tour italy in 14 days

How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)

Planning your first trip to Italy may feel overwhelming–but this (repeatedly) tried-and-tested itinerary for 2 weeks in Italy will have you relaxing into la dolce vita in no time!

For those who are new here, we are Kate and Jeremy Storm, travel bloggers and Italy travel addicts who have cumulatively spent more than a year each, over the course of many trips, exploring Italy in-depth.

After more trips (and plates of pasta) than we can count , our desire to return to Italy just keeps growing: there will always be more villages to explore, natural beauty to marvel at, and, of course, pasta and wine to enjoy.

Helping travelers plan their Italy itineraries is one of our passions, and we have repeatedly tested this guide to 14 days in Italy on friends, family, and ourselves many times over the course of several years!

So far, we have personally made our way to 14 of Italy’s 20 regions, from the imposing Dolomites of South Tyrol to the beaches of Sicily.

We’ve also “lived” for 2 months in Rome, and one month each in Florence and Bologna , enjoying a slower pace of Italy travel.

Suffice it to say that after all the time we’ve spent in Italy, we have some opinions about how to make your first trip to Italy truly unforgettable… and this Italy itinerary is what we suggest.

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For first-time visitors, 2 weeks in Italy is the perfect amount of time to hit the country’s most famous and classic spots, see which ones you love, and (if you’re anything like us) fall head-over-heels in love with the country to the point that you’ll leave planning your next trip back.

This is the 2 week Italy itinerary we recommend to first-time visitors, including our friends and family, and we won’t be straying off the beaten path much here.

These first 14 days in Italy will be all about the classics–follow this trip and you’ll be spending a lot of time watching postcards come to life!

(And yes, this is a fairly long Italy blog post–feel free to use the table of contents below this paragraph to jump around as needed.)

Table of Contents

After Planning Your 2 Week Italy Itinerary…

How we structured this itinerary for 14 days in italy, the perfect itinerary for 2 weeks in italy, more (or less) than 2 weeks in italy, getting around italy, when to visit italy for 2 weeks, what to pack for italy, your 2 week italy itinerary map.

… we’d love to help continue to plan your trip to Italy in more detail here on Our Escape Clause!

We have been writing about Italy travel since 2016, and have amassed a collection of 100+ Italy blog posts available for free on this website, covering everything from the best hidden gems in Rome to what a coperto is (and why you should expect to pay one).

Cities like Rome and Venice are among our absolute favorites in the world, and we write about them extensively–but if you’re interested in getting off the beaten path in Italy, we have lots of options for that, too, from enjoying the mosaics of Ravenna to taking a road trip in Puglia .

One of my favorite things to write is detailed itineraries (like this one!), and we have suggestions for  Rome ,  Florence ,  Venice ,  Cinque Terre , the  Amalfi Coast ,  Milan ,  Naples , and more (and in the cases of some cities, several versions depending on how long you have to explore!).

I’ll link relevant blog posts throughout this 2 week Italy itinerary, but of course, I could never hope to include links to them all!

Head to  our Italy archives  to view all of our Italy blog posts in order, or if you’re looking for details on a particular destination, the search bar at the top right of the page (or at the top of the pop-out menu on mobile) is a great tool to use.

You also may want to check out the comment section at the bottom of this post–over the years, dozens of travelers have refined their own Italy itineraries there!

We structured this 2 week Italy itinerary as a point-to-point trip covering Rome, Florence, the Tuscan countryside, Cinque Terre, and Venice.

In this way, you’ll have a chance to experience many of the most popular places to visit in Italy over the course of 2 weeks, without doubling back or over-stuffing your schedule.

While some travelers like to include Milan, Lake Como, and/or the Amalfi Coast over the course of 2 weeks, we have found that with roughly 14 days (and often some jet lag) to work with, less is more.

We’ve opted for Venice over Milan and Lake Como due to personal preference, and opted for Cinque Terre over the Amalfi Coast due to geographic convenience and the ease with which it can be seen over a short period of time.

However, ultimately, the destinations that appeal to you most should be at the top of your Italy bucket list, and this itinerary for Italy in 2 weeks can be adjusted accordingly.

Days 1-4 in Italy: Rome

Rome’s highlights rank among the most famous sights in the world: who hasn’t dreamed of seeing the Colosseum in person, of walking across St. Peter’s Square, and of admiring the masterpiece that is the Sistine Chapel?

Three full days in Rome (excluding travel days) will give you plenty of time to see the best of what Rome has to offer, while also leaving plenty of time in your 2 weeks in Italy itinerary for all of the other destinations along the way.

If you happen to be lucky enough to have an extra couple of days in Italy, though–say 15 or 16 days, or perhaps less jetlag to contend with than some visitors–we highly recommend extending your time in Rome before adding time to any other destination on this 2 week Italy itinerary.

It’s simply impossible to run out of incredible things to do in Rome, which is why we have happily spent months there!

(It’s also worth pointing out that if you do have a bit of extra time in your schedule, booking an organized day trip to the Amalfi Coast is doable, if a long, day that is popular with ambitious travelers!).

Top Things to Do in Rome

Tour the colosseum + palatine hill..

Strolling through the center of Ancient Rome for the first time is an unforgettable experience!

Definitely don’t miss it during your first trip to Italy: you can buy skip-the-line tickets here (highly recommend for people visiting during summer/high season), or book the tour we enjoyed here .

Visit Vatican City.

The magnificent Sistine Chapel, the iconic St. Peter’s Basilica, the lovely St. Peter’s Square: for being such a tiny country, visiting Vatican City has a lot to offer!

We recommend using skip-the-line passes here as well, you can purchase them here .

We wrote a full guide to visiting Vatican City , so won’t repeat ourselves too much here, but in short, plan ahead, cover your shoulders, and touring the Vatican Museums on Friday night is worth it if you have the chance.

Stroll through Centro Storico.

The Trevi Fountain, the Pantheon, the Spanish Steps, Campo de Fiori: what do all of these famous things to do in Italy have in common with each other?

They’re all within walking distance of each other in Rome’s Centro Storico!

We also recommend seeking out a few of Rome’s hidden gems as you explore, including easy-to-access spots like Galleria Sciarra and Galleria Spada .

One of the best things about visiting Rome is just how much beauty is hidden in plain sight.

Things to Consider When Visiting Rome

Rome has two major downsides for a tourist: crowds and heat.

You can beat the bulk of both by traveling in the shoulder season (we personally think that October is the perfect month to visit Italy, and Rome is remarkably uncrowded in winter ), and/or waking up extra early to enjoy the city before everyone else gets out of bed.

For example, some of the best photos of the Trevi Fountain, Colosseum, and Spanish Steps that we’ve taken were snapped around dawn!

That being said–there are a million ways to get off the beaten path in Rome no matter when you visit!

While touristic hotspots like the Colosseum and Spanish Steps are nearly always crowded, fascinating places like the Capuchin Crypt, the Palazzo Doria Pamphilj, the Basilica of St. Paul Outside the Walls, plus the neighborhoods of Testaccio, Ostiense, and Monti in general, are just a few of the many great places to enjoy Rome without dense crowds.

Where to Stay in Rome

La Cornice Guesthouse  — We loved this little guesthouse! It was extremely clean and comfortable, and VERY affordable for Rome.

La Cornice is set slightly outside the main tourist areas, but an easy 5-minute walk to the metro and a 20-minute ride got us to the Colosseum and other major sights.

Our favorite part of La Cornice? Eating a nearby Joseph Ristorante for lunch, which we not only enjoyed during this trip but have returned to repeatedly in the years after.

Check rates & book your stay at La Cornice Guesthouse!

Hotel Condotti  — Located just around the corner from the Spanish Steps (and consequently the Piazza di Spagna metro station), you couldn’t ask for a better location in Rome!

Well-reviewed and boasting exceptionally clean rooms, Hotel Condotti is the perfect choice for a traveler with a midrange budget (or even a luxury traveler–this hotel also holds some impressive-looking suites!) who would like to be within walking distance of the best that Centro Storico has to offer.

Check rates & book your stay at Hotel Condotti!

Pantheon Inn  — If you’re looking for a building with classic Italian charm in the heart of Rome, this is it.

Located right behind the Pantheon and within reach, the Pantheon Inn offers a quiet, peaceful escape in the middle of bustling Rome.

You will need to walk a bit to the metro stop–but since the walk will take you through the heart of the beautiful Centro Storico, we doubt you’ll mind.

Check rates & book your stay at the Pantheon Inn!

Days 5-7 in Italy: Cinque Terre

No first trip to Italy would be complete without a visit to this beautiful coastline!

After leaving Rome, head north to Cinque Terre for coastal views, hiking, adorable fishing villages, and plenty of fresh seafood.

We recommend traveling from Rome to Cinque Terre (specifically Monterosso al Mare) via train , which should take about 4-6 hours depending on the route.

Since all 5 of the Cinque Terre villages are easily connected by train (or ferry during the summer!), feel free to stay in whichever one appeals the most, or even in nearby Levanto or La Spezia to save a tiny bit of cash.

Top Things to Do in Cinque Terre

Hike between the villages..

Sadly, many of the hikes at Cinque Terre have been closed for landslides–but the magnificent Blue Path trail between Monterosso al Mare and Vernazza (which is highly recommended!) and between Vernazza and Corniglia are open and ready for visitors!

We recommend stopping by one of the visitor centers for the latest information on available hikes.

Watch the sunset from Manarola.

Arguably the most famous of Cinque Terre’s villages due to its postcard-worthy view, Manarola is the perfect place to watch the sun sink behind the sea (preferably with a glass of local wine in hand).

Eat all the pesto and seafood.

Pesto is local to the Ligurian coast, and that makes Cinque Terre one of the best places to indulge in it in all of Italy!

Pesto happens to be one of my favorite foods, so I may be slightly biased, but in my opinion, it’s an unforgettable part of visiting Cinque Terre.

As the villages of Cinque Terre are fishing villages at their heart, the seafood here is also absolutely delicious.

Things to Consider When Visiting Cinque Terre

While it would be tempting to bring a car to Cinque Terre to have access to your own transportation and a more direct way to get to Cinque Terre from Rome and to Florence after your visit, the roads do not make for an easy drive.

Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train, ferry, or the famous trail to get around Cinque Terre .

Keep an eye on closures to both the trains and the trails between the villages, however.

Strikes can happen that will shut down the train (which happened to us way back in May 2016!), and the trails can sometimes be washed out and therefore closed.

The trails also often close during the offseason, so if you’re planning a winter trip to Italy, don’t count on being able to hike between all the villages.

Why Cinque Terre instead of the Amalfi Coast?

I addressed this above, but it’s understandably a popular question when planning a trip to Italy for 2 weeks, and I wanted to expand on it here!

Italy’s Amalfi Coast is truly a marvel, but it makes less geographic sense for this itinerary than Cinque Terre.

Visiting the Amalfi Coast would require traveling south from Rome when the bulk of this 2 weeks in Italy itinerary focuses on the northern half of the country.

If you have your heart set on visiting the Amalfi Coast, you can certainly swap it out for Cinque Terre, but bear in mind that the travel times involved would be cumbersome, especially if you don’t want to cut days from the rest of the destinations on your Italy itinerary.

Cinque Terre also has the benefit of being smaller than the Amalfi Coast, making it easy to explore most or all of the villages over a short amount of time.

If you absolutely don’t want to cut any destinations and are determined to visit both Cinque Terre and the Amalfi Coast, handing the reins to the experts and booking and organized day trip to the Amalfi Coast from here is your best bet ( this one gets rave reviews ).

Where to Stay in Cinque Terre

Of the 5 villages of Cinque Terre, the only one we would recommend not staying in is Corniglia, as it’s the most difficult to get in and out of.

Other than that, all the villages have their perks–Monterosso al Mare has the biggest beach, Manarola has the most Instagram-famous viewpoint, and Vernazza and Riomaggiore are simply drop-dead gorgeous.

Bear in mind that many properties in Cinque Terre can involve a climb to reach them, so if mobility is a concern, be sure to double-check the location.

Most properties will offer porters to carry your luggage for you for a small fee, so if clamoring through town with your luggage doesn’t sound like fun, be sure to ask your hotel about their services!

Here are a few very well-reviewed properties to consider during your time in Cinque Terre:

Luciano Guesthouse (Riomaggiore)  — This is where we stayed during our most recent visit to Cinque Terre, and we can’t recommend it enough!

The property was clean and lovely, and the customer service offered by Francesco and his wife during our stay was absolutely top-notch. We would be thrilled to stay again!

Check rates & book your stay at Luciano Guesthouse!

Scorci di Mare (Riomaggiore) — Want to stay a 3-minute walk from the beach and see the sea from your window?

If so, the popular Scorci di Mare is the perfect spot for you!

Check rates & book your stay at Scorci di Mare!

Da Baranin (Manarola) — Cinque Terre is expensive, there’s no getting around it.

For a budget option, consider Da Baranin–you’ll need to climb up and down a steep hill as a trade-off, but you’ll get to stay in Manarola for a very affordable price tag!

Check rates & book your stay at Da Baranin!

Days 8-11 in Italy: Florence + the Tuscan Countryside

Tuscany is one of our favorite regions in Italy–and not just because we could spend a lifetime eating and drinking there (though we could).

The towns are beautiful and distinct, Florence is a dream of a city, the history is interesting, and the golden tinge to the light that you see in pictures of Tuscany isn’t photoshop–it just really looks like that.

While there’s no such thing as too much time in Tuscany, 3 days in Tuscany will give you a chance to explore the best of Florence in about 1.5-2 days, and also give you time to visit at least one other Tuscan city or small town, and/or head out wine tasting.

Pisa is a popular choice that is close to Florence, but unless you’re truly dying to see the leaning tower, we’d recommend Siena, Lucca , or Montepulciano instead.

If you’re looking for small-town day trips from Florence , San Gimignano, Volterra , Arezzo , and Montefioralle (near Greve in Chianti) are all stunning, and though it is in Umbria rather than Tuscany, we adored our visit to the village of Orvieto as well.

If you’re hoping to enjoy some wine tasting and town-hopping, this is an excellent opportunity to get a lot of value out of a guided tour: this wildly popular day trip from Florence is a fantastic way to taste a variety of what Tuscany has to offer (literally and figuratively).

Top Things to Do in Florence

Visit some of the best renaissance art on the planet..

The Uffizi Gallery (home of the Birth of Venus) and the Galleria dell’Accademia (home of Michelangelo’s David) are both home to undisputed world treasures that deserve to be admired during your 2 weeks in Italy.

We definitely recommend booking skip-the-line tickets to both galleries to avoid waiting in their very long lines (we once showed up to the Uffizi without pre-booked tickets and ended up giving up on visiting after nearly an hour of waiting).

You can purchase skip-the-line tickets to the Galleria dell’ Accademia here and to the Uffizi here .

Try your hand at a cooking class.

We may be a bit biased, given how much we adore Tuscan food, but if you want to take a cooking class during your 14 days in Italy, we recommend doing it here.

We adored our day taking this cooking class and years later, we still talk about it being one of our favorite days spent in Tuscany!

From the views of the countryside to the beautiful farmhouse the class is hosted in, to the sublime food, it is truly an experience to remember.

Seek out the best views of the city.

From the ever-popular viewpoints of Piazzale Michelangelo and the cupola of the Duomo to lesser-known spots like the Rose Garden and Palazzo Vecchio, there’s no doubt that Florence is a city that deserves to be admired from all angles.

We’ve rounded up the best views of Florence here –personally, we have a soft spot for the view from the top of Palazzo Vecchio.

Take a day trip to the Tuscan countryside.

Wine, plus incredible Tuscan food, plus rolling countryside, plus stunning villages–a day trip to some of Tuscany’s remarkable villages and wineries is bound to be a day that you’ll never forget.

This incredibly popular day trip is a fabulous option!

Things to Consider When Visiting Florence and Tuscan y’s Countryside

Three days in Tuscany gives you a couple of options as far as lodging: you can either stay in Florence the whole time and take day trips out, you can stay in a smaller city the whole time and simply take a day trip to Florence, or you can split it up–two nights in one city, and one in another.

Personally, we’d recommend sticking with one place to stay–this Italy itinerary is already fast-paced, so there’s no reason to take up extra time moving hotels in Tuscany.

We’ve visited Tuscany many times with both structures , and love both for different reasons .

You truly can’t go wrong with either option–I’d stay in Florence if you’re more of a city person, and in a surrounding Tuscan town if you’re more interested in the countryside.

If you stay in the countryside, you will definitely want to rent a car for this portion of your Italy itinerary.

Where to Stay in Florence

B&B Le Stanze del Duomo  — Though Florence hotels can be a bit pricey and stretch the definition of “budget”, B&B Le Stanze’s beautiful rooms and impeccable location in Florence will be sure to have you swooning!

Check rates & book your stay at B&B Le Stanze del Duomo!

Hotel Silla — Located just a hop, skip, and jump from the Arno River, we loved our stay at Hotel Silla!

The hotel itself is lovely and quiet, the included breakfast a nice touch, and the location perfect: you have easy access on foot to all that Florence has to offer, without having to worry about crowds or noise.

We’d be happy to check in again!

Check rates & book your stay at Hotel Silla!

Hotel Lungarno  — Nestled right against the Arno River and home to one of the best views of the Ponte Vecchio in Florence (not to mention some of the best views of the rest of Florence from their top deck), Hotel Lungarno is our personal “if we ever  really  want to splurge” hotel in Florence.

You can’t go wrong using Hotel Lungarno as your base during your Italy vacation!

Check rates & book your stay at Hotel Lungarno!

Days 12-14 in Italy: Venice

Canals, canals, and more canals: Venice is simply a ridiculously beautiful place, and despite its somewhat controversial reputation, we absolutely adore it (yes, even during the summer !).

Definitely make sure that you climb St. Mark’s Campanile for an amazing view of the city, check out Libreria Acqua Alta (one of our favorite bookstores in the world!), walk across the Rialto Bridge, and spend ridiculous amounts of time wandering aimlessly around the small streets and lesser-known canals–that is truly Venice at its best.

If you have good weather while in Venice, also consider a day trip out to Murano or Burano for another view of Venetian life!

We’ve written extensively about Venice, in large part because we adore the city and know that unfortunately, not everyone walks away with the same impression.

We recommend taking a look at our suggested 2 day Venice itinerary and guide to the best hidden gems in Venice as you plan your trip here!

Top Things to Do in Venice

Tour the doge’s palace + st. mark’s basilica..

Venice has a truly fascinating history–for a city that is now known mostly for its beauty, flooding, and risks of sinking, it can be hard to recall that once upon a time, there was a true and powerful Venetian Empire.

Learning about the history of Venice’s government (it included  many  councils) and how it acquired its wealth is a fabulous way to get to know the city on a deeper level–and the buildings themselves are incredibly impressive, too.

We recommend taking a tour here if at all possible–it truly adds so much context.

This tour of the Doge’s Palace + St. Mark’s Basilica is very popular and a great option!

Stroll through Venice’s beautiful sestieri.

Venice is divided into six districts, or sestieri, and each sestiere has its own distinct flavor and beauty.

San Marco and San Polo are the most popular (read: crowded), and while they are absolutely gorgeous, we recommend making time for a walk through some of the others as well.

Castello, Cannaregio, Dorsoduro , and San Croce all have a lot of beauty, canals, and quiet streets to offer.

Hit the water and enjoy Venice’s canals.

While the gondolas are (deservedly) famous, there are indeed ways to experience Venice’s canals on any budget.

Whether you want to splurge on a private gondola ride, opt for the mid-range shared gondola option, or stick to a budget and tour the Grand Canal via Vaporetto , there’s a canal option open to you!

Our guide to gondola rides in Venice will help you know what to expect, or, if you want to find a way to enjoy a gondola ride for just 2 Euro (not a typo!), here’s how to find a traghetto .

Things to Consider When Visiting Venice

Especially if you’re visiting during the summer, Venice will be both crowded and expensive.

It’s still absolutely worth it to go, but like in Rome, consider early wake-up calls to get the most out of your experience.

Some of our best memories of Venice are of walking through the city before the shops even start opening–and we’ve often found that we get our best photos of Venice then, too.

Keep in mind that if you want to take an iconic gondola ride, you’ll be paying a pretty penny–80 Euro/gondola worth.

After enjoying more than one gondola ride in Venice, we can confirm that they are worth it to the right traveler–but you can absolutely have a fabulous trip to Venice without one, too.

Where to Stay in Venice

Hotel Casa Boccassini  — This cute hotel easily met our needs during our first trip to Venice!

The room was simple but clean, and the shared bathroom was a fair trade in exchange for their competitive prices in a great location in Cannaregio.

The bathroom was clean and we had a sink in our room, both of which always make shared bathroom situations much easier.

The courtyard of the hotel was beautiful!

The hotel was a simple and beautiful 10-minute walk from the Rialto Bridge and just a 5-minute walk from the Vaporetto to the airport.

Check rates & book your stay at Hotel Casa Boccassini!

Hotel Lisbona  — We decided to check into Hotel Lisbona for one reason: we wanted to stay on a canal!

If you’re looking to stay right on a canal in Venice without paying luxury prices, we can heartily recommend Hotel Lisbona.

The building is beautiful and definitely has that oh-wow-I’m-in-Venice effect (especially when you look out the windows), the customer service is great, and the included breakfast is tasty.

The central location (it’s around a 5-minute walk to Piazza San Marco) couldn’t be better.

The downside? The room we stayed in was  tiny –but to be staying right on a Venetian canal in such an amazing location, we definitely considered the trade-off worth it.

Check rates & book your stay at Hotel Lisbona!

Hotel Danieli  — If you’re looking for a true luxury experience for your 2 days in Venice–the kind of hotel stay that you’ll remember for the rest of your life–look no further than the iconic Hotel Danieli, located inside 3 former palazzos along the Riva degli Schiavoni.

Every detail has been looked after here, and everything from the furniture to the breakfast to the location (mere steps from the Bridge of Sighs) to the truly stunning lobby will ensure you have an absolutely unforgettable trip to Venice.

Even if you don’t check in, consider dropping by the bar to see the beautiful lobby for yourself!

Check rates & book your stay at Hotel Danieli!

Italy has an endless amount of places to see, and no 2 weeks in Italy itinerary could dream of covering the whole country.

If you’re visiting over the summer (or over the winter and you like to ski) and find yourself with more time in Italy, consider heading to the South Tyrol region to experience the Dolomites (also known as the Italian Alps).

You could also head to Lake Como and stop off at Milan along the way, or stay further east after leaving Venice and hit up the stunning Verona .

Bologna , which is known as one of Italy’s great foodie cities, is another wonderful choice, and also includes the option of a day trip to the microstate of San Marino .

And, while Bologna is the most famous place to visit in Emilia-Romagna, we’d be remiss not to point out Ravenna (home to absolutely incredible UNESCO-recognized mosaics) and Parma (the origin of parmigiano-reggiano and a delightful city) as well.

South of Rome, you could head to the incredible Amalfi Coast or the stunning island of Capri , and stop off for a day along the way to eat pizza in Naples .

Further south, the stunning beaches and towns of Puglia make for a memorable summer trip to Italy.

Even with all that, you’re still barely scratching the surface of Italy (and of course, every single one of the destinations included in this 2 week Italy itinerary could easily take up more time as well)–but that’s ultimately a good thing.

If there’s one thing that we’re certain of after more than a year of exploring, it’s that there is always a reason to plan another vacation in Italy.

With One Week in Italy

If you only have roughly one week to spend in Italy, we–heartbreaking though it is–recommend cutting at least one of the destinations suggested on this 2 week Italy itinerary. 

Personally, we’d first cut Cinque Terre (especially if you’re visiting outside the summer season), leaving the trifecta of Rome-Florence-Venice intact.

We go into this further in our guide to spending a week in Italy , as well as provide other suggestions on how to make the most of a short Italy itinerary.

If you need to cut a second destination, let geography be your guide, and trim off whichever destination will take the most time to reach based on your travel plans.

I know it’s incredibly hard to cut destinations, but rushing to a new place almost every day will eat up way too much time that should be spent experiencing Italy.

And ultimately, any given two, or even one, of the destinations covered in this Italy itinerary, could make for a magnificent trip.

With 3 Weeks in Italy

If you have an extra week to tack onto this 2 week Italy itinerary, lucky you!

You’re in for a real treat with a whole 3 weeks in Italy.

Our personal recommendation would be to use that extra week to add on Naples, Pompeii , and the Amalfi Coast.

If you’re a fast-paced traveler, you could cover those destinations in 4-5 days and spend the remaining time sampling Milan and Lake Como ( the town of Bellagio is just as picturesque as the pictures imply).

With that, you’ll cover the vast majority of the country’s best-known sights on your trip to Italy!

Alternatively, if you’re more of a slow, immersive traveler, use the extra week to really dig into one of the regions already included on this Italy itinerary.

Tuscany or Rome would be our pick (and you can technically take a very long day trip to Pompeii or Naples from Rome if you want to try to get the best of both worlds).

Within each of the destinations outlined in this 2 weeks in Italy itinerary, walking will likely be your most common method of getting around, and also half the fun of traveling Italy!

You’ll probably want to mix in some public transportation as well, particularly in Rome, but strolling through destinations like Venice and Florence is by far the best way to explore them.

Getting between destinations, however, is a different story–here’s a quick outline of transportation within Italy.

Trains rule on-the-ground travel in Italy: if you’re not going to rent a car, it’s likely you’ll be getting around Italy by train.

Every train we have taken in Italy has been comfortable and pleasant, but keep in mind that strikes can occasionally interfere with travel.

We definitely recommend booking your train tickets in advance if you’re traveling on Italy’s high-speed trains, as these tickets can increase in price as the dates get closer.

If you’re traveling on the regional train, you don’t need to worry about booking ahead, as the prices are fixed. 

We typically travel Italy by train with Trenitalia, Italy’s national company, but Italo (a private company) is also excellent for some routes.

In Lombardy (where Milan and Lake Como are located), you’ll also see Trenord-branded trains.

You can check prices and compare rates, schedules, and more on Omio to ensure you’re getting the best deal on train (or bus) travel in Italy.

We use Omio regularly throughout Europe and have always had good experiences with it.

If you do happen to buy a train ticket at the station (for a day trip, perhaps), keep in mind that paper train tickets  must  be validated before boarding the train in Italy, and failing to do so could result in a hefty fine, being thrown off the train at the next stop, and an enormous headache.

As far as we’re concerned, that’s another reason to book online, as showing the tickets on your phone to the conductor is just fine.

Shop train tickets for your 2 week Italy trip today!

Renting a car to drive through Italy is a popular option, especially in places like Tuscany, but there are a few things you’ll want to consider before you do.

Keep in mind that cars are restricted from driving into the historical centers of most cities, including Florence and Venice, and failure to adhere to these rules (even accidentally) can result in strict fines that you sometimes find out about through the mail months after the fact (my dad and a good friend have both been fined for driving in Italy via a summons after returning home).

For that reason, as well as issues with extremely limited parking in cities, we recommend limiting car rental when possible to time spent in smaller villages and towns.

While we love taking road trips in Italy , this itinerary for 14 days in Italy doesn’t require one, with the possible exception of renting a car for a couple of days to explore smaller villages in Tuscany.

If you do want to rent a car in Tuscany, know that an international driver’s permit is required for renting a car in Italy and must be obtained in your home country before arriving.

Sometimes car rental companies ask for it, sometimes they don’t (same with the police), but in our opinion, it’s not worth taking the risk–add this to your list of things to take care of being starting your 2 week Italy trip if you plan on renting a car.

Also, keep insurance in mind!

Thanks to Italy’s (somewhat deserved) reputation for less-than-cautious drivers, some travel insurance companies will not cover you while driving in Italy, or charge an extra fee to do so. Be sure to double-check before you book.

If renting a car is the right choice for you, we recommend browsing Discover Cars , and aggregate for finding rental cars in Europe (and beyond, though they’re most popular in Europe).

Discover Cars will search both local and international brands that have available cars for your dates, and allow you to compare prices, reviews, and inclusions side-by-side.

Shop rental cars for your Italy vacation today!

Bus travel in Italy is much less common than in some other European countries, mostly because of their well-developed train system.

You can find some buses available, however, especially among smaller cities and villages (we’ve used local buses in South Tyrol several times), as well as throughout certain parts of southern Italy.

If you’re having trouble deciding how to get around a certain destination.

In addition to trains, you can also browse some long-distance buses via Omio .

If you’re hoping to be careful of your budget during your 2 week Italy trip, we recommend looking into flights for the Rome to Venice (or vice versa) leg of this itinerary.

Trains are a comfortable, romantic, and easy way to travel, and they also often cost more than budget flights do!

There’s no such thing as a bad time to spend 2 weeks in Italy, but some seasons are definitely more convenient to travel in than others.

Summer is the most popular season and will bring warm weather, lots of sunshine, and lots of tourists.

Prices will be at their highest, but the beaches will be at their best–if you’re hoping to swim at Cinque Terre, you’ll want to plan a summer trip.

Winter is the offseason and will bring colder temperatures, rain, and gray skies.

Prices will be at their lowest, and crowds will be as small as they ever get.

The Christmas season can bring increased crowds, but also the benefit of experiencing Christmas decor and markets (though fair warning–these have nothing on the Christmas markets in Austria and Germany! Check out Bolzano for something close.).

Personally, our favorite times to travel to Italy are the spring and especially the fall.

T he crowds are less than in the summer, spring brings beautiful blooms, and fall brings the olive harvest (after tasting fresh olive oil in Tuscany, I don’t know how we ever lived without it).

The weather is a bit riskier during the spring and fall than during the summer, but we have never had much of an issue with it.

T he occasional rainy or cool day is worth it to us for the tradeoff of not being hot and crowded, and October is our personal favorite month to visit Italy.

Ultimately, though, whenever you have a chance to plan a 14 day Italy trip, take advantage of it: every month of the year brings distinct upsides and challenges, but each and every one of them is worth the trade-off.

Planning a packing list for 2 weeks in Italy can be a challenge of its own!

We have a full Italy packing list here, but to get you started here are a few things to be sure to bring on your trip to Italy.

These days, we prefer just to leave valuables in our Pacsafe during the day.

Option C: Hope you get lucky with the weather (but fair warning, we’ve never been avoided rain entirely during a trip to Italy!).

Bring a small pack of tissues, toss them in your day bag, and you won’t have to worry about it.

I’ve been using it for more than 5 years now and am now working on my second volume, and I absolutely adore it!

I use them on all boats and the occasional bus, and if things get really bad, take some Non-Drowsy Dramamine as well.

Before heading off for your 2 weeks in Italy, be sure to read through our complete Italy packing list !

Take This Map With You! Click each highlight to pull up the name of the destination. To save this map to “Your Places” on Google Maps, click the star to the right of the title. You’ll then be able to find it under the Maps tab of your Google Maps account! To open the map in a new window, click the button on the top right of the map.

About Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

148 thoughts on “How to Spend 2 Weeks in Italy (Itinerary for 14 Perfect Days!)”

I’m in Veneto, and so am biased about what I write about Italy. You covered some great places like CInque Terre and beautiful Toscana. I totally agree about heading to see the Alps, the Dolomiti is a must too. Beautiful photos to accompany the post too!

Thanks, Lisa! We’re hoping to make it back to see even more of Italy in 2018–maybe we’ll make it to more of Veneto this time!

Do the 3 chimney hike, you will not be disappointed!

Italy, why can’t I quit you… I have been reading about how dreary Italy can be in the winters. I think you are right that fall would be the best time to visit. I loved how clear all of your photography was.

Thanks, guys! I know what you mean–we can’t quit Italy, either.

I went in October 1-14, 2021, we had one evening of rain in Venice but we went to a concerto and the rain was over when we came out of the concert!!! I had the best trip ever!!!!!! My daughter planned it and she did an excellent job, Naples to Rome to Florence to Tuscany to Venice to Cortina to Venice train to Naples to Mt. Vesuvius to Pompeii to Verti to Amalfi Coast. It was an amazing trip and I want to go back too.

How many days did you stay in each of these places on your trip to Italy?

What was your itinerary day to day. What method of transportation? Thanks!

Could you please share more details? would love to do this itinerary Summer of 2023!

A great article for first timer to Italy. I have sent this to my partner and I hope he reads it, I have dreamed of coming to Italy since I was a young girl. My parents went to Italy and always spoke of Venice and Muranos Island and of course glassware. Your photos are spectacular.

Hope you get to make that trip happen soon, Nicole! Italy is as amazing as advertised. 😀

Italy is such a cool destination and this is the perfect guide to plan a trip in two weeks. I have been to Rome once and your pictures of Trivi Fountain is amazing as during my visit it was mainly crowded. Did you explore the islands near Venice too ?

No chance to go to the islands, sadly–the weather didn’t cooperate with us too well in Venice. Hopefully next time! We’d especially love to go to Burano.

I was actually wondering where you were off next, after reading your Rome post 🙂 although not a big fan of Italy overall, I am a huge fan of Tuscany… I only got to spend 2 days in Florence a few years back, so it is definitely on my travel list! Love your pics!

Florence is definitely worth a return visit–the food alone would be, in our opinion! 😉

I visited Italy for the first time last year, travelling to Rome and it was magical. The amount of culture is unbelievable, I would love to travel to Florence or Naples next time!

I hope you get that return trip, Lottie! Italy never gets dull, that’s for sure.

Your pictures are really enticing. A trip to Italy would be incomplete without taking up a culinary class or 2 in Tuscany. Cinque Terre looks particularly interesting too. Will get back to you for travel-planning. 🙂 Cheers!!

You’re totally right, Aditi–our cooking class in Tuscany was one of our highlights of our month there this year! Food in general is such a big part of traveling in Italy, it really adds something to the whole experience.

I agree with you that one cant get enough of Italy…and this time I really mean it! So much cosy villages and site to explore…and not to mention the food! I have been to Italy many times before living in the country next to so I think you have chosen a great destinations for a two weeks itinerary for a first-timer! I hope to visit the northern and souther part of Italy this summer!

Oh, it must be so much fun to live in Italy! I’m sure it comes with its challenges as well, like any destination, but if we could pick somewhere to live for a year, Italy would be VERY high on the list!

Eat, Pray, love put Italy on my map. And, I am so glad it did. I really enjoyed my time in Italy. And, without knowing I almost followed your first-time visitor itinerary. The country is so beautiful that one time is not enough. I am aching to go back. Maybe this year it will happen.

Hope you get to go back, Archana! No such thing as too many trips to Italy, right?!

A nice itinerary that you have suggested. Did all these except for cinque Terre. Wish someone had advised me then to do that. I hope to go back to Italy again to see this. Cheers

Agreed–we hope we get to go again soon, too! 🙂

Curious, how did you decide the order of your destinations? We’re doing 15 days in Italy and flying into Rome. We’re trying to visit Venice, Florence, Cinque Terre, Tuscany then Amalfi Coast before returning to Rome for our flight home. Any advice on the best order?

We actually put this itinerary together based on a couple of months worth of travel in Italy, so we didn’t follow these steps exactly in order (though we’ve visited all of these destinations, some more than once!).For your trip, assuming you’re flying out of Rome as well, I’d personally probably structure it as: Rome to Cinque Terre, Cinque Terre to Florence/Tuscany, Florence/Tuscany to Venice, and Venice to the Amalfi Coast (you’ll need to stop by Rome again) before returning home.

No matter what way you do it, you’re going to have a lot of travel time in there–you’re covering quite a bit of the country.Honestly, I’m tempted to say you should skip either Cinque Terre or the Amalfi Coast (the Amalfi Coast would make more sense to cut geographically, hence why it didn’t make this itinerary) and slow the pace a bit, but I know that’s much easier said than done–when you have a limited number of days, you want to see it all!

Not sure how you’re planning on getting around, but I’d consider saving some time and flying from Venice back to Rome–budget airlines (including Ryanair) fly in/out of both those cities, and if you plan in advance, you may be able to get very low fares. Also consider booking any train tickets you need in advance–fares go up dramatically the closer your dates get.

Hope you guys have an amazing trip! Italy is absolutely incredible. ?

Hi Jeremy and Kate, Warm greetings from India. I discovered your blogsite recently and this is really amazing 🙂 I wanted a favor from you guys, I will be travelling to Italy soon, for some office work in mid march. I will stay at Siena for 14 days. Can you please please please recommend me a travel plan or at least help me with details of rail travel? I intend to see Rome on one weekend, Venice and Milan on other weekend. I intend to travel Florence and Pisa during weekdays, when we get time off. I wish to hear from you guys… Love from India <3

Hi, Akshay! That’s not a service that we offer, but I can say that we used Trenitalia for our train tickets and were very satisfied with them. I recommend booking as soon as you know your dates, because prices do get more expensive over time. I think seeing Venice and Milan in a single weekend will likely be too much–unless you’re dying to see Milan in particular, I’d recommend skipping it and heading right to Venice. Good luck!! Hope you have an incredible trip.

We leave for our first Italy trip next week! I am so excited! When we were first planning our trip we were trying to pack too much into 14 days. We settled on flying into Venice for two days, heading to Modena for two days, traveling to the Umbria region for 5 and ending in Rome where we fly out.

Oh, that is so exciting! It’s definitely tempting to try to stuff too many destinations into too few days, but your trip sounds wonderful. I hope it helps you fall in love with Italy!!

Hello- We are traveling to Italy for first time in August 2018. Flying in to Venice and staying for 3 nights. Then to Florence for 4 nights, and on to Rome for 6. Flying back to US from Rome. Question– Should we decrease time in Rome to add 1-2 nights in Naples or Sorrento to see Amalfi Coast? We will do day trip from Rome –> Naples –> Pompeii, but just curious if we should try to squeeze in Amalfi Coast. Thank you!

Hi Vicki! It’s hard to say without knowing your general travel style (how badly do you want to see the beach?), but our recommendation would be to stick with Rome for 6 nights, or to add on an additional night onto Florence and potentially use that as a day trip to Cinque Terre (you’ll need a car to do that, but it’s a shorter drive than Rome –> Sorrento). Good luck with your planning–your trip sounds fabulous!

Thanks so much Kate! The attraction to Amalfi Coast is b/c we have heard how beautiful it is- but it does does sound far for a day trip from Rome. I keep reading about Cinque Terre but we are not big hikers (knee issues…!). Would Cinque Terre be worth a day trip (train?) on the way to Florence from Venice? Thank you so much for your help! Vicki

A day in Cinque Terre on the way to Florence, perhaps… but you’d need a whole day, and likely need to spend a night. There’s no direct train from Florence to Levanto (the larger village near the Cinque Terre villages), unfortunately, so traveling by train between the two without a car is harder than it appears looking at a map. Travel from Venice to Cinque Terre will likely take an entire day as well, but you could add one Cinque Terre day in between two travel days if you’d like! 🙂

Kate, Thank you so much– this has been enormously helpful! I think we’ve decided to take the train from Venice to Florence, spend 4 full days in Florence and just explore that beautiful area. We know we need at least two full days in Florence, but welcome any/all suggestions about surrounding area day trips. Grazie!!

Hi Vicki! Some of our favorite Florence towns include San Gimignano, Volterra, and Lucca–all great day trips. 🙂 Siena is also popular. If you have a car, there are natural hot springs in Tuscany that are supposed to be beautiful, but we haven’t made it there ourselves yet. Our “Romantic Things to Do in Tuscany” post has some great ideas as well–you don’t necessarily need to be traveling with a partner for them, either! 😉

Vicki- who are you booking with. This is the exact trip myhusband wants but couldn’t find it. flying to venice for 3 nights, florence for 4 nights, then Rome.

I’m not sure what Vicki is planning, but if you guys are planning the trip yourselves, I’d fly to Venice, take the train to Florence, and then the train to Rome before flying home. I’m not sure of any group tours that follow that route, though I’m sure they exist!

Hi Kate, in your scenariou do you fly back home from Venice or Rome back home

It’s up to you and how the flights work to/from your destination.

In a perfect world, it’s easiest to fly into Rome and out of Venice.

However, if flights are much more expensive that way vs booking a round trip ticket, you can also take the high-speed train from Venice back to Rome to fly out. The fastest trains on that route take just under 4 hours, but you’d need to book those tickets in advance.

This post is a great guide for traveling through Italy. My friends and I traveled to Italy on a rented car and visited some of these places. I advise everyone to visit here!

Thanks, Dylan! So glad you guys had a great time.

Parking can also be a challenge around the villages–if possible, we’d recommend relying on the train or Cinque Terre’s famous trail to get between the villages. And it is very good, because in Ukraine it is big problem!^(

Yes, absolutely, but it can be convenient to drive to La Spezia and take the train into the 5 villages from there. 🙂 Easier than taking the train all the way from Florence for sure!

This is amazing blog! My husband and I are traveling to Italy for our honeymoon in June. Could you guys shed some light on car rental and driving in Italy? Is it driver friendly with interpretable directions? My husband wants to bring a GPS – is this too ridiculous? Thank you!! Also, have you been to Capri?

Hey Natalie! Congrats on your wedding–we got married 5 years ago this June. 🙂 🙂 Italy is reasonably simple to drive in when you consider the quality of the roads (decent) and navigation (decent). That being said, drivers are aggressive and driving in cities is a headache–at the very least, I’d ditch the car in major cities. Depending on your itinerary, I doubt you’ll need a car for your whole trip–I’d consider where it would be more of a hindrance than a help (basically any large city and any surrounding smaller cities/towns that you can connect to by train) and go from there.

I am so happy I came across your blog! We leave 9/8/18 from California and arrive in Rome on Sun. 9/9 @ 6pm My initial thought was to take the fast train to Venice on Mon. 9/10 and then work our way down to Florence, CT, Rome.. but now i am wondering if i should fly to Venice on 9/10 after a good nights rest instead of train to save time.. its the same price! Or do you suggest head straight to CT from Rome, then on to Florence, Venice and fly back to Rome to finish our trip there?? I saw you suggested above to go to CT from Rome..

I am trying to not overwhelm ourselves as i really don’t want to spend all my time on a train or stressed out.. But i feel like these are the 4 places we want to see this time around.. (i had to talk myself out of Amalfi, Lake Garda, etc.!.. i want to see it all!) Also, this will be our honeymoon! We will be there for a total of 13 nights.

Hey Amanda! Congrats on your upcoming wedding!!

September is the perfect time for a honeymoon in Italy, it’s one of our favorite months here. 🙂 I definitely understand the difficulty of cutting things down, lol–there’s never enough time!

As far as starting in Rome or Venice, it’s mostly personal preference. I wrote the itinerary this way for two reasons: 1) most people fly into Rome, and 2) If I had to choose, I think Venice makes a better last destination than first. They’re both crowded and touristy, of course, but seeing the best of Rome requires a lot of effort and activities–the Colosseum, touring the Vatican, etc.

Venice definitely has some great sights, but you could also spend a couple of days strolling aimlessly around the city while eating endless gelatos and still come away feeling like you “saw Venice”–in other words, it’s not as demanding as Rome IMO.

Plus… after flying all the way from California, I’m guessing you’ll be ready to see Italy once you get here, not jump on another train/plane! But ultimately, it’s your call–I don’t think either direction would be a mistake.

I do definitely recommend flying over train travel for the Rome to Venice route, as it’ll definitely save you time–anything that saves you time and stress on a honeymoon is a good idea. 🙂

Hi there, I am taking my wife for 2 weeks coming up next month. We are staying in Cortona, Italy in Tuscancy and making day excursions to Florence, Pisa and other towns within a day of Cortona. For the second week, would it be better to start off in Venice and make our way to Rome and/or Cinque Terre or do I see about a last minute cruise from Venice through the Mediterranean. Downside would be that we wouldn’t see as much of Italy. We don’t want to be on the go 24-7 but we do want to experience Italy. Your comments are appreciated!

Both of those options sound amazing, so it’ll really just be down to personal preference!

I don’t know the cruise itinerary, but I would imagine that the cruise will focus more on natural beauty + beaches, and a a trip to Rome would be more focused on history (with still a sprinkling of beaches in that week if you hit up Cinque Terre).

If this is your first trip to Italy, I personally would forgo the cruise to focus on Italy itself, but there is definitely no right or wrong answer to that!

Great advice and itineraries, thanks so much! We’re planning an 8-10 day trip to Italy during the last 2 weeks of August and are thinking Venice, Florence and Rome (not necessarily in that order). I’m wondering if it would be a better plan to split the time between Venice and Florence and plan to see Rome during a trip during a shoulder season (we also have 2 weeks available to travel after Christmas ). Your thoughts on whether to cut the itinerary to 2 vs 3 cities during the hotter “touristy” time of year? Thanks!

That’s a tough question! Knowing you have another opportunity to travel after Christmas, I would probably lean toward cutting one city and sticking to two–it’ll be a more relaxing trip that way, and there’s more than enough to do in any two of those cities to keep you entertained for 8-10 days. I know it’s a hard call, though!

Hello, it was nice reading your and other people’s ideas. We are going to be 71 and 72 this coming April-May when I am planning our trip to Italy. I have been before and love the trains and agree with all. But, dealing with luggage on trains is not the easiest especially as we get older. I need to book lodging before the flights and we have enough miles. If we take the train, are there taxis at all the stations to get us and luggage to where we stay? And, any idea how much or if they take credit cards like I know they do in NYC? He suggested driving for that reason, but I think finding parking with the lodging, or at the sights, would be the worse problem. Do you agree? I was thinking of mid May, but have read that May is pricey. Do you think late April is warm? I don’t want to lug jackets. My idea for 2 weeks: fly to Rome, 3 days; to Assisi, Perugio, Siena- find a place in either area for a day or 2; Florence, 3 days;Pisa 1 day; Cinque Terre/LaSpezia, 2 days; Venice -maybe drive thru Verona, 2 days.

Hi Roberta! Yes, I can definitely see how the luggage on and off trains can be difficult. There are taxis at most of the stations, but they don’t tend to take credit cards. Uber is available in Rome, but no other city on your itinerary. I would say that driving is definitely more trouble than it is worth for larger cities like Florence, Rome, and Venice–you could consider driving to Cinque Terre, but you’ll likely just be leaving the car at the hotel the whole time.

I’m not sure what your budget is, but some hotels will also offer an airport (and possibly train station?) pick up service–for a fee, of course, but they would be able to help with the luggage.

Late April is a bit unpredictable with the weather–it may already be getting warm in Rome, but Venice will almost certainly still be jacket weather. You never know, though! We were in central Italy during late April this year (Bologna/Emila-Romagna) and we still wanted light jackets until around the beginning of May.

Hope this helps! 🙂

Hey! Came across your blog and this is super helpful. Even reading through all the comments.

My wife and I are flying into and out of Rome in September and have 14 days in Italy. We were thinking after arriving in Rome hopping on a train to Venice and staying there for about 3 and a half days then taking the high speed train to Naples and spending some time in Sorrento and that area for about 4 days and ending in a Rome for about 4-5 days. I’m not counting the days where it’s mostly traveling.

Do you think this is feasible? Should we add a city worth seeing or is it too spread out to really enjoy it? We want to make the best of it since we may not get back there soon but I also don’t want us running around so much that it becomes in enjoyable.

I appreciate your feedback!

It is feasible! You’ll be tired, but it looks like you have enough time to work with. If you have your heart set on those destinations, I’d look at a budget flight instead of a train for Rome/Venice and back–round trip fares can be quite inexpensive on discount airlines like Ryanair, and I know they have lots of flights between both cities.

With a 14 day trip, I would personally be tempted to trim a day from each of those destinations and add in another city (Florence/Tuscany would be my personal first pick), but you certainly don’t need to, and you guys know your pace best.

If you’re 100% sure on dates, I’d check on flight and train prices *now*–the high-speed trains that go between multiple regions of Italy (ie, the Rome–>Venice and Venice–>Naples trains) can be pricey, and the prices do increase as the dates get closer. With regional trains that stay in one area (just Lazio or just Veneto, for example), the prices are fixed and you can just buy whenever. 🙂

Have fun!! September is a magical time to be in Italy, I’m sure your trip will be wonderful.

Hi I Loved your itinerary, am thinking of something similar in October for my family. Could I ask what your final budget was for travel and accommodation / tickets etc please? Many thanks Carly

We put this itinerary together based on several months traveling in Italy, so it’s hard to extrapolate out what we would have spent. Speaking generally, I would say 140 Euros/couple/day, adding additional funds for kids, is a comfortable midrange budget in Italy, though you can easily do it on a far smaller or far bigger budget as well. If you plan to rent a car in Italy, that will eat into costs and you may want to budget extra for that.

Your travel blog is perfection! We are looking to surprise our daughters with a trip next summer and you have covered everything on our wish list.

Thanks, Jodi! That sounds like so much fun–I would have been thrilled to have my parents surprise me with an Italy trip! 😀

Hello I am in the process of planning a summer trip to Italy with our kids. We are flying into Venice ( award travel) and was planning to stay 2 nights, then stay 5 nights in Tuscany and then head to Positano for 5 nights. Will fly home from Naples or Rome. On our first trip to Italy we did Florence, Cinque and Rome. I was dreaming of a farmhouse/villa stay in Tuscany but so far they are all a Saturday to Saturday stay. We arrive in Venice on a Monday and was planning Tuscany for a Wednesday arrival for 5 nights. Wondering if we should skip Positano and go somewhere for 5 nights before Tuscany? Or should we fly from Venice to Naples , visit Amalfi area and then head back to Tuscany? Or maybe you know a place that doesn’t require a week stay in Tuscany? Is there a Tuscan town you recommend for a good home base? Trying to make the best use of our time. I am getting confused 🙂 Our kids are teens. Appreciate your thoughts!

Hi Sally! It all depends on what you’re looking for–Positano is beautiful, but if you’d rather stick to a closer geographic area, Verona and Emilia-Romagna (possibly based in Verona) would be good options between the two. For beaches, there’s always Elba in Tuscany (though that can be a little harder to get to). I don’t know of any Tuscan villas offhand that aren’t only Saturday-Saturday, but I would guess that VRBO and maybe Airbnb would be your best bets for that. We use VRBO for our multi-generational family trips to Tuscany. 🙂 Tuscany is one of our favorite places, so I’d have a hard time saying you can go wrong with a base there! Siena and Lucca are both great options if you’re wanting something smaller than Florence, but you’ll definitely need a car for day trips if you’re wanting to explore the region (and especially if you’re staying outside the city center).

I enjoyed reading your blogs very much. My family and i will have only 5 days in Italy, as a side trip from Germany. Where would you recommend that we must visit, as a first timer to Italy? Also, are there flights/trains that go directly to Florence?

Ahh, that’s a hard one! The answer is, of course, wherever you are most invested in going–but in my personal opinion, I’d pick Tuscany. It’s easy to navigate, incredibly beautiful, and very classically “Italian” for first-time visitors. It’s also one of our favorite places in the world, so I’m a bit biased. 🙂 There are flights and trains that go directly to Florence, but on that timeline and coming all the way from Germany, I’d definitely fly. If you’re open to budget airlines, be sure to check Pisa–it’s about 20-30 minutes outside of Florence, and most of the budget airlines fly there instead of directly to Florence.

We are heading to Italy (first time for me) next fall with 2 other couples and are just now starting to research. Your blog is amazing and really is helping us formulate our trip. Have you ever cruised the coast of Italy ( i want to see as much as possible going for 2 weeks) and know we cant see it all but wondered how a cruise (small less then 300 people) might help us see all those amazing sights on the water – 7 day then heading into shore and seeing the other parts of Italy.

We haven’t had the chance to cruise the coast of Italy (yet), but it’s actually on our list of Italy trips we hope to take one day.

If your goal is to see as much as of Italy as possible, I would say the benefits of the cruise depend on where exactly it goes and what your priorities are. I’d check and see how much land time there is vs cruising time, etc. It’ll definitely cut into your time in Italy itself, but it would also undoubtedly be a beautiful and unforgettable experience in its own right. The coast of Italy is incredibly gorgeous!

Did you take the picture of the Tuscan countryside that is right before the “Cars” section of this blog? If so, where is that at?

Yes we did!

It was taken at a winery outside of San Gimignano–those are the towers of San Gimignano that you can see in the far distance. Unfortunately, I didn’t note the name of the winery at the time, but there are similar views all throughout the area!

Kate, My husband and I are planning to go back to Italy next October.our past trips were Florence, Tuscany and a Rome. This time we’re going to Umbria area and the Amalfi coast probably 14 days total. My question is what order do you suggest? Last trip we felt like we should have done Rome first then Tuscany, Rome was hustle bustle and Tuscany was laid back and relaxing..we felt we should have stayed in Tuscany last. What place would you suggest starting and ending with.

If you’re looking to start with hustle and bustle and then end with somewhere relaxing, I’d recommend starting with the Amalfi Coast and then heading onto Umbria! As a bonus, you’ll then be near the coast a tiny bit earlier in the season, so hopefully some of the warm weather will hold out for you (and it very well might–we’re in Rome right now, and even though we’re into the second half of October, it’s 80F and sunny out!).

Hi, Thank you for sharing this itinerary – so helpful as we have never travelled to Italy and are planning our first trip later this year. We would also like to visit Pompeii. How long would you spend there and where would you stay to include this stop. Thanks so much

I’m actually working on a Pompeii/Mount Vesuvius guide that should be published sometime this month, so be sure to check back for more detail, but here’s the short version–it depends on how much time you have.

If you only have right around 2 weeks in Italy and don’t want to cut any other destinations, you can do Pompeii as a day trip from Rome. However, the only way to feasibly do that well (especially on a first trip to Italy) is to book an all-day tour, and it’s about 6 hours of driving roundtrip.

Alternatively, you can stay in Naples and visit independently. Naples feels very different from the rest of this Italy itinerary, which focuses on north and central Italy instead of the south of the country, but it is a lovely city with some fascinating things to do, the world’s best pizza, and easy access to Pompeii. It’s considered “dirty” by many, but it doesn’t personally bother us a bit, and we don’t think time there is wasted.

For Pompeii itself, you really only need one day, and with some solid planning, a base in Naples, and an alarm clock, you can squeeze in a visit to the crater of Mount Vesuvius or Herculaneum that day as well.

If you wanted to visit via Naples and keep most of this itinerary structure, add on a stop after Rome. You could then double back to Cinque Terre or simply swap Cinque Terre for the Amalfi Coast, which is very close to Pompeii and Naples, before heading up to Florence + Venice.

Hi. I am visiting Italy in April and would like to go to the Dolomites. I will be staying at Peschiera del Garda for 5 nights. Will I be able to visit the Dolomites from this place? Will Dolomites be accessible in early May?

We haven’t been to Peschiera del Garda, but there are plenty of day trips to the Dolomites sold that leave from there, so you should be safe. 🙂 The Dolomites are pretty accessible–depending on altitude you may still see some snow in early May and certainly some colder temperatures, but you should be able to access the mountains to experience some beautiful views (I’m assuming you’re not planning on doing any intense hiking since you’re basing yourself near Lake Como).

Hi! I am trying to plan a trip to Italy for May. We want to go to Venice, but have also heard that there are new laws for tourists and how expensive it is during this time of year. I know it is so overly visited by tourists, and just wanted to ask you if you think it is worth it. It would be at the end of our trip, and only 2 days. If not, we may stay south. Thanks!

It’s an interesting question, Hannah. We’ve personally only visited Venice in the late fall, so we haven’t experienced the summer crowds ourselves–but we know they are intense.

If you have always wanted to see Venice, I do think it’s worth it–no matter how many cities call themselves “the Venice of X place”, there truly is only one Venice. It’s an incredibly unique and beautiful city.

However, you will definitely pay for the privilege–it’s expensive, and there will be crowds in May, especially if you go toward the end of the month.

I’d recommend pricing out hotels and activities for your dates, adding up the estimated cost, and asking if you think that number–including the cost of getting to/from Venice–is justified based on how much you want to see it.

If you don’t mind crowds, have always wanted to see the city, and don’t mind the cost (much)–go.

If you’d prefer to visit somewhere less congested and Venice is somewhere you’re considering visiting just because it’s an obvious choice and not because you’re excited to see it specifically, look at staying further south.

This is WONDERFUL! My fiance and I are planning a two week trip to Italy from the States. Any chance you have a rough estimate on how much to budget for all of this? Thanks so much!

Thank you, Marissa! Plane tickets will be incredibly dependent on where you are flying from in the USA–Las Vegas, Orlando, NYC, Chicago, Atlanta, and sometimes Boston are all places to check for budget airline flights if you’re looking to save cash and those are an option for you. To help with budgeting on the ground, we put together this post: https://www.ourescapeclause.com/trip-to-italy-cost/

Hopefully that helps give you a general idea!

That’s a really informative article Kate!

I need some advice from you. I am planning to visit Italy on my honeymoon in late November. I know it’s not an ideal season for sightseeing and getting around, but would you recommend including Catania or Malta in the itinerary during that time of the year? With some quick research I noted that these locations offer warmer weather, but I never saw these places covered in any itineraries available online. Would you be aware of any reason for that?

Thanks in advance!

Late November will really be too late in the year for any swimming, but Sicily and Malta will still be beautiful.

Catania is not generally considered to be a great place to sightsee in Sicily–Taormina, Siracusa, and even Palermo are all more popular. We skipped Catania ourselves for this reason, so I can’t offer any personal advice there. We did love Palermo, which is Sicily’s other major airport hub.

The best way to find itineraries for Malta would be to search for those itineraries alone–it’s not usually combined with Italy (not sure if that’s what you were searching?). It is a lovely place, and if you’re content to sightsee on land and skip some of the more summery activities, I think a November trip could be fun.

Other than weather, etc, if you want to include either Catania or Malta in your trip, the other two things I’d check on are flights (many budget flights to/from beach destinations are seasonal and won’t be running in November), and for Malta, whether anything you want to do is closed for the season.

Also, I’m not sure if you’re looking for a particular kind of trip, but depending on how late in November you go, you may be able to check out some Christmas markets in Italy and/or Malta, so keep an eye out for those!

Congratulations on your marriage–hope you have a wonderful trip!

Great article thank you so much! We just really don’t have interest in Venice (I know it’s weird) but would you suggest we could easily sub in Milan/Como for Venice?

You can! Milan and Venice can be reached in roughly the same amount of time from Florence, give or take depending on your train route. If you’re looking for other places in northern Italy to consider, you might like to take a look at Verona or Bologna as well. 🙂

This is a great and detailed article to aid in starting up creating one’s itinerary! I doubt 2 weeks would be even close to being enough if I wanted to see most of Italy in one go, especially since I am dying to see Milan, Lake Garda and Amalfi Coast!

– Laura

I’ve finally come to the conclusion that no amount of time is enough for Italy! I don’t think we’ll ever be done going back. 🙂 We still need to make it to Lake Garda (and Lake Como, and Lago di Braies, and Lago di Sorapis…) ourselves.

Thank you for the information. Q: If we ignore the time to travel, cost and all other extranal factors. Which is a better place to see Cinque Terre or Amalfi Coast?

Q: What other place in a differnt country in europe can I travel from Italy for a three day trip?

Have a good say!!

For your first question, personally we slightly prefer Cinque Terre, but it really just comes down to personal preference at that point! Both are phenomenal, neither is objectively better.

You can go just about anywhere in Europe for 3 days from Italy, as there are budget flights from all the major cities to just about anywhere on the continent! If you are looking for something geographically close and/or you don’t want to take a plane, Slovenia, Austria, Switzerland, France, etc, are easy to reach from the north, San Marino is accessible from Emilia-Romagna and the surrounding area, and Malta, Spain, and Croatia are accessible by ferry, just to give you a few ideas!

Very engaging and informative read! Enjoyed your blog. In process of planning trip to Italy in mid November. Flying in at Milan and out from Rome. 1N(Night) Milan 3N Dolomites 2N Venice 3N Cinque Terre 3N Florence/Tuscany 2N Rome 2N Naples

Love for mountains and offbeat places (less crowded) places. On a budget trip, depending on public transport.

(1) If you can suggest base location /or (BnB or Hostel) for Dolomites and Naples (2) Any other location, where exploring around would not be straight forward as will be dependent on public transport (3) Is the itinerary good mix of days and routes? If you think by any ways can swap days / location..please do recommend

Thanks so much, Niket! That trip sounds amazing, if a little fast-paced for our tastes. 🙂

For the Dolomites, Cortina d’Ampezzo and Bolzano are two of the “bigger” cities (and I use bigger loosely) that people use for a base. There are plenty of small towns as well, but keep in mind that in November there could be snow, etc, to contend with the higher you go, and public transportation options will be fewer and a bit more complicated.

For Naples, the biggest thing to keep in mind is the hills! The further you stay from Piazza del Plebiscito, the more hills you’ll climb. We stayed in the budget hotel linked in this post on our first visit to Naples and liked it well enough (the nearby escalators to get down the hill definitely helped): https://www.ourescapeclause.com/one-day-in-naples-itinerary/

As for the route, I personally would cut Cinque Terre and/or the Dolomites, as in mid-November the weather isn’t likely to be great and you have a lot of places that you’re covering. I’d be tempted to give over another night to Venice and another two nights to Rome in exchange, but that’s entirely personal preference!

I’d also recommend not counting too much on getting to see a particular hike, etc, in the Dolomites. It’s very likely that it will be cold, rainy, and maybe even snowy by mid-November, though undoubtedly still beautiful!

Thanks for the great ideas and tips. We’re a family of 4 thinking of a 2-week trip to Italy next summer and your itinerary could be a possibility (in reverse, as we’d start in Venice). Can you suggest any good self-catering or apartment rental options for the itinerary? Or trustworthy websites to try? Thank you in advance!

Hi Dee! Depends on what you’re looking for, size of group, etc, but for self-catering apartments we generally book through Booking.com or Airbnb. For villas/large groups, we’ve found excellent properties through VRBO. We highly recommend a country villa for a couple of nights in Tuscany if it fits your group and budget!

Hi Kate, very helpful blog indeed, thanks. I am struggling to work out the perfect itinerary because I need to visit Bologna for business. My plan ( which can be tweaked ) is to fly into ROME March 2 arriving 7 am and fly out March 16 at 11 am. I need to arrive Bologna 11th evening, and leave 14th evening or 15th morning. I can move my dates 1-2 days before or after. I am very keen on Amalfi coast, tuscany ( since i love tuscan wine ); florence, rome and Venice. Cinque terre is captivating in the pics too. I can skip pisa/ lucca. Would love to hear your comments, thanks

Personally, I’d strongly recommend cutting a couple of destinations from your list. While technically you can make it work (especially using day trips), that will be a very exhausting trip and the coastal destinations won’t be at their best in March. At most, I’d pick 3 destinations in addition to Bologna to visit.

You could potentially do something like this, give or take:

Rome Florence + Tuscan countryside (as one stop, you can day trip to the countryside from Florence or visa versa) Bologna 11-14 Venice OR Amalfi Coast with your remaining days (Venice would probably be easier).

That’s my suggestion, but ultimately it’s your call! I’ve certainly squeezed extra destinations I couldn’t bear to leave out before. 🙂

Hi Karen, Thanks for your advice. I will now consider the following, feel free to let me know if this is doable. day 1-3 Venice day 4-7 Florence ( 2 days in city; 1 day trip siena/ san gimignano/ chianti; 1 day trip hiking in cinque terre ) day 8-10 roma day 11-14 bologna for business What do you think? Tony

That sounds very doable and like a great trip!

We are in the planning stages of our 2+ week adventure of Italy. Travel is slated for May of 2021 which will include my wife, 2 daughters and I. We plan to fly into Milan or Venice depending flight tickets. We will rent a car and go for it. We want to drive along the entire coast of Italy with possible multi day stops in some of the bigger cities. Plan to stay in hostels, BnB and occasional hotels. For sure spend a 3 days in Silicy. Thoughts?

Hi Daniel! Sounds like quite the odyssey you guys have planned!

My first thought is that I hope that “+” on the 2+ weeks is pretty flexible if you want to drive the whole coast of Italy! That’s an extremely ambitious plan if you want to stop and see much along the way and also fit in 3 days in Sicily.

If your time frame is set at around 2 weeks in Italy, I’d consider road-tripping one portion of the country (since you mentioned flying into Venice or Milan, maybe driving from there to a few stops in Tuscany and/or Emilia-Romagna/Veneto/Lombardy along the way depending on what you want to see and then flying to Sicily to close out your trip.

If you have your heart set on driving the whole thing, I’d either try to extend your time or accept you’ll spend a lot of time in the car, finding and paying for parking, walking from parking lots into the towns and villages you’re visiting, and generally getting from place to place. Driving in Italy isn’t impossible by a long shot and we’ve done it plenty, but by the time you add in all the logistics, Google maps estimates tend to fall a bit short of how long it actually takes to get to each place!

Your blog is so incredibly helpful, thank you! Planning my 1st trip to Italy with my teen girl who’s graduating. Will us two females traveling alone feel safe? I want to not hassle with buses and need some tour guides, private cars. Etc over buses. I can probably do train but needs to be easy cause I get lost easy LOL. I will need everything bought ahead of time and planned out to the T so I won’t be stressed. I want to go about 20 nights but want to see allot then.

Sorry clicked send before I asked my question LOL. Can you please help me itinerary order. I want to spend 20 nights total. 2 in Rome, 2 in Lake Como, 4 in Florence Tuscany area (please list 2 towns for me to stay in there), 2 in Dolomite area, then 1 night in these places venice, Almfia coast, postitano, sorrento, Vernannza, riomaggiore, portofino, bolzano, and Bari. Am I missing any must see places? Is this doable? Also one last place is I want to see at least one place in Croatia. I don’t know which is better dubernick or split and how to fit it in? Maybe fly out of there? Help please thanks so much!

Hi Becky! Sounds like some amazing destinations you have on your list!

In Tuscany, if you want to stay in two places I’d personally probably do Florence + Siena or Lucca if you don’t want to drive, or Florence + a country house/apartment near Montepulciano or Siena if you do plan to drive!

Your wish list sounds amazing but honestly, with 20 nights that’s probably going to be a bit too much. I’d probably cut Bari altogether, and choose two coastal destinations max (Amalfi Coast area with Positano/Sorrento, or Cinque Terre with Riomaggiore/Vernazza, or Portofino, or Croatia).

For choosing between Split and Dubrovnik if you do decide to do Croatia, we have a whole post on that–search “Split or Dubrovnik” in the top righthand corner of the site and it’ll come up. 🙂

I haven’t personally taken a whole trip in Italy alone, but I have many friends who travel solo as women in Italy and love it, and I’ve never had any big problems going out alone, etc. Italy is very used to tourists and generally feels very safe to travel.

Hope that you guys have a wonderful trip, and happy graduation to your daughter!

Hello – planning to go in January for 30th bday. How do you feel about this choice of month?

Thanks, Haylee

It all depends on what you’re looking for!

You’ll need a coat, and gray/rainy days are worth preparing for, but on the other hand, prices will be lower (in a normal year, who knows what will happen this year), the crowds MUCH lighter, and all the sights still beautiful.

We sure wouldn’t turn down a January trip to Italy!

Thanks Kate Storm , Your article is so incredibly helpful. Verona, Liguria, Sicily, Abruzzo, Milan the best places you can live in Italy. I like u r article.

Thank you for your very informative article.I am interested in staying in Puglia.Could you recommend a small authentic village on the coast with access to public transport.What would your ideal itinerary for the Puglia region be.Thanks again

Hi Frances! Sadly our planned 2020 trip to Puglia got cancelled, so I can’t offer any personal recommendations there yet. Hope that changes soon!

Kate, I can’t get enough of your articles!! We are a family of 4 (2 teen boys), traveling to Italy for the first time! We will be flying into Venice the morning of June 2 2022 and out of Rome June 16. I would love your opinion on our proposed itinerary- trying to keep everyone happy and see a lot without cramming in too much! We will likely be hitting the “high points” when it comes to museums and churches. Right now, we’re looking at… 2-6 Venice 6-8 Cinque Terre 8-11 Tuscany/Florence 11-15 Rome 16 fly home Would you allocate it any differently traveling with two teen boys (14 and 17)? And/or add in any day trips? Thank you so much!

Aw, thank you for making my day, Rachel! Truly my favorite part of my job is knowing I help people plan their trips. 🙂

Your itinerary looks great! I’d consider moving one day from Venice (I adore it, but it’s a small city) to either Cinque Terre or to Florence/Tuscany.

A second full day in Cinque Terre would allow you to either spend some time at the beach or hike more, while an additional day in Florence/Tuscany would give you a chance to spend 2 full days in Florence (here’s our suggested itinerary for that: https://www.ourescapeclause.com/2-days-in-florence-itinerary/ ) as well as take a day trip out to the countryside.

There are some wonderful day trip options from Rome that you may want to look into since you have 4 full days there (here’s a post: https://www.ourescapeclause.com/best-day-trips-from-rome-italy/ ) but you can easily keep yourselves busy in the city as well!

Hope you guys have an amazing time! June is a beautiful month to be in Italy. 🙂

Hello, We are planning to travel to a Italy for 3 weeks (the end of March – beginning of April). Do you have any extra insight for traveling with children? Ages: 13 yrs, 8 yrs, 1yr old. I want an easy, mellow trip but still want to hit the major sights. What should we add or take away from your itinerary?

Hi! Unfortunately, we don’t have any experience traveling in Italy with children that young, but generally speaking, the itinerary should work as long as you’re willing to cut down the number of activities in each destination (so fewer museums, basically). I’d definitely recommend skip-the-line tickets everywhere you go! I know that Rome has a popular children’s museum, as well, and several of the popular hikes in Cinque Terre are doable with your 8 and 13-year-old.

Your blog is amazing, Kate! I am booking a surprise trip for my partner and we are set to visit Italy for 14 days in April 2022. He is a huge history and art buff, I am definitely planning on including Rome, Florence/Tuscany and Venice from your 2 week itinerary. In your opinion would adding in Naples in place of Cinque Terre be stretching it too thin?

Thanks in Advance! Dani

Thanks so much, Dani!

A surprise trip to Italy–that’s one lucky partner you have! LOL.

Yes, you can absolutely swap Naples for Cinque Terre, and I’m sure an art/history buff would love it. A fast train (not regional train) from Rome will probably be your most efficient way of getting there.

Fair warning, since I’m not sure of your travel style, Naples is definitely a bit less manicured than the other cities on your list. I adore it and highly recommend a visit, but just got in expecting a bit more grit (and the best pizza of your life).

Day trips to Pompeii, Herculaneum, and the Amalfi Coast are very doable from Naples as well.

Amazing post! I have always been fascinated by Italy and its historic colosseum. However, I never got a chance to visit there due to my hectic work schedule and other commitments. But, I will be getting some time off during Christmas. And while I was looking for an interesting travel itinerary, I stumbled upon your blog. It does give me some amazing suggestions that will help me to experience the best that Italy has to offer.

Hello…we are looking to go in 2023 to Italy and were considering this itinerary…We need to make sure we are in Florence/Tuscany on June 18…Is this a bit agressive? Would you consider something different and what is the best way to get around…Car or Train? You also noted day trips from these different places…would Naples be one?

Travel to Venice 1 Venice 2 Venice 3 Travel to Lake Como to Milan 4 Milan 5 Travel to Cinque Terre 6 Cinque Terre 7 Cinque Terre 8 Cinque Terre 9 Travel to Florence 10 Florence/Tuscany 11 Florence/Tuscany 12 Florence/Tuscany 13 Travel to Rome 14 Rome 15 Rome 16 Rome 17 Travel Home 18

That looks like a wonderful itinerary, and very reasonable for the most part!

The only exception is that you have “travel to Lake Como to Milan” in one day… doing a quick stopover at Lake Como would be difficult, I’d choose either Lake Como or Milan to visit.

You may also want to move one day from Cinque Terre to either Tuscany or Milan/Lake Como, but that’s a personal preference.

You can easily use the train for all of these places except possibly some of the smaller Tuscan towns, if you plan to visit them. For that, you could either rent a car for a couple of days or book a day tour!

For Naples, you can take a day trip from Rome, but it’s fairly long. If you plan to visit Pompeii and/or the Amalfi Coast as part of that, plan for a VERY long day and absolutely book a tour! We have a very reputable one listed in our Rome day trips guide: https://www.ourescapeclause.com/best-day-trips-from-rome-italy/

Hi! Thank you for sharing this wonderful itinerary. We are leaving San Francisco 5/25 and arriving in Rome on May on 5/26 and flying out of Venice on 6/9. I’m hoping we are getting in and out just before the big summer rush and heat! We were considering adding one extra day in Rome and I was wondering what the logic is for going to C/T before Florence? On the map it appears going Rome/Florence/CT/Venice might make the most sense, but I’m sure there is a reason I am not seeing. Would also love to hear your recommendations for the three full days in Florence for a family of 4 including a 15 and 18 year old! Thanks!

That’s an excellent time to be in Italy, you guys are going to have an incredible time. 🙂

The logic for going to Cinque Terre before Florence is two-fold. First, if you travel by train instead of by car (which I highly recommend for this itinerary), you can travel from Rome to Cinque Terre along the coast without switching trains, and you won’t go through Florence or need to double back at all. You’ll also have some beautiful views of the coast along the way!

The second is simply to break up what you’re seeing on the trip. While Florence and Rome are two very different cities, they’re the most similar of the 4 destinations on this itinerary, and going to Cinque Terre in between them gives you an opportunity to mix things up instead of condensing more art museums/churches/cobblestone streets (all things I adore, just to be clear!) into one portion of the trip and risk getting burned out.

For the 3 days in Florence, I would recommend more-or-less following our 2 day Florence itinerary (which I’m going to be updating with a bit more detail in the next few weeks, as we just got back from our latest trip!), and then taking a day trip into the Tuscan countryside with the 3rd day, whether that’s by booking a tour or going independently.

Here’s the itinerary: https://www.ourescapeclause.com/2-days-in-florence-itinerary/

For day trips, many popular tours include Siena, a small town like San Gimignano, and a winery visit. If you’d like something a bit different due to having teens with you, other options include Lucca (you can also add a stop in Pisa if you like), Volterra, Arezzo, Bologna… the sky is the limit! We have a full guide to day trips from Florence here: https://www.ourescapeclause.com/best-day-trips-from-florence-italy/

Hello! I am so happy I found your blog! Such great hints and tips for each of the areas you are recommending. We are heading to Italy for a wedding in Volterra. Flying into Florence and renting a car. After the wedding we are staying and for a week and ultimately ending up in Milan. What are your thoughts on breaking up the trip? Some of the places of interest from your blogs: Livorno, Pisa, Lucca, Cinque Terre (?), Rapallo or a beach, Genoa (?), Milan, Lake Como

I feel like we definitely have too many places we want to see be for such a short time. Would love your input, given we will have a car. 4 adults

Thank you so much! Back to google!

What a beautiful place for a wedding! Volterra is incredible (here’s our post on the town if you haven’t seen it: https://www.ourescapeclause.com/volterra-italy/ )

As for where to go the week after the wedding, you’re right that your dream list is a bit long, but which areas you pick are totally up to you!

Personally, I’d recommend doing either Lucca + Pisa + Cinque Terre or Milan + Lake Como + *maybe* one other Tuscan town/city before leaving the area after the wedding.

Lucca makes a great base in Tuscany (here’s our post: https://www.ourescapeclause.com/things-to-do-in-lucca-italy/ ) and also has the benefit of being within a quick ride of Pisa for a day trip. You can realisitically day trip to Cinque Terre from Lucca more easily than from Florence, too, or move to the beach and stay a couple of days.

I love that area, so that’s what I would do if it were my trip. 🙂

However, Lombardy is also stunning! In addition to Milan and Lake Como, with a full week you could also add a visit to Verona, Bergamo, or even Venice. However, I’d be tempted to split the difference and do about 2 days in Milan, 2-3 days in the Como area, and stay in Tuscany after the wedding to explore a different Tuscan city before heading to Lombardy.

Hope that helps! You have the benefit of your wish list being pretty well grouped geographically, which gives you more flexibility. 🙂

Hello! Wow your blog is so incredibly helpful. My husband and I are planning a ~2 week trip to Italy at the end of July/early August (I know… it’s soon!), and we’re looking at doing basically this itinerary. I’m curious though – this is a 14 day itinerary but I believe only 9 days are accounted for in your post. 2 days in Rome, 2 days in Cinque Terre, 3 days in Florence/Tuscany, and lastly 2 days in Venice. Is that right? Am I missing something? My husband is really interested in seeing the Dolomites. Is that something you think we could throw in there with that 9 day itinerary? Thanks so much! Really appreciated your recommendations.

Yes, it’s because the way I laid out this itinerary doesn’t include the days you’re actually traveling between destinations, these are the full days you’re in each area. 🙂 I know it’s a bit confusing, which is why I switched to a day-by-day layout on future itineraries!

It would be hard to squeeze the Dolomites (or any 5th destination) into a 2-week trip without being extremely rushed, especially because the Dolomites really need more than a day. If he has his heart set on seeing them, I’d consider swapping one of these destinations for the mountains!

Fantastic descovery is your site as Ive just decided last minute to go to Italy. Im under a particular schedule going there since Im going for 6 weeks but two of those will have to be remote work. So after two weeks of travel one week of remote work. Have 100 questions for you but if there would be just one, what would be the places you would stop for about a week,considering most my days will be working.

for sure will have more questions for you as I was thinking of using one of those week to go travel in a near by country etc.

Ah, that’s a delightful problem to have but a very hard question to answer!

Really, any city or reasonably-sized town that appeals to you is a great option. If you need to use video or send large files, I’d opt for a city and keep an eye on wifi speeds. If you don’t need particularly fast wifi, just about anywhere (other than perhaps some very rural places) will do.

We’ve worked for a month at a time from Rome, Florence, and Bologna, and for a week from many, many places including Naples, Palermo, Otranto, Verona, Venice… basically, the sky is the limit!

Personally, we find quiet neighborhoods in medium-to-large cities generally excellent to work from–plenty of convenience and infrastructure, as well as lots to see on your times off.

I just found your blog today & I’m actually obsessed with all the info you’ve posted! I’m trying to jump start my exploration of the world with my boyfriend so I’m currently trying to plan our Italy trip for 2024! It will be both of our first times & I’ve just been hooked onto reading this 2 week guide… I wanted to ask though as first timers, what would the best itinerary breakdown of each city be for us? As far as how many days in each city & what to do in order to check it off our first timer list? Also if you had to choose between Sept/October to travel to Italy which one would you choose?! I love love love this blog of yours & will continue to reach for it as I plan future trips for my boyfriend & I! (:

Thank you so much, Tori!

The itinerary here, as written, is great for first-timers, but where you start and finish can be swapped depending on whether Rome or Venice is easiest to fly in and out of based on where you’re coming from.

September and October are two of my absolute favorite months to visit Italy, so it’s hard to choose!

September will be warmer and a bit more crowded, and depending on the year and which week in September you may even enjoy some late-summer style weather. That’s great for visiting places like Cinque Terre.

October is cooler, with a higher risk of rain (especially later in the month), but the food is delicious, many of the harvests start, there are fewer crowds, and many perfect weather days. I often say Tuscany is the perfect October destination.

You really can’t go wrong with either month!

Hi Kate, So happy I stumbled upon your blog – most helpful of everything I’ve found online so far! Would love guidance on planning our trip for March 11-25, 2023. This will be the first time in Italy for my husband and near-adult kids – ages 16 and 18. I was in Rome, Florence, Siena and San Gimignano for about ten days, 25yrs ago and have been dreaming of going back ever since!!

The challenge is that we have to spend about 3 days in Paris as part of this 2-wk trip, and i don’t know how best to organize that. I’d like to go to Rome and Florence for sure; everything else is open. We’ll be flying to/from Florida and don’t know if we should go to Paris first, last… or if it’s just unrealistic to try to do all of it. Maybe we should do 5 days in Paris and the rest in just Rome and Florence? Also, ideally, we’d be in Paris for all or part of a weekend, which makes it even more challenging! (Meeting French cousins there and they have to work during the week.)

Here’s a bit about us: we have lots of energy and are willing to get up early and stay out late and take trains and planes at odd times :). We’re good travelers and are flexible, and yet this shouldn’t be a wild ride – it should have an easy pace but be full of sights, sounds, tastes, and discovery. Cities and small quaint charming towns are superb; we can probably skip coastal towns on this trip since we live near the beach in FL 🙂 If you disagree, do speak up! Happy to take trains and walk a lot, and use the discounted airline you mentioned, as long as it’s safe (!).

I haven’t looked at the rest of your blogs yet; wondering if you also have recs for olive oil and/or a balsamic tastings/tours and if there’s a guide or an app for being gluten free in Italy!

Thanks SO much in advance for any advice you can offer! Much appreciated!

Happy to help! You guys seem to be the perfect candidates for a busy trip, which is a great thing. 🙂

If you want to squeeze it all in, I’d recommend either starting in Paris or ending in Rome, or vice versa. If you can find good open-jaw tickets to these cities, your plan is ambitious but doable.

Assuming you start in Paris, I’d plan about 3-4 days there.

Your long travel day will be between Paris and Florence–you can either fly, or take a high-speed train to Milan followed by one to Florence (book early to ensure the best prices and direct routes). Both will be a long day, but the train is more fun. 🙂 We use Omio to plan our long train routes.

In Florence/Tuscany, you can allot 5-6 days. I’d plan to spend at least 2 full days in the city, and then more in smaller towns. You can either take day trips from Florence (by train, car, or tour), or head to southern Tuscany for a few days.

Southern Tuscany is where you’ll find the Val d’Orcia, as well as gorgeous towns like Montepulciano: https://www.ourescapeclause.com/things-to-do-in-montepulciano-italy/

If you want to take a day trip to Florence but are looking for a different (but still convenient) home base, Siena (as you know) and/or Lucca are amazing cities: https://www.ourescapeclause.com/things-to-do-in-lucca-italy/

From there, you can wrap up with a few days in Rome, which will give you time to see the major sites. We have lots of Rome posts, but here’s an example of what you can see with 2 days there: https://www.ourescapeclause.com/2-days-in-rome-itinerary/

Olive oil tours will be at their peak in the late fall (when the harvest is), so it doesn’t overlap with your trip. Traditional balsamic vinegar hails from Modena, which is out of the way for you. However–a good enoteca will be able to offer you delicious tastings of both, and you’ll find those all across Italy (you’ll be spoiled for choice in Tuscany in particular).

As far as being gluten-free goes, that is not my area of expertise, but I can recommend checking out the guides and translation cards from Jodi at Legal Nomads–she’s a longtime foodie and travel writer who has traveled the world with celiac.

Have an amazing trip!

Hi Kate, I am planning for the first ever european trip for my wife (40) and son (14). I have travelled in other countries of europe for business purpose. I have decided for a two weeks trip to Italy in 2nd half of May 2023. The following is a very very high level itinerary. I am yet to drill down. I have 13 full days. Day 1 – Arrival in Rome @ 2 pm. Take a walk in the evening. Day 2 – Colosseum, Roman Forum etc. Day 3 – Vatican City Day 4 – Travel to Florence Day 5 – Florence Day 6 – Florence Day 7 – Florence Day 8 – Cinque Terre Day 9 – Cinque Terre Day 10 – Cinque Terre/Camogli??? Day 11 – Travel to Venice Day 12 – Venice Day 13 – Venice Day 14 – Venice Day 15 – Travel to Rome and take a departure flight @ 4pm

I am not sure if I should cut down somethings and include any other spots. Can you please review the itinerary and suggest amendments?

Sounds like the workings of a great trip!

I’d consider moving one of your Florence days to Rome unless you’re planning to use the third day in Florence to take a day trip to the Tuscan countryside/smaller towns. You could also move your third day in Venice to Rome instead. Rome is definitely the biggest city of what’s on your list!

If you want to see the Riviera beyond Cinque Terre, I’d look into Portovenere–it’s sometimes called the “sixth town” of Cinque Terre, is easily accessible by ferry, and is much less crowded due to being a bit harder to access than the others.

I’d recommend booking your trains from Cinque Terre to Venice and Venice to Rome well in advance, as you’ll definitely want to take the high-speed trains for those routes.

Hope you have a fantastic first trip to Italy!

Thanks Kate for such a quick response! After doing some more research, I changed the sequence of the travel so that it is easier to fly out of Rome. Some people suggest to remove CT and increase the days for other 3 big cities. I am confused. 🙂 What do you suggest? Day 1 – Fly in to Rome @ 2pm. Travel to Venice by train. Day 2,3 – Venice (Yet to plan detailed itinerary) Day 4 – Travel to Florence Day 5,6,7 – Florence and nearby areas (Yet to plan detailed itinerary) Day 8 – Travel to Cinque Terre Day 9,10,11 – Cinque Terre (Yet to plan detailed itinerary) Day 12 – Travel to Rome Day 13, 14 – Rome ( 1 day colosseum etc. and 1 day vatican city) Day 15 – Travel back from Rome to India

I definitely agree that it’s a good idea to move some of your Cinque Terre time to Rome!

While you definitely can enjoy 3 full days in Cinque Terre, with your schedule, 1-2 is plenty. Better to have another day in the Eternal City. 🙂

Hi, Kate: We are traveling to Italy in May and June. Your site has been invaluable in our planning. My first of what I’m sure will be many questions is what train stations in Venice (to travel to Florence) and Florence (to travel to Rome) do we want to use? We are staying as close to the center of those cities as possible.

Hi Elizabeth,

I’m so glad to hear that!

In Venice, you’ll want to use Venezia Santa Lucia (which is right on the Grand Canal).

For Florence (both to and from), you’ll want Firenze Santa Maria Novella (which is a 10-minute walk from the Duomo).

Those are the “main” train stations in each city, so most ticket-booking options should suggest them to you automatically!

I have never been to Italy but am going in July so found your blog really helpful! My daughter will be doing an abroad program in Siena so I will fly over with her 12 days early. Is it a stretch to want to visit Rome, Florence, Cinque Terre, Venice and Lake Como within this time frame when she has to be in Florence on day 12? It would mean flying to Rome and going north from there to hit everything but would have to circle back to Siena. I’d love your two cents on where to fly into- thinking maybe even Switzerland since wanting to see Lake Como. Thank you!

Your daughter is going to have such a wonderful time!

All of the places you mentioned are fantastic, but yes, that’s really too much to fit into 12 days (since you mention your daughter needs to be in Florence on day 12, I’m assuming this is more or less an 11 day trip).

If it were me, I’d focus on Venice, Rome, and Florence.

Flying into Venice would probably be most convenient, though Rome would work as well.

Taking the high-speed train from Venice to Rome (you’ll want to book those tickets in advance) and then traveling from Rome to Florence by train after sightseeing down south will likely make the most sense.

As far as Cinque Terre goes, a day trip from Florence to Cinque Terre isn’t ideal, but it can be done and in your case may be a way to squeeze in a taste of the coast. We go into more detail on how to do that well here: https://www.ourescapeclause.com/florence-to-cinque-terre/

I hope that helps a bit and that you guys have a magnificent time in Italy!

HI Kate! your blog was very helpful. I would love to have your opinion on my upcoming trip. I am taking a transatlantic cruise from NYC to Rome; arriving in Civitavecchia on 10 May 2024. I am lucky and don’t have a time frame. Since Italians take their time… I’m going to embrace that after years of a stressful job, I’m traveling solo as at 37. I want to be loose with my plans, do you think buying tickets for places like the Colosseum just a few days in advance is risky? I was planning on my travel day to purchase tickets for those things. I also have a general route planned and I would love your opinion one this. Since I disembark in Civitavecchia I was going to spend 4 nights in Rome (this is the only things I have booked). -4 night in Rome -2/3 nights in Naples/ Amalfi Coast (I also would like to go further south but not sure where.) -Travel Day to Florence I might stay a night in Assisi or Siena -3/4 nights in Florence with a day trip to Pisa and Lucca -2 nights in Cinque Terre -I think I should go to Genoa or Milan after – I also want to spend a night in the Tuscan country side (Under the Tuscan Sun like) -1 night in Bologna -1 night in Bolozno/ Ortisei for the Seceda -2 nights in Venice I would really like to experience some real Italian life and this trip is really a scouting trip for a possible move to Italy.

Sounds like a wonderful trip!

In May, booking a few days in advance for most places (including the Colosseum) should be just fine in mid-May. There are a few attractions in Italy (climbing to the top of the Duomo’s cupola in Florence and visiting The Last Supper in Milan are two of them) that require planning further in advance year-round, but for travelers who are flexible with their plans, most things are doable a few days in advance.

All of the places you have mentioned are wonderful, but I do think you’ll find there are too many of them! Since you’re going to be booking as you go, I’d just stay open to extending your stays and visiting fewer places.

I’m not sure if you have a timeline for your trip, but after weeks of traveling it’s safe to say continuing to change hotels every night to every other night will stop being appealing. Plus, traveling more slowly is one of the biggest benefits of traveling for longer–it’s worth slowing down for.

We are going to Italy in September/October for about 2-3 weeks. Will visit Rome, Florence, Tuscany and Umbria areas. At the end of our trip we would like to visit Assisi, montepulciano , perugia. Our concern is how to get around in those areas. We don’t really want to rent a car but will if that is our only option, what is your suggestion on this?

It’s doable, but takes a bit of finagling!

The train stations for each of those places are outside the city center (1-3 miles away or so), so you’ll need to take a bus or taxi from the train station to the historic center.

I have been reviewing your site for the last few weeks and my fiancé and I have decided on two weeks in Italy. We’re thinking of flying into Rome and flying home from Venice.

We have never taken such a huge trip before and I’m curious if it makes sense to book the flights and have the book ends planned and then start doing booking of the meat of travel afterwards? Or should we have everything planned and booked before we even book the flights?

Hi Jessica!

Personally, we always opt to book the flights first and then fill in the rest of the trip from there. Flight deals and times can impact your starting and ending points, and possibly even shuffle your trip around by a day here or there.

Everything else–with rare exceptions like festivals, very trendy hotels, etc–is much more flexible compared to flights.

Just going over your blog and absorbing everything! I have a trip planned that has us arriving in Milan on April 29th and leaving out of Rome on May 19th so I’m planning on working our way from top to bottom.

Rough plan currently is Milan -> Venice -> Bologna -> Florence -> Cinque Terre? -> Naples -> Amalfi Coast? -> Rome With some day trips mixed in there, most likely to Siena, Pompeii, maybe Lucca/Pisa or somewhere else.

Would you recommend going to Cinque Terre which we would do closer to the start of May or go to Amalfi Coast which would be closer to mid May? Since you mentioned a day trip from Florence to Cinque Terre is not the easiest, would it make sense to go to the Amalfi Coast instead so I don’t have to backtrack through Florence to get down to Rome or Naples? I’m also concerned about the weather as Cinque Terre is more north and it will be earlier in the month vs Amalfi Coast being more south and more mid month.

What would your itinerary look like with roughly 3 weeks that works top to bottom?

For both Cinque Terre and the Amalfi Coast in May, you’ll really be gambling with the weather–it might be gorgeous swimming weather, it might be rainy and chilly (happened to us on our May trip that covered both places a few years ago–you’ll notice I’m wearing long sleeves and jeans in some Cinque Terre photos), or anywhere in between.

Weather aside, since we can’t control that, prices will probably be a bit lower in early May than mid-May, and the Amalfi Coast is the more expensive destination of the two overall–if cost is a factor, that’s something to keep in mind.

If you’re open to trimming Cinque Terre, it will certainly streamline your itinerary by cutting a transition, so I’d consider it if you’re not married to the idea of visiting two coastal destinations.

A few other day trip ideas you might consider if you have time: Parma or Ravenna from Bologna, Lake Como from Milan, and Montepulciano and/or some of the other Tuscan hill towns from Florence.

Your route is very similar to what we’d cover if trying to hit the highlights in 3 weeks, I’d just make sure to cut anywhere that feels like an obligation in order to give more time to the places you’re most excited for (any one of those cities would be an amazing place to spend a week or more).

Happy planning!

Thanks for the info! I’ve done some more research and currently have the following plan

Day 1 – Milan – Arrive late at night Day 2 – Milan – half day and then train to Venice. Half day in Venice Day 3 – Venice – Full Day Day 4 – Venice – Check out of hotel and explore Venice until ready to leave for Bologna. Night in Bologna Day 5 – Day trip to Modena and Parma Day 6 – Check out of hotel. Day in Bologna until ready to leave for Florence Day 7 – Florence – Full day Day 8 – Florence – Full day Day 9 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour. Day 10 – Florence – Sienna or Pisa/Luca day trip or Chianti wine tour. Day 11 – Train from Florence to Naples or Sorrento and then day trip from Sorrento to Naples. Day 12 -Sorrento – Day trip to Pompeii? Day 13 – Sorrento – Day trip to Capri? Day 14 – Amalfi Coast Day 15 – Amalfi Coast Day 16 – Amalfi Coast Day 17 – Rome half day? Or full day or arrive late night and just have 3 days in rome? Day 18 – Rome Day 19 – Rome Day 20 -Rome Day 21 -Half Day in Rome fly home

I’d like to do a wine tour of the Chianti region but I’m not sure if it’s something I should try to do with a Siena, San gimignano, and Chianti tour or dedicate a full day to it and have Siena/San gimignano as it’s own day. If I dedicate a full day to it I would have to take a day from Bologna, Rome or Amalfi coast. What are your thoughts on this? Do you think we have too much time in the Amalfi coast? I’m thinking of using Sorrento as a base for a few days as I’d like to visit Pompeii, Naples and Capri and then a few days stay possibly in Ravello. Or maybe take Day 17 away from Rome and give it to Florence. That would leave us with 3 and a half days in Rome.

Love to hear all your thoughts on my above plan and what changes you would make or places that you would switch out.

These are the places that I’ve wrote down that I don’t think are worth visiting this trip Assis Lake Como Cinque Terre Padova Vicenza Verona

and these are the places that I’m still thinking about Orvieto Arezzo

Do you think Orvieto or Arezzo are worth swapping out for Siena or Lucca/Pisa.

I’d actually recommend taking any extra time to smooth out the very beginning of the itinerary–day 2 in particular isn’t going to leave a lot of room for sightseeing, in between checking into/out of two hotels, transiting to a new city, etc. Depending on which city interests you more, I’d consider adding a day to either Milan or Venice. As it stands, you probably won’t do more than a few hours of actual sightseeing in Milan–up to you if that’s the pace you’re looking for!

I do think you can get away with 3 full days in Rome–more is always lovely, but 3 is a solid start.

Same with the Amalfi Coast–you can certainly have a wonderful time there with the extra day, but I wouldn’t say you need it. Sorrento is an excellent base and you can easily see a lot of the region from there.

Siena, Orvieto, Arezzo, and Lucca are all wonderful. Pisa is fun, but I wouldn’t call it an absolute must-do unless you’re dying to see the leaning tower–of the five, it’d be the one I’d prioritize least. Other than that, you can’t go wrong with any of them.

As far as whether to visit the Chianti region as an entirely separate day or combine with Siena/San Gimignano, I’d say that depends on how much of a wine fan you are. Personally, we enjoy wine tastings but one in a day (especially the way they pour in Tuscany!) is plenty for us, and we prefer to mix in sightseeing. If you’re visiting Tuscany for wine in particular and are very interested in learning about the various varietals, etc., though, you might consider separating them out.

Thanks so much Kate!

I was not overly interested in Milan other than the Duomo and Galleria Vittorio which is why I was only planning on spending the afternoon there before heading off to Venice. I didn’t want to skip over Milan entirely but I feel like our time is better spent in other locations.

Do you think it makes sense to split our time in Naples and Sorrento? Stay in Naples for say 2 days to explore Naples and Pompeii and then move onto Sorrento for 3 or 4 days to explore Capri and the AC? Or would you recommend sticking in one place the whole time? I have heard there is not as much to do in the town of Sorrento and by not having to do day trips to Naples and Pompeii from Sorrento could save some money on transportation?

Honestly we’re not much wine fans but I thought it was something we should try while we are there. Sounds like mixing all 3 locations into a tour in one day is the way to go!

If you think the time we have in AC is enough without adding more and 3 days in Rome is enough then it looks like I have an extra day to allocate somewhere. I’ll have to do some more thinking on where to place that extra day. Thanks for all your help so far!

Anytime, Edmond!

Sounds like a solid plan for Milan.

Personally I love both Naples and Sorrento, though they’re very different–just depends on what you’re looking for. You can day trip to Pompeii pretty easily from either, so I wouldn’t let that sway your decision. But the pizza, views, archaeological museum, underground, etc, in Naples are well worth your time if you can fit it in!

Great work on the site, it’s been super helpful.

Was wondering if you could gife me your opinion on an issue I am facing. My nieces wedding is in September so we are planning 16 days and wanted your thoughts if this is doable.

We are arriving before the wedding and have to end in Florence.

Arrive Rome – 3 nights Assisi – 1 night Bologna – 2 nights Venice – 3 nights Modena – 2 nights Florence – 5 nights

Would love your thoughts and thanks in advance!

Hi Michael,

Thank you so much!

The first thing that jumps out is that you have Bologna and Modena separated–I would definitely combine those! Modena is only a 15-25 minute train ride or so from Bologna, and virtually every train to it is going to require passing back through Bologna regardless.

Personally, I’d probably base yourself in either Bologna or Modena for one 3 or 4 night period, and take a day trip to the city you’re not staying in. It’ll be much more efficient and if you only stay 3 days, buy you an extra night to add to another city of your choice.

Bologna is the traditional choice for where to stay between those two: it’s bigger, there’s more to do, and as the capital and transportation hub of the Emilia-Romagna region, it’s easy to navigate to and from. However, Modena is beautiful and offers the benefits of being a more affordable and less crowded place to stay.

Other than that, your route looks wonderful and is very doable by train, so navigation should be very convenient. 🙂

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The Ultimate 14-Day Italy Travel Itinerary

LAST UPDATED: 2/25/24 – Ultimate 14-Day Italy Travel Itinerary

The country of Italy is a beautiful and exciting place with a seemingly endless number of amazing things to see and do. It is no wonder then, that Italy is one of the world’s top tourist destinations. If you are planning a trip to Italy soon, you will want to review my Ultimate 14-Day Italy Travel Itinerary to make sure you don’t miss out on some of the country’s most popular sights and activities.

Without a proper plan in place, it is very easy to miss out on an important sight or activity and regret it later. Using this itinerary as a blueprint, you can start to build your big Italian adventure knowing that you have a wealth of information and experience at your fingertips.

See Many of Italy’s Top Destinations

While my itinerary doesn’t cover every region of Italy, it does cover some of the most popular tourist destinations within this amazing country. On your two-week Italian adventure, you will get to explore all of the treasures in the amazing cities of Rome, Venice, and Florence. You will also have the opportunity to explore breathtakingly beautiful regions such as the Amalfi Coast and Tuscany. To top it off, you will even get a chance to visit the amazing island of Capri, which is widely considered to be one of the most beautiful places in Italy.

Included in this Italy travel itinerary are numerous links to in-depth guides that I have developed for each of these regions of Italy. As you start to fill out your personal travel itinerary, these guides will be invaluable resources that you can use to choose the proper accommodations, decide which restaurants you want to try, lay out your daily plans for sightseeing in the region, and book fun and exciting tours and excursions that you will remember for a lifetime. With this wealth of information in hand, you can relax and enjoy the process of planning your trip and focus on the fun, less tedious aspects of planning your trip.

Italy Travel Itinerary Overview

This includes tasks such as making sure you have a valid passport and VISA for entry into the country. It also means confirming that you are up-to-date on the vaccinations that are recommended and required. Once you have done that, you will need to understand what you should and should not pack for your trip.

You will also need to determine what time of year to take your trip and how you will get around the country. Using the links below, you can quickly and easily navigate to the relevant sections of this guide as you start to check these items off your list.

Italy Travel Itinerary Guide Navigation Menu

The best times to visit italy.

When planning your big trip to Italy, one of the most important decisions that you will need to make is when to visit. Before you start looking at accommodations and arranging transportation, you need to know when you will be traveling. For many travelers, this is often one of the most stressful parts of planning a trip because there are so many different variables to consider.

In my opinion, the most important of these variables that you will want to consider are the weather and the number of other tourists that will be visiting when you do. The better the weather, the more time you will be able to spend outdoors exploring this amazing country. And with fewer other tourists around, you will have fewer crowds to contend with when you set out to see and do what interests you.

To make things easier for you as you start to plan this trip of a lifetime, I have compiled all of the weather and tourism data that you will want to consider when scheduling your trip to Italy within my Italy travel itinerary. Using this data, you will be able to pick the time of year that you find the weather to be the most enjoyable.

Average Temperature (°F)

One of the most important factors that you will want to consider before deciding when to visit Italy is the average temperature throughout the year. In the graph below, I have compiled the average high and low temperatures for Venice, Rome, Florence, and the Amalfi Coast for each month of the year. Using this data, you can easily determine which month of the year will be the most comfortable for you as you start to put together your Italy travel itinerary.

Average Precipitation Level (Inches)

Another factor that you will want to consider when deciding when to visit Italy is the average amount of precipitation that each region of Italy you will be visiting typically gets. After all, it can be difficult to get outside and enjoy the beautiful landscapes and cities when it is raining a lot. If you take a look at the graph below, you will see the average amount of precipitation for Venice, Rome, Florence, and Amalfi Coast throughout the year.

Using this data, you can decide which time of year gives you the highest probability of having nice weather during your trip as you start to fill in your Italy travel itinerary.

Average Number of Visitors (Millions)

The last major factor that you will want to consider when determining which time of year is the best time for you to visit Italy is the number of other visitors that you can expect to be visiting while you are there. To give you an idea of how many other tourists you can expect to encounter in Italy throughout the year, I used Statista’s analysis of the number of tourist arrivals and guest accommodations in Italy.

In addition to having an impact on the crowds you will encounter, the number of other tourists visiting during your trip will also impact the availability and price of excursions and tours. However, most importantly, it will be a large factor in the price of your airline tickets and accommodations while in Italy.

The Best Months to Plan Your Trip to Italy

As you look at the temperature, precipitation, and visitor numbers for Italy, it is clear that some months are better for visiting than others. For instance, the months of June through August tend to be quite hot in Italy. This is especially true for July and August. If you want to avoid the heat, you should avoid visiting during these months.

I would also avoid visiting during the autumn months of October through December, as those are typically the wettest months of the year in Italy. Not to mention, it can also get quite cool between November and March. Unless you like wet and rainy conditions, I would avoid planning your trip during late autumn or winter.

In my opinion, the best months to visit Italy are the shoulder months of May and September. The weather is typically warm, but not too hot, and there is usually little rain. This gives you the best weather window to get out and enjoy the sites during your adventure in Italy.

How to Get to Italy for Your Trip

There are many different international airports in Italy, so if you are planning on flying in from outside of the country, you have a lot of options to choose from. If you follow the Italy travel itinerary that I have outlined for you here, there are four major international airports that you can choose from to fly into and out of. For your reference, I have listed those airports for your review.

Major International Airports You Can Fly Into for This Itinerary

• Rome – Leonardo da Vinci International Airport (FCO)
• Venice – Venice Marco Polo Airport (VCE)
• Naples – Naples International Airport (NAP)
• Florence – Florence Airport, Peretola (FLR)

To save time, I would strongly suggest that you fly into and out of different airports. This will prevent having to backtrack significantly when it is time to fly home. However, if you would prefer to fly into and out of the same airport, or find significantly cheaper airfare by doing so, then you can easily modify this Italy travel itinerary to meet those needs. As you start to plan your trip, there are several different options that you can choose from when laying out the logistics of your trip.

There Are Multiple Ways to Plan This Trip

You can start by flying into Venice and then work your way down to Naples, where you will fly home. There is also the option of flying into Naples and then working your way up to Venice, where you will end your trip. For the sake of this guide, I am going to outline a modified Italy travel itinerary where you fly into Rome, work your way down to the Amalfi Coast, then work your way back up to Venice, where you will fly home at the end of your trip. This will allow you to fly into and out of two of Italy’s largest airports where there are more flight options. However, feel free to modify this itinerary in any way that you see fit to meet your travel needs.

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Italy Passport Requirements

When visiting Italy, you must have at least 6 months of validity on your passport beyond the date on which you are planning on arriving in the country.  You will also need to have at least two blank passport pages to be processed into the country. 

Presently, you do not need to have a Visa if you are planning on staying in the Schengen area of the EU for less than 90 days, but starting in 2025 American citizens will be required to get a  European Travel Information and Authorization System (ETIAS) authorization . Before you start making your travel plans, I would strongly suggest you review the passport and Visa requirements I have laid out in my Italy travel itinerary guide below.

Recommended Travel Immunizations for Italy

Before you leave for your trip to Italy, you need to make sure you have all of the proper vaccinations.  Not only to protect yourself but to protect others.  You may have questions on what immunizations you need and what to look out for when getting them. If you do, I have included some general guidelines I can pass on to you from my experience below.

• Most specialized travel clinics will not accept insurance so you will have to pay for your travel consultation and immunizations and then request reimbursement from your insurance company later.
• Some immunizations aren’t accepted by every insurance company, so check with your insurance provider before getting your immunizations.
• Check with your regular doctor first, as often they can do a travel consultation for you and write you the necessary prescriptions for your immunizations, even if they aren’t able to give them to you.  This way you can ensure that at least your travel consultant will be covered by your insurance up-front.
• Check with  Walgreens   or other drug stores that give flu shots to see if they have any of the immunization shots that you require before going to a specialized clinic that doesn’t accept insurance to get them.  Walgreens can give you many of the immunizations necessary for international travel, and they accept insurance up-front.
• The  Centers for Disease Control (CDC) website   can be a great resource for answering any travel immunization questions that you have.

Italy Immunization Recommendations

In case you are unsure of what travel vaccinations you might need, I have compiled a list below of some of what you might expect your physician to recommend.

• Hepatitis A & B  (if you haven’t had them).
• Tetanus  (if you aren’t current).
• Transderm SCōP Patch (for motion sickness) or at minimum Dramamine pills if you get motion sickness easily and you plan on getting out on the water or doing adventure activities.

Italy Travel Packing Tips

Outside of knowing the entry and immunization requirements, there is no pre-travel task more important than packing. Don’t worry, I am here to make sure you are packed and prepared for your trip. I have included links to my packing resources in my Italy travel itinerary guide below for you to review.

Planning Your Transportation in Italy

When it comes to arranging your transportation for the trip, getting from Italy is just half the battle.  Once you arrive in Italy, you are going to need a way to get around.  There are several different methods of transportation you can choose from, depending on the amount of time you will be in-country and your comfort level with driving.

The two most popular options to choose from are renting a car and using the train system. Before you decide which method of transportation is best for you, I have outlined the important considerations for each of these transportation methods for you to review in my Italy travel itinerary below.

Renting a Car

If you are comfortable driving a car abroad, renting a car to get around while in Italy is one option that you can consider. Unlike public transportation, you aren’t subjected to a schedule when planning your travel from one place to another. Ultimately, this means you have much more freedom to do what you want when you want to do it while in Italy.

Italy Car Rental Tips

However, it does come with responsibilities that you don’t need to worry about when using public transportation. This includes paying tolls, finding parking, and filling up with gas when you run low. If you are considering renting a car for your trip, I have included some important tips for you to consider below.

Airport Rental Tips

• The main car rental companies in Europe are Avis , Hertz , Budget , Europcar , and Sixt .
• If you choose to pick up your car while at the airport, you will likely get charged an extra fee.  To save money, you can consider renting from a location outside the airport.   Whether the cost savings on the rental is worth it or not will depend on the cost of transportation to pick up the car and the amount of time it will require.
• In Italy, CDW car rental insurance is mandatory in Italy and rental companies will not let you leave the lot with a car without it. You will be asked to sign a waiver stating that you have car insurance that covers you overseas and you will be responsible for all damages to the vehicle you rent. If you plan on purchasing insurance from the rental company, it is almost always cheaper to select when you make the reservation than it is to add it at the rental counter during vehicle pick-up.
• Unless you specify that you want an automatic transmission when you make your reservation, you will almost always be given a vehicle with a manual transmission.
• Most car rental companies in Europe will charge you an extra fee to take your rental car outside the country, so I would check with the car rental company you decide to use before taking your rental car outside of Italy.

Driving Regulation Tips

• The legal driving age in Italy is 18 years of age, but you also need to have your license for a year before you can rent a car. Most car rental companies will charge you an extra fee if you are under the age of 25 years.
• Never drive in zones marked as Zona Traffico Limitato  (ZTL) or  Area Pedonale . These pedestrian zones are often monitored by traffic cameras and you will be fined.
• The maximum speed limit on highways is 130 kilometers per hour and 60 kilometers per hour within most towns, so be aware of your speed when you aren’t sure of the posted speed limit.
• Never turn right on red lights. While this is commonly acceptable in the United States, it is generally against the law in Europe. So unless you see a sign that explicitly says that you are allowed to turn right on a red light, always wait for the light to turn green.
• As long as you have a valid US driver’s license, you should not need an international driver’s license to drive in Italy.
• In Italy, motorists drive on the right side of the road and the driver’s seat is on the left side of the car.
• Italy uses the metric system, so mileage is listed in kilometers instead of miles.

Using the Rail System

If you aren’t comfortable driving while overseas or just want to avoid the hassle of having to find parking for your rental car, navigate from city to city, and deal with the heavy traffic in some of Italy’s largest cities, a popular alternative is to use Italy’s amazing rail system to get from city-to-city and then use taxis or ride share services to get around each of the cities you visit.

Italy Rail System Tips

The downside of using the train system is that you will have to be aware of your time and make sure you plan your train rides well in advance so that you don’t miss out on some of your trips by not getting where you need to go when you need to be there. If you are considering using the rail system during your trip, I have included some important tips for you to consider below.

Purchasing Rail Passes

• If you are only planning on traveling within Italy, it may not make sense for you to purchase a rail pass. Instead, it will likely be cheaper for you to purchase point-to-point tickets for your train rides separately. The rail passes in Italy tend to be more than $50 per day and you will likely spend less than that amount on second-class point-to-point tickets between Naples, Rome, Florence, and Venice. Before you make a decision on whether or not to purchase rail passes, I would suggest using the railway fare map I included below to price out how much you would be charged for all of your point-to-point tickets and then compare that total price to the cost of a rail pass on the Eurail website .
• Be aware, that even with a rail pass, some routes require that you purchase a reservation for some routes. These reservation costs are included in the fare route map I included below but are not included in the cost of the rail pass.
• The Italo trains run between Italy’s largest cities. If you purchase a rail pass, stick to the Le Frecce trains, which are covered by the rail pass and are typically quicker and run more frequently.
• The Circumvesuviana and Campania Express trains run between Naples Pompeii and Sorrento. If you plan on visiting the Amalfi Coast, this will impact you as the Circumvesuviana and Campania Express trains are the main options to use for getting from Naples to the Amalfi Coast region by train. These tickets typically only cost around $5.

Purchasing Train Tickets

• I would recommend purchasing tickets ahead of time if you know when you will be traveling to ensure that you get on the trains that you want. However, if you do need to purchase point-to-point tickets or reservations while in Italy, I would recommend taking advantage of the ticket machines at the train stations as opposed to waiting in the ticket lines to save yourself time.
• If you are 60 or older, you can buy a  Carta d’Argento , which gives you a 15% discount on most train tickets. They cost €30 for individuals between the ages of 60-74 and are free to those over the age of 75.
• Individuals under the age of 25 can purchase a Carta Verde , which gives you a 10% discount on most train tickets.
• Note that children under the age of 3 ride free on Italian trains. And while not free, kids between 4-11 ride for half-price on regional trains, and kids between 4-14 ride for half-price on long-distance routes.

Italy Travel Itinerary Outline

Now that we have covered some of the basics that you will need to know before you start planning your specific Italy travel itinerary, it is time to start putting your itinerary together. To make that process easier for you, I have included my recommended itinerary below. Your trip will essentially be broken up into four different stages, centered around four different major tourist destinations within Italy.

You will Start Your Trip in Historic Rome

You will start by flying into the city of Rome, where you will tour the city and the Vatican City for the first leg of your trip. After getting to see all of the amazing things that Rome has to offer, you will head south to the Amalfi Coast region. Here, you will enjoy the beautiful beaches, amazing coastline, and wonderful seafood that this region is known for.

As soon as you are finished touring the Amalfi Coast, you will head north to the city of Florence. After taking a day or two to tour the city, you will venture into the countryside to experience the beauty of the region of Italy known as Tuscany. In addition to enjoying the rolling hills and beautiful vineyards, you will get to tour some of Italy’s most amazing wineries.

You will End Your Trip in Beautiful Venice

When you have had your fill of wine, you will keep heading north until you get to the final destination on this Italy travel itinerary. In Venice, you will get to enjoy one of this world’s most amazing cityscapes. Between the breathtakingly stunning canals, beautiful bridges, and amazing historical buildings, you will really enjoy your time touring Venice before getting on a plane and heading home.

Day 1: Arriving in Rome

On the first day of the Italy travel itinerary that I have laid out, you will be arriving in Rome, Italy to begin your two-week adventure. When booking your flights, I would recommend trying to find a flight that gets you into Rome as early as possible.

This will give you time to settle into your accommodations and start exploring the city. If you would like some assistance in finding the right accommodations for you, I have included some recommendations on hotels and hostels in Rome in my Quintessential Rome, Italy Visitor Guide for you to review.

I have included an assortment of options at a variety of different price points near the top attractions in Rome to give you options when choosing the right accommodations for your trip. I have also included several restaurants that I recommend in my guide in case you are looking for a good restaurant to try for dinner after getting settled.

Day 2-3: Tour Rome

Rome is an amazing city with a wealth of history to explore. Because there is so much to see and do in the city and the surrounding area, I have set aside two days for you to explore Rome. To help you fill out your itinerary, I have included a link to my Quintessential Rome, Italy Visitor Guide below.

In my guide, I outline the top things to see and do in Rome during your visit. In addition, I have also included several different tours and excursions that I would recommend checking out if you have the time. Using my guide, you should have no trouble getting around the city and seeing all of the wonderful things that the city of Rome has to offer during your visit.

Day 4: Tour the Vatican

On the fourth day of my Italy travel itinerary, I have scheduled some time for you to explore the wonderful Vatican City near Rome. It’s a large and amazing place, so I would recommend setting aside the entire day to fully explore the Vatican.

I would recommend booking a tour of the Vatican rather than exploring it on your own. Not only will it ensure that you see everything and make your visit more memorable, but tours get priority on entrance and it will save you a bunch of time that you would otherwise spend waiting in line.

Expert Tip: I would strongly recommend booking a tour of Saint Peter’s tomb. They only let a very limited number of people tour the tomb each day, so you will need to make sure you book your tour well in advance (at least 3 months in advance). If you are using a tour company to tour the Vatican, I would let them know you are interested in this tour and they can help you get a reservation.

Day 5: Travel to Sorrento

After touring Rome and the Vatican, the next phase of my Italy travel itinerary has you heading south towards Naples, and then on to Sorrento, which will be your base of operations while you tour the Amalfi Coast.

Depending on how much time you want to spend in Rome, you can travel to Sorrento either early in the day on Day 5 of your trip or later that evening. I would recommend not getting in too late so that you can make sure you get settled properly and are ready to get out and explore right away on Day 6.

If you are looking for accommodations and restaurants in the Sorrento area, I would recommend checking out my Definitive Amalfi Coast Visitor Guide for recommendations. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 6: Visit Capri

On Day 6 of my Italy travel itinerary, I suggest that you take a trip to the island of Capri to explore for the day. The island of Capri is one of the most beautiful places in Italy and an absolute must-see if you are visiting the Amalfi Coast.

You will need to arrange a ferry ride from Sorrento to Capri and back, so make sure you either purchase tickets in advance if you are sure about your travel dates or leave yourself ample time and flexibility to buy your tickets when you get there.

If you would like more information on travel from the island of Capri, as well as what to see and do while you are there, please refer to my Complete Capri Travel Guide linked below for my recommendations.

Days 7-8: Tour the Amalfi Coast

The next stop on the Italy travel itinerary I have laid out for you is one of the most beautiful regions in Italy. The Amalfi Coast is famed for its breathtaking coastline, colorful cities built up on the coastal bluffs, and delicious seafood and citrus fruits.

You will get to spend the next few days traveling down the Amalfi Coast and exploring all of the treasures that this quaint Italian region has to offer. If you are looking for recommendations on what to see, where to grab a bite to eat, and what tours and excursions are recommended in the area, I would suggest that you check out my Definitive Amalfi Coast Visitor Guide linked below.

Day 9: Travel to Florence

Once you have finished exploring all of the beauty on the Amalfi Coast, the next stop on the Italy travel itinerary I have laid out is the amazing city of Florence in Northern Italy. If you decide not to rent a car while in Italy, you will need to take a train from Sorrento to Naples, where you can catch a high-speed train to Florence. Considering the distance, the 3.5-hour train ride really isn’t that bad.

If you are driving, it will take you roughly 5.5 hours to get from Sorrento to Florence, so you might want to consider making your way North slowly or consider doing this trip from the top-down (starting in Venice and ending in Naples) or bottom-up (starting in Naples and ending in Venice). This will save you a considerable amount of driving time on your trip.

If you are looking for accommodations or restaurant recommendations in Florence, I would recommend reviewing my Florence, Italy Visitor Guide for recommendations. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 10: Tour Florence

Few cities in the world, let alone Italy, have as much wealth of history as the amazing city of Florence. After arriving in Florence on Day 9 of the Italy travel itinerary, you will get to spend the rest of that day and the following day exploring all of the treasures that the city has to offer. I would suggest that you make the most of it, as there are many amazing things to see and do in the Florence area.

If you are looking for suggestions on what to see, where to eat, and what tours and excursions are recommended in Florence, I would suggest reading my Florence, Italy Visitor Guide linked below for my recommendations.

Day 11: Take a Tour to Tuscany

On the eleventh day of your Italian vacation, you will be taking a tour into one of the most popular tourist spots in Northern Italy. The Tuscany region of Italy is famed for its beautiful rolling hills and fantastic vineyards and wineries. If you have some extra time to extend your trip, this is one of the spots where I would recommend spending an extra few days if you have the time.

If you don’t have extra time, you should be able to get a good sense of the region by taking a day tour into the Tuscan countryside and touring some of the most popular vineyards and wineries in the region.

There is a wide range of tours available, so make sure you take the time to research the tour that is the most interesting to you. To give you a head start, I have linked TripAdvisor’s list of the best Tuscany wine tours and tastings for you to review below.

Day 12: Travel to Venice

When you are finished exploring Florence and Tuscany, the last stop on my Italy travel itinerary is one of the most amazing cities you will find in the world. Renowned all across the world for its romantic canals, its amazing annual Carnival festival, and its wealth of history, Venice is an absolute must-see destination when visiting Italy.

It’s roughly a three-hour trip from Florence to Venice, both by car or train, so you will want to decide how you spend your time on this travel day. You can travel mid-day and spend portions of each day touring each of these cities, travel in the evening if you need more time in Florence, or depart early in the morning if you would like to spend more time in Venice.

When I visited Venice, I was able to see what I wanted in one full day, so my personal recommendation is to spend at least some of the travel days further exploring Florence and Tuscany.

Venice is a large city, so there are a lot of options for you to choose from in terms of accommodations. If you are looking for recommendations, I would suggest reviewing my Venice, Italy Travel Guide for my suggestions. If you are interested, I also outline the top restaurants in the city that I would recommend trying during your stay. I have included an assortment of accommodation and restaurant options at a variety of different price points in my guide so that you can easily find what you need.

Day 13: Tour Venice

When most travelers think of Venice, the first thing that comes to mind is the beautiful canals and romantic gondola rides through the city. While this is a popular activity to enjoy while visiting Venice, it is just the tip of the iceberg when it comes to the wonderful things to see and do while visiting the city.

The last full day of my Italy travel itinerary is dedicated to exploring Venice and all of the amazing things there are to see and do. If you are looking for suggestions on what to see, I have included my list of the top things to see and do in the city in my Venice, Italy Travel Guide linked below. I also outline some of the best tours and excursions you should consider during your stay in case you have extra time and would like to try something unique.

Day 14: Depart From Venice

On the final day of my Italy travel itinerary, you will be wrapping up your sightseeing and preparing to depart for home. If you follow my itinerary as I have laid it out for you in this guide, you will be departing for home from the Venice Marco Polo Airport (VCE) in Venice.

In which case, you will want to leave yourself some extra time to get to the airport as you are going to need to catch a boat from the city back to the mainland of Italy. From there, you can take a taxi or rideshare to the airport.

If you adjust this itinerary to follow the top-down or bottom-up options, you will either be flying out of Leonardo da Vinci International Airport (FCO) in Rome or Naples International Airport (NAP) . You will want to ensure that you have your transportation prepared so that you get to the airport in plenty of time to make your flight.

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Published by Josh Hewitt

Avid traveler and photographer who loves to see new places, meet new people, and experience new things. There is so much this world can teach us, we just need to explore! View all posts by Josh Hewitt

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Your blog is amazing! We’ve travelled through Italy and your guide is thoroufh and valuable for anyone who is considering Italy as a travel destination.

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2 Weeks in Italy – A 14-Day Itinerary for First-Timers

A trip to Italy has something for everyone: artistic masterpieces, ancient history, amazing food, fabulous landscapes and local folklore.

A 14-day itinerary allows you to discover all the facets of this unique country, from its main cities to some of its most fascinating villages.

Are you ready to spend 2 weeks in Italy?

There are two ways to travel, by car a do an Italy road trip or by train as described below.

Don’t forget to check: my Italy packing list .

Disclaimer: This post contains affiliate links. This means that should you click on certain links, and then subsequently purchase a product, I will receive a small commission.

Table of Contents

How to Spend 14 Days in Italy – 2 Week Itinerary

Day 1: Flight to Rome and Transfer To Naples

Fly to Rome, which is not only the Italian capital but also one of its main transportation hubs allowing you to easily reach any other large city.

To find the cheapest flight options from your city, you can use the search form below

Catch a high-speed train to reach Naples in about 1h. Try to be there around lunchtime to be able to spend a few hours visiting the city.

But first, enjoy a real Neapolitan pizza and a well-deserved lunchbreak!

In the afternoon, you can choose between:

• A visit to the National Archeological Museum (if you’re not too tired!) for a real blast from the past. Book your skip the line tickets for the museum here.

• a visit to the mystic Sansevero Chapel to admire the famous Veiled Christ. Click here to book a small group guided tour to the Old Town and the Veiled Christ.
• In the evening, take a stroll in the trendy Chiaia neighborhood and have a drink outdoor like a local

Where to stay in Naples

Check out my guide on where to stay in Naples here. 

Renaissance Naples Hotel Mediterraneo : This 4-star hotel, a member of the Marriott Group, is located centrally close to the main attractions of Naples and the ferry terminal. Rooms are comfortable and modern while the rooftop where breakfast is served has lovely views of the Bay, Castel Nuovo, and Mount Vesuvius. Click here for more information and to check the latest prices. Grand Hotel Europa – Sea Hotels Group : Located near the main station, this hotel is an excellent choice for those thinking about visiting Pompeii or the Amalfi Coast. It provides excellent 3-star value with comfortable rooms including Wi-Fi, satellite TV, air-con, and safe. Click here for more information and to book the Grand Hotel Europa.

You might be interested in: 3 days in Naples.

Day 2 Pompeii & Sorrento

Visiting Pompei is a must and you cannot miss this stop during your 2week stay in Italy! You can easily reach Pompei by train and it will surely be an emotional visit making you feel like an ancient inhabitant of these places. To see the main points of interest and make the best of your time, join a guided tour ( Pompeii: Small-Group Tour with an Archeologist ). As an alternative, get a fast-track ticket ( Pompeii Fast Track Entry Ticket ).

An organized tour will take around 2- 3 hours, but armed with the knowledge already gained, you may want to spend more time there on your own before returning moving on.

No matter how you choose to visit the site, know that it is very busy especially from May to October. Bring a hat and sunscreen, wear comfortable shoes and drink plenty of water.

In the afternoon, head to the lovely town of Sorrento . How can you spend a few hours?

• take a stroll in the picturesque alleyways of the Old Town
• visit the beautiful S. Francesco Cloister
• linger in a café in Piazza Tasso

• meet local fishermen in Marina Grande village
• watch the sunset from the panoramic terrace of Villa Comunale

As an alternative, you can join a walking tour. If you are looking for an organised skip the line guided tour starting from Naples I suggest this full day guided tour that combines a visit to the Pompeii ruins and the mount Vesuvious .

Day 3 Amalfi Coast

Option 1 : rent a car and spend your day driving around to explore all the picturesque villages along the coast. A few tips?

• Positano : winding alleys, a medieval flair, and some wonderful views. If you feel like being active, don’t miss the Path of the Gods.
• Amalfi: the main and largest town on the coast, full of historical buildings and monuments. Visit at least S. Andrea Cathedral and the Cloister of Paradise .

• Ravello : up in the Lattari Mountains and overlooking the Mediterranean Sea. Visit the Gardens of Villa Cimbrone to take the most amazing pictures!
• Cetara: a lovely fisherman village where you can taste a local gastronomic specialty named “colatura di alici” (anchovy extract)

Option 2 : a guided tour from Naples to the Amalfi Coast.

Option 3: It is very easy to do this day trip on your own as well. You just need to catch a train to Sorrento from Naples. There are about 3 trains per hour depending on the season and the journey is about an hour depending on the type of train. As soon as you exit the train station there is a kiosk where you can buy a bus ticket to either Positano or Amalfi. The buses are in front of the station and tickets cost 2-3 euros one way.

It takes around an hour to get to Positano by bus as the road is small and there is huge traffic especially during the summer and you need even more time to get to the Amalfi village because it is further away. Also, during the high season, the queues to take the bus are huge and you might have to ride standing. Also, the road is very curvy and a lot of people get sick.

Option 4: There is an alternative way to get to the villages, which is by ferry from Sorrento. You can get the ferry from the port. It is a 10- minute walk from the train station. From Sorrento to Amalfi it is one hour by ferry and the ticket was 16 euros in September that I visited. The ferry makes also a stop in Positano before arriving in Amalfi. There are many small boats connecting Positano with Amalfi and the other villages of the Amalfi Coast. Tickets can be bought at each port.

You might also be interested in: 11 Amalfi towns to visit. An Amalfi Coast itinerary and a guide on where to stay in the Amalfi Coast. A guide to Positano

Day 4 Capri

Take a ferry from Naples to reach Capri island in about 40 minutes. The fast ferry takes 50 minutes to Capri from Naples and tickets cost around 21,50 euros one way.

Start your visit with a boat tour taking you to the wonderful Blue Grotto ( Capri Boat Tour With Stop by the Blue Grotto )

Catch a bus and reach the village of Anacapri . Its highlight is the beautiful S. Michele Arcangelo church with its precious majolica floor ( Chiesa di San Michele (chiesa-san-michele.com) )

Now you can either take the chairlift and reach the top of Mount Solaro ( The Chair Lift Monte Solaro (capriseggiovia.it) ) or go back to Capri to visit its Old Town and the medieval Certosa di San Giacomo

Don’t miss a visit to the Gardens of Augustus to enjoy some local nature

If you still have some time to spend on Capri island, reach Villa Jovis on Mount Tiberius

Alternatively, you can book a full-day tour to Capri from Naples.

Click here for my post: Things to do in Capri

Day 5 Naples to Rome

Spend your last hours in Naples taking the Underground Tour to learn more about some important archeological findings ( Naples Underground (napolisotterranea.org) )

Catch a high-speed train to reach the second stop of your 14day itinerary in Italy: Rome !

Spend the afternoon walking around the city center. Start from Piazza Navona and take a moment to admire the Fountain of the Four Rivers by Bernini

Reach Piazza di Spagna and climb its iconic stairs to reach the panoramic terrace in front of the church of Trinità dei Monti

Admire the neoclassical beauty of Piazza del Popolo with its Egyptian obelisk and its twin churches

Reach the Trevi Fountain and wait in line to throw a coin into the basin!

If you still have some time, enjoy some shopping in via Condotti and via del Corso

Where to stay in Rome

Royal Rooms – Via Del Corso : The Royal Rooms are just 200 meters from Via Margutta and many amenities are in the immediate vicinity. They include shopping, piazzas, and cafes. Within the Royal Rooms, you will find everything you need for comfortable accommodation. Click here for more information and to check the latest prices. Palazzo Medusa : Palazzo Medusa is regularly selected by its guests as one of the best in the whole city. Comfortable accommodation includes a large TV, an en-suite bathroom, and a hairdryer. You can even rent a bike if you wish. Palazzo Medusa has gained a reputation for its fine cuisine; enjoy it! Click here for more information and to check the latest prices. Navona Colors Hotel : Located less than 200 meters from Piazza Navona, its situation is ideal for visitors wanting to walk or cycle around. The food is good and the bedrooms are comfortable in this beautiful Baroque building. Click here for more information and to check the latest prices. Piazza Del Gesu Luxury Suites : Situated on the Piazza Navona, a 5-minute walk from one of Rome’s highlights, the Pantheon. Facilities you will enjoy include free WI-FI, lovely furnishings, and a modern bathroom. The views over the City are stunning. Click here for more information and to check the latest prices.

You can also check a local’s guide on where to stay in Rome .

What’s best than starting off the day with a visit to the Colosseum ?

Dive into ancient times by also visiting the Roman Forum and the Palatine Hill . You can also take a guided tour with skip the line tickets to make the best of your time as lines are huge .

In the afternoon, head to the Pantheon and watch the light entering from the hole in its dome.

Enjoy some nature in Villa Borghese Park , but not before taking a tour of the beautiful Villa Borghese Gallery housing some famous statues by Canova. Book your skip the line tickets here to avoid the queues.

Tonight, taste some typical Roman dishes in Trastevere !

You might also be interested in: 5 days in Rome .

During your 2week stay in Italy, you should absolutely spend a whole day visiting the Vatican . Start from the Vatican Museums and save enough time for the Sistine Chapel, the Galleries, and Raffaello’s Room.

Tip: Visiting the Vatican is an essential Rome experience, and it will be quite overwhelming! Before anything, you should know that the queues are huge. No matter how much you think you can wait, you can’t. The queues go on for seemingly forever, so I recommend a skip a line tour. Another way to enjoy the Vatican if you don’t have much time is by this Pristine Sistine, early entrance small group Vatican tour . The reason I like this tour is that you get inside the Vatican one hour before it opens, the group is small and you get to see the Vatican in under 4 hours. All 3 times I’ve been there were with the skip-the-line guided tour, and it added to the overall comfort and convenience of my entire visit there.

Visit St. Peter’s Basilica and get lost among its many artistic masterpieces and stunning architectural features like the dome.

Leave the Vatican by walking along the majestic via della Conciliazione and take one last picture of the Basilica

Reach S. Angelo Castle and watch the Tevere river from the homonymous bridge lined with huge stone Angels. Book here your fast-track ticket to Castel San Angelo or a guided tour.

Spend a romantic evening walking along the Tiber river .

Day 8 Rome to Florence

Get up early and catch a high-speed train to reach Florence in about 1h30.

Start your tour from the Duomo Complex , the beating heart of Florence. It consists of: Santa Maria del Fiore (Cathedral), Brunelleschi Dome (belonging to the cathedral), Baptistery , and Giotto Tower . A guided tour of the Cathedral is always a great idea.

Tip: There is a dress code to enter the church. Women must wear clothes covering their knees and their elbows. Men must wear long trousers. Tip: The queues to enter the Duomo and to climb the Cupola are long and you might have to wait for hours to enter. A great way to skip the lines is by taking a guided tour or if you are using the Firenze Card (The Firenze Card works like a three-day fast pass to your favorite attractions. This is a great option for visitors trying to pack as much sightseeing into a Florence vacation as it lets them skip the long queue lines at most of the most popular sites. It is a great buy if you are staying in Firenze for 3 days). Here are some recommended tours of the Duomo: Duomo skip the line guided tour. Guided Tour of the Duomo Including the Rooftop and View the Terraces

Head to the elegant Piazza della Repubblica with its beautiful Triumphal Arch and the ancient Column of Abundance

Now reach Piazza della Signoria with the iconic Palazzo Vecchio and the famous Loggia dei Lanzi .

Cross the picturesque Ponte Vecchio , but not before having touched the nose of the wild boar decorating a small fountain nearby (it brings good luck!)

Your last stop will be Santa Croce Basilica , with its marble façade, its frescoes, and the tombs of some famous people like Galileo Galilei and Michelangelo.

Taste the famous Fiorentina Steak for dinner!

Where to stay in Florence

Tourist House Battistero : This accommodation in a 15 th Century building is close to the Ponte Vecchio and the Scudieri Café. You will get a comfortable room with lovely views over the City. Click here for more information and to check the latest prices. C-Hotels Ambasciatori : You will be close to Florence’s main attractions if you stay at this 4-star hotel. It is a chic, modern hotel surrounded by a wonderful history. Click here for more information and to check the latest prices. Plaza Hotel Lucchesi : Built in 1860, this is 4-star accommodation situated close to the Arno River. You will have lovely views of Florence during your stay. Click here for more information and to check the latest prices.

Day 9 Florence

Spend the whole day admiring some of the most famous artistic masterpieces in the world! An example? The iconic David by Michelangelo! Where to find it? In the Galleria Dell’ Accademia .

Tip: There are usually long queues for the Accademia. To save time you can either buy a timed entrance ticket beforehand or book a guided tour. Skip the line entrance ticket to the Accademia Another great option is to book a skip-the-line half-day tour to both the Accademia and Uffizi.

Another iconic museum is waiting for you: the Uffizi . Skipping the endless line at the entrance is a must, but a guided tour is what you really need to see everything without spending the whole day wandering around and getting lost!

Tip: The queues for the Uffizi are long. To save time you can either buy a timed entrance ticket beforehand or book a guided tour. Here are some great options: Skip the line Ticket to the Uffizi Skip the long queue with a guided tour of the Uffizi

As an alternative, you can replace one of these visits with Palazzo Pitti , especially if you love Renaissance art. If you go there, step outside and visit the beautiful Boboli Gardens !

Don’t miss the sunset from Piazzale Michelangelo and remember to take a picture of the iconic city’s skyline

The Piazzale Michelangelo has become famous because of its wonderful views of Florence and the neighbouring areas. It is equally impressive by night with its flickering lights or as the sunsets.

Check out here my 2 day Florence itinerary. 

Day 10 Tuscany Tour or Cinque Terre

There are interesting day trips from Florence to see the larger region. The choice is yours from a few alternatives:

• San Gimignano and Siena and Chianti are medieval towns within a famous wine region of Italy. It is a lovely region of rolling hills so even the journeys there and back are fun.
• Pisa with tickets to the leaning tower, another alternative especially if you want to see the Leaning Tower of Pisa.
• Cinque Terre is a region of lovely small villages that can be done by train from Florence or with an organized group.

You might like: How to spend one day in Cinque Terre . How to get from Florence to Cinque Terre. The most beautiful hilltop village in Tuscany.

Day 11 Florence to Venice

Get up early and take a high-speed train to reach the third stop of your 14day itinerary in Italy: Venice ! Try to be there as early as you can to be able to spend the whole day exploring the city.

Start from Piazza San Marco . Enter the majestic San Marco Basilica and enjoy its golden decorations and its byzantine vibes. It’s always extremely crowded, so it’s best to skip the line .

Visit also Palazzo Ducale (Doge’s Palace) and learn who the famous Doge was

Recommended: Skip the line tour to Doge’s Palace & St Mark’s Basilica.

Learn something more about the other two landmarks of San Marco Square: San Marco Tower and the Clock Tower . You can enjoy a complete visit to the Square and its monuments by taking a guided tour .

In the afternoon, relax and slowly stroll along the canals . Cross Rialto Bridge and don’t forget to take a picture of the Canal Grande !

Your first night out in Venice shall involve some “cicchetti” and an “ombra” in a local “bacaro” (meaning tasting some local tapas and a glass of wine in one of the typical taverns of Venice!)

Where to stay in Venice

Hotel Al Codega : This comfortable hotel has regularly received positive reviews from its guests. That is because of its location close to some of Venice’s top attractions as well as the facilities they have found within their accommodation. Click here for more information and to check the latest prices. Hotel Rio : Hotel Rio is central within Venice so that you will find attractions close by including the Rialto Bridge. The Venezia Santa Lucia Train Station is near and so it is convenient for arrivals and departures. You can expect every modern amenity including satellite TV and Wi-Fi. Click here for more information and to check the latest prices. Hotel Ai Reali – Small Luxury Hotels of the World : An eclectic mix of Baroque and Neoclassical architecture with plenty of marble, this hotel is among the top tourist selections in Venice.  St. Mark’s Basilica is just a short walk away; perhaps the first major attraction you will see in Venice if you book here? Click here for more information and to check the latest prices.

Day 12 Venice

Start your day with some Venetian art at the Accademia Galleries . Save at least 2h30 for this visit!

If you love modern and contemporary art, replace this visit with a tour of the Peggy Guggenheim Collection. Click here to book your skip-the-line tickets.

Spend the afternoon visiting the smaller islands of the Venetian Lagoon: Murano, Burano, and Torcello . They are well connected to Venice by water taxi, but you can also choose a combined tour Find here more information and book a cruise to Murano, Burano , and Torcello islands.

The perfect Venetian night? It shall start with a romantic gondola ride . Find here more information and book a 30-minute gondola ride.

Check out my detailed post about 2 days in Venice .

Day 13 Venice to Milan

Today, you’ll reach the last stop of your14day itinerary: Milan ! You can reach it in about 3h by high-speed train

Since you only have 1 day left, focus on the city center and start with the symbol of the city: the Cathedral in Piazza Duomo . This gothic masterpiece deserves a thorough visit and you should absolutely climb up to the rooftop to take in a breathtaking view of the Alps and to see the golden Madonnina (a golden statue of the Virgin Mary protecting the city).

To make the best of your time, choose a fast-track Milan Cathedral and Terraces Guided Tour .

You won’t probably have enough time for a visit, but you should spend a moment to watch the medieval Sforza Castle .

Take a moment to also enjoy some nature and get out of Milan’s crazy traffic in the lovely Sempione Park !

How to spend your last night in Italy? At La Scala Theater of course! It doesn’t need to be super expensive, just have a look at the discounted shows offered by ScalAperta – Teatro alla Scala . Check the regular schedule at Teatro alla Scala

Where to stay in Milan

NYX Hotel Milan : This 299-room hotel near the Central Station is close to a number of the City’s attractions; “La Scala” Opera House, the Sforzesco Castle and”Golden Triangle” (Quadrilatero Della Moda). There is a bar, restaurant, gym, and Wi-Fi. Click here for more information and to check the latest prices. Mandarin Oriental Milano : This 104-room hotel takes up four 18 th Century buildings in Quadrilatero della Moda. Its elegant décor, spa, pool and gym, and excellent service combine with a Michelin-starred restaurant, one of two in the hotel, to provide a memorable stay in Milan, no matter how brief. Click here for more information and to check the latest prices.

You can also check my one day Milan itinerary.

Day 14 Fly Home

Book your flight in the afternoon to be able to enjoy an unmissable artistic masterpiece also included in the UNESCO’s World Heritage List: The Last Supper by Leonardo da Vinci . It is kept in the Cenacolo Vinciano, which is part of the monastery of Santa Maria delle Grazie. Visitors are admitted a few days a week and in small groups, so plan your visit in advance ( Last Supper, Leonardo Da Vinci | Cenacolo Vinciano Official Website ). As an alternative, take a guided tour .

Time to fly home!  Reach Malpensa international airport by bus ( By Coach | Milan Malpensa Airport (milanomalpensa-airport.com) ) or by train ( By Train | Milan Malpensa Airport (milanomalpensa-airport.com) ) and say bye to Italy…or better, see you soon!

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Looking to extend your trip to Italy? Check out the following 20 Northern Italy cities you should visit. One day in Verona. Best Towns on Lake Como. Things to do in Lake Garda. Best towns in Lake Garda.

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2 Week Italy Tours & Trips

Filter for departure dates and price to find the right 2 week Italy tour with TourRadar. Choose from 139 trips with 1,179 customer reviews, that range from 11 up to 14 days.

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139 italy 14 days tour packages with 1,179 reviews.

• In-depth Cultural
• Christmas & New Year

Tutta l'Italia

It was smooth and successful having the hotels and transfers between each city. The first seven days were extremely busy with full guided tours and then the pace slowed down to have more free time and relaxing moments the second half of the trip once we were along the coastal cities of Sorrento and Cinque Terre. This was a good tour to see many cities and the guides were knowledgeable and helpful in sharing the history of Italy. I know know which areas I will be going back to for longer time periods in my next trip.

• Coach / Bus

Italy's Best

This was a great taste of Italy. I made friends from all over the world and enjoyed my time on this trip. Our tour guide Stefano was funny and knowledgeable and Claudio our driver was amazing. My only critique is I wish they would add visiting the museum in Naples after visiting Pompei.

Italia Amore Mio (Small Group)

Best of Italy (Summer, 13 Days)

The skip the line tickets are worth it for quicker entry and are a valued benefit of the tour. Most included meals were good and included drinks. The convenience of the coach is great too.

• €100 deposit on some dates Some departure dates offer you the chance to book this tour with a lower deposit.

Highlights of Sicily

Iconic Italy National Geographic Journeys

Amazing tour facilitated by an amazing guide! Great balance of planned activities and free time to explore. Highly recommended!

Best of Italy

Loved the free time to explore personal interests.

Shrines of Italy - Faith-Based Travel

Mamma Mia! - 13 Days/12 Nights

Take the trip! We look our two adult children with us and this was a trip of a lifetime for us all! Worth every single penny! The memories are priceless and they are still talking about it two years later. If you want to take the vacation without worrying about figuring out transportation and lodging in a foreign country...this is the trip for you! Though not always exactly what we expected, the nuances were part of the charm. Like I said...TAKE THE TRIP!!!!! You won’t regret it!

Ultimate Italy

I travelled as a single & joined this tour May 2015. The tour leader was a local lady from Lake Como. She advised us of all the best local restaurants, attractions & importantly gelato vendors! It was a small, mixed age group of 11 which made for getting to know the other travellers well. Accommodation was always with local owners and was clean although basic but quite acceptable. Travelling through Italy was very well organized with using local transport & a lot of extras included. We also had lots of time to adventure on our own. I highly recommend this tour.

Best of Italy: Tuscany, Cinque Terre & The Amalfi Coast

Italy Jewels : Venice to Amalfi

Grand Cycling Tour of Sicily

I really enjoyed the Sicily trip, especially all the cultural experiences that Experience Plus adds to the trip. I also like following the chalk arrows. I find it an easy and a relaxing way to get to that days destination. The tour leaders are always great and make the trip extra special.

• Educational

Renaissance Italy

Italy: Amalfi Coast to Puglia (Naples to Alberobello) (2024) (Standard)

What people love about 2 week italy tours.

This tour is great for seeing numerous cities and historical sites in Italy, a one day trip over the border into Lugano, Switzerland was just a true delight and icing on the cake. I have now learned that the Cosmos level is the "budget" label for Globus, so expect mostly 3 star hotels that are located outside of the major cities. This wasn't too much an issue as public transportation (metro/bus) or taxi's are available from each hotels if needed. Some of the hotels have poor air conditioning so if that's a priority for you then consider a Globus level tour instead. Overall, the hotel we clean. We found it difficult to plan our excursions as the itinerary they provide is very vague with regards to the times of the optional excursions, but these were clarified on day one as we asked our tour director and she was able to tell us if we had enough time to do some of things we wanted to do that weren't offered. Expect to get up early as the bus is usually on the road by 7:30 am, but that's necessary to get to the sites before the crowds. As far as the optional excursions go, the first dinner in Rome was a bit of a disappointment as it wasn't in central Rome, the food was mediocre and the service was fair, the highlight was two elderly Italian men playing and singing live music - famous old Italian songs- a lot of us complained about this so maybe Cosmos will change that venue? The other excursions are well worth it, takes the hassle out of dealing with transportation and getting tickets. The ones not to miss are the Tuscan Farm Dinner, Lugano Switzerland Cable Car, Capri, Pompeii. I would recommend this tour for those who don't require a luxury hotel, I am glad we were able to experience it!

Overall good, seemed a bit rushed with not enough time to absorb the sites.

Regions in Italy

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• Tuscany (7)
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Other Regions in Italy

• South Italy 10 day Tours (218)
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• Italy Travel Guide | All You Need to Know
• Itinerary Ideas for 10 Days in Italy, 2022-2023
• Best 7 Day Italy Itineraries 2024/2025 (with Reviews)
• Discover the Best Italy Vacation Packages 2024/2025
• What is the best time to visit Italy in 2024/2025?

Fearlessly Italy

2-Week Italy Itinerary – A Step-By-Step Guide To 14 Days In Italy

You’ve been planning a 2 week Italy itinerary for a while and still feel in a stalemate? Don’t worry, you’re not alone. The country is so packed with things to do, wonderful places to visit, and great Italian food to try that anyone traveling to Italy for the first time is bound to feel overwhelmed.

If you don’t want the burden of the logistics, you can book one of the best Italy tours , but if you prefer to travel independently, fret not, we’re here to help.

This guide of ours, even though extensive and detailed, will only touch the most popular cities you can’t miss in 2 weeks in Italy. Those places you really can’t afford to miss if it’s your first time in this beautiful country.

We will squeeze as much as we can into a two-week Italy tour itinerary. It’s not strictly a Rome Florence Venice itinerary, it includes also other places, but it’s pretty classic.

Table of Contents

Is 2 weeks long enough in Italy?

If it’s your first trip, 2 weeks is a pretty good amount of time to get the grasp of what to expect from an Italian holiday, to experience the local culture, to visit the most famous and classic landmarks, and to fall in love with the country.

Two weeks in Italy is enough if you do proper planning. Whether you are planning a classic 2-week Italy itinerary or a more alternative one, you need to keep in mind that there will always be places you won’t be able to include. Which is the best excuse to plan a second trip or more!

Should I go to Italy for 2 weeks or 3 weeks?

If you are planning a country-wide itinerary, I think you will need at least two weeks to cover the most important landmarks. Of course, if you can afford 3 weeks in Italy you can either include more regions and places or stay longer in the cities you are visiting.

For example, you could stay a week in Rome, 5 days in Florence, or devote 4 to 5 days to the Campania region and enjoy a more complete experience.

14 Days In Italy – A Step-By-Step Itinerary

Granted, with so much to see, planning your best 2-week Italy itinerary is not easy. Our extensive guide will provide you with the essentials to organize a perfect vacation on your own. If you are visiting for the first time, 2 weeks in Italy are enough to see the main attractions in the main cities.

Planning 14 days in Italy allows you to explore the classics such as Rome, Florence, and Venice. If you want to enjoy a place longer, visit more attractions or take some day trips, you can easily spend 3 weeks in Italy. If you have less than two weeks in Italy, you can avoid some of the attractions in each city and stay one day less. Here, we give you the tools to plan a trip to Italy on your own.

If it’s not your first time or you have more than two weeks in Italy, check out our other guides on specific areas like Sardinia, Sicily in the cities of Catania and Agrigento, and Trentino Alto Adige, both its cities and the Dolomites mountain range.

We will see when is the best time to visit Italy depending on what type of holiday you want, we will suggest the best car rentals in case you want to embark on an Italy road trip, we will tell you what to pack and obviously what to visit to make your holiday smooth and unforgettable.

This guide will empower you to plan a trip to Italy on your own. For each city, we will provide you with the best day tours if you wish to optimize the time of your 2 weeks Italy itinerary and have more in-depth information. At the end of this guide, you will also find a selection of the best tours to Italy in case you want a hassle-free holiday where expert organizers take care of the details and the logistics for you.

Map Of Your 14 Days In Italy

Where to go: a cool itinerary for two weeks in italy, milan – 2 days.

Milan is Italy’s “Wall Street”, a bustling financial hub that attracts businessmen for work or business-oriented travelers. However, with a long history and a good deal of historical landmarks and artistic attractions, Milan has been imposing itself also as an exciting tourist destination for travelers from all over the world. On your 2-week Italy itinerary, we suggest spending 2 days in Milan . If you want to stay less, you can also visit most attractions in Milan in 1 day .

Some of the most important places to visit in Milan are:

• The Duomo. The most popular among Milan’s landmarks, the city’s cathedral is a must. Its Gothic facade never fails to bedazzle visitors and passers-by, the inside is a fascinating journey into Milan’s history and culture, and its rooftop gives you a great view of the city and its architecture.  Click here for Walks of Italy’s Best of Milan Tour that includes a visit to The Last Supper and the Duomo’s rooftop .
• Sforza Castle. Residence of one of Milan’s most prominent families, the Sforza Castle today hosts several exhibitions, both temporary and permanent, as well as being a cultural center.
• Galleria Vittorio Emanuele II. Known as Milan’s parlour, this long covered gallery is lined with cafes and shops of the most exclusive brands. It’s close to the Duomo’s square, so you can’t miss it!
• Da Vinci’s The Last Supper. Don’t miss the famous mural painting by Leonardo Da Vinci in UNESCO-listed Santa Maria delle Grazie church, beautiful Renaissance building by architect Donato Bramante.
• La Scala Opera House. Milan’s opera house, this is a beautiful Neoclassic building worth a visit even if you are not going to see the performances. You can visit both La Scala and the museum but call first because if there are rehearsals you can’t visit the theatre hall.
• Navigli. Milan’s canals are a great place for a walk both day and night. This is one of the favorite hangouts for aperitivo , dinner or a night out.

READ MORE: Check out our extensive guide to Milan to find out what to do if you have more time .

Hotels in Milan – Some suggestions

• High-end. Bulgari Hotel Milano , Four Seasons Hotel Milano , Mandarin Oriental, Milan .
• Mid-range. Hotel NH Collection Milano CityLife , Hyatt Centric Milano Centrale , Hotel Milano Scala , The Street Milano Duomo .
• Budget. B&B Hotel Milano Portello , Hotel RossoVino Milano , QUO Milano hostel .
• Apartments. CA Foscari Loft & Factory , ApartHotel Bossi .

Check out Booking for more accommodation options in Milan for every type and price.

The next stop in your two-week trip to Italy is La Serenissima, so book your Milan to Venice train and get to one of the world’s most romantic cities. Click here to check timetables and prices with Omio .

Venice – 2 to 3 Days

One of the most popular destinations in Italy, Venice is as gorgeous as it gets. Unprecedented views, a unique urban landscape, and a long history are the perfect combination for an unforgettable trip. And if you go for the Carnival, the colorful and fascinating masks will add to the charm of the city.

How many days in Venice? We suggest 2 to 3 but it really depends on how much time you have, how much you want to enjoy and explore the city and, last but not least, on your budget.

Some of the things to do in Venice in your two weeks in Italy are:

• Piazza San Marco. One of the key landmarks in Venice that make the city famous is its central Piazza San Marco, the very first place tourists visit. Surrounded by San Marco Basilica and the Doge’s Palace, this piazza is really gorgeous.
• St. Mark’s Basilica. One of the most symbolic buildings in Venice, San Marco Basilica is a gorgeous piece of Oriental-style architecture dating back to the 11th century. Click here to book the exclusive tour of St. Mark’s Basilica after closing time .
• Doge Palace.  Standing exactly where it stood throughout the centuries, the majestic Palazzo Ducale is an important piece of the city’s republican past. Get a VIP entrance to the Doge Palace with Walk of Italy’s Secret Passages tour .
• Jewish Ghetto. Europe’s oldest Jewish ghetto, Venice one was created in 1516 and is now a lovely neighborhood to stroll around the city’s traditional architecture and eat delicious local treats.
• Canals and Bridges. The beauty of Venice is in its architecture and this is directly related to its unusual layout. Instead of streets, in Venice you have canals and bridges, instead of buses, you will take the boat or if you don’t mind forking out good cash, a gondola. One of the most scenic things to do in Venice is certainly strolling around its bridges, Rialto and the Bridge of Sighs being the most famous. Click here to book Venice Boat Tour to visit the city and its bridges from the water and cruise the Grand Canal .
• Gallerie dell’Accademia. This art gallery hosts the largest collection of Venetian paintings from the Byzantine and Gothic 14th century to the Renaissance.
• Basilica dei Frari. Often neglected by the hasty traveler, this monumental Basilica is 102 meters long and boasts an impressive collection of artwork and 17 altars. It’s also the resting place of several notables, from Antonio Canova to Titian to several Doges.

Hotels in Venice – Some suggestions

• High-end. The Gritti Palace , The St. Regis Venice , Hotel Danieli, Venice .
• Mid-range. Hotel Papadopoli Venezia , Hotel Monaco & Gran Canal , Palazzo Veneziano – Venice Collection , Ruzzini Palace Hotel .
• Budget. Ca’ Pedrocchi , Dimora Marciana , Locanda Antica Venezia , Ai Cherubini .
• Apartments. Corte Barozzi Venice Suites , San Gregorio Venice Apartments , Casa del Carro 2 Grand Terrace Apartment , Palazzo Paruta & Wellness Suites .

Check out Booking for more accommodation options in Venice for every type and price.

Unless you are part of an organized tour, from Venice to the Cinque Terre, I definitely suggest you take the train as it’s cheap, comfortable and you can find different times of departure. Click here to book and see the prices on Omio (GoEuro) .

If you are skipping the Italian Riviera, check out our Venice to Florence train guide to keep planning your trip!

Cinque Terre – 2 Days

The quaint villages of the Italian Riviera never fail to bedazzle travelers from all over the world. If you want to spend three weeks in Italy, you can stay a bit longer in the Liguria region and explore also cities like Genoa and La Spezia.

Close to La Spezia, the capital of the province, are also beautiful places like Lerici and Tellaro, sea resorts cherished by writers and artists. Being on the coast, you will find great fish restaurants. Alongside the five scenic villages, part of the Cinque Terre , La Spezia’s coastline boasts also other towns worth a stop, such as Portovenere, Le Grazie, and Levanto.

The five villages known as Cinque Terre are:

• Monterosso al Mare. It’s the largest of the five towns and boasts also the largest beach on the coastline. Which is why it’s the most popular both day and night for evening parties and entertainment.
• Manarola. Famous for its Nativity Scene set for Christmas , here you can also visit 14th-century San Lorenzo Church and the remains of the local stronghold.
• Vernazza. This is a very scenic village, some consider it the most beautiful. It has two beaches and several nice restaurants. You will spend your time wandering up and down its cobbled alleys.
• Corniglia. The smallest and tallest village of the Cinque Terre, here you can visit its famous churches and sanctuaries as well as the remains of old Genoese strongholds.
• Riomaggiore. The closest village to La Spezia city, from its train station you can start the famous Via dell’Amore hiking route and the dock from where to take the ferries for the local tours and cruises.

From Cinque Terre to Florence, too, you can take the train. First, a regional to get to La Spezia and Genoa, then a high-speed train to Florence. Click here to check timetables and prices with Omio .

If you are visiting the Italian Riviera as a day trip from Florence, you can check out our guide on the different ways to reach it and how to get to Cinque Terre from Florence by train .

Florence – 3 to 4 Days

The birthplace of the Renaissance and included in most tours, very likely your Italy travel itinerary will have at least two days in Florence . Here, we suggest three to four days, but if you have only ten days in Italy , two is also enough to get a taste of the city.

The city’s history was heavily influenced by the rule of the Medici family, and today we can still see much of their legacy. Walking around Florence will fill you with beauty and culture. Enjoy its ancient art and architecture all around the city center, walk along the Arno River and linger on the Ponte Vecchio bridge for some shopping and photo snapping.

Best things to do in Florence

We wrote a full guide to Florence , if you wish to stay longer and see more places.

• Duomo and Giotto’s Bell Tower. Santa Maria del Fiore Cathedral and the adjoining bell tower and gorgeous Baptistery are possibly the most photographed and visited landmarks in Florence. For sure one of the first places travelers head to as soon as they arrive and a must even if you are wondering what to do in Florence in one day . Click here for a full experience of Florence Duomo and Michelangelo’s David.
• Uffizi Gallery. A huge art collection, at the Uffizi you will find the paintings and statues of some of the world’s most famous artists such as Leonardo Da Vinci, Botticelli, Caravaggio, Raphael, Cimabue and many others. Here the line is very long, so if you want to skip it and optimize your time inside the museum with a guide, check out Walks of Italy’s 3-hour Uffizi Tour comprehensive also of Palazzo Vecchio.
• Santa Maria Novella Basilica. Located near Florence’s main train station, this beautiful Dominican basilica built with a mix of Gothic and Romanesque styles includes great artwork, paintings, chapels, a big garden, and a cloister.
• Pitti Palace. Residence of many of Florence’s ruling families, Palazzo Pitti today is a large complex of art galleries and royal apartments.
• Boboli’s Gardens. Adjoining the Pitti Palace, the elegant Giardini di Boboli were built in 1418 when Luca Pitti bought this vast land intending to build a mansion (Pitti Palace will be built 40 years later). One of Florence’s largest parks, Boboli Gardens are one of the most important examples of Italian gardens of the 16th century.
• San Lorenzo Cathedral. The personal cathedral of the powerful Medici family, San Lorenzo huge church also hosts a museum showing the donations received over the centuries, most of them by the same Medicis. Close is also the burial place of the Medicis, known as Cappelle Medicee.

Hotels in Florence – Some suggestions

• High-end. Portrait Firenze – Lungarno Collection , Rocco Forte Hotel Savoy , The St. Regis Florence , Four Seasons Hotel Firenze , Hotel Lungarno – Lungarno Collection .
• Mid-range. Donati Luxury Tower Suites , Hotel Bernini Palace , Hotel Number Nine , Arte’ Boutique Hotel .
• Budget. Il Gattopardo B&B , Eco Urban B&B , Cicerone Guest House , Hotel Art Atelier .
• Apartments. Modarno Exclusive Apartments , Windows on Florence , Casa del Sarto , Residenza Marchesi Pontenani .

Check out Booking for more accommodation options in Florence.

The whole region of Tuscany is amazing, so if you can stretch your holiday a couple more days, you might like to explore also other cities such as Siena and Pisa  and the countryside with a day trip from Florence to the Chianti region and San Gimignano town. Click here to check availability and price .

Florence is not too far from Rome, with Trenitalia’s Frecciarossa or Frecciargento high-speed trains, it takes an hour and a half. Click here to book and see the prices on Omio .

READ MORE: How to plan a perfect trip to Florence

Rome – 4 to 6 Days

The capital of the ancient Roman empire boasting some 3000 years of history and rich civilization, the places to visit in Rome are endless. From the archaeological sites of the Roman Forum to the quaint neighborhood of Trastevere to the Vatican City, the more you manage to devote to Rome, the better you will experience the city. It goes without saying that Rome is a must-see, especially if it’s your first 2-week trip to Italy.

Having a hard time planning your Rome trip? We design your itinerary and guide you through the planning!

Some of the things to do in Rome in your 2 weeks in Italy include:

• Colosseum. Possibly the most famous and photographed landmark in Rome, the Coliseum was built in 70 AD to host fights among gladiators, public shows, animal hunts and even naval battles.
• Roman Forum. Located in the valley between the Palatine and the Capitoline Hills, the Roman Forum was the heart of ancient Rome, where senators and public figures held their speeches, where they organized the city’s markets, court trials and pretty much everything concerning public life. Click here for the VIP Colosseum and Roman Forum Tour .
• Baths of Caracalla. Gorgeous ancient public baths, they included also a gym, a library, and different rooms for the bath experience and a wellness center. They are often skipped for lack of time, but if you can make it, they are really beautiful.
• Vatican City. The seat of Christendom and papal residence for centuries, the Vatican City is packed with sites to visit such as the Sistine Chapel, the Vatican Museums and obviously St. Peter’s Basilica. If you want to fully enjoy the Vatican, the best thing you can do is to skip the lines, especially to the museums and the basilica. In this case, the convenience of booking a tour, apart from VIP access, is that your guide will take you directly to the places you shouldn’t miss. The Vatican is really big!  Click here to see Walks of Italy’s Private Vatican Tour .
• Trastevere. A gentrified former working-class neighborhood, Trastevere is the place to go for a good night out. During the day, however, you can also visit the Museum of Roman Popular Traditions which sometimes also hosts temporary exhibitions and Villa Farnesina where are Raphael’s frescoes.
• Hadrian Mausoleum. Built by Emperor Hadrian as his own funerary mausoleum in the 2nd century, this is also known as Castel Sant’Angelo and is located along the Tiber River, giving beautiful views both day and night.
• Pantheon. A very old building, it was a temple devoted to all gods built with an “oculus”, a hole in the big dome to symbolize direct contact with the divine. Now it’s a Catholic church that hosts several tombs of members of the former royal family and of the famous painter Raphael.
• Piazza Navona. Huge elliptical piazza in the city center not far from the Pantheon, Piazza Navona has three fountains, the largest being Bernini’s Four Rivers Fountain standing in front of Borromini’s Sant’Agnese church.
• Spanish Steps. Rome’s most famous staircase, the Spanish Steps lead to St. Trinità dei Monti church, ordered by French king Louis XII, while at the bottom you can view Bernini’s sculpture known as La Barcaccia.
• Trevi Fountain. An absolute must, especially if you are visiting Rome for the first time, is Trevi Fountain, the gorgeous baroque fountain built between 1732 and 1762.

Rome is divided into “Rioni”, neighborhoods, and each of them has its own landmarks and personality. From Prati to Trastevere to Testaccio and Ostiense , countless are the things to see in Rome, the restaurants where you can try the traditional food, the park where to run, jog or chill out for an afternoon, the museums, the palaces and more. To get around and see how to best enjoy Rome, check out my full guide of the city , or click here to see what are the best Rome tours if you wish to save some time but still visit the most important sites.

My eBook “ Tasting Rome by Neighbourhood ” suggests five daily Rome itineraries in as many districts, giving you the chance to explore the popular and lesser-known areas of the city stopping to eat in the best restaurants along the way. All the meals of the day are covered, from breakfast to dinner, with some suggestions also for aperitif and gelato.

Hotels in Rome – Some suggestions

I wrote several guides to navigate the huge landscape of Rome hotels:

• Best 5-star Rome hotels
• Best boutique hotels in Rome
• Best budget hotels in Rome
• Best cheap hotels in Rome
• Best hotels near Termini Station
• Best hotels near the Pantheon in Rome
• Top hotels near the Spanish Steps in Rome
• Top hotels near Piazza Navona in Rome
• Top hotels near the Trevi Fountain in Rome
• Best hotels near the Colosseum in Rome
• Best hotels in Rome city center
• Best hotels near the Vatican in Rome
• Best family-friendly Rome hotels
• Best hotels in Trastevere
• Most romantic hotels in Rome

Check out Booking for more Rome hotel options.

Your next stop when planning a 2 week trip to Italy for the first time is Naples, the gorgeous capital city of the Campania region not too far from Rome. With Trenitalia high-speed trains you will reach it in a little more than an hour. Click here to book and see the prices on Omio (GoEuro) .

Naples and the Amalfi Coast – 3 Days

Famous for having invented the pizza, alongside delicious cuisine, Naples has a lot to offer to the curious traveler who wants to dig deep into the local history and culture. If you stay for 2 days in Naples , you will have plenty of time to walk around its city center, enjoy the view of the Vesuvio volcano and the beach, explore its wonderful coastline, and soak in its rich tradition.

Some of the best things to do in Naples in your 2 weeks in Italy include:

• Royal Palace. Naples’ Palazzo Reale is located in Piazza del Plebiscito, an old square that in the Middle Ages was used for public tournaments and shows in the age of the Bourbons. It has been made pedestrian so now it’s the place where locals and tourists like to relax in a historical promenade.
• Archaeological Museum. Launched in 1816, Naples’ Museo Archeologico displays a huge collection of ancient relics, among which you will find relics from Pompeii and others from the Greek-Roman age, Etrurian and Egyptian, and ancient coins from a private collection.
• Duomo.  Naples’ Santa Maria Assunta Cathedral shows the paintings of Luca Giordano and is the place where locals worship San Gennaro, patron of the city. Here you can also see the Treasure of San Gennaro and all the precious donations given by kings, presidents, and leaders of the world for centuries.
• Spaccanapoli. This is the long road built by the Romans to better organize the city, and it runs from the Quartiere degli Spagnoli to Forcella district. Wandering this road you will also wander the city’s history and multifaceted society. Here, in fact, you are going to see old buildings, churches, shops, abusive street vendors, and local restaurants that release the unique scent of Napoli’s cuisine.
• Sansevero Chapel and the Veiled Christ. A hidden gem near Spaccanapoli is Cappella Sansevero where you can admire the incredible sculpture of the Veiled Christ (Cristo Velato), a masterpiece by Giuseppe Sanmartino where you will totally mistake the marble veil that covers the body of the Christ for a fine fabric!
• Underground Naples. Beneath the surface, you can visit another Naples, the hidden spots, and nooks that citizens have used for different purposes such as shelter during the bombings, the hideout for the runaway criminals, and the water springs. Today, you can visit also museums, the relics found after ongoing archaeological diggings, and the Bourbons Gallery.
• Pompeii and Ercolano. I know time is short, but once you are in Naples, we recommend you devote a day to visit the ruins of the ancient cities of Pompei and Ercolano, destroyed by the Vesuvio eruption in 70 AD. They are very easy to reach via a short ride on the Circumvesuviana train and you can spend there the whole day. Click here to see reviews and prices for the tours and activities available in Pompeii .

Hotels in Naples – Some suggestions

• High-end. Grand Hotel Parker’s , ROMEO Napoli , Grand Hotel Vesuvio .
• Mid-range. Santa Chiara Boutique Hotel , Prestige Rooms Chiaia , NapoliMia Boutique Hotel .
• Budget. Le Corti del Re , Hotel Bella Napoli , Sant’Angelo Suites .
• Apartments. Appartamenti Mergellina , Borgo 1313 Apt , La Casa sul Nilo .

Check out Booking’s website for more hotel options.

Hotels in the Amalfi Coast – Some suggestions

• High-end. Hotel Conca d’Oro in Positano, Positamy in Positano,
• Mid-range. Le Muse Suite in Sorrento, Villa Setteventi in Positano, Amalfi Luxury House ,
• Budget. Ambrosio Relais in Sorrento, B&B MoMi Sorrento , Residenza Ester .
• Apartments. Sorrento Apartments , Lucy’s House in Amalfi, Amalfitano Apartments .

Once your 14 days in Italy are over, you can either take your flight back home from Naples or take a train to Rome and your flight from Fiumicino International Airport.

Hidden gems + alternative Italy itineraries

If you like to discover also more offbeat destinations or you can afford a longer holiday, say 3 weeks in Italy, you can really add some interesting places to your Italy itinerary.

For example, let’s say that you are back in Rome after this two-week Italy trip and you have one extra week.

For a lovely alternative, you can catch a plane to Sardinia and enjoy a fantastic offbeat destination! To be able to stray off the bigger cities and explore its traditional soul, make sure you rent a car.

Your experience in Sardinia will depend on the season. If you are traveling in summer, especially in July and August, what you can do will be pretty much limited to the beach because it’s really hot. Not too bad, considering that Sardinia is surrounded by wonderful beaches and the turquoise Mediterranean Sea. Famous are the beaches of the Costa Smeralda and the northern coast where you can find cool European vacation rentals .

If you go in spring or fall, you can enjoy a more authentic experience by exploring the towns of the inland. Places like Orgosolo, Oristano, Ghilarza, and San Sperate will make for lovely trips to immerse in the local culture.

In winter, I suggest a stop in Mamoiada for their Mamuthones festival. You can see these ancient masquerades on the night of the 16th of January or in February for Carnival. Carnival is a fantastic occasion to visit also towns like Oristano where they celebrate it with the Sartiglia or Ottana where they have the masks of Boes and Merdules, always coming from ancient times and farming-themed.

If it’s your first time in Sardinia, I also suggest you explore the city where you land, which is going to be either Cagliari, Bosa, or Alghero . All of them are extremely fascinating and are surrounded by interesting places for a potential day trip.

Northern Italy

If you enjoy the northern cities and want to explore more of them, a nice alternative is to explore the Trentino Alto Adige region or the beautiful city of Turin .

The region of Trentino Alto Adige is heaven for nature lovers. For scenic treks, choose any of the destinations in the Dolomites from the stunning Madonna di Campiglio to Molveno Lake to the Marmolada.

If you are more of a cultural traveler, you can explore charming cities like Trento , Bolzano , Rovereto, and Merano, or quaint towns like Bressanone and Levico. In Trentino Alto Adige, when you are not skiing, you can visit the castles scattered around the region like Castel Thun and Castel Beseno or sacred places like San Romedio Sanctuary perched on a cliff.

City slickers will probably enjoy a couple of days in Turin. The cool capital of the Piedmont region opens up to a myriad of different opportunities.

If you are fond of Christian history, you can visit the Duomo to see the Holy Shroud, while other types of spirituality will be attracted by esoteric places such as Piazza Statuto, Portone del Diavolo (Gates of Hell), and Chiesa della Gran Madre di Dio.

In Turin, you can definitely enjoy great food, indulge in an evening aperitif, and sip their traditional bicerin coffee drink . For some great day trip, head to the Baroque Basilica of Superga or Venaria Reale royal palace.

Not sure if you’d rather visit Milan or Turin ? Our tips will help!

Bologna and Emilia Romagna

Foodies on the lookout for some alternative destinations to include in their 2-week Italy itinerary should consider Bologna . Showcasing a very elegant architecture, the streets of the city center are covered with porticoes, making it more pleasant to walk in both summer and winter.

Being the capital of the Emilia-Romagna region, it goes without saying that the food in Bologna is hearty, delicious, and pretty fulfilling. Tuck into lasagna, piadina, tortellini, and all types of stuffed pasta in ragout sauce before moving on to the next destination.

Other fantastic places to visit in the region are Ravenna, the last capital of the western Roman Empire and packed with gorgeous Byzantine mosaics that have been declared UNESCO world heritage sites, Parma and the surrounding castles, Modena and Maranello for sports cars fans, and Rimini and Riccione in summer.

It’s really hard to leave Sicily off your trip. Whether you are following a classic 2-week Italy itinerary or a more alternative one, Sicily is the largest Italian island and packed with amazing cities, activities, foods, and historical sites to discover.

Whether you land in Palermo or Catania, I suggest taking your time to explore your port of arrival before moving on. Palermo is Italy’s “most Arab” city. Showcasing a suggestive combination of Christian and Muslim sacred sites and decorative patterns, in Palermo you can easily spend a week doing every day something different.

Of course, the region deserves to be visited far and wide, so I’ll understand if you move onto the next harbour sooner. Get lost in the maze of alleys of Mazara del Vallo where you will spot architectural and artistic influences from the Romans, the Punics, the Saracens, and the Normans. This beautiful town is famous for its pristine beaches lapped by a crystal azure sea.

Carry on to Agrigento where, apart from enjoying the local beaches, you can also visit the town and the famous Valle dei Templi Greek ruins. Before leaving Sicily, make sure you consider visiting also places like Syracuse, Ragusa, Taormina, and the beautiful Catania for its charming architecture and an excursion on the Etna Mount.

Take more day trips

Alternatively, you can spend more days in some of the cities suggested in our classic 2 weeks in Italy itinerary and take some day trips.

From Florence, you can enjoy a great day trip to Pisa , Lucca, or Siena . Or other fantastic towns such as San Gimignano, Arezzo, and obviously the wonderful vineyards of the Chianti region.

There are also plenty of day trips you can take from Rome . You can visit the beautiful Viterbo also known as the city of popes, the scenic Bracciano on its namesake lake, Cerveteri for Etruscan history and necropolis, and Tivoli for two wonderful UNESCO World Heritage Sites.

From Venice, you can head to Verona for a day and come back in the evening. Venice is a big group of islands, so when you are done with the main attractions in Piazza San Marco and the Jewish Quarter, head to the picturesque harbors of Burano, Torcello, Pellestrina, and Sant’Erasmo.

Some other great day trips from Venice in the Veneto region include Treviso, Padova, Rovigo, Vicenza, and Belluno for a great holiday in the Dolomites.

From Naples, I highly recommend you visit Pompeii. History buffs can even devote two days to this wonderfully preserved ancient Roman city because it’s huge and all parts are very interesting and revealing of the local life before the Vesuvius destroyed it. More great day trips from Naples include Sorrento, the Amalfi Coast, and the city of Caserta for its gorgeous “Reggia” royal palace.

The possibilities are endless, and soon we’ll be publishing a full northern Italy itinerary and an exciting offbeat Italy itinerary!

Essential tips for two weeks in Italy

Best time to travel to italy.

Boasting a mild climate and the advantages of four seasons, depending on what your ideal holiday is, any time is good to visit Italy.

Do you like skiing? Explore the beautiful Dolomites in Trentino Alto Adige. Do you prefer chilling out in the sun? Discover the gorgeous beaches in Sardinia in summer.

As far as the main cities go, any month is good to visit. In Rome, Florence and Venice there are so many things to see and do that really any season is good. If you are quite free to choose your holiday time, I would probably avoid July and August as they are very crowded and can be very hot. So not so pleasant to walk around the city center.

Spring and Fall are both great seasons to visit the big cities both to avoid the crowds and to have a more pleasant climate.

How to get around Italy

Italy has a great and very widespread railway system, so if you are traveling independently, you can totally rely on Trenitalia or Italo Treno. After each major city, I mentioned the transport you can book to get to your next stop but Italy railway is great to reach also smaller towns and even tiny villages. The perfect way of traveling around Italy for two weeks.

If you are visiting the cities and towns within the railway network, you are covered. But if you are planning on getting off the train route, relying solely on the buses might not be as straightforward. So for example, if you want to visit the Tuscany countryside or some parks outside Rome, I suggest you rent a car. Definitely, the best option when planning a 2-week Italy road trip. Click here for more info and to book a car in Italy .

What to pack for Italy

As Italy has four seasons, you can decide what to pack once you know when you are traveling. Spring is a very popular season thanks to its mild weather, but it can sometimes be tricky as temperatures change all of a sudden.

My advice would be to wear different layers so that you can cover in the evening when it’s usually colder. If you are planning a 2-week trip to Italy in Spring, make sure you pack some pretty flexible clothes.

The beginning of the Fall in Italy is pretty nice as the summer heat is mostly gone and the winter cold has not arrived yet. Mostly, you can wear light clothes and carry a jacket, a light jumper, and a light scarf for the evening. Make sure you pack an umbrella.

If you are wondering what to pack for Italy for the winter, it’s pretty straightforward: warm clothes, a jacket, a coat, warm trousers, and sweaters. Quite straightforward is also packing for a summer Italy trip: shorts, t-shirts, sandals, or summer runners, and obviously a bikini if you are going to the beach!

For some peace of mind, especially on public transport, you might want to wear anti-theft clothes. Clever Travel Companion has a pretty wide choice of models, colors, and clothes such as scarves, boxers, leggings, tops, t-shirts, women’s underpants, and more. Click here to check models and prices.

How much money do you need for 2 weeks in Italy?

If you are really traveling on a budget, you should consider putting aside around 1500€ (1600$), international flights excluded. If you prefer mid-range accommodation rather than hostels or cheap B&Bs and to treat yourself to some restaurant lunch or dinner, a budget of 2000€ (2100$) per person will be more likely.

Accommodation prices will vary depending on the location and on the season. Rome in November will be cheaper than in December , April , or even August . Generally speaking, Italy in December will be more expensive than in January or in November . Also, hotels in Naples will be more affordable than in Venice.

When it comes to food, if you wish to save some good bucks, you can opt for street food on the go, which is delicious and you are bound to find plenty of specialties.

The cost of local transport depends on how you travel. Domestic flights are usually more expensive than trains and buses, including bullet trains. You can find some offers and promotions but it’s a matter of luck. Of course, if you need to go from Milan to Palermo quickly, a flight is the best option.

High-speed trains are more expensive than regional and Intercity trains, but obviously faster. They are more affordable than flights and in some cases I think a better choice. For example, if you are going from Milan to Rome, or from Florence to Rome, the bullet train will take you from city center to city center so you are going to save time and money of the airport transfers.

Regional trains are recommended if you wish to stop in smaller towns where Trenitalia’s Freccia trains and Italo fast trains don’t stop.

Finally, if you are traveling on a shoestring and want to save also in public transport, check out bus schedules and routes. This is the cheapest option but also the slowest. This means that you either need to stay in Italy for more than two weeks, sacrifice some destinations, or skip some landmarks.

READ MORE: Tips for planning a perfect trip to Italy

Which is better Amalfi Coast or Cinque Terre?

If you are traveling with kids and planning cultural sightseeing, the Amalfi Coast should be your choice. The Cinque Terre is a good option if you want to do some hiking between the towns and visit other cities of the Italian Riviera and Liguria region such as Levico, Genoa , and La Spezia.

Amalfi Coast is the destination for celebrities and families. Its location close to Naples, Pompeii, Caserta, and Sorrento allows for a great cultural holiday.

Both Amalfi Coast and Cinque Terre are summer destinations because they are on the coast and in winter most tourism resorts and facilities are closed. Plus, bad weather might cause landslides and heavy rain.

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Delightfully Italy

The insider's Italy travel guide for independent travelers

Italy in two weeks: the perfect 14 days Italy travel itinerary

Discover Italy in 2 weeks. Visit classical destinations such as Venice, Florence, Tuscany, Rome, Cinque Terre and the Amalfi coast. 

Two weeks in Italy are probably the minimum time needed to give you a fair view and feeling about this wonderful country: you should be able to see many of Italy highlights and spend a decent time in each one of them.

This Italy in 2 weeks itinerary is based on my experience, personal tastes and on a tight 2 weeks schedule (reasonable days in brackets). I’m assuming you will purchase  an “open jaws” ticket (meaning: landing and departing in two different airports),  to save valuable time. A round trip would imply at least half a day more.

I tried to use train / public transportation as far as possible, and showed (in brackets) average transfer times.

However, you may wish to rent a car, especially to explore Tuscany at your own pace, and to discover beautiful hamlets off the beaten path. If this is the case, I recommend you have a look at   www.rentalcar.com , and book your car as early as possible , to ensure availability and to get the best rates. It’s an aggregator, and allows you to compare offers from the main car rental companies.

These are just ideas, with optimized logistics. Days to be spent in the different places can be modified based on your tastes and interests. Feel free to mix everything up, it’s your Italy in 2 weeks very personal trip!

Would you like some help on your Italian trip planning? Then have a look at my Italy Travel Consultant page!

Destination 1:   Venice  – (2-3 days)

Ferry Boat in Venice + a lot of walking (and maybe a romantic gondola ride  ). Of course Rialto, San Marco and Palazzo dei Dogi, but also fancy Museums like Punta della Dogana . If you are travelling with kids, have  a look at a  child oriented itinerary . On the third day visit Murano, Burano and Torcello (1 day, by ferry).

Venice main highlights, and especially San Marco church, suffer from very long queues. To skip the line and to know more about its masterpieces, a guided tour could be a clever option. Click here for a good San Marco guided tour .

Where to stay in Venice:

• The Foscari Palace : enjoy a room on the Canal Grande, just in front of Rialto market
• The Hotel Pausania : a charming hotel in the off the beaten path Dorsoduro Neighborhood.

Want more choice? Click here to find the best places to stay in Venice

Destination 2: Florence (1-2 days)

The length of your stay in Florence will depend on how much time you wantto dedicate to Florence Museums.

Key highlights are Uffizi, Michelangelo’s David (in Galleria dell’Accademia, the one in front of Palazzo Vecchio is a copy) , Palazzo Vecchio, Santa Croce, San Miniato, piazzale Michelangiolo, Via Tornabuoni, Palazzo Pitti, Boboli, Fiesole (20-30’ out of town). Have a look here for a one day walking itinerary. 

You may consider a guided tour, to better appreciate Florence history and culture. If you would be interested in taking a g uided tour, or to skip the line in the main museums , just follow the link.

Where to stay in Florence:

The Grand Hotel Cavour : lots of atmosphere and history for this fascinating hotel located between Santa Maria del Fiore and Palazzo Vecchio. The roof bar will seduce you with its fantastic views over the Santa Maria del Fiore cathedral.

Want more choice? Click here to find the best places to stay in Florence

Destination 3:  Florence >> Pisa  (Lucca) >> Cinque Terre (1 day) .

It takes a little less than 3 hours to go by train from Florence to the Cinque Terre area, via Pisa. Lucca is half an hour from Pisa by train. If you decide to visit also Lucca, you could consider spending the night in one of the two towns (I personally prefer Lucca).

Destination 4:  Cinque Terre .

It’s worth spending 1-2 days at Cinque Terre, but should also visit Portofino and San Fruttuoso (convenient boat services/tour available). Sestri Levante, lovely little town located between Portofino and the Cinque Terre could be a good Base. Don’t use a car, parking is a nightmare. (2 days).

Destination 5: Cinque Terre – Siena / Tuscany country side .

Here you could consider renting a car,  to provide you with all the freedom you want to explore this fascinating countryside. Tuscany country side >>> Rome. Chianti, Monteriggioni, Siena, Montalcino, Val d’Orcia, Pienza, Montepulciano >>> Rome. (1-2 days, even more if you like the countryside and the good food).

This itinerary assumes you rent a car, by far my suggested option. In case you didn’t feel comfortable driving on Tuscany country roads, then you can use Florence as a hub and join Tuscany country side guided tours. Here are my recommended ones .

Where to stay in Tuscany: Monteriggioni (Siena)

• The Hotel Monteriggioni : a charming and romantic hotel, located in a fortified medieval village
• The Castel Pietraio , a true medieval castle, now four star hotel, to treat yourself like a king

Destination 6:   Rome (3-4 days or more) .

You don’t want to have a car in Rome; walk + hop on – hop off buses ( follow this link to reserve on line, no need to print the receipt ). Bicycles or scooters, if you dare, are fantastic solutions!  Spanish steps , Piazza Navona, Panteon, Fontana di Trevi, Campo dei Fiori, Old Ghetto,  Trastevere . St Peter (consider  climbing on the Cupola ) + Vatican Museum ( RESERVE! queues are terrible – click here if you wish to reserve your visit with Ticketbar ).

Mercati di Traiano, Fori Imperiali (including Orti Farnesiani), Colosseum, Palatino are unmissable destinations, and for this reason may be crowded. Purchasing the ticket in advance is a clever way to skip the line and to save time .

Don’t miss Trastevere + Isola Tiberina (very lively area in summer time, funny & crowded). Appia antica + Catacombs (best by bike, you can rent one in via Appia),  medieval Rome and its underground treasures .   If you are a running fanatic, don’t miss Villa Borghese and the awesome  Borghese Gallery .   Villa Adriana and Villa D’Este , both in Tivoli (30 km from Rome) make a pleasant day trip out of town .

Where to stay in Rome:

• The  Hotel la Lumiere , a delightful hotel hidden a few blocks away from the Spanish steps, in posh via Condotti. Great roof top, have your breakfast while admiring Rome century old roofs!

Want more choice? Click here to find the best places to stay in Rome

Destination 7: Rome >>Naples/Sorrento (2/3 days) .

You can sleep in Naples or, better, in Sorrento. Visit Pompei, Sorrento, Positano , Ravello, Capri. Naples is also worth a visit. You can use public transports: boat service between Sorrento and Positano is very convenient, while buses, especially to Ravello, could be extremely crowded (consider sharing a taxi with fellow travelers). Renting a car could be an option in high season, but car parks are very expensive (and driving on the costiera is an experience on its own!).

Looking for a hotel? Click here to find the best places to stay in Sorrento

For more info about Amalfi coast visit my posts: Capri: breathtaking Faraglioni and Natural Arch walking tour and Best of Amalfi coast

Enjoy your Italy in two weeks itinerary!

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27 Replies to “Italy in two weeks: the perfect 14 days Italy travel itinerary”

Thank you for the post and a wonderful blog! I am using your itinerary for our first trip to Italy.

Tks Phoenx, enjoy Italy!

I must state that yours is a very well written blog. We spent two weeks in Italy’16 and very much followed an itinerary similar to what you have proposed. However we added Milan as our flight out was from there. We did not include CT as we had read that cramming CT to a 2 week trip in Italy would have been rather hectic. We are middle aged and wanted to take things rather laid back. Mine was a complete DIY trip and I thought I should share my experience with other first- time would be travellers to Italy. So I have started a very hands- on kind of travel blog which is almost 75% complete.diytravelexperiences.wordpress.com. Glad if you can critique the same and hope that others will visit my blog and benefit. Regards. Dhiraj

Hi, nice blog. I particularly liked the hands on tips and the “myths about Italy”!

Hi grateful for visiting my blog and thanks a ton for your comments. Good luck. Regards. Dhiraj

Hi- we are taking our 2 boys in 2018. My favorite is Venice and my husband loves the Amalfi coast. Is this doable in 2 weeks adding CT, Pisa, Pomeii and Rome?

How old are your boys? Children have their own pace, and need time to relax and play, on top of visiting. By the way, you are not mentioning Florence and Tuscany, unless you have already seen them you may probably wish to spend some time there. So, coming back to your question: yes, you can do it: Day 1: getting to Venice, check in, relax Day 2-3: Venice and the lagoon (Murano, Burano) Day 4: Venice >> CT (this will take close to one day, change train in Milan) Day: 5-6 CT Day 7: CT >> Pisa (visit the leaning tower, reserve in advance!!!) Sleep in Florence Day 8: Florence >> Rome (1,5 hours) >> Check in, city center walk (look for my post for detailed itinerary) Day 9-10: Explore Rome Day 11> Rome – Sorrento Check in, relax (yu may squeeze Pompei in day 11 if you leave early) Day 12: Visit Pompei (or Capri if you already seen Pompei on day 11) Day 13: Visit Amalfi coast: Positano, Ravello, Amalfi (renting a car could be a good idea) Day 14: Back to Rome & fly home

In my opinion, this is doable if your children are at least 8-9 and used to travel, otherwise too tiring.

Hi, thank you so much for this. It looks like your first flight coming in drops you off in Venice, but tell me at what point do you take another flight other than back home, is there one needed at all other than home?

Hi Arlene, you don’t need any additional plane for this itinerary, you can just use trains. I’m available in case you need any help for your Italy trip planning. You can also follow delightfully Italy Facebook page for additional travel inspiration https://www.facebook.com/delightfullyitaly/

Enjoy Italy!

Hi, we are headed back to Italy for our second trip. We will have 2 weeks and starting from London. We would like to spend a few days in Amalfi Coast and also Tuscany. Maybe Milan, CT, Lake Como, Naples. Not sure how to plan this. We will not be going to Venice or Pompeii or Pisa as we already did this. Would appreciate any help.

Sure Lydia, with pleasure. I will send you an e-mail with some suggestions.

Would love to see this itinerary!

Hello. We are planning trip to Italy beginning of June this year. I was thinking 2 weeks and would like to visit the following places Venice, Milan, Florence, Amalfi Coast, CT, Pompeii and Vatican. Is this doable in 2 weeks. I am flying from Tampa, FL and was thinking of arriving in Milan or Venice and then come back home from Rome or Naples. Or do it the other way around arrive to Naples or Rome and come back from Venice or Milan. Any thoughts?

Hi Ana, would fly to Venice and come back from Rome, or the other way round, depending on the air rates. Will send you additional details on your mail.

thank you for your blog it is very helpful. few questions, what is the best way for transportation between the 7 destinations? is renting a car for the whole trip possible or you recommend taking the train? also flying back the last day from Naples or Rome what you suggest. thank you!

Hi, I recommend to use the train, and hire a car only to visit specific areas such as Tuscany. The reason is taht trains are much faster and taht you are not allowed to use private cars in city centers such as Rome or Florence (and of course you don’t need a car in Venice!). If you can find a suitable flight from Naples (meaning: good time slot and not too expensive) then a flight from Naples makes a lot of sense.

Hi Jean, thank you for the blog – very helpful!! Would love to get your recommendation on a 14 day travel with 2 kids, 3 & 11 in July. We love the beaches and would like to visit few historical sites. We are flying into Milan. I was thinking about renting a car, driving down to CT, Pisa, Florence, train to Rome/Naples/Amalfi Coast. Any recommendations? Kids love train rides. I thought a car would be convenient to do things at your own pace. Thanks!

Hi Brian, thanks for your appreciation! I’ll send you a separate mail with my views and suggestions

Hi Jean, I wish to also have the same trip plan exactly like Brian. Flying into Milan and flying out from Rome for a 14 days travel, but in December. Appreciate your advice as well. Thanks.

Hi, I just answered to Brian specific points, I didn’t design a bespoke plan. For a 2 weeks itinerary you can get inspiration from my “Italy in 2 weeks” post or subscribe to my Italy Trip Planning” service.

Hi Jean love your Blog , I’m flying in to Rome with my Husband and meeting my Brothers . We have 4 days booked in Rome and then 10 days who knows , I really like to be organised my Brothers want to wing it . What’s your thoughts on this and best places to go .. thank you Karen

Hi Karen, the needed level of organization and pre-booking depends on three factors: A) when you are planning your trip: if you are planning to come in low season (ie, winter), not much need to plan ahead, in July and August you may hardly find decent accommodation and trains availability B) Were you are planning to stay, mainstream destinations: Venice, Rome, Florence, Cinque Terre, Amalfi coast get overbooked long ahead, while off the beaten regions (Apulia,marche, …) are less crowded C) Your visiting ambitions: if you want to limit your visit, say, to Rome, Tuscany and Umbria, then you have a reasonable amount of time to decide day by day where to go and stay, also based on availability. On the other side, if your plan is to squeeze the mainstream destinations in 14 days (Rome, Amalfi Coast, Florence, Tuscany, Cinque Terre, Venice, …), then you need to design an optimized itinarary and make sure the logistics is fixed much ahead.

Hope this is useful. Enjoy your visit and don’t hesitate to contact me should you need some help on your trip planning.

We are planing for three weeks in Italy in either may or September. Starting in Milan and ending in Sorrento and fly to back to the US from either Naples or Rome . the second week of our trip we plan on staying in Greve in Tuscany for a week and travel from there. Any suggestions.. Thanks.

Hi Mike, I would rather choose September, weather should be nicer and it’s a better period to visit the vineyards. Milano deserves 1, max 2 days, from tehre you can get to Como Lake in one hour by train (train to Varenna, then ferry to Bellagio) You may want to have a look at my post about Chianti, there’s lots of information about what to do, where to sleep…and where to wine taste! Once you are finished with Tuscany, take a high speed train to Naples, and start your Amalfi coast exploration from there. Try to dedicate one day to visit Naples, it really deserves it. Do spend a night in Capri (avoiding the week end), it’s a magical place and for a real off the beaten path experience the island of Procida will seduce you (no tourists there, just colored housed and a lost in time feeling). Even though Sorrento is a perfect hub to visit the area, in my view it’s not the most beautiful place to stay, I would rather select Positano.

These are the first things that come to my mind. If you wish help on your Italy trip planning (select best accommodations, optimize logistics, select the unmissable experiences) don’t hesitate to contact me, I’ll be more than happy to help.

Thank you for your quick response. We travel to Italy almost every year and rent an apartment in a small town just south of Florence. (Qurco)..The name of the place is Le Torri. This coming trip we are going to rent a car and drive from Milan down south and visit friends in Rome and Lake Bomba In Abruso.. then on to Sant Agata del golfi near Sorrento. then depart either from Naples or Rome depending on the flights. I would like to know if you know a good route and any good bed and breakfast places on the way. We come there to visit the people and and and enjoy your beautiful country and try not to stay at large hotels. Thanks again. Mike

Thanks for a great itinerary, am using it as a foundation for our first trip to Italy!

Hi Douglas, apologies for the late reply. I’m glad you liked my suggested itinerary. In case you need any further help for your trip planning don’t hesitate to contact me.

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How To Spend 2 Weeks in Italy: Itinerary Advice From An Italian

Posted on Last updated: February 2, 2024

Need help planning your Italy 2-week itinerary? You’ve come to the right place!

Italy is located in the middle of the Mediterranean Sea and is home to some of the most beautiful views and experiences (and no, I’m not just saying it just because I’m Italian).

Being Italian I get asked a million times for Italy travel advice, so I decided to put together this ultimate Italy 2-week itinerary that covers all the major sights and cities.  

This Italy two week itinerary starts with the history and beauty of the Eternal City, Rome, to then head over to Tuscany for a bit of exploration in Florence and Pisa, before heading to Cinque Terre for an amazing hiking experience.

Exploring Piazza del Duomo in Milan, Italy

After that this Italy travel itinerary continues on to the city of fashion, which also happens to be my hometown, Milan, and then ends in Venice, the city of lovers.

Two weeks in Italy aren’t enough to see the whole country, I’ve lived here for 18 years and there are regions I still haven’t been to either!

But it’s a great start and a good enough amount of time to travel comfortably around Italy and see all the main tourist hotspots.

I’ll also go over useful travel information like how to get around Italy, where to stay, what to pack and more. Ready to discover how to spend 2 weeks in Italy?

• 1 Do you need travel insurance for 2 weeks in Italy?
• 2.1 Day 1: Arrive in Rome – Colosseum & Trevi Fountain
• 2.2 Day 2: Rome – Visit the Vatican
• 2.3 Day 3: Rome – Pantheon & Fori Romani
• 2.4 Day 4: Travel from Rome to Florence
• 2.5 Day 5: Florence – Gallery and Gardens
• 2.6 Day 6: Explore the Old Town of Siena
• 2.7 Day 7: Travel to Pisa & explore Piazza dei Miracoli
• 2.8 Day 8: Pisa to Cinque Terre
• 2.9 Day 9: Hike the Sentiero Azzurro in Cinque Terre
• 2.10 Day 10: Cinque Terre to Milan
• 2.11 Day 11: Explore Piazza del Duomo in Milan
• 2.12 Day 12: Travel from Milan to Venice
• 2.13 Day 13: Explore Venice
• 2.14 Day 14: Fly home from Venice or extend your trip
• 3 How to travel around Italy
• 4 What to pack for 2 weeks in Italy

Admiring the colourful houses of Manarola, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

Do you need travel insurance for 2 weeks in Italy?

After my personal experience spending two nights in a private hospital in Tenerife, and having to pay for it out of pocket (it wasn’t cheap), I always recommend getting travel insurance.

You might not end up needing it, but for a small fee you can travel without worries. Personally, I suggest getting your Italy travel insurance with  Heymondo .

Heymondo offers tailor made travel insurance, providing the best value for money for your specific trip. You can also buy it once you’re already abroad and have forgotten about it before flying (which, if you’re anything like me, is quite likely).

Besides the usual cancellation, medical expenses, luggage coverage and general travel insurance services, Heymondo also has a 24/7 doctor chat and instant assistance through their app.

As a Greta’s Travels reader, you get 5% off your Heymondo travel insurance !

Click here to get your 5% off Heymondo travel insurance!

Exploring the Golfo di Orosei and Cala Luna by kayak in Sardinia, Italy

Italy Itinerary: 14 days of exploring

Let’s dive right in to our 2-week Italy itinerary ! If you want to do this itinerary, without having to worry about booking hotels, tours and transfers yourself, you can book my customised Italy itinerary by Designer Journeys here !

Day 1: Arrive in Rome – Colosseum & Trevi Fountain

You should start your 2 week trip to Italy in Rome . After all it’s the capital of Italy, the Eternal City and it’s home to some of the worlds most ancient and beautiful history and art.

You’re only going to spend three days in Rome , so you’ll need to hit all the major attractions on your first day.

Plan your flight strategically, so that you land in Rome in the early morning. This gives you the ability to see a decent amount of the gorgeous ancient city right on day one. 

The first stop on your Italy route will be the ancient Colosseum!

There are many guided tours of the Colosseum , which will provide you with the knowledge about the brave gladiators, and the bloodthirsty entertainment that took place in Rome’s most famous monument.

The queue to go inside the Colosseum can get pretty huge so make sure to book online beforehand , or check out this guide to skipping the line at the Colosseum on a budget . 

Another way to skip the queue, is to join a night tour of the Colosseum . That way you’ll skip the crowds, and see this iconic attraction lit up at night. It’s one of the most popular Rome by night tours , and it’s easy to see why.

Click here to book your Colosseum skip the line tour!

Or click below to see prices & availability for your chosen date!

Enjoying the beauty of the Colosseum in Rome, Italy

Next, you’ll want to visit Trevi Fountain. It’s a beautiful monument decorated with sculptures and is a must-see when in Rome . I recommend walking there from the Colosseum, as this will take you past the famous Fori Romani.

These are a series of public areas that are centred around a monument. These were an integral part of Roman culture, and each served a different purpose in ancient times.

With its beautiful statues and white marble, the Trevi Fountain is without a doubt one of the most Instagrammable places in Rome .

They say if you throw a coin in the Trevi Fountain, you’ll get the chance to visit Rome again. I do it every time I go to Rome, just to be sure (and so far I’ve always gone back so I think it’s working)!

From the Trevi Fountain you can walk onwards to Piazza del Popolo and Piazza di Spagna, to see the famous Spanish steps and enjoy the view from Villa Borghese over the rooftops of Rome.

I love this part of Rome in spring , when all the trees are green and the flowers in bloom.

The Trevi Fountain in Rome, Italy

You can end your first day in Rome with a dinner out in Trastevere. Trastevere is one of my favourite areas in Rome, with lots of osterie and trattorie to choose from for your aperitivo or dinner options.

It’s a beautiful area of Rome at night , when the warm lights of the trattorie overflow into the cobbled streets, and especially so if you’re in Rome in summer , when locals and tourists alike mill around the streets and enjoy the long days and warm evenings of Italian summers .

I’ve eaten before at Osteria Cacio & Pepe and loved it, but most restaurants there will be good. It’s also a fun area to go bar hopping after dinner.

Eating spaghetti carbonara in Rome

Where to stay in Rome

My ex-boyfriend is from Rome so we tried our fair number of bnb and apartment rentals in Rome . That said, my personal favourite are places close to the Colosseum or Pantheon , as they’re in a great position to explore Rome.

If you want to save a little, here are some great places to stay in Rome for every budget. 

Budget: Palladini Hostel :Budget option for the backpackers or hostel lovers; this hostel is super central, close to the train station and all the action of Rome, with spacious dorms and a lively atmosphere

Mid-range: Tridente Rooms : Mid-range option, the rooms are simple but spacious and it’s right next to Villa Borghese, in the heart of all the Rome attractions

Luxury: Hotel Eden – Dorchester Collection : If you can squeeze it in your Italy trip budget , this beautifully decorated hotel is very conveniently located in the centre of Rome

Click here to book your accommodation in Rome!

Castel Sant’Angelo & Ponte Sant’Angelo in Rome, Italy

Day 2: Rome – Visit the Vatican

On the second day of your Italy travels, I recommend paying a visit to the famed Vatican museum. It’s one of the most popular tourist attractions in Rome, and it’s not hard to see why.

The best Italian trips include something ancient and something beautiful. This attraction just happens to include both!  Especially if you visit Rome in winter , it gives you an excuse to be indoors and out of the rain and cold for a while!

You can take a guided tour of the Vatican Museum and the Sistine Chapel , where you can ogle at masterpieces done by the great Michael Angelo, admire the incredible architecture, as well as learn about the cities fascinating past.

V isiting the Vatican Museum will easily take up a whole half-day, if not more depending on how long you want to spend in the museum. You can also go to the top of the dome and see an epic view over Rome .

I recommend buying your tickets online beforehand or you might end up queueing for hours just to get in.

Click here to book your Vatican Museum & Sistine Chapel skip the line tickets!

The Basilica di San Pietro and main square of the Vatican in Rome

In the late afternoon and early evening you can grab dinner and drinks around Campo Dei Fiori, where all the students and young people in Rome go out in evenings.

Once it’s properly dark you can also wander around the Fori Romani, where they play projections and light shows that aim to teach the public about these areas that played such an important part in Roman history.

You’ll see what the Fori Romanis looked like when they were built, which is an interesting insight into the past of this wonderful city.

| READ MORE: THE ULTIMATE ITALY BUCKET LIST |

Lost somewhere in the side streets of Rome

Day 3: Rome – Pantheon & Fori Romani

Start your third day in Italy off the right way by visiting the Pantheon ! It’s an ancient Roman temple that was later converted into a church, and holds great cultural significance within the Italian community.  

The architecture is absolutely stunning! This circular building is beautiful both inside and out, and it is also free to visit.

However, with free attractions comes queues, so I recommend you head to the Pantheon as soon as it opens to make sure you miss the crowds.

Alternatively, you can take a guided tour of the Pantheon , which allows you to skip the line, and learn the history of the Pantheon from a knowledgeable guide.

Close to the Pantheon is Gelateria 100 Palme, an ice cream shop that sells over 100 different flavours. Needless to say every time I go to Rome I try a different flavour.

Click here to book your Pantheon skip the line tour!

Or click below to see prices & availability!

The Pantheon in Rome, Italy

Best tours in Rome

These highly rated tours are a must during your time in Rome!

Vatican Museums & Sistine Chapel Skip-the-Ticket-Line Entry   – Like I already said, if you only have two days in Rome you don’t want to waste part of that time queuing up for things! 

Rome: Colosseum, Roman Forum, Palatine Hill Priority Tickets   – Same goes for the Colosseum, don’t waste time and don’t miss out on this awesome Italian attraction!

Rome: Street Food Tour with Local Guide   – Italians take food very seriously, the best way to discover true Roman cuisine is with a local!

Exploring Piazza Navona in Rome

Day 4: Travel from Rome to Florence

On your 4th day in Italy, you’ll travel from Rome to Florence. You can get to Florence either by plane or train. I personally recommend the train.

The flight might be one hour, but you still have to factor in travel time to and from the airport, and you usually have to be at the airport at least one hour before.

If you get the fast train from Rome to Florence this takes you from the centre of Rome straight to the centre of Florence in roughly the same amount of time as the total flying travel time.

Once you arrive in Tuscany , you’ll have plenty more activities to take part in and areas to explore. No matter how many days in Florence you have, you’re sure to fill up your Italy itinerary with a multitude of awesome things to do.

Your first stop in Florence should be the grand Florence Cathedral . It’s possibly the most celebrated cathedral in the world, making it one you don’t want to miss!

Known as Duomo or the jewel of the city, the incredible building was built in 1436 but wasn’t finished being built until the 19th century. 

The architecture is amazing and is an absolute must-see if you’re looking for Italian vacation ideas!

Click here to book your skip the line guided tour of the Florence Cathedral!

Getting up close to the majestic Duomo of Florence

Next, you should visit Ponte Vecchio, which is a historically significant bridge that stretches across the river Arno. The bridge is enclosed and has become famous for the many quaint shops built into its sides.

The earliest recordings of the bridge date back to 996, but nobody really knows its true origins. Take a meander along the bridge as you browse the shop windows.

| READ MORE: HOW TO SPEND 2 DAYS IN FLORENCE |

Light reflections at the Ponte Vecchio in Florence

You can end your first day in Florence at Piazzale Michelangelo. This is a park with a beautiful view over Florence. The huge dome of the cahedral towers over the rooftops of the houses, and makes for a stunning sunset spot.

When I visited Florence with my mum we stayed at Palazzo Riblet .

This hotel is a family-run business with only a few room within a historical building, with beautiful decorated bedrooms and original Renaissance affrescos on the ceilings.

It’s a great place to stay in Florence also thanks to its convenient position, close to both the train station and centre of Florence. 

Check out the latest prices and  availability at Residenza d’Epoca Palazzo Riblet here!

Sunset over Florence from Piazzale Michelangelo

Day 5: Florence – Gallery and Gardens

On your second day in Florence, you should aim to fill your day with as many beautiful Florence sights as possible.

Galleria dell’Accademia is a wonderful gallery that houses some of the most incredible sculptures from the Renaissance period. 

You can expect to see original sculptures from Michelangelo, as well as masterpieces from a multitude of other incredible artists. 

After a visit to the wonderful gallery, spend the afternoon exploring the Boboli Gardens! The gardens cover an area of 45 000 square metres, making them the largest gardens in Florence.

If you love being out in nature, this is the perfect Italy vacation idea. The gardens were created in the 16th century and feature rolling lawns with a scattering of beautiful sculptures to admire.

A stroll through these gardens is the perfect escape from the hustle and bustle of the city!

The Duomo of Florence and Battistero of San Giovanni in front of it

Best tours in Florence

Here are some tours with awesome reviews to check out for your time in Florence.

Florence: Uffizi Gallery Timed Entrance Ticket  – Skip the queue for your visit to the Uffizi!

Florence: City Walking Tours with entry to Accademia  – Discover Florence on foot with a local guide, and then explore the Accademia with them!

Florence: Small-Group Tour on E-Bike  – Try something a little different and discover Florence by bike!

Aerial view of Florence – Photo by Garrit Wes Anderson on Scopio

Where to stay in Florence

Besides Palazzo Riblet, I wanted to suggest a few places to stay for every budget.

Budget:  Plus Florence   – This hostel has spacious dorms, a sociable atmosphere and a spectacular rooftop with views over the Florence skyline.

Mid-range:  Palazzo Riblet   – I stayed here when I visited Florence with my mum and can highly recommend it. This family run hotel is situated in a historical building, with affrescos on the ceiling and in a great location.

Luxury:  Firenze Rentals Corso 12  – This lovely apartment has a balcony directly overlooking the Duomo of Florence. It doesn’t really get any better than this!

The view from the top of the dome of the Duomo of Florence – Photo by Giuseppe Trimarchi on Scopio

Day 6: Explore the Old Town of Siena

But Tuscany isn’t just about Florence, so travel on to Siena on day 6. In Siena you’ll discover a different side of Italy, as you explore the well preserved medieval city. 

There are plenty of things to see and places to explore in this wonderful town in the middle of the Tuscany region.

Start your tour of Siena at the central square, called Piazza del Campo, and learn about its great historical significance before paying a visit to the Gothic town hall.

Every year they run an important horseriding competition in this square, called Palio di Siena, and it’s a huge event much loved by the local people of Siena.  

Visiting the Cathedral of Santa Maria Assunta is an absolute must when you’re in the beautiful town.

It was constructed in the 13th century, and just like many of the other wonderful buildings in Italy, it has incredible architecture that rivals the worlds best.  

You can take a guided tour that will take you to both the Piazza del Campo and the Siena cathedral.

Click here to book your Siena highlights guided tour!

Piazza del Campo in Siena

You’ll also want to visit the Siena national gallery, which is housed in a former palace, making for a wonderful destination to tour.

Inside the gallery, you’ll find wonderful artworks from famed artists between the 12th and 16th centuries.

If you don’t feel like being indoors, spend some time wandering around the streets of Siena. Siena has one of the best preserved medieval old town centres and even just getting lost in its quaint streets will be a fun experience. 

We only spent one night in Siena and we stayed at Hotel Athena , within the old town walls.

The rooms were spacious and they included a tasty breakfast, but the highlight for me was by far the stunning view they had from the rooftop restaurant of the Tuscan countryside.

Click here to see the latest prices and availability at Hotel Athena

View over the Tuscan countryside from our hotel in Siena

Best tours in Siena

Here are some tours in Siena with excellent reviews.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry – Discover the beauties of Siena with a local guide and without wasting time in a queue.

From Siena: San Gimignano, Montalcino & Wine Tasting – Explore the surroundings of Siena and taste delicious local wine!

From Siena: Vespa & Chianti Tour in the Tuscan Hills – Live your Italian travel movie dreams and zoom around the Tuscan countryside in a traditional Italian vespa!

View over the rooftops of Siena, Italy – photo by Roberto Destarac on Scopio

Where to stay in Siena

Besides Hotel Athena, I wanted to include a few accommodation options for every budget.

Budget: Camping Siena Colleverde – For something a little different, you can stay in this unique camping with epic views of Siena!

Mid-range: Hotel Athena   – The hotel I stayed at, it has cozy rooms and great views of the Tuscan countryside.

Luxury: Grand Hotel Continental Siena  – If you want to treat yourself, this is the place to do so!

Sunset views in Siena – Photo by Giuseppe Trimarchi on Scopio

Day 7: Travel to Pisa & explore Piazza dei Miracoli

After a week in Italy, you’re sure to have fallen in love with the beautiful country! However, there’s still plenty more to see if you’re feeling up for it!

On your 7th day in Italy, I recommend you travel from Siena to the wonderful town of Pisa. 

As soon as you arrive you should head straight for the famous Leaning Tower of Pisa, which was completed in 1372, and yes, it was leaning then too.

It’s incredible that this tower has managed to stand for hundreds of years at what seems to be a dangerous angle.

The Leaning Tower of Pisa is located in Piazza Dei Miracoli, which houses also the Baptistery and Duomo of Pisa. With one visit you can tick off all the main landmarks and attractions of Pisa.

| READ MORE: ONE PERFECT DAY IN PISA |

The Leaning Tower of Pisa

These aren’t as famous as the tower (nothing crooked or unusual about their architecture after all) but they’re still important parts of Italian history.

You can do a guided tour of Piazza Dei Miracoli where they will take you into both the Leaning Tower, the Baptistery and the Duomo, so that you can learn everything about this stunning city. 

You should then head to Borgo Stretto, a street that combines magnificent architecture and high-end shopping.

The street is located in the heart of the city and features many branded stores, boutique shops, designer clothing labels and quaint cafes that offer the perfect break from your shopping experience.  

A fter an incredibly scenic shopping experience, head to the Mezzo bridge that spans over the river Arno. It’s a great place to take pictures during sunset and it provides beautiful views of the sleepy town.

Click here to book your Pisa guided tour!

The baptistery of Pisa in Piazza dei Miracoli, Italy

The Duomo of Pisa with the Leaning tower in the back

Where to stay in Pisa

I haven’t slept in Pisa myself but here are some suggestions for places to stay.

Budget – Hotel Cecile : A good budget option, with finely decorated rooms and conveniently located in Pisa

Mid-range – Grand Hotel Duomo : This mid-range hotel is in an amazing location, with a rooftop terrace with a stunning view over the rooftops of Pisa and you can also get a glimpse of the Leaning Tower of Pisa. The rooms are also spacious and finely decorated

Luxury – Allegroitalia Pisa Tower Plaza : This luxury hotel is a bit outside Pisa but has a beautiful swimming pool, for those searching for a quiet place to take a break in the middle of this busy Italy itinerary

Click here to see the latest prices and availability for accommodation in Pisa

Exploring the off the beaten track courtyards of Pisa

Day 8: Pisa to Cinque Terre

After spending a wonderful night in Pisa, it’s time to move on to another wonderful part of Italy! Cinque Terre is a string of ancient sea-side villages that stretch along the Italian Riviera coastline.

Travelling from Pisa to Cinque Terre by train will take you between 1 – 2 hours, and gives you the chance to enjoy spectacular views along the way.

If you want to stay in Cinque Terre I recommend staying in either Monterosso or Riomaggiore. These are the two towns at the two ends of the Sentiero Azzurro, and as such are great starting points for your hike tomorrow.

It’s cheaper to stay outside Cinque Terre and travel in, but these towns really are beautiful and if you’re only going to spend 2 weeks in Italy, I get it if you want to absorb more of their atmosphere. 

The First – La Vista di Marina in Riomaggiore is a lovely apartment with absolutely gorgeous views. They’re right on the sea front and have epic views both of the sea and the colourful houses of Riomaggiore.

Click here to see the latest prices and availability at The First – La Vista di Marina!

Admiring the colourful houses of Riomaggiore in Cinque Terre, Italy

Many travellers only do a day trip to Cinque Terre , but in my opinion, they don’t realise how much they’re missing. It’s better to plan a longer Cinque Terre itinerary , so you can relax a bit too.

By day 8 I imagine you’ll be pretty knackered with all this intense sightseeing, so I suggest that after your train journey to Cinque Terre you take some time to relax.

Riomaggiore seemingly rises out of the ocean, leaving the entire town with exquisite views! You can spend some time exploring the town, wandering around the harbour or basking in the sun.

The coastline in Cinque Terre is rugged, but there are a few beaches in Riomaggiore worth exploring. Batteria beach is one of them. 

Fegina Beach in Monterosso al Mare, Cinque Terre

Hiking along the Sentiero Azzurro in Cinque Terre

Day 9: Hike the Sentiero Azzurro in Cinque Terre

You should spend a full day in Cinque Terre hiking the Sentiero Azzurro , a wonderfully scenic hike.

The trail passes passes through Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore, giving you the option to explore each town individually.

The trail is 12 kilometres long, but if you’re not up for the entire hike, you can do segments of it instead. You can start at either end of the trail, depending on where you’re staying, and then take a train back.

All the towns are connected via train. Access to the Cinque Terre national park and the Sentiero Azzurro hike costs 8 EUR for just entry, or 15 EUR for a combined park plus hop-on hop-off ticket to the trains.

Wineries somewhere along the Sentiero Azzurro in Cinque Terre, with Monterosso in the distance

Admiring the colourful houses of Vernazza, one of the five towns along the Sentiero Azzurro in Cinque Terre, Italy

If you can handle 12km in a day, I highly recommend doing the hike. While the colourful houses of Cinque Terre are the highlight of this trail, there are stunning views all throughout.

Along the way, you’ll enjoy the beautiful scenic views of the ocean and sheer rock faces that rise up out of the sea. It’s a wonderful hike for photographers or Instagrammers looking for the perfect shot. 

Be sure to find a great spot to watch the sunset in the evening, as the views from the trail are absolutely exquisite. Although it’s easy enough to head down to a seaside restaurant and watch the beautiful views from there.

The beautiful streets of Manarola in Cinque Terre, Italy

View over Vernazza from the start of the Sentiero Azzurro, enroute to Corniglia

Best tours in Cinque Terre

You can explore Cinque Terre on foot by hiking the Sentiero Azzurro, but these highly rated tours can add a special something to your holiday!

Cinque Terre Sunset Boat Tour   – Admire the coloured houses of Cinque Terre as the sun goes down and the sky turns golden!

From Monterosso: Cinque Terre Kayak Tour  – Combine a workout with a unique experience, and see Cinque Terre from a completely different angle!

From La Spezia: Cinque Terre Full-Day Boat Tour   – Spend a whole day sailing along the beautiful Ligurian coastline.

Sunset over the perched colourful houses of Riomaggiore in Cinque Terre, Italy

Where to stay in Cinque Terre

I’ve already given you my opinion on the best place to stay in Cinque Terre, but here are some optons for every budget.

Budget:  Grand Hostel Manin   – This hostel has spacious dorms, a friendly atmosphere and is located in the heart of La Spezia. It’s the perfect place to use as base to explore Cinque Terre on a budget!

Mid-range:  ALTIDO Villa Monterosso Apartment Bellavista   – This modern villa is tastefully decorated, with gorgeous views of the Ligurian coastline and sea. It’s also in an excellent position in Monterosso.

Luxury:  La Vista di Marina by The First   – This apartment combines modern furnishing with exposed bricks for a rustic vibe, plus spacious rooms and white décor for an airy feel. It also has a spectacular terrace with view over the sea and iconic perched houses of Riomaggiore.

The harbour and colourful houses of Porto Venere

Day 10: Cinque Terre to Milan

After your hiking and seaside break it’s time to take the train from Cinque Terre to Milan (my hometown)!

By now you’ll be very familiar with taking the train in Italy, and learning to enjoy the journey as the views are usually spectacular!

The slight delays that often happen on Italian railways are just part of the journey.

The train trip should take you around 3 hours, leaving you with plenty of time in the afternoon and evening to explore the wonderful city of Milan and its nightlife .

Piazza del Duomo in Milan, Italy

This city is one of the fashion capitals of the world, so you can be sure its a creative city with loads to explore!

The best way to start a trip to Milan is by visiting the Brera District. You can walk through the charming cobbled streets, admiring the architecture and taking in all the wonderful sights and smells.

Sit down for a meal at one of the charming cafes or restaurants before exploring some of the amazing art galleries in the area.

Especially if you’re visiting Milan in winter , it gives you an excuse to be indoors while still discovering the culture. 

And, if you need a little retail therapy, there’s plenty of high-end shops that can provide you with just that!

Galleria Vittorio Emanuele seen from across Piazza del Duomo in Milan, Italy

Where to stay in Milan

Wondering where to stay in Milan ? Being from Milan I’ve never had any need to stay in a hotel there, however there are a couple thatI’ve had friends stay at before that I can recommend:

Budget – Ostello Bello : There are two hostels of this chain around Milan and both are good budget options, with a lively atmosphere, spacious dorms and convenient central locations

Mid-range – Ibis Milano Centro : Part of the Ibis chain this is a good mid-range hotel, with a guaranteed standard of room set up and a great central location

Luxury – Galleria Vik Milano : If you’re looking to splurge a bit, this is the place to do so. Located in Galleria Vittorio Emanuele this luxury hotel couldn’t get any more central than this, with stunning views over the galleria just outside your window

Click here to see the latest prices and availability for accommodation in Milan!

The inside courtyard of the Accademia di Brera, Milan

Day 11: Explore Piazza del Duomo in Milan

You should spend your full day in Milan  around Piazza del Duomo, this is the central square in Milan and all the main tourist attractions are located around it. It’s a great meeting place amongst locals and tourists alike.

You’ll see unbelievable architecture, intricate sculptures and the wonderful Duomo itself.

You can start with a guided tour of the cathedral which is very informative, however the highlight of the tour for me is the rooftop tour that comes along with it. 

It allows you to enjoy a view over the city while seeing the spires and architectural intricacies of the rooftop sculptures and designs.

This is also a great place to take photos, especially as the sun is rising or setting in the background!

Book your fast track tour of the Milan Duomo here!

Exploring the rooftop of the Duomo cathedral in Milan, Italy

Sunset over Milan from the rooftop of the Duomo, Italy

After exploring the wonderful interior of the Duomo, it’s time to head outdoors and enjoy the scenery that Milan has to offer!

From Piazza del Duomo you can easily visit Galleria Vittorio Emanuele, the Teatro della Scala and Castello Sforzesco, two must-sees that are close in the area.

Some of my favourite food places can also be found close to he Duomo; Luini for panzerotti (these are tiny fried calzone) and Spontini for pizza.

You can end the day by going for a stroll around the navigli. Not many people realise that Milan has canals (yes like Venice!) even if it only has two.

The Naviglio Grande canal was built in 1177 and has been expanded since then. This is one of the hip areas to hang out in evenings, where you can have a lovely aperitivo or dinner out amongst locals.

Admiring the perfect symmetry of Galleria Vittorio Emanuele in Milan, Italy

Best tours in Milan

Here are some of the best tours you can’t miss during your time in Milan.

Milan: Fast-Track Milan Cathedral and Terraces Guided Tour  –  Discover the beautiful Duomo and its stunning rooftop, without having to waste time queuing!

Best of Milan Tour with Skip-the-Line to Duomo & Last Supper   – For the art lovers, no visit to Milan would be complete without seeing the Last Supper!

Milan: Grand City Highlights E-Bike Tour  –  Discover all the highlights of Milan on bike!

Castello Sforzesco in Milan, Italy

Day 12: Travel from Milan to Venice

Travelling by train from Milan to Venice offers some amazing views along the way.

The trip should take just over 2 hours, if you set off in the morning it will give you plenty of time to start getting your bearings around the famed city of Venice.

As soon as you get to Venice, after you drop off your bags, you should visit San Marco square, where you’ll find some some of the most beautiful basilicas in Venice.

If you love exploring old churches, why not take a tour of the basilica and the palace ? This will give you a chance to learn a great deal about Venetian history and the culture of the city.  

Click here to book your skip the line tour of St Mark’s Basilica and the Doge’s Palace!

Piazza San Marco in the early evening

On the way back from San Marco square you will come across Ponte di Rialto, which is the most famous of the 400 bridges that are scattered throughout Venice.

The bridge offers magnificent views over the romantic city and it’s a wonderful spot to enjoy the sunset.

I spent one night in Venice with my mum and we slept at Hotel alle Guglie . This was ideal since it was located just outside the main touristy area of Venice, but was still within short walking distance of all the attractions.

The rooms were a bit small but they made up for it with an abundant breakfast, good price for value and great location.

Click here to book your stay at Hotel all Guglie!

Sunset on the grand canal in Venice from Ponte di Rialto

Day 13: Explore Venice

Seeing as you only have one full day in Venice , you need to make the most of it by doing as many sightseeing activities as possible.

You can start the day with a gondola ride through the canals of Venice. These are a bit expensive but it’s such a traditional Venetian experience, how could you possibly miss it?

It will give you a unique and lovely view from the waterways, since you can see the ancient buildings that seemingly rise up out of the water.

I recommend starting your gondola cruise by Rialto Bridge, as it offers the best views and calmest waters.

There’s no need to book beforehand, since there are plenty of gondolas all over Venice waiting to take tourists around (kind of like taxi stands in any other city) and the price is standardised.

However if you want to be sure to have your experience confirmed you can also book online .

Click here to book your private gondola cruise in Venice!

Enjoying my gondola cruise around Venice

Our gondola ride took us close to Rialto Bridge

After your gondola cruise you should visit the Bridge of Sighs or Ponte dei Sospiri, which is a very famous bridge in Venice. Despite popular stories, the name isn’t inspired by love stories.

The bridge connects the interrogation room to the prison, and it’s said that prisoners would sigh while crossing the bridge, as they took in their very last sight of Venice.

Not as romantic as you’d think right? But it’s still a beautiful spot in Venice and definitely worth a visit.

The Ponte dei Sospiri in Venice

From here you can take a tour of the Basilica di Santa Maria Della Salute . It’s a beautiful church with some of the best architecture you’ll ever find in the city (which is really saying something).

You can explore it yourself, or take a guided tour if you’d like to learn a little more about its history. Just across from the Basilica there’s also a killer sunset spot so you can sit here and enjoy the end of your Italy itinerary.

Best tours in Venice

Book one of these highly rated tours for your time in Venice!

Venice: Private Gondola Ride to Rialto Bridge   – Go for a private gondola ride amongst the most beautiful canals of Venice!

Venice: Doge’s Palace Priority Admission Ticket   – Skip the queue and visit this iconic site in Venice!

Venice: Small Group Wine Tasting and Food Tour with a Local   – Go for a guided tour of all the best places to eat and drink in Venice with a local guide!

Sunset at the Basilica di Santa Maria della Salute in Venice

Where to stay in Venice

I’ve already mentioned my great stay at Hotel alle Guglie, but I wanted to include some more accommodation options in Venice for every budget.

Budget:  Combo Venezia   – This hostel has a combination of modern dorms and a traditional courtyard. It’s also in a great location and has a very sociable atmosphere.

Mid-range:  Hotel alle Guglie  – I stayed here with my mum and found it a perfect compromise for those looking for a comfortable room, great location and affordable price.

Luxury:  Ai Patrizi di Venezia   – These luxury apartments are the perfect place to treat yourself during your Venice stay.

Cruising the canals of Venice in our gondola

Day 14: Fly home from Venice or extend your trip

It’s the 14 th and final day of your Italy trip! The time has sadly come to fly home. However, if you manage to get a few extra days in, there is still so much more of Italy to see!

Want to do this Italy trip without the hassle of booking all the tours, transfers and hotels yourself? Book this itinerary on Designer Journeys !

Click here to book your customised Italy 2-week itinerary on Designer Journeys!

Exploring the Greek amphitheatre of Taormina at sunset

Alternatively, after hitting all the main cities and tourist landmarks of Italy, I imagine you’ll be ready to head out off the beaten track!

If you’re not ready to leave Venice just yet you can go on some awesome day trips from Venice . You can easily get to beautiful cities like Verona , Bologna and more.

If you want to see a completely different side to Italy, it’s time for a nature escape!

If you’re looking for beautiful beaches, I recommend you head to Sardinia for a boat trip  (one of the best beach destinations near Milan ), where you’ll get the chance to explore the beautiful archipelago and see a more tropical side to my wonderful country.

I’ve seen a lot of beaches all over the world, but I’m yet to see beaches that are better than the ones in Sardinia . If you’re looking for a mixture of sea and culture, you can also head to   Sicily .

Here you can spend your afternoons with the sunshine warming your skin and your toes in the sand, before cooling off in the turquoise waters, but also exploring the food scenario and wandering around the cute towns. 

A relaxing boat trip day in Sardinia, Italy

If you’re not a beach bum, or you’re visiting Italy in winter , you can head to Trentino for an adventurous escape.

In summer in Trentino you can entertain yourself with some magnificent hikes and epic views over alpine lakes , whilst over Christmas you can ski in world famous slopes .

Either way, you’ll get your heart pumping and your blood flowing. I’ve visited Trentino loads of times as a kid in winter, but only recently in summer and I can honestly say this region is stunning at any time of year.

It’s the perfect place for a nature escape after 2 weeks of city sightseeing in Italy.

Hiking at Rolle Pass in Trentino

Another beautiful place in Italy, which I haven’t included in this Italy 2-week itinerary is Lake Como. Lake Como is one of the most popular tourist spots in Italy.

With its stunning natural landscapes, picturesque towns and relaxed vibe, it’s easy to see why. Many travellers only do a day trip to Lake Como from Milan , but I always say it’s well worth spending at least three days in Lake Como .

If you stay in Lake Como overnight you can go on a beautiful Lake Como boat tour , discover the towns of Bellagio and Varenna, go on a scenic hike and much more!

The picturesque streets and views of Bellagio in Lake Como, Italy

You could also head to the south and visit the Sassi of Matera . This city went from being considered the “Shame of Italy” to being the European Capital of Culture in 2019. 

Also in the south of Italy, is the famous Amalfi Coast . I recently spent five days in Amalfi Coast , hiking the Path of the Gods , going on boat trips to Capri , exploring Positano and discovering the ruins of Pompeii .

I didn’t include Amalfi Coast in this video since there’s just too much to do in the area. Even if you only do day trips to Pompeii and Capri , and skip the Positano boat tour , it would take up too much for your two weeks in Italy, leaving little time for other destinations.

Don’t have two weeks to travel around Italy? Check out this Italy 10-day itinerary or my 7 days in Italy itinerary instead.

Wondering how much all this would cost? Check out my Italy 2-week trip budget to find out!

Enjoying the view over the Sassi of Matera in Italy

How to travel around Italy

Travelling within Italy is fairly easy.

We have a pretty decent railway system (Trenitalia is often late but it always gets you where you need to go), lots of bus companies, internal flights that connect most major and minor cities to each other, and pretty good roads for driving.

My personal favourite way to get around, as you may have guessed from this itinerary, is by train.

On long distances the Frecciarossa (the high speed train here in Italy) is often faster than flying, if you were to factor in also travel time to the airport, airport faff time and then travel time from the airport to home.

Driving in Italy is also great if you have a licence and friends to share the journey with, as it gives you more flexibility than the trains.

What to pack for 2 weeks in Italy

I’ve written a full Italy packing list  with all the essential items you might need in Italy, however if you don’t want to open a new tab (I get it, it’s the end of the article, you’re tired and excited to start planning your trip) here’s a couple absolute must haves you don’t want to forget.

International adaptor  – depends on where you come from but I like to always carry with me an international adaptor just to be sure.

It’s a bit more expensive than the one country adaptors but at least I only need one that I can take everywhere

Power bank  – you don’t want to be wandering around the medieval streets of Siena and then all of a sudden your phone dies! You want to always be charged both for Google Maps and let’s be real, photo opportunities!

Steel water bottle  – In Italy we’re not as ahead as other countries with water dispensers in restaurants and other public places, but generally speaking the tap water is drinkable everywhere, so if you want to cut down on your plastic consumption and save some cash in the process, don’t forget your own water bottle!

Exploring the side streets, canals and bridges of Venice, Italy

Final thoughts on the best Italy itinerary

If you’re looking for the best way to visit Italy in 2 weeks, you’ve just found it! I’ve made sure that this Italy itinerary is jam-packed full of exciting entertainment, sightseeing opportunities and adventures you’ll treasure forever.

Yes it’s a bit of a touristy itinerary, but after all tourist places are so for a reason, usually because they’re beautiful! 

Travelling to all the major cities and tourist destinations is a must during your 14 days in Italy trip. However that doesn’t mean you shouldn’t venture a little off the beaten track to find the hidden gems that will keep you coming back. 

If quaint cities, beautiful architecture and ancient history all sound right up your ally, then Italy is the place for you to roam. I hope you find this 2-week Italy itinerary useful in planning your own trip.

From an Italian point of view, I tried my best to include all the most beautiful cities that I would want any new traveller to visit. I hope you’ll fall in love with my country as much as me! 

I f you’re still looking for more Italy inspiration, check out my guide on the 10 things to know before travelling to Italy , or these 60+ inspiring quotes about Italy .

Enjoyed reading my Italy 2-week itinerary? Pin it!

BEST of Italy in 2 Weeks: Detailed 14-Day Itinerary (+Map & Planning Tips)

By Author Jurga

Posted on Last updated: February 4, 2024

Planning a trip to Italy for the first time and getting overwhelmed? You are not alone! We get this question all the time: ‘What is the best Italy itinerary for a first trip’ ?

In all honesty, there is no one ‘best’ way to plan a trip to Italy. It’s a big and incredibly beautiful country and pretty much everywhere is worth visiting. But if this is your first trip to Italy and you don’t know where to start, I recommend focusing on the ‘musts’ – some of the most beautiful places in Italy that everyone should see at least once in a lifetime.

To help you plan a trip, in this guide, we share a detailed 2-week Italy itinerary that brings you to all the most famous places in the country : Rome, Florence, Venice, Milan, but also the famous Leaning Tower of Pisa, Tuscan countryside, Cinque Terre, Amalfi Coast, Pompeii, and a few other destinations that should be at the top of every Italy bucket list.

Will you see everything in Italy in two weeks? No, definitely not! But if you want to see the main highlights and get a good idea of what Italy is about, this itinerary is a great first introduction to this amazing country. And take my word for it – you will want to go back and explore more!

So why do we recommend 2 weeks? In my opinion, you really need at least two weeks in order to quickly see all the ‘musts’ in Italy. If you have just a week or ten days, don’t worry – Italy is still more than worth a trip (it always is!). But if you want to cover all the main highlights, you’ll really need at least 12-15 days.

In this article, we focus on helping you make the most of your first trip and plan the most complete Italy itinerary in 2 weeks. At the bottom of this guide, you can also find our additional suggestions on places to see if you have more time.

Good to know: You can visit Italy in any season and this trip itinerary is suitable for any time of the year. Some coastal areas might be a bit deserted in winter, but if you absolutely want to see them, it’s possible too.

Also, this itinerary is structured in such a way that you don’t have to change hotels too often . This will save you time for practicalities and leave more time to explore.

Since most of the places covered in this Italian itinerary are cities, we DO NOT recommend renting a car for this trip . You can’t do much with a car in Rome or in Venice and you can easily travel between the main cities by train . And for those few places where it would be useful to have a car, you can take day tours (you can find all this info in our article).

If you want to explore a few places in northern Italy deeper, you could rent a car after you visit Venice and then return it in Milan . Depending on what exactly you want to see, it might make sense to consider hiring a car for this part of the trip.

How to use this itinerary: As you’ll see, this 2-week trip starts in Rome and ends in Milan . Both cities have major international airports and it’s quite easy to find flights to/from Rome or Milan from pretty much anywhere in the world. Of course, you can do the trip in the other direction, or you can also make a round trip starting and ending at any of the cities mentioned below . This itinerary is solely meant to give you an idea of what can be done and how you can plan a 2-week trip to Italy.

MAP: To help you get a better idea of where all these places are located, we also created a map indicating all the places covered by our itinerary.

Take a look!

This is our recommended Italy itinerary that covers all the best places in two weeks:

Day 1: Arrival in Rome

There is no better place to start your Italian vacation than in the Eternal City – the capital city of Italy – Rome .

For this itinerary, I recommend that you spend at least 3 full days in Rome: 2 days in the city itself, plus make a day trip to Pompeii and the Amalfi Coast. This way, you won’t have to change hotels too often and can see (albeit very shortly) some of the best places in southern Italy as well.

Depending on when your flight arrives, you might be able to see some of the landmarks of Rome on the first day already.

TIP: If you can make it, I highly recommend joining an evening walking tour of the city’s highlights – it’s a great first introduction to the city!

Accommodation: Stay in Rome for 4 nights. Here you can find our guide to the best area to stay in Rome . We recently stayed at 9Hotel Cesari and loved it (especially the breakfasts on their rooftop terrace). On a bit lower budget, Hotel Accademia is an excellent choice, and you’ll find many other hotels in the same area.

Days 2-3: Rome

While two days are really short for Rome, if you plan well, you can see most of the ‘musts’ in just 2 days.

We recommend focusing on the main attractions, such as the Vatican , the Colosseum , and all the famous sights in the historic city center (Trevi Fountain, Pantheon, etc.). In addition, you can also add one or two more local experiences such as e.g. a food tour . It will make your visit more memorable and also a bit more relaxing!

Good to know: Be sure to book your tickets/tours for the Colosseum and also for the Vatican in advance!!! Both are extremely popular attractions and tickets often sell out (in high season, sometimes a few weeks in advance). Tip! This Rome Tourist Card allows you to book timed entry tickets for both these attractions in one place, so you’ll also immediately see what is open on the day when you are there (and can adjust your itinerary if needed).

TIP: If you didn’t get the tickets in advance and they are sold out, you can usually still join one or the other guided tour (they usually have access to tickets that are reserved for tour groups). In any case, at least for the Colosseum and the Roman Forum, we highly recommend going with a guided tour rather than on your own. We took this amazing tour that also includes the Colosseum Underground and Arena Floor (these levels are not included with the regular ticket).

For more info on what to see and how to best plan your time, please see our 2-day Rome itinerary below . This itinerary includes all the top sights that you absolutely shouldn’t miss, a detailed schedule, as well as our experience-based tips on how to make the most of your short visit. Check it out!

LEARN MORE: How to see the best of Rome in 2 days

Day 4: Pompeii & Amalfi Coast day trip from Rome

You could easily spend this day in Rome and find plenty to do too. But if you want to make the most out of your two weeks in Italy, we recommend visiting Pompeii and the Amalfi Coast as a day trip from Rome . You don’t necessarily have to do it on day 4 of this itinerary; days 2 or 3 would work too, so you can move things around depending on your preference.

It’s quite a long drive to get to Pompeii from Rome, but if this is your first time in Italy and you want to see as many of the most famous places, then it’s probably worth it.

There are various tours that visit Pompeii and either Mt Vesuvius , Amalfi Coast , or Naples from Rome in one day. Any of these tours will be rushed if you only have a day, but all are really nice and you can’t really go wrong with either option.

• If visiting in the warmest months (+-March to October), we recommend this tour . It includes Pompeii and the Amalfi Coast.
• If visiting in the lower season, we recommend this tour . In winter, it brings you to Pompeii and Naples.

TIP: If you’re just interested in the city of Naples, you can also easily come here for a day by train from Rome. In that case, see our recommended 1-day Naples itinerary . Here you can also find a more detailed guide to the best things to do in Naples .

And if you have a few days extra to add to your Italy itinerary, definitely consider spending more time in this area. In that case, you could probably better fly to Naples first, before going to Rome.

Alternative: If you don’t feel like doing a 12-13-hour day tour to Pompeii and rather stay in Rome, it’s a great choice too. In that case, we recommend getting a bit off the beaten path and visiting some of the most incredible ancient sites in Rome .

We recently did this amazing e-bike tour that brings you to the famous Appian Way, Roman aqueducts, and catacombs.

And with the extra time left in the city, you could visit some of the hidden gems of Rome or see some of the best viewpoints .

Day 5: Rome to Florence & visit Florence

Next on your Italy itinerary is Tuscany , one of the most beautiful regions in the country. We recommend basing yourself in Florence for the next few days. Florence is one of the most beautiful cities in Italy and is well worth a visit, but there are also some really nice places that you can see nearby. With just a few days here, you’ll have difficulties choosing where to go and what to skip!

Florence is just a short ride from Rome (+-1.5 hrs by train). Try to get an early train so you have enough time to explore the city after you arrive and drop off your luggage at your hotel.

On the first day in Florence, be sure to visit the musts, such as the Duomo Cathedral, the Uffizi Gallery, and/or Accademia Gallery . Depending on your interests, you can visit one or all three, but be sure to plan it well.

Good to know: All these places require a ticket and are extremely popular, so it’s essential to get tickets/tours in advance! Having your sightseeing itinerary well-planned upfront is the only way not to miss any of the most important sights and keep your Italian vacation enjoyable without feeling overwhelmed.

TIP: If you want to see as many of the musts in a short time, we recommend this popular tour that includes both – Uffizi Gallery and Accademia Gallery. Afterwards, visit the Florence Cathedral and climb the Dome (be sure to get a timed-entry ticket !).

Then, stroll the streets of the city center and see some of the main highlights that don’t absolutely require tickets or reservations – such as Ponte Vecchio, Piazza della Signoria, Basilica Santa Croce, etc.

LEARN MORE: One Day in Florence

You’ll still have some additional time to explore Florence in the next days, but – depending on the day trips you choose – it will likely be just a few hours in the evenings after you get back from a tour. That’s why we recommend visiting the places that require a ticket on your first day already.

In the evenings, you can also enjoy some of the best sunset views from the nicest rooftop bars in Florence .

Needless to say, if you can add an extra day in Florence, you’ll be able to explore the city at a much more relaxed pace. But this counts for pretty much every place in this itinerary…

READ ALSO: Best Things to Do in Florence

Accommodation: Stay in Florence for at least 3 nights. Florence city center isn’t that big, but – to make things easier with the luggage and tours, stay somewhat close to the railway station. For one of our recent trips to Florence, we booked Hotel Croce di Malta – the location is excellent, they have a pool, and you can’t beat those rooftop views! On a bit lower budget, B&B Le Stanze del Duomo is one of the best price-quality hotels in the center!

Day 6: Tuscany day tour from Florence

While there’s plenty to see and do in Florence to fill a few days, you’ll likely want to see some of the famous Tuscan countryside as well.

So on your second day in Florence, we recommend taking a day tour to some of the nicest towns of Tuscany .

You could just take a train and visit the cities like Siena or Pisa on your own, but you would likely only see one town that way (and waste too much time in transit). Also here – if you want to make the most of your time, it’s best to go with an organized tour that visits a few of the very best places in a day.

TIP: We recommend this highly-rated day tour . It brings you to the Leaning Tower of Pisa, the beautiful city of Siena, the charming medieval town of San Gimignano, and more. You could never see all these places in just a day on your own.

If you rather not join a tour, then take a train to Siena. Here you can find our guide to the best things to do in Siena , including a sample itinerary for your first. As an absolute minimum, don’t miss the Siena Cathedral !

Day 7: Cinque Terre day trip from Florence

Next is another place that’s probably high on your Italy bucket list – Cinque Terre . The famous 5 villages on the Ligurian coast are among the most visited and most photographed places in Italy.

If you plan well, it’s possible to see the best of Cinque Terre in just a day, also if you are visiting from Florence. You could take a train to La Spezia and on to Cinque Terre, following our detailed 1-day Cinque Terre itinerary . If you decide to go on your own, be sure to also read our practical tips for visiting Cinque Terre .

However, Cinque Terre is very popular and extremely busy (especially in the high season from March to October). So planning a quick visit here might be overwhelming…

TIP: If you want to see all the best places without having to plan anything, you’ll be glad to know that there are also some organized day tours from Florence to Cinque Terre. This highly-rated tour is one of the very best options for a day trip from Florence and covers all the musts in Cinque Terre.

Alternative/ addition day: If you are visiting Italy in the low season, you may want to skip Cinque Terre and visit Bologna instead (it’s just 40 minutes by train from Florence). Or, you could also add a stop in Bologna when traveling between Florence and Venice.

One day is enough to see the main sights in Bologna and it’s worth it if you can squeeze it in. But – as already mentioned before – you can add extra days pretty much everywhere in this itinerary and still not see it all…

READ ALSO: Florence to Bologna Travel Info & Best Things to Do in Bologna

Day 8: Florence to Venice & explore Venice

The second part of this 2-week Italy itinerary takes you to northern Italy. The next stop is Venice , just about 2.5 hrs from Florence by train. Venice is one of the most unique cities in the world and so no Italy trip itinerary would be complete without visiting here!

If you take a train early in the morning, you’ll be in Venice by noon, which leaves you plenty of time to get acquainted with the city and see some of the main highlights. We recommend spending 2 nights here, so you have 1.5 days, plus two evenings in Venice. Venice is magical at night – the city is so pretty and you can appreciate it so much more without all the day tourists around.

On your first day, you could tick some of the must-see places on your Venice bucket list. One of the musts is St. Mark’s Square and Cathedral (one of the most beautiful churches in Italy ), and the other – Doge’s Palace , just next door. Needless to say, these are very popular attractions, so also here you have to book your tickets (or tours) in advance.

TIP: We recommend a tour like this that covers some of the musts in the most efficient way. Ideally, opt for an afternoon tour, so that you don’t have to rush in order to get there on time.

After that, explore the city center on foot, see Rialto Bridge and the Grand Canal. You should also take a Venetian gondola ride , which is another must-do in Venice!

READ ALSO: How to see the best of Venice in 1 day

Accommodation: Stay in Venice for 2 nights. To make things easy for yourself, you could stay close to the railway station – e.g. Hotel Carlton On The Grand Canal is a very good option and usually great value for the money. Alternatively, if you don’t mind taking a water bus to the more centrally-located places, check out H10 Palazzo Canova close to Rialto Bridge or Bauer Palazzo not too far from San Marco Square. For the ultimate Venitian experience, take a look at the famous luxury Hotel Danieli .

Day 9: Venice

Today, you have an entire day to explore Venice and its surroundings . You could opt to spend the day in the city, or you could also take a half-day trip to the nearby islands Murano, Burano, and Torcello (there are various boat tours that visit the islands in 4-6 hours ).

While not an absolute must, a visit to these islands is a nice opportunity to see some smaller Italian towns. Murano is famous for its glass-blowing factories, Burano – for its lace, and Torcello – for its Byzantine basilica. In addition, the towns are very colorful and picturesque, and completely different from Venice.

There is so much to see and do in Venice that you will easily fill the entire day in the city. So it all depends on your interests and how many activities you want to pack into your itinerary.

As a minimum, in addition to the places mentioned before, we recommend going to the top of St. Mark’s Campanile for some of the best views over the city and the Venetian Lagoon. In some seasons, it is now possible to reserve the tickets in advance (do it!). Otherwise, you’ll have to queue and wait a long time. If you can do it first thing in the morning or in the late afternoon, it will be easier to plan the rest of your day.

TIP: If you are looking for something special to do in Venice in the evening, check out this dinner cruise on the Venetian lagoon . Alternatively, see if there’s something interesting going on at Teatro La Fenice .

And if you can squeeze in an extra day in your itinerary, Venice is definitely worth a longer stay. In that case, check out our 3-day Venice itinerary for some inspiration on what to see and do depending on how much time you have.

READ ALSO: Best things to do in Venice

TIP: Next on your itinerary is Verona, Lake Garda, and Lake Como. If you want to explore these areas deeper, Venice would be a good place to rent a car for the remainder of this trip ( see here for the best car rental deals ). You can easily visit Verona by car, drive to (and maybe even around) Lake Garda, visit Lake Como, and then return the car in Milan.

Renting a car in Italy is normally not expensive, but driving and parking in the small towns by the lakes – especially in high season – can be very challenging.

Anyway, the rest of the itinerary below is created assuming you take a train. But you can easily adjust it if you decide to drive.

Day 10: Venice to Verona & explore Verona

The next stop on this Italian itinerary is Verona , one of the most romantic cities in Italy. It gets this reputation because of Shakespeare’s “Romeo and Juliet”, and Juliet’s House is one of the top attractions in the city.

The train ride between Venice and Verona takes about 1.5 hours, so you’ll have a big part of the day left to explore Verona. The city is quite compact and you should be able to see all the musts in a day.

As a minimum, be sure not to miss the Verona Arena , built 2000 years ago (best get a priority ticket for this one). Also the views from Torre dei Lamberti and the earlier-mentioned Juliet’s House with its famous balcony are must-see in Verona.

Just as in all the other cities, you can also find some really nice Verona city tours led by locals. There are walking tours , a very nice bike tour , and this food tour is very popular as well. The nice thing about Verona is that it’s not that big, and so you can see a lot at a rather relaxed pace.

LEARN MORE: Best Places to See & Things to Do in Verona

Accommodation: Stay in Verona for 2 nights. We recommend Hotel Milano & SPA***S – it offers excellent price/quality in the city center. And yes, it also has a beautiful rooftop terrace with an amazing view – something we recommend in every city in this itinerary because we love staying at hotels with nice rooftop terraces ourselves. It makes any city visit so much more memorable!

Day 11: Lake Garda day trip from Verona

Lake Garda is one of the most beautiful lakes in Italy and if you have an extra day in your itinerary, it’s well worth planning a short visit here as well. This is especially the case if you are traveling in the warmer months.

If you don’t mind changing hotels more often, you could stay in Sirmione on your way between Verona and Milan. However, keep in mind that there is no direct train from Verona to Sirmione, so you’ll have to travel by bus or train + bus, or arrange a private transfer. To make it easier and simpler to plan, you can just visit Lake Garda as a (half) day trip from Verona. It’s good not to have to pack/ unpack every day.

You can come here by public transport and explore on your own. In that case, be sure to decide in advance where you’ll visit – just Sirmione or also some other towns along the lake, and research the public transport options to get back to Verona in the evening. See our Lake Garda itinerary suggestions on how to spend a day here.

There’s also a nice half-day tour from Verona that visits Sirmione town and includes a short boat ride on the lake. Sirmione is one of the best places to see at Lake Garda and the one that’s the easiest to visit if you don’t rent a car and/or don’t have at least a few days in the area.

TIP: If you take a half-day tour to Lake Garda, you’ll have a free afternoon in Verona. If visiting on weekends in summer (Thursday to Sunday, from +- mid-June to early September), you can attend an opera at the Verona Arena . It’s a really special experience!

Alternative: If you decide to skip Lake Garda altogether, then you could add an extra day in Florence or in Bologna as mentioned before. Or – if you visit Lake Garda with a half-day tour, you could take a train to Milan in the afternoon already and save some time in your itinerary this way.

Day 12: Verona to Milan & explore Milan

The final destination in this 2-week Italy itinerary is Milan , where you can also visit the beautiful Lake Como nearby.

One of Italy’s biggest and richest cities, Milan is also one of the most fascinating places in the country. It has such a unique mix of old, historic places and modern contemporary lifestyle and architecture. Plus, if you like Italian fashion and want to do some shopping, Milan will not disappoint either.

The train ride from Verona to Milan takes about 1.5 hours, and since you have almost two days for the city alone, you should be able to see all the musts in a rather relaxed way.

On your first day in Milan, you could visit the two main attractions – the Duomo Cathedral and see Leonardo Da Vinci’s Last Supper . There are also some great tours that visit The Last Supper and some of them also bring you to the Cathedral. It’s also well worth visiting the Duomo rooftop , but you can leave it for the next morning as well.

Good to know: Also here, whatever you decide, be sure to book tickets/ tours for the most popular places in advance! Tickets for The Last Supper are often sold out a few months upfront, but finding a guided tour is much easier (they pre-book tickets and can usually accommodate last-minute bookings as well).

Accommodation: Stay in Milan for 3 nights. Hotel Dei Cavalieri Milano Duomo is a great option right in the heart of the old town.

Day 13: Milan

Today, you have an entire day to explore Milan . Visit the highlights in the old city center, but don’t miss the modern part of the town either!

For more information on what to see and do and how to plan your day, please see our recommended 1-day Milan itinerary . It includes all the musts and the details on how to best plan your time.

If you already visited the Duomo and/or Duomo Terraces and/or Da Vinci’s Last Supper the day before, just adjust your itinerary accordingly.

If you have some time left, you can go shopping in the center or visit Designer Outlet Serravalle (although this one will likely require an entire day).

In the evening, head to the Navigli district , aka the canals of Milan. It’s a very nice and lively neighborhood with lots of restaurants, bars, and cafes – a perfect place to end the day of sightseeing.

LEARN MORE: Best Things to Do in Milan

Day 14: Lake Como day trip from Milan

On the last day of your 2 weeks in Italy, we recommend visiting another famous lake in northern Italy, Lake Como . Located just near Milan, it’s an easy day trip destination and a wonderful addition to any Italian itinerary!

Just as with Lake Garda, you could visit Lake Como on your own. In that case, simply take a train from Milan to one of the towns (Como or Varenna are both good options) and then explore further.

However, ideally, you also take a boat trip on the lake and visit several of the nicest towns of Lake Como instead of one. And for that, it’s easier to join an organized tour and have them guide you to all the best places without having to plan or arrange anything.

TIP: We recommend this highly-rated day tour. It brings you to Como (including Villa Olmo), Bellagio , and Varenna – some of the most scenic places on Lake Como. It would be very difficult to plan a similar trip and see all of these sights in just a day on your own (mainly because tours use private transportation and don’t have to waste time waiting for trains or delayed ferries).

Also here, you could easily spend more time at Lake Como than just a day. In that case (or if you rather not take a tour even if visiting for just a day), you may want to read our guide with tips for visiting Lake Como .

READ ALSO: Top Places to See & Things to Do in Lake Como

So, this is it – the ultimate Italy itinerary that allows you to see ALL THE BEST PLACES in 2 weeks. Of course, there’s much more to see and do in Italy than the destinations covered here. But if you want to visit all the ‘musts’, this sightseeing itinerary does exactly that.

We planned this Italy itinerary in such a way that it starts and ends at the biggest towns with major international airports, Rome and Milan. There are lots of direct flights to/from both of these cities to many other places in the world. So it should be quite easy to plan your trip in such a way that you can fly home from Milan.

And if you absolutely want to make a loop, a round trip starting and ending in Rome, you can simply take a train from Milan to Rome, and fly out of there. The fast train between the two cities takes about 3.5 hours.

Good to know: If you take regular trains in Italy, you can just get a ticket at a station. However, if you opt for high-speed trains between the main cities (recommended), it’s best to reserve your seat in advance. You can use the official Trenitalia website for that, but keep in mind that standard tickets are usually non-refundable. We also recommend checking this website for all the best options for train tickets .

If you have more time…

If you have more time in Italy, you could add extra days pretty much anywhere in this itinerary and you’ll find plenty to do. We already included some additional recommendations above. And here are a few extra suggestions:

• You could add some extra time at the Amalfi Coast and also visit Capri Island and Naples . So instead of visiting this area on a day trip from Rome, you could stay here for several days. See our Amalfi Coast itinerary and Naples day trips for more suggestions on what to see and do there, and this guide for more information about the best areas to stay in Naples . You could easily add at least 5 days to your Italy trip itinerary just for this area – there’s so much to see!
• If visiting in summer, I also highly recommend adding at least a few days in the beautiful Italian Dolomites . You could rent a car in Venice and visit the mountains for a few days, continuing past Verona and Lake Garda and on to Milan. Here you can find some Dolomites itinerary suggestions a,d our guide on where to stay in the Dolomites .
• Tuscany is another area where you could easily add a few extra days. There are so many beautiful places to see! See our Tuscany itinerary for some additional inspiration for the best Tuscan towns .
• Bologna , one of the foodie destinations in Italy, is another nice addition to any Italy itinerary. You could just visit for a day from Florence, or spend several days here as well. Also Rimini , Ravenna , and San Marino are all worth a visit. See our Emilia Romagna itinerary for more information about these places.

…. I could go on and on. As you can see, there’s plenty to see in Italy to fill another few weeks or months. And once you visit this incredible country, you’ll definitely want to come back and explore more.

But for your first trip, this is a very complete itinerary that shows you the best of Italy in two weeks .

Yes, this itinerary is quite packed and yes, you’ll probably want to stay longer at many places you visit. But it gives you an amazing overview of what Italy is about, and you can always plan a repeat trip to the areas that you liked the most. You can also find a lot more travel inspiration in our Italy travel guide .

READ ALSO: Italian Food – traditional dishes to try in every region

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Tuesday 5th of March 2024

Please offer your ideas and suggestions for a 1-week trip to Italy in May 2024. We only have a short time to visit so any guidance to enjoy Italy in a few days will be so helpful!

Thursday 7th of March 2024

Hi Shannah, there are so many options, so pick the places that interest you the most. And don't overdo it in terms of too many different locations. With a week in Italy and if it's your first trip, you could visit Rome (2-3 days + potentially a day trip to Pompeii/Amalfi e.g. like this), Florence (1 day in the city and one day trip, e.g. to Tuscan towns like this or to Cinque Terre - see this tour), and Venice (1-2 days). Of course, you can just visit one specific region, but there are literally thousands of options, so you have to see what interests you the most. Hope this helps. For more details about all these places, please see our article above.

Monday 26th of February 2024

We are to Italy/Switzerland for 3 weeks in August. We are starting in Switzerland for a week then two weeks in Italy starting with Milan and working our way down as far south as the Amalfi Coast. We are a bit stressed because we finally booked our flights and then read that August is the worst time to travel to Italy due to the weather, horrendous crowds and Italy national holiday starting August 15 when Italians and other Europeans go to the coastal cities (where we wanted to end our trip) an overcrowd those areas.

Do you have any tips on places to go to make an August trip most enjoyable? We prefer some areas that are beautiful, nice to stroll around, eat and see some sights, but don't have to go to all the main tourist attractions. We'd love some suggestions that help us get off the beaten path vs. all the main highlights. I've been to Venice, Florence, Rome once before and my husband has not been at all, but doesn't care too much about all the 'must sees' besides Rome. We plan to leave from Rome airport, but want to try to make it further south to Amalfi coast first.

Any suggestions would be super helpful!

Tuesday 27th of February 2024

Hi Erica, I'm afraid that what you read is correct. Italy can be crazy busy in August, especially in coastal areas. That being said, the cities are usually deserted (=locals are gone), but places like Rome are full of tourists so you won't be alone. The best way to avoid the biggest crowds is to skip the most popular seaside destinations. Amalfi Coast, Italian Riviera, Cinque Terre, Capri, Rimini, etc. will be crowded at that time of the year. But if you book accommodations in advance and plan your sightseeing activities in the mornings, it could be manageable. Of you visit places like e.g. Amalfi Coast, you will have to pre-book everything, not just hotels and excursions, but also restaurants. If you go more inland and stay in smaller villages, you can have a perfectly enjoyable trip. A few years ago, we were in Tuscany in the second half of August and it was great. But we started our days early, did most of the sightseeing in the mornings, and when it started to get busy everywhere, went back to our accommodation and spent the warmest hours by the pool. In the evenings, we usually visited smaller towns, but it was really busy everywhere, parking was not easy, etc. So you need more patience, especially if you go to the main tourist hotspots. Take a look at these articles for some additional tips: Amalfi Coast Travel Tips (don't rent a car here!!!) Where to Stay on the Amalfi Coast Where to Stay in Capri Rome Travel Tips Lake Como Travel Tips If you like nature, consider spending some time in the Italian Dolomites. It will also be very busy, but different than at the sea. Also there, top places and most popular hikes will be crowded, so start your days early. Or avoid the top places and you can have a very enjoyable visit. The nearby Trentino region is much quieter, but it's popular with locals = August is the peak season. You can find some inspiration in this article - most activities are definitely not just for kids. Having said all this, when you travel somewhere from the other side of the world, it's just normal that you want to see the top spots. The best tip I can give you is to try to get a bit off the beaten path in addition to the top places, AND book as much as possible in advance. Good luck and enjoy your trip. Italy is always a good idea and I'm sure you'll have a wonderful time!

Sunday 22nd of October 2023

Hello Jurga,

A great article to read through! Me, the wife and two kids (11 and 14) are planning a trip through Italy next Summer. He have 6 weeks off for summer, so we're looking at a 2-3 week trip through Italy probably. With the kids I don't want to be rushing so do you recommend staying longer in some of these locations? More hotels don't phase us.

Monday 23rd of October 2023

Hi Matthew, so much depends on your interests! With the kids in the summer, you may want to spend some more time in the nature rather than sightseeing in big cities. So you could add Italian Dolomites to your itinerary. Also, you could spend more time at the Naples/Capri/Amalfi Coast and/or Italian Riviera (around Cinque Terre). Also places like Lake Garda and Lake Como offer a great mix of nature, sightseeing, and some relaxing time by the pool. There are so many options. That's why it's really difficult to help our readers with specific itineraries. Pick the places that interest you the most, plan a few longer stays once in a while so that you can all wind down and relax a bit, and realize that whatever you do, there is no way you can see everything in Italy in 3 or even 6 weeks. You'll want to go back ;). Good luck with the choices!

Madonna Hanes

Thursday 19th of October 2023

I'm thinking of coming out to Italy for 10 days, 2 days for flights, and 8 days for touring Italy. What do you recommend and where? Thanks advance.

I was thinking September.

Hi Madonna, so much depends on your interests and on the season when you travel and - as you can probably imagine - the possibilities are endless. But if it's your first trip to Italy and you want to see 'the musts', then I'd probably concentrate on the main cities - Rome (3 days), Florence (3 days), and Venice (2 days). In Rome, I'd probably just stay in the city - there's a lot to see. Take a look at this itinerary for some ideas. In Florence, take a look at these suggestions on what to do in a day. In addition, you can always take one or two day trips from Florence like this day trip that visits Siena, Pisa, and Tuscan countryside, and/or a day tour to Cinque Terre. In Venice, see this itinerary. In addition, you could take a (half)day trip to the nearby islands. Hope this helps.

Friday 11th of August 2023

Hello, Jurga. Your article is an absolute gem!!! I learned so much from it. I am planning a trip to Italy and i was going to follow your itinerary but we are only going for 12 days not 14. What do you recommend skipping? Thank you in advance

Hi Maya, that's a tough one since there is so much to see. You also didn't say when you are traveling. For example, in the winter you could skip some of the coastal areas/nature (e.g. Amalfi Coast from Rome on day 4, Tuscan countryside or Cinque Terre (days 5-6), or Lake Garda and Lake Como (days 11 and 14). In the warm season, the choice is much more difficult. Just see what interests you less and let it go. There is no way to see everything in Italy in 3-4 weeks, let alone 12 days, so you always have to make choices. Good luck!

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The Best of Italy: Ultimate Two Week Italy Itinerary (14 Days)

Ahh, the land of pizza, pasta, and gelato – what’s not to love about Italy? This boot-shaped country boasts so much to see, that it’s difficult to plan an itinerary for a limited amount of time. So, in an effort to take the guesswork out of it for others, I’ve put together this epic two week Italy itinerary for fourteen glorious days in Italy, now that I’ve visited multiple times. It hits all the main sights – Rome, Florence , and Venice – plus some extras so you can come back home seeing more than the bare minimum.

This guide (prices, links, and all other details!) was last updated in March/April 2024.

Now, I have to warn you. This two week Italy itinerary is super detailed . Like, how-the-hell-do-you-have-time-to-write-all-this detailed. And I did that on purpose. You can go to any old website to get a vague “two nights in here” and “one night here,” bare-bones itinerary for Italy. But those itineraries don’t tell you what to do in each place, or how to get from each city to city. You’d have to go look that up after. But not with this itinerary.

Basically, what I’m trying to say is: get ready for a long article! (About a 30 minute read.) You might definitely want to save this for later right now by bookmarking it or saving it on Pinterest, just in case you don’t finish all in one go . Then, grab a cuppa, sit back, and let’s get to it!

Pssst! Debating a shorter trip to Italy? Definitely skim through my detailed itineraries for ten days in Italy or one week in Italy .

The Perfect Two Week Itinerary

Let’s start off with an overview of this epic, fourteen day Italy itinerary, so you can have an idea what to expect.

If you’re the average traveler with limited vacation days, I suggest breaking it down like below. This way, you only need to use ten vacation days , but you get fourteen actual days in Italy.

What is the Best Time of Year to Visit Italy?

The absolute best time to visit Italy is definitely the shoulder seasons of April – May and September – October . This allows you to see everything in comfortable weather, but to avoid the extreme crowds (And heat! And prices!) of the summer. If you plan to swim, aim for September – October, so that the water has had all summer to get warm.

That being said, I’ve traveled to Italy in the middle of August and still had a wonderful time. So if July and August are the only time you have available, you’ll still have a great trip. Just come mentally prepared for the crowds.

Winter in Italy is generally warmer than winter in central Europe. However, I would avoid winter if possible for this itinerary. There are places that flood often during rain (Venice) and places that practically shut down out of peak season (Cinque Terre and the Amalfi Coast). If you can’t stand large crowds, I would also avoid Easter in Rome. Other than that, any time in Italy is a great time to visit Italy !

If you have more specific questions about your trip timing and what I think, definitely leave a comment at the bottom of this page. I’ll get back to you with my advice. Think of me like a free travel agent…!

Best Way to Get Around Italy?

One of my favorite things about Italy is how ridiculously easy it is to travel Italy without a car . This country gets a lot of slack for being inefficient and disorganized, but you have to admit, they do public transport just fine! This itinerary is completely car-free, relying solely on trains, buses, and ferries.

In my opinion, trains are the best way to travel Italy. This is especially true for your first time in the country. I do have dreams to one day complete a grand Italian road trip. But that is only because, after multiple trips, I now have places on my list that are remote and therefore easier to reach by car. All the more-typical destinations are much easier to visit without the hassle of Italian driving, filling up gas, finding and paying for parking, etc.

One very important tip for train travel in Italy is to always validate your ticket! Otherwise, you will be fined, and the fines ain’t cheap . (Like, truly. The fines are low-key high-key ridiculous.) How do you validate your train ticket in Italy? Simply stick the paper ticket into the machines before you enter the train. It’ll make a noise and time-stamp your ticket. These little validation machines are typically at the entrance to each platform. If you have trouble locating them, just ask a train station employee. If you buy your ticket online or via the mobile app – no need to stress!

In this itinerary, I include all the details and prices for each time you’ll use public transport to move around. I’ve got you covered!

Free Printable 2-Week Italy Itinerary E-Book

But once actually in Italy, you definitely don’t want to be walking around on your phone all trip trying to get to each next spot. So, I’ve made a printable, condensed version of this post with every important detail from this fourteen day Italy itinerary you’re about to read. Just download the PDF, print it double-sided (so four pages total), and you’re good to go for your trip. It even has a map! Click below to get it emailed to you.

(Finally) The Actual Two Week Itinerary for Italy

Beforehand, I just want to let you know you can do this itinerary in the order I have it or the reverse. Just look up flights and see which direction is cheaper. Also, at the very end of this page, I have a section on how to adjust this itinerary if you need to. Ready?!

Rome. The Eternal City. This place needs no introduction , since I’m sure you learned plenty about it in school. As the former capital of the Roman Empire and the current capital of Italy, Rome is a mix of old and new like you’ve never seen. Huge, crumbling ruins from 2000 years ago contrast against beeping Vespas zipping through the cobblestoned streets. Try to ignore the street vendors with no regard for personal space selling selfie sticks and whizzing gadgets, and I’m sure you’ll fall in love with Rome as I have.

How to Get to Rome

This is the start of your trip, so you’ll need to fly in. Rome has two airports, so be careful you fly into the correct one. The main international airport in Rome is Fiumicino (FCO) . This airport is the further out one. To get to the city center from FCO, you have two options.

• Option 1: Take the train. Follow signs in the airport to the train platform. From FCO, take the Leonardo Express train to Roma Termini train station. This costs €14 (or €40 if bought for a group of four!) and will take 30 minutes. The train departs every 15 minutes, so you shouldn’t need to wait too long. From Roma Termini, you can either walk to your accommodation, or use the Metro to take the subway if your accommodation is further away. Be very careful of pick-pocketers in this train station! Do not accept or ask help from anyone except official employees, and wear your backpack facing your front.
• Option 2: Take a taxi. Taxis from FCO into central Rome are a fixed fare of €50. Make sure you get into an official taxi (they’re white with a sign saying “TAXI” on top) at the taxi pickup line. They should accept card, and you can double check this as well as fare before getting in. This will take 30 minutes, just like the train.
• Option 3: Take a bus to Roma Termini train station. Terravision offers a €6 ticket, and the ride takes 45 minutes.

Rome’s other airport is Ciampino (CIA) . This smaller airport is actually slightly closer to central Rome. However, it is only used for budget airline flights within Europe, like RyanAir and EasyJet. If you’re flying here (or anywhere!) with RyanAir, definitely skim through my guide on how to not get ripped off ! Once again, you have two options on how to get to central Rome from CIA airport.

• Option 1: Take a bus to (right near) Roma Termini train station. There are multiple options you can explore here . Some include SITBusShuttle for €6 one-way, or Terravision for €6. This ride takes 40 minutes.
• Option 2: Take a taxi. Taxis from CIA into central Rome are a fixed fare of €31. Again, make sure you get into an official taxi at the taxi pickup line and confirm the fare before getting in. This ride takes 30 minutes.

What to Do in Rome (Three Days)

Three days in Rome is the minimum amount of time to “see everything.” Below is exactly how to see Rome in three days. Take it easy on day one , since it’s the day your flight gets in. But feel free to interchange days two and three as works best for you. If you get in way too late on day one, you can tack it onto day three.

Walking straight through this route as I have it below is 30 min (2km or 1.25 miles), just to give you an idea of total distance on day one. Start at whichever end is closer to you.

• Scalina Spagna: Otherwise known as the Spanish Steps, this beautiful staircase gets busy at night as a popular hang-out spot.
• Trevi Fountain: This is Rome’s largest and most-famous fountain. Prepare for major crowds, and start practicing major patience needed to get your perfect pic!
• Pantheon: Built in 120AD as a Roman (pagan) temple for all gods, it was transformed into a church in 609 AD. Still, everyone calls it the Pantheon, which means “honor all Gods” in Greek. Entry will set you back €5. You can purchase tickets in advance by visiting this site , typing “Pantheon” in the left-hand search bar, and clicking the result.
• Piazza Navona: I’m pretty sure this square is just popular because it’s beautiful! Lots of cafes line the edges of the piazza, which also has two impressive fountains, and a church in between them.
• Largo di Torre Argentina: This is where Roman senators assassinated Emperor Julius Caesar by stabbing him 23 times (dramatic much?) to death in 44 BC.
• Colosseum: Gladiators. Need I even say more?! Though it is now in ruins, back in its heyday, this thing sat 50,000 guests and even had retractable shades. Tickets are €16 for this plus the next two sites, plus €2 if purchased online from the official si te . This price quote is the highest price, but those 25 years and younger get discounts !
• Roman Forum: These are the ruins of numerous important government buildings during the ancient Roman Empire. It’s so cool walking around, seeing how huge the ruins are, and wondering how it must have been back then – almost 2000 years ago!
• Palatine Hill: This is where all the cool kids lived during the Roman Empire – the aristocrats and emperors and all that jazz.
• Arch of Constantine: This arc, built in 302 AD and the largest surviving one of its kind, is right outside the Colosseum.
• Via dei Fori Imeriali: This street is my favorite part of Rome, especially at dusk! You can look down on the Roman Forum from above on one side and view other incredible ruins on the other. It connects the Colosseum to the next attraction below.
• Vittoriano: This huge, marble building almost doesn’t fit in with its ancient surroundings.  But I love it, nevertheless. It is a memorial to Victor Emmanuel II, the first king of the united Italy as we know it today.
• Vatican City: Technically, this area isn’t Italy! It’s its own country – the smallest country in the world – and it’s ruled by the Catholic Pope. There are basically three things to see while here: St. Peter’s Square , St. Peter’s Basilica , and the Vatican Museums . St. Peter’s Basilica is free to enter, but dress code is very strict. Make sure your shoulders and knees are covered. This goes for all genders and ages. There is a slow moving-crowd-slash-line to get in, but I found it moved quickly enough when I went. Once in the basilica, you can climb up to the dome for iconic views. To the right from the entrance, there should be a “Cupola” sign. Follow the sign until at the ticket office, where you can purchase a ticket to either climb the whole way for €8 or one to take an elevator partway up for €10. As far as I know, you can only buy tickets (that aren’t with a guide) in person. The Vatican Museums house the world-famous Sistine Chapel. You’ll pay €20 for entry, plus a €5 online booking fee if you book in advance on the official site , which I highly recommend you do. Entry to the Museums is free on the last Sunday of every month. Seeing Vatican City should take up a whole morning.
• Castel Sant’Angelo: Emperor Hadrian originally commissioned this as a mausoleum for himself and his family, but it’s since been used as a fortress, castle, and currently a museum. I didn’t enter the museum, so I can’t recommend entering, but I think this castle over the river just looks so cool!
• Wander: Explore on your own! Get lost! You’ve checked off all the “can’t miss” things everyone else does, but who wants their trip to be just the same as everyone else’s? If you just run around ticking off attractions, I’m not sure you’ll like Rome. But wandering it’s less-crowded streets, strolling along the river, popping into a random church – these are the things that will leave you loving Rome.

What to Eat in Rome

Food in Italy is good just about everywhere. But each region is known for something different , so why not try all your favorite Italian dishes (and some new ones!) right in the specific regions or cities that they were invented? So throughout this guide, I will be listing and explaining some must-try foods from each place you will be overnight-ing. To start, here are some traditional Roman foods to keep an eye for while in Rome!

• Spaghetti alla Carbonara : This famous Roman dish actually arrived on the Italian scene relatively recently, in the mid-1900s. It is made by mixing whisked eggs and grated cheese into cooked spaghetti, then adding in cured pork, and topping with black pepper and, of course, some more cheese.
• Cacio e pepe : The name of this Roman dish translates literally into “cheese and pepper,” and that’s a pretty good description of what it is!
• Pizza al taglio : While pizza itself was not invented in Rome (don’t worry – you’ll stop by the city where it was born later on in this Italy itinerary!), pizza by the slice, or pizza al taglio, was. But it looks far different to the triangularly-sliced pizza you may be used to back home. Here, the slices are rectangular, and they often come piled high with meats and/or vegetables. It’s considered street food, so it makes the perfect quick lunch if you don’t have enough time for a sit-down meal as you explore the attractions in Rome.
• Supplì : These are another perfect Roman snack to grab while on the go! They are fried, breaded balls of seasoned rice with cheese and sometimes meat inside (essentially, croquettes).
• Bruschetta : This beloved Italian appetizer does not hail from Rome itself, but its origins date back to the Roman Empire, or perhaps even the Etruscans who preceded it. Regardless, as the capital of the Roman Empire, Rome makes a pretty good place to try some authentic bruschetta alla Romana, which is grilled bread rubbed with garlic and topped with olive oil. Of course, no one will blame you if you get the version with tomatoes as well!

Pompeii was an ancient Roman city, famous now for coming to its demise after a tragic volcano eruption . The city, along with nearby Herculaneum, was preserved under all the ash. It has since been excavated, which allows visitors to see a frozen-in-time snapshot of Roman civilization almost 2000 years back!

How to Get to Pompeii from Rome

First, take an early train from Roma Termini train station to Napoli Centrale train station . This takes either one, two, or three hours, depending on what type of train you take! Naturally, the costs are different, too. If you are buying a ticket for the next morning, you can expect to pay €13 for a 3-hour Regional train, €27 for a 2-hour Intercity train, or €48 for a 1-hour Frecciarossa train. If you are buying one month out, the prices for the faster trains drop to €20 for a 2-hour Intercity train, or €25 for a 1-hour Frecciarossa train. And if you buy three months out, the 2-hour Intercity train drops to €15.

Moral of the story? Always buy your long-distance train tickets online as soon as you know your schedule to save money in Italy! If you are taking regional trains, just buy them at the station on the day of, to allow flexibility in case plans change.

OK! So once you arrive at Napoli Centrale, follow signs to the connected underground station called Napoli Piazza Garibaldi . From here, take the Circumvesuviana train for 40 minutes to Pompeii Scavi Station for around €4. (This part was honestly very confusing for me! I accidently went to the Metro 2 area instead of the Circumvesuviana area. So my tip to you is to ignore the Metro 2 signs, and ask for help from staff if you need to.)

At Pompeii Scavi train station, there is a luggage storage service. Drop your bags off here for around €8 per bag. From here, it’s a 5-minute walk to the Pompeii site.

What to Do in Pompeii (Half Day)

The only thing to do in Pompeii is… tour Pompeii ! Entrance to this historical site costs €18, and you should plan to spend 2 – 3 hours here. You can buy tickets at the gate in person or online (for an additional €1 fee) at the official ticket site . Entry is free the first Sunday of every month. You can also check opening hours for the month you are visiting on the site.

If there is any place in all of Italy where you need a tour , it is Pompeii! Otherwise, you’re really just staring at a lot of old rocks with no idea why. There are a few options on how to actually know what’s going on in Pompeii.

• You can join a tour group by paying around €12 in cash on the day of. Guides hang out near the entrance, and the ones certified by the region of Campania have official ID badges. A private guided tour will, of course, cost more.
• You can buy an official audio guide set at the Porta Marina entrance for around €8 and tour at your own pace.
• You can get an audio tour for free by downloading Rick Steve’s audio guide for Pompeii. I did the live tour while in Pompeii, but I’ve used his guides for other Italian sites, and I was satisfied! It’s a great way to save money while still getting info.

While Pompeii is the more-popular site due to its much larger size, Herculaneum is actually the site that is better preserved. Personally, I only toured Pompeii, due to time constraints. But if you are a history buff and don’t mind a busy day, consider trying to squeeze both in!

Sorrento is a perfectly charming place, and it boasts seriously beautiful views over the Bay of Naples and Mt Vesuvius (that really destructive volcano way back when). However, its purpose in this itinerary is as a convenient jumping-off point for the Pompeii-Amalfi Coast-Capri area. I recommend using this as a base for the three nights to limit dragging your luggage around. However, if you prefer to be in the heart of the action, you can head straight to Positano (or Amalfi) after getting to Sorrento from Pompeii.

How to Get to Sorrento from Pompeii

Head back to Pompeii Scavi train station and pick up the bags you dropped off. Then, hop back on the same Circumvesuviana train route and ride for 30 minutes and around €3 to Sorrento. It’s the very last stop on the route , so don’t worry about missing it!

What to Do in Sorrento (Half Day)

If you decide to stay in Sorrento overnight or even use it as a base, I recommend simply walking around town at your leisure. It’s a super cute place to window shop (or actually shop), eat, and enjoy views of the Bay of Naples and Mt Vesuvius.

Amalfi Coast

I know all of Italy is stunning, but get ready for some insane beauty over the next few days exploring the Amalfi Coast! Unsurprisingly, this area is filled with lots of couples and is popular as a honeymoon destination. Though the area is named after the town of Amalfi, it is the town of Positano that truly steals the show. This area is a really special place, and it’s impressive to think about how the Italians built the curvy roads and quintesential houses into the steep cliffs.

How to Get to the Amalfi Coast from Sorrento

There are a few options on how to do this. Two of them include an insanely curvy and crowded two-lane road, so keep that in mind as you decide, especially if you’re prone to motion sickness.

• Option 1: Take the bus. This is the most budget-friendly option. Board the SITA bus 5070 from Sorrento (map below for exactly where). It takes either one hour to Positano or 1.5 – 2 hours to Amalfi. Unfortunately, this bus is crazy crowded , even in shoulder months. You’re not guaranteed a seat, so you might have to stand. I actually had to sit on the floor of the bus and couldn’t even enjoy the views approaching Positano *tear*. If you do snag a seat, sit on the right side for better views. Bus tickets cost €10 for 24 hours unlimited rides and are sold at “tabaccherie” (cigarette shops) or newspaper stands in every town on the route. They can’t be purchased on board the bus! I recommend buying yours in Sorrento at the ticket booth at the Circumvesuviana station, since you’ll already pass through here after Pompeii. You can buy them ahead, but the 24-hours starts once you board the bus and validate your ticket. Check out the bus schedule here .

• Option 2: Take the ferry. This is definitely the most beautiful way to pull up to each town. From Sorrento, this is 40 minutes and €18 one-way to Positano and 1 hour and €19 one-way to Amalfi. Though it won’t happen often, ferries get cancelled if sea conditions are too rough, so allow some flexibility in your plans. Below is a map of the ferry station in Sorrento. You can’t tell from the map, but it requires walking down a staircase . Check out the ferry schedules here .

• Option 3: Hire a private car. This is not a cheap option, but might be worth it with a large enough group. You’ll have to search for price quotes online depending on the car size, company, and pick up and drop off locations. But as an idea, a private transfer from Rome to Positano or Amalfi might cost around €500. If you do hire a private car, I recommend including a stop in Pompeii between Rome and the Amalfi Coast. That way, you’re saving a good amount of hassle between all the train transfers, luggage holding, and buses!

What to Do in the Amalfi Coast (Two Days)

These days are totally interchangeable however you please. There aren’t a lot of “attractions,” per se, in the Amalfi Coast. The main thing to do is to just take in the beauty, whether by shopping in the tourist-geared shops, eating with a view, or taking a swim. You really can’t go wrong! But, if you like to have a plan, I recommend you split two days in the Amalfi Coast like below.

• Positano:  This unreal village is the star of the whole area. You definitely want to get here earlier rather than later, if you can, to avoid midday crowds. For the best view, splurge on a meal at Le Sirenuse Hotel’s La Sponda Restaurant .
• The beach: After exploring during the morning, cool off from the midday heat by taking a swim. The easiest option would be the main beach right in front of the town, Marina Grande beach. If you have your own ride or are willing to bus back and forth 35 minutes each way, check out Fiordo di Furore beach. These two beaches are the most insta-famous ones in the area, but there are many more!
• Amalfi: This is the town after which the area is named. It boasts a beautiful church, the Amalfi Cathedral, which you can enter for €3. It’s actually pretty cool inside, but the exterior is the main show-stealer, in my opinion!
• The Path of the Gods: I didn’t get to do this, but I really wanted to and had planned to! This hike between Amalfi and Positano takes you along the very top of the cliffs and is supposed to be ahhhmazing. Just Google “Sentiero degli Dei” and follow the route. It starts in Bomerano, which you can reach by SITA bus 5080 from Amalfi. It ends in Nocelle, the upper part of Positano. I definitely recommend doing it this direction, since it’s all downhill, and you’ll get better views. Definitely check out the official page for more deets if you’re interested.

• Ravello: This tiny little village high up in the mountains has the area’s most famous villa – Villa Rufolo . Entry costs €8, and you can take the SITA bus 5110 from Amalfi. The ride takes 30 minutes.

What to Eat in the Amalfi Coast (and Nearby)

These are some traditional Italian foods from the Amalfi Coast and Naples.

• Mozzarella di Bufala : This famous Italian cheese is made from the milk of the Italian water buffalo, instead of milk from cows, like mozzarella without the “di bufala” is. It hails from the region of Campania (the region where Naples, the Amalfi Coast, and Capri are), but especially Salerno, a city just to the east of the Amalfi Coast. A great way to try this item would be in a caprese!
• Lemoncello : You will find this sweet, lemon liquor practically everywhere you look upon arriving in the Amalfi Coast.
• Pasta al Limone : With all the lemons in this area, it’s no surprise they found their way into the pasta dishes as well. This creamy dish with cheese and lemon is so unique and a must try when in the area.
• Anything Seafood : Since this area hugs the coast, get your fill of fresh seafood pasta dishes while in this region!
• Pizza : The birthplace of pizza is Naples, and while you won’t have time to stop for a bite when transferring from Rome to Pompeii, you might have time when transferring from Capri to Florence (covered in the next section of this itinerary). If not, the Amalfi Coast was part of the former Kingdom of Naples, so it’s the next best place to try the Italian staple. Authentic Neapolitan pizza is made in a wood oven (this part is crucial!) with only the simple ingredients of dough, tomatoes, mozzarella, olive oil, and a couple fresh basil leaves.

The celebrity-favorite island of Capri makes for the perfect final day in south Italy before your itinerary takes you up north. It’s known for yacht-studded waters, glowingly-blue grottos, and upscale shopping. Maybe just reading this hurt your bank account a little bit… but not to worry! I’ve got you covered with how to visit Capri on a reasonable budget.

How to Get to Capri from the Amalfi Coast

The only way to get to Capri is by boat (it’s an island – duh!). Ferries will be from Sorrento, from Positano, and from Amalfi. Expect €25.50 for a 50-minute ride from Amalfi, and less from the other two.

You’ll need to drop your bags off in storage while you explore.

You should be able to either near the main docks in Marina Grande on Via C. Colombo, to the left of Bar Grotta Azzurra, at a souvenir shop with a “deposito bagaglio left-luggage” sign above the door… or under the funicular station, past the signs for “toilette,” along the tunnel part of Via Acquaviva. This was my plan when I did this trip, but I couldn’t locate either storage place!

Luckily, an Italian waiter came to my rescue and offered to hold our bags in the restaurant all day if we ate at his place. Honestly, I’m sure you would have no trouble arranging the same.

But if you want to be more prepared, another baggage storage option (which I haven’t tried) includes Bounce . You can book in advance online for €5 a day. Just search “Marina Grande, Capri” and select an available location in the Marina Grande harbor.

What to Do in Capri (Half Day)

There is so much to do in Capri that you’d have trouble fitting it all into a single day, let alone a half day. So you’ll have to pick and choose what interests you most from the below . The island’s official site actually has a pretty good itinerary you can follow, too.

• Marina Grande: No need to even add this to your list. You’ll inevitably walk by this colorful harbor-front area after disembarking the ferry.
• Boat tour around the island: This is the best way to truly appreciate Capri’s magnificent cliffs. You’ll also go past Faragolioni , that ultra-iconic arch in the water. Boat tours can also include an add-on of the Blue Grotto. Without the Blue Grotto, expect €21 for an hour-long tour.
• Blue Grotto: This cave is probably the most famous attraction in Capri! Unfortunately though, it’s a bit of a time-suck because of that. We were told we would have to wait on a small, bobbing rowboat for an hour before our turn to enter, so we skipped the grotto, even though our boat tour included it. The only way to avoid the long wait is to be the first ones out, but the best time for viewing is noon – 2pm, so it’s quite the dilemma. Tours departing from Marina Grande cost €18.
• Piazzetta: This is the island’s most famous square. Be sure to stroll down the Via Camerelle while in the area.
• Anacapri: The island of Capri actually has two towns; Capri and Anacapri. Anacapri is less crowded than Capri, and it has more artisanal shops, rather than just high-end boutiques. While here, definitely pass Piazza Vittoria , the main square. You can also ride the chairlift 12 minutes to Mount Solaro for a view (€12), or walk there in 30 minutes.
• Villa San Michele: Entry costs €10 for some spectacular views.
• Gardens of Augustus: From here, you get that classic Capri viewpoint of the Faraglioni . Entry only costs €1.50!
• Marina Picola: If you’d rather spend your half-day relaxing at the beach instead of running around the island, this beach is a classic.

As the birthplace of the European Renaissance , Florence is known for all things art. It houses world-famous masterpieces, such as the David statue by Michelangelo and The Birth of Venus painting by Botticelli. Personally, I was expecting a bit more from Florence than I got, since everyone and their mothers raaave about it in comparison to Rome. (For the record, I’m staunchly team Rome!) But maybe I’m just not into art enough? That being said, though, it’s definitely still a can’t-miss Italian destination with plenty to do.

How to Get to Florence from Capri

(Psst: You’ll actually be doing this transfer from Capri to Florence on the same day that you visited Capri. Then, the next day, you’ll wake up in Florence to start your two full days there. Just scroll back up to the itinerary summary at the top of this page if you’re confused!)

First, get back to Napopli Centrale from Capri . I recommend taking the ferry directly to Naples from Capri. This will be 1 hour 25 minutes for €12.30 or around an hour for €20 – €25. Then, take a taxi from the ferry station in Naples to Napoli Centrale. When I did this, the taxi cost me €20. I also stopped and picked up a pizza to go while in central Naples. After all, Naples is the exact birthplace of pizza! How could I not?!

Alternatively, you can take a ferry from Capri to Sorrento. This takes 20 or 30 minutes minutes and costs around €21. Then, go up those stairs to the Sorrento Circumvesuviana station, and ride the Circumvesuviana train to Napoli Piazza Garibaldi for 70 minutes and around €4. From there, walk the underground connection to Napoli Centrale. This is a little more hassle – hence why I recommend the ferry straight to Naples – but it’s cheaper.

Either way, once in Napoli Centrale train station, take a direct, 3-hour train to Firenze S. M. Novella train station . Since this is a long distance, don’t even think about taking one of the Regional or Intercity trains ! These will set you back 2 – 4.5 hours. Trust me – just book the Frecciarossa train for this route as soon as you have your dates to get the cheapest price you can. As an idea, it will cost €86 if you buy the day before, €35 – €55 (depending on departure time) if you buy two weeks in advance.

What to Do in Florence (Two Days)

Many people recommend considering the Firenze Card , which covers a lot of attractions in the city. For two days in Florence (or even three days in Florence), the card is not worth it. Instead, I recommend purchasing the Brunelleschi Pass . This grants entry into the Duomo, a climb to the dome of the Duomo (the Cupola), a climb to the bell tower (the Campanile), entry into the baptistery, entry into the Duomo museum, and entry into the crypt beneath the church. It costs €30 if bought on the official website .

Now that that bit’s out of the way, here’s everything to do in Florence in two days! I haven’t split it out into separate days here, because I think it’s better if you decide . Do you like to visit one museum a day, or have one single day devoted to all the museums? Do you want to avoid climbing stairs twice in the same day, or do you not care? Do you prefer a viewpoint for sunset, sunrise, or can’t be bothered? These are the things that will determine what you do each day, so I can’t recommend that for you. But don’t worry – most sights in Florence are rather compactly located, so planning a route shouldn’t be an issue!

* Items with an asterisk are totally skip-able if you’re not interested, but I’ve included them since they’re included in the ticket I recommended above. If you want a more-detailed breakdown of the below, plus pictures, check out my full guide on everything to do in Florence .

• Basilica di Santa Maria del Fiore (aka, the Duomo): It’s the third largest church in the world, was instrumental in the Renaissance, and is the symbol of Florence. Entry is free, but prepare for a massive line at least an hour long.
• Cupola: Bruneschelli’s Dome, named after the architect who designed it, is actually the most impressive part of the entire church. Architecturally, it was the first of its kind. He literally had to invent new tools and architectural systems to do it! Definitely climb up the steps for the view from the top. You’ll have to select a specific time slot, though, when you buy your ticket! Otherwise, you will be turned away and asked to return.
• Campanile di Giotto: Yes you already climbed up the cupola, but there’s another viewpoint! This time, the view is the cupola itself.
• Battistero di San Giovanni: This is the building right across the main cathedral. The Byzantine-like mosaic inside was actually pretty cool in contrast to all the typical-Renaissance paintings. Everyone will be snapping pics of the gold doors outside, but those are copies. The real ones are in the Duomo Museum!
• Duomo Museum*: Since you already paid, it might be worth a quick visit. It will help you understand why all this Duomo stuff in Florence is such a big deal!
• Crypt of Santa Reparata*: This is included in the Duomo combo ticket, which was the only reason I saw it. But once I got there, it was actually much more than I expected! It’s basically church ruins from 405AD inside the main church. The unfortunate thing about the crypt is that you have to wait in the same line as for the free Duomo entry. So definitely time these two activities together!
• Piazza della Repubblica: One of the main squares in Florence.
• Piazza della Signoria: This square has a lot going on! The best part is definitely the Loggia dei Lanzi . It’s basically a free, open-air museum of dramatic sculptures that really should be in one of the museums. (Like really though, I’m super surprised these are just out there!) Also in this square is a copy of the David statue , for those of you who don’t pay to see the real thang.
• Palazzo Vecchio: I didn’t enter except for the free courtyard. But apparently it’s supposed to have a great view of the Duomo.
• Ponte Vecchio: This iconic bridge has become synonymous with Florence itself! It was originally a passageway so the Medicis (a super rich family that basically made Florence….well, Florence) didn’t have to walk with the commoners on their commutes from their palace. Since then, shops have been added and create the look it has today. Prepare for major crowds!
• Piazzale Michelangelo: The best viewpoint in all of Florence – hands down! I recommend trying to time your visit with sunset, but it’s gorgeous anytime. (I went three times in my visit….so I would know.) It requires an uphill walk and is the furthest out you’ll get from the city center. So make the trek worth it! Bring some snacks and hangout for a while like everyone else does.
• Accademia Gallery: Unfortunately, the only reason to enter this gallery is for one piece of art. The David. Don’t at me, art fanatics. You decide if that’s worth it for you, but y’all know me! I have such FOMO that I had to pay €16 and see for myself. Pro-tip: avoid the lines AND the €4 online skip-the-line fee to book by visiting on one of the days they allow night visits! I got in lickety-split! No one really knows about it, which is why it’s so empty, so let’s try not to tell too many people? *wink* Confirm the night time hours, or book online, here .
• Uffizi Gallery: Uffizi actually means “offices” in Italian, which makes sense, because this building used to be the Medici’s offices. Now, it’s a museum, and a world-famous one at that! Its most-famous art piece is the Birth of Venus painting. Entry costs €25, plus €4 for the skip-the-line online booking fee on the official site . Everything I read beforehand swore up and down that wait times are upwards of three hours. But when I went (mid September, early afternoon) there was no line in sight.
• San Lorenzo Market: This is Florence’s most-famous market. Stop by here to shop leather and eat in the indoor food stalls.
• Santa Croce: I didn’t enter this church, since admission was not free, but I do think it’s in a picturesque area and warrants passing by!
• Palazzo Pitti: Normally, palace equals royalty…not in Florence! This palace belonged to the Medicis (shocker). I personally have seen way too many European palaces at this point. So I forwent paying the €16 entry fee (€22 if seeing the gardens as well) and only observed from outside. But I did regret maybe not having arrived earlier in the day than I did, to buy just a Boboli Gardens ticket (€10)! You can purchase online in advance from the official site (the same site as for the Uffizi) for an additional €3 fee, but it was not very crowded at all when I was there.

What to Eat in Florence

These are some Florentine and general Tuscan traditional dishes to try while in Florence.

• Bistecca alla Fiorentina : You will have no trouble finding Florentine-style beefsteak to try in a restaurant in Florence. Keep in mind that since it’s a pretty thick cut, getting the inside well done would be difficult without ruining the outside of the steak!
• Gelato : Yep – everyone’s favorite frozen Italian dessert made from milk, cream, and sugar is from the city of Florence! Now, that absolutely does not mean you should wait until arriving in Florence to try authentic gelato (after all, if you’re not having gelato at least once a day, are you really even on vacation in Italy?). But, maybe it does mean taking a gelato making class at the Carpigiani Gelato Museum ?
• Biscotti : These dry, crunchy, oblong-shaped almond cookies are traditionally called cantucci. They originally come from the Tuscan city of Prato, which sits just north of Florence.
• Crostini Neri : Also known by the names of crostini di fegatini and crostini Toscani, this typical Tuscan appetizer is toasted bread with a chicken liver paste spread atop.

Is there anything more quintessential Italy than the image of the leaning tower of Pisa? It’s funny how such a famous Italian landmark is from the most random of Italian cities! Luckily, Pisa is a necessary transfer station on the route between Florence and the Cinque Terre, so you lose almost no time making a couple-hour stop to get out of the station, snap your cliché photographs, and get right back on your way .

How to Get to Pisa from Florence

Take a regional train from Firenze S. M. Novella train station to Pisa Centrale train station . This is a 1.25 hour ride and costs €9.30. Once at the train station, head to the luggage storage in the station, and drop off your things for €5 per bag. Check out the storage website . Two other storage options near (but not inside) the station include this and this .

What to Do in Pisa (Half Day)

Personally, because this two week Italy itinerary is so jam packed, I recommend you head straight to the leaning tower, snap your pics, and head back to the train . The walk is about 30 minutes each way, plus I expect you’ll spend about 20 – 30 minutes trying to get that perfect leaning picture. So budget 1.5 – 2 hours for your stop in Pisa. The reason I recommend this is so that you can have as much time as possible in Cinque Terre.

But , if you want more than just a photo, there actually are a decent amount of things to do in Pisa.

• Climb the leaning tower: It’ll cost you €20 and you’ll need to choose a time-slot! The line looked long as I passed by.
• Go inside the Duomo (for free!): You still have to get a ticket, though, and time slots do book out. Do this at the building with all the signs, right by the leaning tower.
• Visit the Baptistery: I didn’t enter, but pictures do look very pretty! This alone will set you back €7, or you can pay €10 or €27 for a four or five-monument combo, respectively. See the official website to understand!
• Chiesa di Santa Maria della Spina: I actually know nothing interesting about this church, but I think it looks super cool. Try to walk by it by using Ponte Solferino bridge on your way back to the train.

Also, Pisa is a really pretty Tuscan city! So there’s absolutely no harm in sticking around longer and actually seeing the city of Pisa. You can just budget extra time to walk around before heading back on the train, or even stop for a meal.

Cinque Terre

Cinque Terre translates literally into the “five lands” in Italian, representing the five villages that make it up. The villages are Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore . I highly recommend not choosing Corniglia as a base, only because there is a 350+ step staircase from its train station to the actual village. (Psst: Check out my guide on alternative, cheaper Cinque Terre bases .)

How to Get to Cinque Terre from Pisa

Take a regional train from Pisa Centrale train station to your preferred Cinque Terre village of choice. All journeys will require a train transfer at La Spezia Cenrale station. You might consider using La Spezia as your base, since it might be cheaper, saves some train hassle , and is included in the Cinque Terre Rail Pass (more on the pass later on – don’t worry!). Train times and prices are below.

• Pisa to La Spezia: 75 minutes and €8.40
• Pisa to Riomaggiore (the southern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €9.45
• Pisa to Monterosso (the northern-most village): 1.5 – 2 hours, because it requires a transfer at La Spezia, and €10 – €12, depending on the time

What to Do in Cinque Terre (One & a Half days)

The main things to do in Cinque Terre are visit all five villages and hike between them. Unfortunately, more than half of the famous trail is closed for reconstruction after an avalanche. Currently, the only open part of this specific trail is from Monterosso to Vernazza and from Vernazza to Corniglia, but you can check here for updates.

To hike it, you’ll need to pay (unless it’s winter when there’s apparently no one checking). For this itinerary, get the two-day €33 tr ails and train card . This grants you unlimited access to the paid trails and unlimited train travel between Levanto and La Spezia. It also allows you free public toilet usage in the villages and free WiFi at the village train stations. You can buy in person at any train station or information desk.

Besides the hikes, there is no real to-do list of attractions for each village, so just stroll around at your leisure, swim when you feel like it, and enjoy the beauty! If you’re looking to get off the beaten path (literally), I wrote about the free Cinque Terre hikes you can do instead of the paid ones. The views are better, too, in my opinion!

Day One (Half Day)

Riomaggiore and Manarola: After settling in from Pisa, I recommend splitting the remainder of this day relaxing and hanging out in Riomaggiore and Manarola. Try to be in Manarola for sunset , to get that cliché Instagram view. That café you see everyone take their pics at? It’s called Nessun Dorma .

Hike Monterosso to Vernazza to Corniglia: Finish up the last three villages, and get some hiking in! You can do the hike either direction you please. I highly recommend hiking with your swimsuit underneath , because there is nothing you’ll want to do more after a hike, than jump into that water!

What to Eat in the Cinque Terre

These are some yummy traditional foods to try while exploring the Cinque Terre.

• Pesto alla Genovese : This beloved pasta sauce made from crushed garlic, pine nuts, salt, basil leaves, olive oil, and cheese hails from the region of Liguria (the region where the Cinque Terre are located). More specifically, it comes from Genoa, as the name implies. But anywhere in Liguria is an authentic place to try a pesto dish!
• Focaccia : A warm slice of this fluffy, oily goodness makes for the perfect snack while zipping from village to village, or even a quick breakfast alongside some coffee before heading out for the day. It is made from flour, water, olive oil, salt, and rosemary, so it’s a great option for vegans as well.
• Farinata : Another delicious vegan food to try, farinata is a flat pancake-or-crepe-like food made from chickpea flour. You can pick up a slice as a snack on the go.
• White wine : Especially if you hike the trails between the Cinque Terre, you’ll notice a lot of white grape vineyards scaling the cliffs of this area. So it’s no surprise Liguria is known for its white wines!

Milan is known as fashion capital of Italy …and honestly not much else! It’s a city many aren’t enthused by, and I wouldn’t recommend it if you only have one week in Italy . But for a two week Italy itinerary, I really do think it’s appropriate. It’s home to the world-famous Last Supper painting, an iconic Duomo…and not a whole lot else! Which, in my opinion, makes a perfect, not-too-hectic stop towards the end of your epic, two week tour di Italia.

How to Get to Milan from Cinque Terre

Take a train from La Spezia Centrale to Milano Centrale . I recommend taking the direct, 3.5 hour InterCity train. Expect to pay around €20 if you book a month out, around €25 if you book two weeks out, and around €29 the day of.

What to Do in Milan (One Day)

• See the Last Supper : Book this is as soon as you can! Tickets to see Leonardo Da Vinci’s masterpiece are available on the official site three-ish months in advance. They cost €15, plus a €2 online fee, and allow you a 15-minute viewing of the famous painting in the Santa Maria delle Grazie church . On the first Sunday of every month, tickets are free, so all you would pay is the online booking fee. Unfortunately, official tickets tend to get scooped up on the first day they’re available by tour operators. So if you don’t get a ticket yourself, the only other way is to book a guided tour. These run for around €40 and above.
• Go to the Roof of the Duomo: Entrance to the roof costs €14 on foot or €16 by elevator, but €20 and €25 respectively if you add entry into the church itself. You can purchase tickets in advance on the official site . Remember to be dressed modestly to be able to enter!
• Galleria Vittorio Emanuele II: It’s to the left of the Duomo, and it’s just way too glamorous not to walk through! It’s also Italy’s oldest active shopping gallery. If you fancy a rooftop view of the Duomo, apparently you can take a €12 elevator up to the top.
• Navigli Lombardi: This area of a couple canals is super cute to walk around or eat in the evening!
• Starbucks Reserve Roastery: I’m not even a coffee fanatic, but I just had to pop my head into the first Starbucks in Italy. Definitely the bougiest Starbucks I’ve ever seen.

What to Eat in Milan

• Risotto alla Milanese : No trip to Milan is complete without trying this famous dish! Its yellow color comes from the saffron used, which just so happens to be the world’s most expensive spice – more expensive than gold.
• Cotoletta alla Milanese : This veal cutlet is similar to the Wiener Schnitzel you might be familiar with from Austria, but it is cooked and served with the bone in.
• Panettone : This world-famous Italian sweet bread dotted with candied fruits and raisins hails from the city of Milan. It is especially popular during Christmas and New Years.

I was worried before getting to Venice that I would hate it. So many people complain about its crowds, its mosquitos, its flooding… The list of negatives seems endless! But after just my first hours in Venice, I really felt like people give it a bad rep. Yes it is way too crowded in the center. But honestly, the crowds are completely justified.

I would describe Venice as: so beautiful, it’s unreal . And can you really blame crowds for flocking to something like that? Try to knock out all the main sights at less-crowded hours. Then spend the middle of the day exploring the rest of the city, where it’s much, much less crowded, but just as beautiful. Do that, and you might just end up liking it!

How to Get to Venice from Milan

Take a train from Milano Centrale to Venezia Santa Lucia . I recommend taking the direct, 2.5 hour Frecciarosssa train if you book a month in advance, when it’s around €29 for the morning train. If you buy closer to the departure date, it’ll be €52. Otherwise, the regional train (the type that costs the same no matter when you buy it) is €21.95, and the transfer in Verona only adds an hour more to your journey.

Once in Venice, you’ll want a vaporetto pass . Trust me – you don’t want to be lugging bags up and down those bridges! If you are 29 years-old or under, I highly recommend buying the Rolling Venice Pass . I wish I knew about it earlier! It costs €6, but in order to buy it, you must also purchase (at minimum) an unlimited three-day vaporetto pass for €27. With the pass, you also get discounts on many attractions , like a €12 discount entrance to the Doge’s Palace! The one-day transport pass alone costs €20, and the two-day pass costs €30, so getting the Rolling Pass quickly pays for itself. You can buy these passes online or in person once in Venice.

What to Do in Venice (Two Days)

Assuming you take a reasonably-timed morning train from Milan, you can get to Venice in the late morning. Add some time for navigating the canals to locate your accommodation, and you basically have a little under two days in Venice. (If that sounds like too little, you can remove the Burano and Murano day trip from the suggested itinerary below. But honestly, you’ll be fine!) If you want a more detailed walkthrough plus photographs of each of the below, check out my article on best things to do in Venice .

• Piazza San Marco: This main square is where most of the (tourist) action is. Firstly, there’s the Basilica San Marco . It’s €3 to enter, but there can be a very long line most hours of the day, so be careful what time you go. I went in the middle of the day when I saw it was shorter, and was in and out in 10 minutes! If you’d rather not risk it, you can book your time slot online during high season for a €3 booking fee. Large bags are not allowed inside, but there’s luggage storage nearby that the basilica will tell you to use. Across from the basilica is the Campanile (the bell tower). You can take the elevator up it for €10 if purchasing in person, or pay a €2 booking fee to reserve online in advance . If you want to skip the line, it’s the same website as the basilica. There’s also the Doge’s Palace . Entry is €25 if booked over 30 days prior, but only €13 with the 29-year-old Venice Rolling Card I mentioned above. See the official site for more deets.
• Bridge of Sighs: Walk around the Doge’s Palace, making a left turn around the corner along the water. From the first bridge, you’ll see the famous Bridge of Sighs. It’s named so because it connects to the prisons, and prisoners sighed while taking one last look over beautiful Venice as they walked through the bridge to their dooms.
• Rialto Bridge: If you haven’t figured out by now, Venice has a lot of cool bridges!
• Accademia Bridge: This was my favorite bridge , because it has such an amazing view.
• Take a half-day trip to Burano and Murano: Honestly, I did find this a little overrated, but maybe I’m just bitter because I got bad weather? I have an in-depth guide on how to visit the islands from Venice , as well as what each island is all about.
• Fondaco dei Tedeschi: This shopping center has free rooftop views of Venice, but you’ll need to book in advance (I recommend at least a day or two prior to get your ideal time slot). It’s located right at the edge of the Rialto Bridge on Calle del Fontego .
• The Grand Canal: The obvious way to float around Venice is on a Gondola. This will set you back €80 per gondola (six people max) in the daytime, or €100 sunset and later. Prices are fixed, so check current gondola prices , and don’t let anyone overcharge you. Alternatively, you can ride the vaporetto between San Marco and the train station, which is free since the vaporetto pass for the Burano and Murano day trip is still valid! I reeeeally recommend timing this during sunset. It’s SO pretty (and a lot less hectic).

What to Eat in Venice

These are some Italian favorites to try that come right from either Venice itself or the Veneto region.

• Tiramisu : This beloved Italian dessert made from coffee-dipped ladyfingers, whip, sugar, mascarpone cheese, and cocoa is not from Venice itself, but rather from the nearby city of Treviso to its north. Nevertheless, anywhere in the region of Veneto is an “authentic” place to try this yummy sweet.
• Risotto al nero di seppia : Some may find the black color intriguing, while others may find it offputting. Either way, squid ink risotto is a must try while in Venice!
• Aperol Spritz : Also called a Spritz Veneziano, you’re sure to spot this bright orange drink all throughout your two week Italy vacation. But this cocktail made from prosecco wine, Aperol, and soda water was actually invented in the Veneto region.
• Belini : Another famous Italian cocktail invented in Veneto – but this time from the exact city of Venice itself. In fact, you can have it right in the very bar where it was invented, Harry’s Bar, in San Marco Square. (But be warned – this is a very expensive way to have it if you sit down at one of the tables there!) This cocktail is made with Prosecco wine and peach purée or nectar.
• NOT PIZZA : If you are looking for an “authentic” Italian pizza, Venice is not the place to have it. As I mentioned above when explaining where you should try authentic pizza (Naples), pizza as it was first invented must be made in a wood burning oven. And Venice has none! Venice is built out of wood, and apparently wood burning ovens were banned after a pretty bad fire in the past. So if you fancy a pizza while in Venice, that’s fine, but know that it’s very far from “authentic” pizza!

How to Get Out of Venice

Alas, your epic two week Italy trip has come to an end! You’ll need to get out of Venice. Venice’s international airport is Venice Marco Polo Airport (VCE) . There are a few ways you can get from Venice’s city center to VCE.

• Option 1: By bus . From the Venice Piazzale Roma ATVO bus stop, ride the bus for €10. The ride takes 30 minutes. Purchase tickets at the ATVO ticket office in Piazzale Roma, from the automated ticket machine outside that ticket office, or online .
• Option 2: By water bus . From any of Venice’s Alilaguna water bus stops at San Marco, Rialto, Fondamenta Nuove, or Guglie, ride the water bus for €15. The ride takes up to 1.25 hours. Purchase tickets onboard the water bus or online for a €1 discount. Private water bus rides are also an option.
• Option 3: By taxi . The fare for this 30 minute ride from Venice Piazzale Roma is around €40. Make sure you get into an official taxi. They should accept card, and you can double check this as well as fare before getting in. You can also purchase online in advance (select “Town > Venice (P.Roma)” for Venice city center).

Adjustments to this 14 Day Italy Itinerary

• Starting in Venice instead of Rome: You can totally do this two week itinerary in reverse order. However, when you get to Florence and head to the Amalfi Coast, keep the Amalfi Coast portion in the same order. That is, still start at Pompeii and end in Capri. Then, head from Capri to Rome to end the trip.
• Flying in or out of Milan instead of Venice: Venice and Milan can easily be reversed in the itinerary, in case you find a good Venice flight. You’ll just train between Venice and the Cinque Terre instead of Milan and the Cinque Terre. This will, however, add about 1.5 hours to the train journey.
• Visiting Siena instead of Milan: If you already know you have no interest in Milan, consider replacing that day with adding an extra night in Florence. From there, you can make an easy day trip into Siena (or any other town in Tuscany!).
• Visiting Lake Como from Milan: If you can add just one extra night in Milan to this fourteen day Italy itinerary, you can squeeze in a lovely day trip to Lake Como from Milan . I detail exactly how to do it without a tour group and on a budget here .
• Skipping Capri if it seems too hectic: If the half-day in Capri and evening train to Florence sounds too hectic, I don’t blame you. It might be more enjoyable to save Capri for a return trip to Italy. Use the extra day as another day in either the Amalfi Coast, or add an extra night in Florence or Milan for one of the day trips I mention above.

Any Questions on These 2 Weeks in Italy?

I know that was A LOT! If you’re planning your own two week itinerary for Italy soon and want some personalized advice, drop a comment below with your questions . Whether it’s a two week Italy honeymoon or you’re backpacking Italy two weeks, I love playing travel agent for people!

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105 comments.

Hi Em! I LOVE this itinerary so much! Thank you for sharing it 🙂

My husband and I are planning on using this itinerary but tweaking it a bit to fit in attending the Formula 1 race Aug 29-Sept 1 at the Autodromo Nazionale di Monza. We are planning for an 18 day trip (2 of which we’ll be flying) and since the race will be a 4 day event, we will need to cut out a few things or condense it quite a bit. Any tips?

That Travelista

I’m glad to know you love the itinerary! 🙂

I would cut out whatever interests you least. It sounds like you have 12 days (18 – 2 for flying – 4 for the race). So you would need to cut two days from this itinerary. Monza is close to Milan so that seems easy to keep in. You could cut out the 2 days for Cinque Terre and Pisa. Or cut out 2 days from the Amalfi Coast (cut out the Capri day trip and combine Positano and Amalfi into one day trip from Sorrento, or only visit Positano and not Amalfi). Or you could cut out all 4 days in the Amalfi Coast since there’s enough there for a week-long trip in the future. And then have 2 extra days to add elsewhere to not move around as fast. Maybe an extra day in Cinque Terre and an extra day in Milan to do a day trip to Lake Como from Milan .

Hope some of those ideas help!

Hi! Your very detailed itinerary is really a welcome! Am planning about a 12 days visit in mid to end June. What are your thoughts on visiting during this time?

I’m glad you like the itinerary!

Like I say in the post, I believe that anytime outside of winter is a good time to do this itinerary! You’ll have a great time. 🙂

Thanks for the response! Need your input on this! Am considering your itinerary for my visit. The issue here is I made a mistake in booking my return flight! I’m flying in to Rome and will be ending my tour in Venice but my return flight is from Rome! Any suggestion?

Not a huge problem! Just take the fast train from Venice to Rome on your final evening if your departure is in the morning, or on your final morning if your departure is in the late afternoon or evening. It takes around 4 hours.

Hey Em! My husband and I are going to Italy May 19-June 2nd! We are flying in and out of Rome, and I’m having a hard time trying to figure out the best trajectory! We will spend the first 3 nights in Rome, then from there I’d like to see a few places and I’d love your thoughts on direction!

We’d love to see:

Almalfi Coast Tuscany Florence Modena Cinque Terre Maybe Venice.. too much?

I just can’t figure out the best way to make the best use of our time. I’d love to hear your thoughts!

It sounds like you have 13 full days in Italy? In order to hit everything on your list in 13 days, I’d suggest:

Days 1 – 3: Rome Days 4 – 6: Amalfi Coast Days 7 – 11: Florence (2 days for Florence itself, 1 day for Cinque Terre day trip, 1 day for a day trip somewhere else in Tuscany (bc you list “Tuscany” and also list “Florence,” but Florence is already in Tuscany, so I assume you mean the Tuscan countryside or a smaller village), and 1 day for Modena day trip) Days 12 – 13: Venice

From Venice, take the fast train back to Rome.

If you want more time in Cinque Terre, you can remove 1 day from Amalfi Coast and move it there.

Hope that helps!

Alexis Pratt

This is incredible! Thank you for all the research and real travel experience. And taking the time to write it all out! My only question thus far.. do you know how much this all cost? I want to get an estimate to know what to start saving for! Thank you so much.

I’m glad it’s helpful for you!

The biggest cost is going to be housing, and that is going to depend on your personal preferences, your party size, and how far in advance you book. So it’s hard for me to ballpark it for you. I would just look at some places on a booking site to get an idea for a per night rate for the type of accommodation that you personally will be ok with.

Besides that, I’ve tried to put all the prices of attractions and transport in this guide, so you can just add up all the attractions you would enter (for example, not everyone will do a gondola ride or enter every attraction) and the transport you would take (for example, using a cab is different than using a bus or ferry).

If you plan to have a restaurant meal 3 times a day, I’d budget around €60 per day to be super safe. But I personally usually spend less than €25 a day on food in Italy, because I have pastries for breakfast and simpler meals for lunch and dinner.

Sorry to not be of more help!

Thank you for the detailed itinerary. We are planning a 12-day trip to Italy (not including the travel time), starting from Venice and ending in Rome. Amalfi Coast/Capri is at the top of our list. We are debating whether or not to add Lake Como and skip Cinque Terra since we are planning to go to Amalfi Coast anyway.

I’m glad the itinerary is helpful!

I think that sounds like a fine plan! The debate between Cinque Terre and Amalfi Coast is a common one! Both are full of pretty, colorful villages along the water. Cinque Terre is easier to get to/around and fun for hiking and then jumping in the sea afterwards. It’s also cheaper. But I think the nature/scenery in the Amalfi Coast is more impressive.

You could do Venice (2 nights) > Milan (2 nights, one day for Milan and second for a Lake Como day trip from Milan ) > Florence (2 nights) > Amalfi Coast via Naples (3 nights) > Rome (3 nights).

I hope that helps!

Thank you so much for reply!

Hi, Do you have recommendations on accommodations in all the cities you have included to visit over the 2 week period? We’re looking to go in September. Thanks, Gemma

Not yet, but I am actually currently working on a guide that will be just that! It will definitely be published before September, but not for a while still. I can let you know through this comment thread when it’s up, in case you still haven’t booked your accommodation by then.

Hi, Is it advisable to rent a car in Venice and make a day trip to Either Dolomite or Lake Como?

I’ve replied to your other comment. 🙂

I’ve never done it, so I can’t speak from personal expensive. But from what I’ve seen/read, I would definitely recommend renting a car to travel around the Dolomites. I can’t speak to whether it’s worth the drive for just one day though, since I haven’t been.

For Lake Como, it’s quite a bit further out (3 hours one way to the best part of the lake). Lake Garda is also popular and is closer, so you might consider that, too.

Thank you so much!!

I’ve responded to your other comment. 🙂

This was a lifesaver! I may ( 99.9%) have more questions as I finalize my trip, however, I have 2 I thought of now. Following your list and ending in Venice, we than are heading to Sicily… Can you provide the best route? Also if I wanted to add 1 additional ( 2 night stop) between Venice and Sicily, what you would reccomend with the travel details as well please.

Hi Jacqueline,

I’m glad this itinerary has been so helpful!

If it were me, I would probably fly to Sicily from Venice, because Sicily is quite far by train from anywhere on this itinerary.

If you do want to go by train, I would probably reverse this itinerary, so that you train to Sicily via either Rome or the Amalfi Coast (or ferry, if from Naples). They are still far, but closer to Sicily than Venice. Puglia might be an interesting stop to break up the long train journey. I haven’t visited it yet, though, so I can’t speak to it personally.

But like I said, if it were me and I had limited time, I would fly. If you are looking to add one more place to your trip, maybe you can add a night or two in Lake Como from Milan, before heading to Venice. Or visit Lake Garda from Venice. I have an itinerary on a day trip to Lake Como from Milan , if you are interested. You could also add extra nights to rushed parts of the itinerary, like Amalfi Coast or Cinque Terre.

Thank you for this detailed itinerary. It’s the best 🙂

We decided to not go to Cinque Terre. We are still planning on going to Pisa after Florence. How would we go from Pisa to Venice? The different train systems confuse me and we want to get there as soon as possible. Also, how did you feel about the luggage storage in some of the trains? We plan to bring a 28 inch luggage to hold everything for 2 weeks.

Hi Jennifer,

I’m glad the itinerary is helpful!

If you see the directions from how to get to Venice from Cinque Terre in this itinerary, you’ll see that there is a transfer at Pisa. So you will do the same journey, just minus the part from Cinque Terre to Pisa, saving one transfer. You will go Pisa>Florence>Venice (but just purchase one ticket with a transfer, not two tickets).

The luggage storage has been fine for me. I traveled with one those medium sized check-in luggages for 5 weeks, and I usually had room to keep it in front of me. One day it was crowded and someone offered to lift it to the racks overhead for me, because it was way too heavy to lift myself, so that he could sit in the seat front of me. There also should be space for large bags at the end of each train carriage, but I’ve never used that before in Italy.

This is a great itinerary. I am planning on taking my three daughters to Italy for 2 weeks in May 2025. This looks just what I was wanting. I am wondering if you could recommend hotels (2 rooms) for each stop. I do not want 5*. We want quaint boutique hotels that give a flavour of the region. I would love to be able to book this trip myself using expedia or similar companies. Thoughts? I would appreciate your feedback.

Hi Elizabeth,

I’ve responded to your email, but to answer your question publicly for anyone else who might be reading, it’s definitely doable to book this trip yourself! 🙂

Hello! I’d love to go visit Dolomites when i go to Italy next year. Do you have any advices on where to put this destination during the trip? And which city can i skip for exchange of Dolomites?? Thanks a lot!

Ah and I love to go to Sicily as well! I plan to arrive in Rome and depart from Milan. 🙂

I haven’t visited neither the Dolomites nor Sicily yet, but both are on my list!

From what I’ve researched on the Dolomites, it’s easier with a car rental. I’m not sure if you plan to rent a car. Without a car, I do think you can see some things, but you might not be as time efficient (i.e. it might require more days). So what cities you can cut out is going to depend on how many days you want to spend in the Dolomites.

Sicily is quite far from the rest of the itinerary, so it will be either a long train ride (from Rome, Naples, or Salerno at the eastern edge of the Amalfi Coast) or a flight. It’s a decently sized island, so again what cities to cut out will depend on if you are satisfied to just see one city and get a taste of the island or if you want to see more of the island.

I would recommend axing Milan, the Amalfi Coast/Pompeii/Capri leg, and/or the Cinque Terre/Pisa leg because they are less “must see” than Rome, Venice, and Florence. The Dolomites are going to be closest to Venice. So I would add them from there. Sicily is very south, but you might need to take a domestic flight to not waste time, so it might not matter where you add it in. But probably from Venice or Rome airports (or Naples if you decide to not remove the Amalfi Coast bit of the itinerary).

I hope that helps a bit!

Hi Em we will be travelling to Italy in late September from Australia, spending several days cycling in the Dolomites and then using your itinerary as a broad guide for the rest of our trip. If we have a couple of extra days spare (we have three weeks in total) would you recommend Puglia? Or somewhere else as a higher priority?

I haven’t been south of the Amalfi Coast area yet, but Puglia looks beautiful, less touristy, and is on my list! That and also Sicily, but I think Puglia would be easier in 2 or 3 days than Sicily, from what I’ve read/seen.

Another option is one of the northern lakes, Lake Como and Lake Garda being two of the most popular. I haven’t been to Garda, but Lake Como was stunning and easy to move around. But quite touristy.

Just some other options to consider, but (keeping in mind that I haven’t been there myself) Puglia sounds like a great addition! With the 2 week itinerary I’ve written out, you’re already going to see all the most “priority” stops in the country, from a touristic point of view, so anything else on top of that is going to be a bonus and just based on your interests!!

My fiancé and I are arriving in FCO on 4/1/24. We have two weeks in Italy, in theory. I wouldn’t mind hitting Croatia for a couple of days, if that is doable. I’ve been to Italy numerous times, and he has not, but is happy just going where I want to visit. Croatia is high on both of our lists, so, if we’re there, why not? Any thoughts or insights about that?

I LOVE Croatia and think it’ll pair perfectly with Italy!

If I were making an itinerary for just your fiance alone, who hasn’t been to Italy nor Croatia, I would recommend combining my one week Italy itinerary and my one week Croatia itinerary to make a two week trip. Each itinerary is what I would recommend for a first timer in each country (so Rome, Florence, Venice for Italy, and Dubrovnik, Split area, Plitvice Lakes for Croatia).

BUT since you’ve already been to Italy, and many times at that, I’d have to ask what you’re hoping to get out of both countries this visit. What places are you interested to see in Italy? Do they have to be new, or are you willing to repeat things for your fiance to see? Do you want to see “all” of Croatia, or just Split and Dubrovnik? If so, Split and Dubrovnik both have airports with flights to/from Italy, so you can even just tack that portion of my Croatia itinerary somewhere in your Italy trip. I’m happy to give more specific recommendations/thoughts if you let me know! 🙂

I think you submitted two comments, so I’ve responded to the other one. 🙂

Hello Em, really enjoyed reading your 14 day Italy itinerary for first timers. My darling wife and I are considering a trip to Italy this fall. We are in our sixties, and while we can walk, we cannot “hike”, so do be gentle, haha. While we would love to cover as much as possible, we do like to take it easy and travel in a leisurely manner.

Based on your itinerary in reverse, here is what we have come up with: Fly into Venice early afternoon. Stay in Venice for 3 nights, (one extra night) as we would need to get over the jetlag from an overnight flight from North America. Florence for 2 or 3 nights. Cinque Terre/Pisa for 2 or 3 nights. (As suggested by you, thinking of staying in La Spezia for ease of train travel to the 5 village and budget as well.) Rome for 5 nights. This would include a day trip to Amalfi Coast and or Naples if possible.

Seeking your guidance to set up the itinerary along with details of places to visit. So this would be a 13 or 15 nights itinerary, depending on your valuable input. Also we cannot decide if we should begin the Italy trip mid September, late September or early October, keeping in mind weather and crowds.

Thanking you in advance and best wishes

I think that sounds like a really nice itinerary!

If you are not going to be staying overnight in the Amalfi Coast, I would recommend switching the order of Florence and Cinque Terre around to save an hour of train travel time. So Venice > Florence > Cinque Terre > Rome.

The later you go, the lower accommodation prices will be and the lesser the crowds will be (especially in Venice, because of cruise ships, though I believe they have limited the sizes ships can be now). But also, the cooler the weather should be (but you never know what weather you will get, of course!). If it were me, I would opt for mid or late September. This is because I’m really affected by weather, unfortunately lol! If you don’t mind the weather being cooler, October might be fine for you.

There are tours on sites like Get Your Guide and Viator for Pompeii and Amalfi Coast day trips from Rome that run around $100 – $150, so that might be an option to consider if you want to see them both in one day.

All my recommendations on what to visit or extra day trips to add are basically what I’ve put in this post, so if there is any question in specific, let me know! I think having more time in each city will just allow you to enjoy it more by not being rushed or having to wake up early to fit everything in, and allowing you free time to meander and discover things on your own. There’s no reason to rush if you don’t have to! 🙂

Hello Em Thank you so much for your time and input for our trip. Noted your suggestion about the routing, CT to Rome. A few questions: 1. Taking the train from Florence to CT, should we stop in Pisa. Is the Tower a thing not to miss. 2. What is best train route from Florence to CT. 3. We decided to spend two nights instead of 3 at CT. Question, should we stay in La Spezia or in one of the towns, maybe Monterosso. Any thoughts. 4. What is the best train route from CT to Rome. I guess we should plan to arrive at Roma Termini station. Thanks once again. Best wishes

1. It’s totally up to you if the tower is worth missing or not! It’s not as impressive as the buildings you will see on the rest of your trip (the Colosseum, Venice’s buildings coming out of the water, the Duomo in Florence which literally had new tools invented to build it). It’s just a very cliche symbol of the country for whatever reason, and not worth visiting on it’s own, so that’s why I’ve put it as a quick photo stop in this itinerary, since you already have to exit the train at Pisa station to make a transfer between CT and Florence anyways.

2. I have the train route from Florence to CT in this itinerary. If you don’t want to see the Leaning Tower of Pisa, you can just skip that and can continue the transfer to La Spezia at Pisa station. From there, you can continue to CT proper if you want, or stay in La Spezia as your base, like I recommend in the itinerary. The only reason I mentioned the switch to you is because you are doing my itinerary from Venice to Rome, so backwards. So I didn’t want you to do Venice > CT > Florence, because since you aren’t doing Amalfi. Then to get to Rome from CT, it will be from La Spezia Centrale to Roma Termini (direct train as fast as 3 hours in the morning, closer to 4 hours later in the day). For all other train journeys, just do the exact reverse of what I have detailed out in this post.

3. I answered this slightly in the previous bullet, but in the itinerary I recommend La Spezia for just two nights. I explain a bit why in the itinerary.

4. I answered this in the second bullet, but I’ll add that when looking for tickets to a city, you can type just the name (in Italian, so Roma, Firenze, Venezia, etc.) and then select “Tutti Le Stazioni” if that option is there in the drop-down. This will include all stations for that city in the search. But yes, for this journey in particular, it’ll be Roma Termini. 🙂

Thank you so much Em You are the best.

Glad to be of help! 🙂

Hi Em! Thank you so much for this detailed itinerary, very helpful! I’m planning on visiting Italy in September for 2 weeks, perhaps a little longer. It’ll be my first solo holiday! I’m really keen to explore Sicily as well as the destinations set out in your article. I’ll be flying from Bristol and planned to begin in Milan and make my way down the country, flying home from Sicily but flights are either a lot more expensive or hours long! Do you think it would be okay to follow your itinerary, ending in Sicily and then flying from Sicily back to Milan so that I can book a return flight from there? Thank you again for your help! ☺️

You can definitely tack on Sicily to this itinerary, and I think a domestic flight to save money/time makes a lot of sense.

I’m not sure if you are planning to connect my itinerary to Sicily by train or do two domestic flights. If you are wanting to use the trains to get to Sicily and just the flight to get home, there are direct trains from Roma Termini and Salerno to Messina Centrale, Palermo Centrale, and Siracusa. Salerno will save you about 2 hours compared to Rome, and it is at the eastern end of the Amalfi Coast. So if you decide to go that route, I would recommend moving my itinerary around to end in Amalfi Coast rather than in Rome. That would also make me recommend moving Florence and Cinque Terre around, to save an hour of train time there.

So Milan > Venice > Florence > Cinque Terre > Rome > Amalfi Coast > Salerno (reached either by train with connection in Torre Annunziata or Naples, or by ferry) > Sicily > flight to Milan.

You could also fly from Naples to Sicily. The train journey is so long that it might be worth looking into.

I hope that helps!! Your trip sounds like it’s going to be amazing!!

Hi Em, Thank you so much for your reply! I ended up missing out Sicily and decided to do it another time. Instead I have tweaked things slightly and planned it Venice – Florence – Pisa – Clique Terre – Rome – Pompeii – Sorrento – Matera – Milan – Lake Como. Thank you so much! ☺️

That sounds like it is going to be an amazing trip! Have the best time!

My husband and I will be visiting Italy in June. I would love to visit EVERY place on the itinerary, but my husband is not looking forward to packing up and jumping on a train every 2 days. I read that you recommended cutting out Capri, but that’s high on my list. Can you tell me if cutting out Cinq Terre is a good alternative?

Hi Camille,

I think that’s a great alternative. If Capri is high on your list, that settles it, in my opinion! My itinerary only allocates a half day to Capri, but by removing Cinque Terre, you can either overnight in Capri with those two nights originally meant for La Spezia/Cinque Terre, or add two nights to the Amalfi Coast, allowing you to do a longer day trip to Capri than you would be able to do if you were going to Florence afterwards, like in my itinerary.

The reason I recommended cutting out Capri in another comment is because (1) it only occupies half a day of my itinerary, so it’s one of the smallest things to cut out, and (2) it added the most inconvenience to the itinerary. But now, the train journey between Cinque Terre and Venice has also gotten about an hour longer than it used to be for some reason. I’m not sure if it is because of work on the route or if it’s a permanent change. But now the inconvenience is kind of similar between the two.

And lastly, I think Cinque Terre on its own is easier to return to on a future trip than Capri on its own is.

I hope that helps you make your decision! Enjoy your trip!

Kelley Strutton

Thanks for this wonderful guide – it paints such a beautiful picture of Italy and all the details are really helpful. We are seniors and looking for info to ease the logistics of things. Specifically: Would it make sense to take a train from Rome to Sorrento, using Sorrento as your base for a few days. Then, on one of the days take a train back to Pompeii for the day to see the ruins – trying to avoid the luggage and train transfer hassles. Also, can you tell me how luggage is handled and where it is stored on the trains? Will there be any assistance available for this? Quick impressions of the best area to stay in Rome, Florence and Venice for convenience to attractions and trains would be helpful. Thanks so much.

I’m glad my guide is helpful!

You can totally day trip to Pompeii from Sorrento if you prefer. You could technically even do it on the same day as you leave Rome, if you don’t mind doubling back on the same day. The train ride is around and hour each way, and it will be the same train you take from Naples to Sorrento, so you’ll already have experience with it.

I’ve always put my luggage above me, if the carriage is so full that I cannot keep it near my seat. I’ve never traveled Italy with anything larger than the medium-sized check-in bag, though. (I mean the kind that are definitely too large to be check-in, but not the standard check-in sized luggage.) There is usually also a designated area for luggage at the end of each carriage. There isn’t impromptu service that I have witnessed. I’ve only ever seen train staff give directions and answer questions. But TrenItalia does have this service to deliver luggage to your hotel. So maybe that will interest you.

I personally always try to stay walking distance from the train stations. In Rome, this area visually seems a little dodgy, so you might want to keep that in mind. You can try to find something still walking distance from the train, but in the direction of the attractions (northeast of the station). But in Florence, I found the area near the train to be fine. In Venice, I would definitely recommend to be near the train, because it is annoying transporting luggage over all the bridges, and it can be confusing to navigate the water taxis right upon arriving and with luggage in hand. Florence and Venice are both rather compact.

I usually use Booking.com to search, because I like that their interface allows you to filter criteria and then move to a map view, which allows me to see where the accommodation is relative to the train and attractions. I’m not currently affiliated with Booking.com.

I hope some of that helps!!

So, do you have to change trains to get from Rome to Sorrento? Or is there a direct train?

As my itinerary details in the section about how to get to Pompeii, you have to transfer at Naples. There are two Naples stations. You go from Rome to one. Then, you walk to the other one and head on a second train towards Sorrento. My itinerary has you getting off this second train at Pompeii on the way to Sorrento, but you can of course just keep on the train and head to Sorrento. 🙂

I see. Thanks for the good info

Shani Damodaran

HI, Planning to do a trip of Italy plus Malta starting in first week of April 24 for 17 days. We are a family of 3 (2 adults and a 15 years old child) Landing in Milan and flyout from Rome Can you advice a complete itinerary with an option of flying in and out of Malta in between this 17 days. Malta can be 2 nights only. We would like to spend some quality time in Rome for sure. (if less also, give an option).

That trip sounds like it will be a dream! I think Malta can be squeezed into this Italy itinerary quite nicely.

What I recommend is to do my itinerary backwards then find a way to squeeze Malta in using the airports of Naples, Bologna, or Pisa.

This could yield something like:

April 24: land in Milan April 25: travel to Venice in afternoon or evening (depending on how much time you had in Milan on day 1) April 26: Venice April 27: travel to Florence in evening April 28: Florence April 29: Florence April 30: travel to Cinque Terre (La Spezia) in morning, stopping in Pisa if interested May 1: Cinque Terre May 2: travel to Pisa Airport (9am flight) and fly to Malta May 3: Malta May 4: fly to Naples Airport, travel to Amalfi Coast (Sorrento), stopping in Pompeii if interested May 5: Amalfi Coast May 6: Amalfi Coast May 7: travel to Rome in morning, stopping in Capri if interested May 8: Rome May 9: Rome May 10: fly home

The flights I reference are all through RyanAir. So be sure to read my guide on flying with RyanAir without getting ripped off before purchasing.

Hope that helps, and have a great trip!

Planning to go to Italy for 2 weeks 15-17 days. I was planning to add Malta too.. do u think I can add Sicily and then Malta after Naples ? and miss Milan from the trip. Please let me know your thoughts on these places. If they all look and feel the same in June then may be I could skip them.

Hi Archana!

There are direct flights between the three places (Naples, Sicily, and Malta), so you definitely can tack those onto the itinerary if you’d like. In that case, I would probably make the trip Venice > Florence > Cinque Terre > Rome > Naples/Amalfi Coast > Malta + Sicily. Or the exact reverse. The only thing is that removing Milan only saves one day, so if you are following the rest of my itinerary, your trip will be longer than 17 days if you tack on Sicily (which is a large island) and Malta. So you might have to cut a bit more out from my itinerary, if that is what you are following.

I haven’t been to Sicily or Malta yet, so I can’t advise on them from personal experience. I’ve heard that Sicily is a bit of a different vibe from the rest of the country. And Malta of course is a separate country. But the three places are going to seem similar compared to, say, Norway. They are all in the Mediterranean, they are all southern Europe, they all have been part of the Roman Empire, etc. So it depends on your definition of “the same.” My own opinion is that I absolutely plan to visit both Sicily and Malta in the future!

Jessica Cloutier

Thank you so much for all the valuable information! We’re doing a bit of a shorter trip as we are staying a few days in Paris as well as Switzerland. We plan to have 11 -12 days in Italy. I am wondering how you would reconfigure the itinerary. I have been to Italy on a school trip and was planning on skipping Rome this time around (been to Florence as well but would like to go back). I also wanted to check out lake como. Any suggestions are greatly appreciated.

Hi Jessica,

I’m glad the information is helpful!

Since the itinerary is 14 days and the Rome portion is 3 days, I would just remove those 3 days and have an 11 day itinerary. That would have you starting in Naples (which has an airport) and ending in Milan, or the reverse – whichever works out better for you.

If you want to see Lake Como on a day trip, it’s possible and would keep the itinerary within 12 days. I detail how in my Lake Como day trip itinerary from Milan . If you want to overnight in Lake Como, I would cut some days out from whatever interests you least and tack on those days to Lake Como. Maybe the half day in Capri because it’s a little complicated, or maybe Milan because it’s not as beloved, or maybe a night from Florence since it’s a repeat for you, etc.

I hope that helps!!

This post is amazing! Would love your input on 14 days flights to and from FCO – Rome (Wednesday arrive, Tuesday depart). We hope to hit Rome, Pescara, Roccamorice, Naples, Pompeii, Sorento, Pompeii, Amalfi, the hike you mention, and maybe Capri. We dont mind paying for some accommodations, but we also have a friend in Naples where we can stay for free. Any tips on itinerary and how to get around?

Hi Ken! I’m so glad to know the post was helpful! 🙂

That’s so awesome you have free housing in Naples!

The bulk of everything you listed is day-trip-able from Naples – just Rome, Pescara, and Roccamorice aren’t. I haven’t been to Pescara or Roccamorice, but based off a quick Google Maps search of public transport, it seems there are trains and buses between Rome and Pescara. It seems that there is a long (5hr) Flixbus between Naples and Pescara, but that a train trip between the two has to transfer at Rome. I didn’t see any way to get to Roccamorice with public transport from Pescara, Rome, or Naples.

Off the top of my head, I would say to combine Rome, Pescara, and Roccamorice as one leg of the trip. Let’s call it Leg A.

Leg A: Day 1: land in Rome, explore if you have time/energy, sleep in Rome Day 2: Rome, sleep in Rome Day 3: Rome, sleep in Rome Day 4: travel (probably train) to Pescara, explore, sleep in Pescara Day 5: day trip to Roccamorice (I imagine there must be some way to get there by local bus? I’d look more into that!), sleep in Pescara Day 6: travel to Rome (or to Naples by Flixbus, depending on the day)

Sorrento, Pompeii, a hike up Mt Vesuvius (if that interests you), and Capri are all super-duper easy day trips from Naples. So, if you’re wanting to save budget, I’d plan all those as day trips (and maybe overnight in Capri if you want, to experience it without the day-trippers) from your friend’s place. And Naples itself also has things to see!

I think it’s worth spending a night or two in either Positano or Amalfi to spend one day in each and do the Walk of the Gods hike. But you technicallyyy can day trip to them from Naples as well. If you do, I’d recommend by ferry, because doing the train from Naples to Sorrento, then the bus from Sorrento to Positano/Amalfi, and then returning…all in the same day…multiples days…just sounds terrible to me! But the ferry would be €30 – €40 ish round trip each time, so multiply that by multiple people and two or three days, and I feel like you can just put some of that money towards accommodation instead, spending more time exploring and less time commuting!

Either way, I’d say to combine Naples, Pompeii, Sorrento, Positano, Amalfi, the hike, and Capri into another leg of the trip. Let’s call this next bit of the trip Leg B.

Leg B: Day 1: travel to Naples from Rome by train (or from Pescara by Flixbus), explore depending on time, sleep at friend’s place Day 2: day trip to Pompeii + Sorrento, sleep at friend’s place Day 3: travel to Positano in morning (probably ferry), explore, sleep in Positano (or Amalfi if you decide) Day 4: take bus/cab to Amalfi, explore, take bus/cab to start of hike, hike to Positano, sleep in Positano (or rearrange this if you decided Amalfi for Day 3) Day 5: take ferry to Capri, explore, take ferry to Naples, sleep at friend’s place (or overnight in Capri, taking ferry to Naples the next day)

So all that puts you at about 10 – 13 days, depending on if you add extra nights to Capri or the Amalfi Coast or Naples, and whether you combine day 6 of Leg A with Day 1 of Leg B.

If you have an extra 2 – 4 days, you can add a Leg C of Naples/Rome-Florence-(+ Pisa if you want)-Rome, or Naples/Rome-Florence-Venice-Rome, or Naples/Rome-Venice-Rome, etc. by fast train. Know that Venice is going to be a long train ride from Naples, though!

And you can rearrange any of the Legs A – C into whatever order fits best with your flights or your friends’ schedule, etc. since Rome is kind of the focal point of them all.

Hope some of that is helpful!! I think it all depends on how much you care to “fit everything in!” If that’s not a concern and you can return to Italy later on to tour the north, I’d say spending all 14 days in the areas you listed and taking it more slowly sounds the most enjoyable! (Renting a car is also an option, but as I’ve never done that in Italy and my itinerary was all public transport, I’ve stuck to public transport in this response.)

I’m sure you’ll love your trip whatever you decide. 🙂

Is it best to book the air first and then find the accommodations? I’m wanting to go to Italy this May…in a few weeks.

Hi Ruth! Italy in May sounds like the perfect time!

I’m a huge planner, so I like to plan a rough itinerary (which includes looking at any train schedules/prices, skimming housing options, flight options, etc.) before booking anything.

Sometimes I book free-cancelation accommodation first before booking my flight/transport. But if I am staying in an Airbnb or something not fully-refundable, or if the flight price is very good, then I tend to book the flight before the accommodation. So there really is no correct order! 🙂

But since your trip is coming up soon, maybe it’d be a good idea to at least look at accommodation first to make sure there are enough options for your destination within your budget before you put down money on a flight.

disfruta2vidagmailcom

So, I’ve decided to change my trip to 21 day in and out of Milan…how would you restructure the itinerary?

How exciting!

With seven extra days I would use one day to travel back to Milan from Rome at the end of the trip (Roma Termini to Milano Centrale, fast train takes 3 hrs) and for the remaining six days, choose what interests you the most from the below options:

– one extra night in Milan to do a day trip to Lake Como (or spend a couple nights on Lake Como) – one extra night in Milan or Venice to do a day trip to Verona (or spend one night in Verona in between traveling between Milan and Venice, or spend two nights in Verona to see Verona one day and day trip to Sirmione on Lake Garda the second day – I meant to go to Sirmione from Verona myself but didn’t because of rain) – one or two extra nights in Cinque Terre to rush less or do a day trip to Portofino ( this guide is from Genoa but is just as doable from Cinque Terre) and/or Portovenere – one extra night in Florence to do a day trip to Siena – one extra night in Florence to do some sort of organized day trip that includes Val d’Orcia and/or Tuscan countryside wine tour (I haven’t done either of these) – one extra night in Florence to do a day trip to San Gimignano (I haven’t been but have heard nice things) – one extra night in Amalfi Coast to rush less (and/or add a night to Capri to spend a full day there and not just a few hours) – a couple nights in the Emilia Romagna region (in between Venice and Florence – main city is Bologna) I only recommend this if you love the food from here (bolognese sauce, parmesan cheese, prosciutto di parma, and balsamic vinegar are a few famous ones) and plan to do food tours, as it’s known as a foodie haven

The above options allow you to stay in the same area and get to know it better/less rushed. But you could also add an entirely different region to your trip if that is what you prefer. You could rent a car and explore the Dolomites in the north, you could travel alllll the way south and see some of Sicily or Puglia (but that would be a very long travel day back to Milan or require a domestic flight), you could spend time on the island of Sardinia, etc. I haven’t done any of these things (yet!) so I can’t give much advice on them. If it were me, I would stick to the first options I listed and save further-away things for return trips to Italy. 🙂

Hope some of that helps!! 🙂

I have a 2 week vacation coming up in May and I’m thinking about going to Italy but have to idea how to plan it; where to go or where to stay!

Hi Stephanie! How exciting! I think May is a perfect time to see Italy (that and September) because the weather is warm but it’s not high season. You’re going to have an amazing time. 🙂

If it were me and my first time in Italy, I would follow this two week itinerary exactly as I have it laid out. I like to maximize places I’m seeing while still having enough time to “see everything” in each place, and the itinerary as I have it laid out does that. It hits the three main, can’t-miss Italy destinations (Rome, Venice, and Florence) plus fits in the next tier of popular destinations (Cinque Terre, Pisa, Milan, Amalfi Coast/Capri, and Pompeii).

The only additional planning you would need to do is your accommodation. I like to use Booking.com because I like its interface and app, that many properties listed allow free cancelation, and that it lists hostels (I’m not doing hostels at the moment though, due to the virus). But other sites you can use include Hotels.com, Airbnb, or HostelWorld. It depends on your budget and style. 🙂 Also, I always check the walking distance from the train station to the accommodation on Google Maps before I book.

If the itinerary as I have it laid out seems too jam-packed for you and you like to travel slower, you can let me know what you’re looking for (beaches/relaxing, focusing on one region and returning to the country later for other regions, art/history/museums), and I can give my thoughts on what to add and take out! 🙂

Karan Sachan

My wife & I are heading to our 2 weeks Italy adventure next week. After Rome, we were thinking of renting a car until the end. Do you know what is the parking situation? Would hotels/airbnbs provide accessible parking options overnight? Is parking fare like insane expensive?

Hi Karan! How exciting!!

I’ve never driven a car in Italy, so I can’t say much from personal experience. But the answer depends on what places you are visiting. 🙂 If you are seeing just the places on this itinerary, for me, a car isn’t worth the hassle because it’s so easy to travel between the main tourist destinations by train. The only parts of this itinerary that I think could be easier to get to with a car would be Positano and Amalfi, so just 2 out of 14 days. But maybe you will be exploring smaller towns of the Tuscan countryside, or heading to Sicily, or something like that, which then would have a different (easier) parking situation than the major tourist cities/spots! So the answer depends a lot on your specific itinerary.

Airbnbs sometimes do have parking and they list it on their Airbnb page if they do. Same with hotels. But if it’s not listed on their page, I wouldn’t expect parking. In my experience driving in other European cities, parking is expensive, but like I said, I can’t speak from experience on Italy.

If you do go with a car because you prefer to not be on a train schedule, I would suggest to plan where you will be parking in advance (Google search or see what others on TripAdvisor have shared). You might be able to find the costs in advance and then decide for yourself if it is too expensive vs the trains or worth it. 🙂

I hope some of that helps!

My wife and I are planning a trip to Italy in late May. Your itinerary has been of great help in coming up with our plan – thanks very much for taking the time to write such a detailed travel plan. The following is our draft itinerary:

17-Mar Arrive Milan 2:30 PM 18-Mar Milan sightseeing 19-Mar Lake Como 20-Mar Morning train to Venice 21-Mar Venice, Train to Florence in the evening 22-Mar Florence 23-Mar Florence, Pick up rental car drive to Tuscany in the afternoon 24-Mar Tuscany (includes Pisa and Cinque Terre among other places) 25-Mar Tuscany 26-Mar Tuscany 27-Mar Drive back to Florence, drop rental car, take train to Rome 28-Mar Rome 29-Mar Rome 30-Mar Vatican 31-Mar Train back to Milan, flight out at 2 PM

We will be meeting my sister and brother-in-law in Florence and will be with them for the Florence and Tuscany leg of the trip. The dates and days for this leg of the trip are kind of fixed so we are going with their plan and will be sharing the AirBnB they booked in Tuscany. We intend to cover Pisa and Cinque Terre while we are there. We intend to rent a car to drive to Tuscany, only place on this trip where we plan to do that.

Initially I had Amalfi Coast in there but reading your comments, I took that out for a later trip that could combine that and potentially Sicily (always wanted to visit Palermo/Bagheria – The Godfather effect!).

Would appreciate your insights on the overall itinerary. A couple of doubts that we have are are we budgeting too little time in Venice and is 3 days too much for Rome/Vatican? Thanks a lot in advance.

Hi Kam! I’m so glad to know my post and comments have been helpful to you. 🙂

What you have looks like an awesome itinerary! You are going to have a great time leaving it just as is. Personally, I liked Rome most between Rome/Venice/Florence, so I may be a little biased in saying that 3 days would never be “too much” for Rome. 🙂 That being said, my own itinerary only allots 2.5 days to Rome, so if you wanted to arrive in Rome one day later so that you take the train from Florence the following morning, arrive in Rome by or even past noon, and have 2.5 days instead of 3, I think you can still see everything in Rome that you would have seen. That would allow you to either have more time in Florence or maybe arrive in Florence from Venice the next morning and have one more night in Venice. (Not sure if that part is already fixed though?)

I think, make your decision on what interests you and your wife most between ancient history (Rome), renaissance art (Florence), and a visually stunning city (Venice). I think you’ll be able to “see everything” in Venice with your current itinerary because it’s a pretty small place, especially the touristic center. So the decision is more if you think you want to “hang out” longer in a visually pleasing city rather than about if you will miss seeing something touristic. As for the Vatican, some people allot a whole day to it. Others half a day. (This also depends on if you are buying skip-the-line tickets in advance.) I personally am not interested enough to spend more than half a day (I love Rome’s ancient Rome stuff more than the Vatican stuff), but maybe you and your wife love art and museums more than I do. 🙂

So to answer your question, I think the itinerary as you have it looks good and you’ll “see everything.” But if you are nervous, I think you can remove 0.5 days from Rome and add it elsewhere without seeing any less of touristic Rome. And I think Amalfi + Sicily for a future trip sounds like a dream!

Many thanks for taking the time for writing a detailed reply and apologies for my late response. We have made one change to our original plan: the more Youtube videos I saw of the Amalfi coast the more it felt like we should get at least a glimpse of it on this trip. So I have gone in the opposite direction and added one more night to Rome (stealing a day from Tuscany)!. In addition to giving more time for the historical sites, we plan to do a quick day trip of the Amalfi run by Walk Tours of Italy which should gives us a glimpse of its wonder and hopefully tempt us for a return trip! Once again many thanks for your help and all the best.

An organized day trip is a great way to quickly see the Amalfi Coast from Rome! It’s very stunning/unreal place, and I know you’ll love it! I would love to know how the whole trip went after you return. 🙂 Have the best time!!

Thanks for your help again and will be sure to write after we return from the trip.

Hi. We are planning on arriving in Naples March 26th or so and want to spend two weeks in Italy. Our final destination will be Marseilles France. We will arrive in Naples from Sicily. What do you recommend for an itinerary for those 2 weeks. Thanks

Hello! I’d recommend this exact itinerary, just in a different order. Since you are arriving in Naples instead of Rome, that’s actually less backtracking. 🙂

I’d say to start with the Pompeii/Amalfi Coast/Capri leg. If you wanted to be based in Naples, it is technically possible to do Positano, Amalfi, Capri, and of course Pompeii each as day trips from Naples. So you would either rent a car, join tour groups, hire a driver, or DIY it by using the buses/ferries I mention. It would just be more time in transit each day vs being based in, for example, Sorrento.

After that, I would take the train up to Rome and do the Rome portion of this itinerary. Then, from Rome take the train to Florence and continue with this itinerary exactly as is for Florence > Pisa/Cinque Terre > Venice > Milan. RyanAir has direct flights from “Milan” (the BGY airport in Bergamo, not the MXP airport) to Marseilles. But remember that they are a budget airline and very strict on baggage size/weight!

Hope that helps! Feel free to respond back 🙂 Sounds like it will be such a lovely trip!!

Thank you for such GREAT information!! We plan to be in Italy in November…Hubby is teaching in Milan & Lithuania the first week of Nov & I will meet him in Rome when he’s finished. We should have 15 days, not including our travel days and I’m thinking Rome, Florence & Venice for sure. We like to be leisurely when we travel 😉 Are there any of the destinations you listed that we should omit due to it being November? Leslie

Hi Leslie! So glad you found the info useful 🙂

As a Californian who’s pretty much only known the drought years, weather (including rain) really impacts where I want to travel! So keep in mind that bias in my response LOL.

Like I mentioned towards the beginning of this post, Venice is prone to flooding during rain. So if it’s raining heavily there on your visit, it might not be enjoyable, but you won’t really know the forecast until closer to the date. I wouldn’t go as far as to say omit it, but just keep that in mind, and maybe you can pack or plan to purchase rain boots worst case.

Personally my own interest in beach-y places (which in this itinerary would be Cinque Terre, Amalfi Coast area, and Capri) is entirely dependent on warm weather. So those would be the ones I personally omit and save for another visit. The order of omission for me would be: Capri, Amalfi Coast, Cinque Terre. Cinque Terre would be last to go for me because it’s all connected by train, so I imagine it would still be just as easy to visit. And apparently no one checks for the ticket to the paid hiking trail in winter, so assuming it is not rainy or just rained (muddy trail would not be fun) that might be a plus to going in winter. Amalfi Coast should still be doable, but I imagine the ferry schedules would be heavily reduced in low season, and potentially more canceled due to sea conditions, so getting to Capri might be annoying. All three of these destinations’ villages/towns are filled with souvenir shops, boutiques, and restaurants, so I would imagine some might be closed in winter, but not all.

Since you like to be leisurely and the itinerary as I have it is very jam packed, * I would omit the entire Amalfi Coast and Capri leg of the itinerary. It’s a lot of moving around in a short time frame, and I don’t know that it’s worth it in cold weather. You can keep the Pompeii portion of the itinerary by just adding 1 more night in Rome and making Pompeii a day trip. So in the end, that would net save you 3 days. * I think Cinque Terre will be worth it if you just wanted to SEE the pretty towns (they’ll look exactly the same in winter as summer, and will be much less crowded!) but not worth it if you’d be very upset if the trails are closed do to mud from rain. If you omit this, that would save you 1.5 days. I’ll assume you don’t omit this for the following bullet. * With the 3 extra days, I would choose the 3 of the following that interest you most: ~ Day trip to Siena from Florence (add 1 night to Florence) ~ Day trip to San Gimignano from Florence (add 1 night to Florence) – I have not been, but have heard nice things ~ Day trip to Bologna from Florence or Milan (add 1 night to Florence or Milan) – I only recommend this if you love the food from here and plan to do a food tour, as it’s known as a foodie haven and is in the region where a LOT of the Italian dishes Americans love/know are from ~ Day trip to Verona from Venice or Milan (add 1 night to either Venice or Milan) – where Romeo and Juliet was set ~ If it happens to be a nice day, day trip from Milan to Lake Como (add 1 night to Milan)

This would be a lot less moving around, so a lot more leisurely. If you want to save moving accommodation from Florence to Cinque Terre, you can also just do Cinque Terre as a day trip from Florence, especially if you do not plan to hike. I detail how I’d recommend fitting all villages (plus the main hikes) into one day here . This way, you would only be based in Rome, Venice, Florence, and Milan for the entire 2 weeks.

Hope some of that helps! Feel free to respond back 🙂

Thank you, thank you, thank you! Your reply is very helpful 🙂 We’re less about the beaches so omitting the Amalfi Coast & Capri makes sense. I hadn’t considered the Bologna region and that idea intrigues me as we do like food 😉 Is it a crazy idea to think that we can plan just our Rome leg from the States & then figure out the rest while we’re over there, according to the weather forecast at the time? That would give us flexibility as to whether we begin or end in Venice before heading back to Rome for our flight home. Again, I appreciate all the time & effort you’ve put into your blog & responses! Leslie

I don’t think that’s crazy at all! You will just have to pay some more for any long distance train tickets due to purchasing them closer to the date of travel vs weeks or months out (which I mention some price examples of in the post as well). November will be off season, and on top of that, we have the lovely pandemic which doesn’t seem to be going away any time soon, so I do imagine you would be able to get accommodation just fine.

One thing I personally would do though is to still plan out what you want to do in each of the non-Rome legs of your trip in advance (at least roughly), and then just mix and match the order of the non-Rome legs later on. So plan what you want to do in Florence, how many nights there, roughly how to do any day trips from there, and then same for Venice and any other base cities, but then don’t book until getting to Rome if you like. That way, you don’t waste your vacation time in Rome searching the internet to plan time-consuming details. You can just spend a few minutes searching the weather, deciding the best order, and booking 🙂

Awesome, that’s good to hear. Thank you again!!

You’re welcome! I’m sure you’ll love your trip 🙂

Hi, my husband and I are planning a 14-day honeymoon this October. I am worried we will spend most of our time on trains if we try to visit too many places. We fly in and out of Rome. Would you recommend skipping out on Amalfi Coast and heading north (Rome-Florence-Cinque Terre-Milan-Venice-Rome) instead? We don’t want to miss out on anything!

Hi Ashley! I definitely understand that sentiment!

If there was any portion of this itinerary to take out, in my opinion, the Amalfi Coast/Capri/Pompeii leg would be the one to go. The main reason for that is that it is a rather high ratio of travel time to non-travel time compared to the other legs of this itinerary, AND it easily could make up its own entire week+ Italy trip if you are able to return. A third reason would be that since you mention you don’t want to miss out anything, I think all the other destinations rank above Amalfi Coast/Capri/Pompeii in terms of what is considered most “must see.”

So yes, what you said is what I would recommend. 🙂 Especially for a honeymoon, slowing down would be a lot more romantic!

Hi, this itinerary sounds amazing. My husband and I would like to travel from the US to Italy for the first time next May. Do you have lodging accommodation recommendations and how to book them?

Hi Jennifer! May is a lovely and comfortable time to travel to Italy. You will love it!

I can’t say I have specific lodging recommendations for each destination, but I pretty much always use Booking.com to look for and book my accommodation. I just really like the interface of their website for searching as well as how it lists your bookings out in chronological order, so it’s easy to keep track of where you are headed next. Plus, a lot of their listings offer free cancelation so that (1) I feel comfortable booking something earlier than I’m totally certain on it and (2) things are easy if plans change. And I find this to be true of both their desktop site and mobile app. They also have a large range, from five star hotels to hostels to guest homes, so I really like it as a one stop shop. (I’m not affiliated with them at all, they just happen to be the site that I almost always use for several years now.)

One tip with them and with any hotel listing site is to check TripAdvisor after you have settled on the hotel but before you book. The photos on those booking sites are always provided by the hotel itself, so I often just do a quick skim of the traveler uploaded photos on TripAdvisor, especially if it is more of a budget accommodation.

A lot of people of course love apartment rentals, so if you and your husband like that experience more, definitely look at AirBnB and Vrbo. I just personally prefer not having to coordinate check in and check out time with each host in an itinerary like this where you are moving around every few nights. I like that at hotels/hostels I can drop off my bag with reception if I arrive before check in or leave it there after check out if I’m sticking around. But the plus side is that you have the whole place to yourself, feel a bit more “like a local,” and can save money on food by grocery shopping and using the kitchen, packing lunches, etc. So kind of just depends on your style!

I hope some of that helps! I just haven’t revisited each destination on this itinerary enough to try out enough different accommodations to be able to give strong recommendations 🙂

This is the most amazing, detailed, helpful itinerary I have seen. Thank you for putting this together, it was SO helpful!

Thank you so much for your kind feedback! 🙂 I’m glad to know it was helpful. I hope you love your time in Italy!

Hello there! Your itinerary is so helpful! My husband and I are a planning a hopeful trip to Italy this summer and since we are coming from the states we will have two less days than your itinerary permits. Do you have any advice when it comes to narrowing it down? Also, we are flying in and out of Rome. Thank you!!

Hi Jenny! I’m so excited for your hopeful trip!!

This itinerary is for 14 full days in Italy, so with two less days I understand you will have 12 full days instead. I would recommend you remove the Pompeii/Amalfi Coast/Capri and head straight from Rome to Florence instead.

This is for three reasons:

-Firstly, this part of the trip is the trickiest logistically (unless you hire a private car the whole way), so crowding it into the 14 day itinerary was already pushing it.

-Secondly, this part of the trip is a little less “must-see” than the other destinations in my opinion. I define the “main” Italy spots as Rome, Florence, Venice, Milan, and in recent years, Cinque Terre.

-Thirdly, this region would make/justify a nice one-week trip on a return visit to Italy.

This would bring you down to 10 full days (which I happen to map out here: https://thattravelista.com/italy-ten-day-itinerary/ ). I would save one day as a travel day back to Rome at the end. That brings you to 11 full days.

I would use the last full day as an extra night in either Cinque Terre, Florence, or Rome. I’d reco Cinque Terre so you don’t have to rush through it as quickly as I have in the itinerary. But you could also see more of Tuscany via a day trip from Florence if that region interests you more (Siena and San Gimignano are two popular ones, or perhaps a wine tasting excursion!). Or if you or your husband love the history of Pompeii, you can do a day trip there from Rome.

Hope that helps! Feel free to respond back if any more questions/thoughts!

I can’t believe how detailed and helpful this is! I will definitely use this when my long-awaited trip happens. ❤️

So glad to hear it’s helpful, Rachel 🙂 <3 I seriously wish I was (safely) traveling Italy right now! But at least we can plan now so everything's ready once we can go later 🙂

Since Italy is my “neighbour” country I’ve been there numerous times and visited majority of the places you included in the itinerary – and I must say you did a great job! Thorough & interesting – definitely super helpful for anybody who is planning their trip to Italy!

Thanks so much, Sandra! Jealous that Italy is so close for you! 😉

Disha Smith

You post has me missing Italy so much! I love how detailed you are in this itinerary. I definitely missed out on quite a few gems in Italy.

The best part about missing something is it’s an excuse for a return trip 😉

Snazzytrips

I love all the detail here. Will use this to plan my next trip to Italy. Amalfi Coast and Capri definitely on my list, including the Blue Grotto, but not sure now if I can do it.

If Blue Grotto is top of your list, definitely don’t rule it out! Just budget enough time and skip out on some other Capri sights 🙂

Melissa Roos

The detal in this post is amazing! I’ve been looking to visit Italy for a few days so these tips are very helpful.

I hope you love your trip! I’m sure you will 🙂

This is such a wonderful and detailed blog, so much useful info. And your photos are beautiful, thanks for sharing!

Thanks, Emma! 🙂

wow!! the detail on this post is beautiful!! 🙂 this is inspiring me to go back to Italy ASAP 😀

Thank you, Daniela!

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How to Day Trip to Burano, Murano, & Torcello from Venice

New zealand female packing list: everything i packed, that travelista.

A STUNNING Italy Itinerary 14 Days | 2 Weeks in Italy

By: Author Charles

Posted on July 12, 2023

If you are looking to put together a 2 weeks in Italy itinerary, you have come to the right place. This guide will go through what 14 days in Italy can look like including routes, logistics, attractions, and more.

Italy is just one of those countries that has so much to offer its visitors. From its historical cities & landmarks to its beautiful mountains & beaches, there is just a never ending list of opportunities in the country.

This itinerary will go through how to put together a comprehensive 14 days in the country that will include a little bit of everything. Venice, Rome, Florence, the Amalfi Coast & more will be included on the route.

So, read on to learn more about all of the scenery, sites, viewpoints, and experiences that will come with this Italy itinerary.

*  Affiliate Disclosure : This post may contain affiliate links, which means I may receive a commission if you make a purchase through the links provided, at no additional cost to you. Thanks for supporting the work I put into TripTins!

Italy Itinerary 14 Days Overview

Before jumping into the full travel route, I did want to give a quick overview of what this Italy itinerary will go over during the 14 days in the country. Overall, the itinerary will look something like this:

Venice : 2 Days Florence : 4 Days (w/ two day trips) Rome : 3 Days Pompeii : 1 Day Amalfi Coast : 3 Days Travel : 1 Day

→ The 14 days essentially includes 14 full days in the country , either arriving early on day 1 in Venice (or the night prior), and then making your way out of the Amalfi Coast & departing on day 14.

→ It is also important to note that the itinerary is set up so that you will be arriving in one city (Venice) but departing from another city (Naples – since it is the closest major city to the Amalfi Coast) . If Naples does not work well for your departure, you should also have no issues flying out of Rome instead on the last day.

→ To get from city to city throughout the itinerary, you will be able to use the well connected Italy train system (in conjunction with some busses & taxis from time to time). While driving is a possibility in Italy, this itinerary in particular is best completed by train.

→ From a logistical standpoint I have set up the itinerary to leave early in the morning when going from one city to the next . You can keep it as is, or you can also easily take a later evening train the night prior to avoid the early wakeup. Whatever travel style works for you!

→ Italy can certainly be a year round destination, but it really depends on what types of activities you are most interested in.

For the purpose of this itinerary, I would recommend a trip in the warmer months (May-September) to take full advantage of the Amalfi Coast. With that said, I would advise leaning towards those shoulder months of May, June, September to avoid the summer high season.

→ For all attractions mentioned in this guide, be sure to check the latest opening days & hours .

Certain places are not open every day of the week, so you may need to move things around depending on how your dates line up. In addition, many of the more popular places offer the chance to book tickets in advance . I would recommend doing so to guarantee your entrance.

→ Before diving into the itinerary be sure to check out the Italy Helpful Tips   section to get you prepared for your trip.

Italy Travel Route Map

Take a look below at where each major city that the itinerary goes through falls on the map.

The northern most point is Venice, where you will begin you trip as you make your way down the country to Florence, Rome and onto the Amalfi Coast to finish your trip .

In addition to the main route, you can find a few additional places pinned down on the map:

→ Siena (day trip from Florence) → Pisa (day trip from Florence) → Pompeii (pit stop between Rome & the Amalfi Coast) → Capri (day trip from Positano)

Hopefully this can give you a better sense of how the country is laid out as you prep for your trip.

Italy Itinerary 14 Days Breakdown

​ Now let’s get on to the actual trip! The following is a detailed breakout of the daily attractions and activities on this Italy itinerary 14 days travel route.

Each of the next sections will go through this day by day view, giving you some more detail and explanations of what to expect out there.

Throughout the remainder of the itinerary, you will also find links for more detailed Italy travel guides that I have put together.

Feel free to check those out if you would like to learn more about a particular city, activity or attraction.

Day 1 – Venice

After flying into Venice early on day 1 or the prior evening, it is time to begin your 2 weeks of exploring Italy. The first two days of the trip will be spent wandering around Venice, visiting some top highlights, and roaming the streets.

The first day of the trip will focus on the main attractions within Venice itself, while the second day will be more of a day trip to smaller islands off the coast of the city.

For those who did not know, Venice is not your normal European city. Intertwined throughout its streets is a labyrinth of canals, making Venice one of the most unique cities in Italy.

During your time in the city, you can walk over and around the canals as you head from one attraction to the next. Or you can even make your way on boat rides within the canals if that is of more interest to you.

After getting yourself settled in, you can begin your day checking out some of the best that Venice has to offer. Below are some of the attractions you can choose to visit on your first day in Italy:

• 1. Piazza San Marco
• 2. St Mark’s Basilica
• 3. St Mark’s Bell Tower
• 4. Doge’s Palace
• 5. Peggy Guggenheim Collection
• 6. The Grand Canal
• 7. Ponte di Rialto
• 8. Taking a Gondola Ride

» Learn more about these attractions in the Best Places to Visit in Venice guide up on the site

In addition to specific attractions, feel free to also just start walking around the streets, alongside the canals, and over bridges. You will pass by plenty of picture worthy spots where you will be able to just relax and enjoy the scenery.

For nights 1 & 2 of your trip (and potentially the night prior), take a look at a few highly rated hotels to choose from:

• Hotel Bisanzio
• Hotel Mercurio Venezia
• Hotel Serenissima

Day 2 – Murano, Burano, & Torcello

On your second day in Venice you will be able to venture a bit further out of the main island area through the Venetian Lagoon to the islands of Murano, Burano and Torcello.

Murano is most well known for its glass blowing, Burano is known for its lace making & very colorful buildings, and Torcello is famous for being where the history of Venice all began.

The day trip can easily be done on your own as you leverage the public transportation boat system around Venice or you can opt for a highly rated guided tour around the islands , which will take care of all logistics for you.

If you opt for a self guided day trip, you will first want to make your way to Fondamente Nove on the northern side of the island. From there, the logistics will look something like this:

(1) Fondamente Nove -> Murano : you can hop on the 4.1, 4.2, 12 or 13 water bus lines to the first stop of your trip – Murano. There are a few water bus stations on the islands but nothing is more than a 15-20 walk away

(2) Murano -> Burano : once Murano is complete make your way back to the Faro waterbus stop and catch the 12 line to Burano

(3) Burano -> Torcello : after Burano, get on the 9 line that will take you to Torcello.

(4) Torcello -> Fondamente Nov e: now that touring for the day is complete hop back onto the 12 line to get back to the starting point of Fondamente Nove.

» For everything you need to know about these islands check out the day guide of Exploring Murano, Burano and Torcello

Day 3 – Travel & Explore Florence

After two days of exploring Venice and its surroundings it is time to make your way to the Venice train station where you will begin your journey to your next destination of Florence – a city filled with incredible museums, art galleries, viewpoints and gardens .

This itinerary gives you the chance to spend an extended time in Florence.

The first two days will be spent within the city itself, while the second two days will be spent as day trips (although you can certainly move things around as you see fit).

» To get the most out of Florence go ahead and take a look at the Two Days in Florence Travel Guide that can help plan your time in the city.

The train ride to Florence should take approximately two hours and there should be plenty of trains heading there at all times of day (check out the end of this guide for more information about train travel).

Try and catch an early train (prior to 7AM is best) so you arrive in Florence by mid morning time and you will have more than a half-day to explore the city. Check into your hotel before setting out for the remainder of the afternoon.

Remember, you can opt to head to Florence the previous night as well if you rather wake up in Florence and have some extra time to explore the city.

Below are a few recommended hotel options for your time in Florence (nights 3, 4, 5, & 6):

• Hotel Paris
• Hotel Degli Orafi
• Firenze Number Nine Wellness Hotel

The first day in Florence will be focused on three main attractions – the Accademia Gallery, the Duomo, and the La Basilica di Santa Croce.

Accademia Gallery 

At the Accademia Gallery you will find numerous rooms and halls that are filled with a variety of different artwork. However the main attraction here is the one and only David Statue by Michelangelo.

Be sure to book your tickets ahead of time to reserve a time slot and guarantee your entrance.

Cattedrale di Santa Maria del Fiore

​A 10 or so minute walk from the Accademia is the Duomo or Cattedrale di Santa Maria del Fiore – one of, if not the most well known building of Florence and its skyline.

This massive building has beautiful architecture inside and out.

A visit to the Duomo can entail various sites all within the area including the Cathedral, Brunelleschi’s Dome, Bell Tower, Baptistery, Museum and Santa Reparata.

There are three different ticket options to choose from depending on your preference.

Brunelleschi’s Dome Climb

One of the highlights of the Duomo is climbing the 463 steps to the top of Brunelleschi’s Dome. From up top, you will get some of the best 360 degree views that Florence has to offer. The climb up is only included in the Brunelleschi Pass ticket option through the link above.

Note: you must reserve a day/time slot for your Duomo climb. The remainder of the attractions within the area do not require entering at certain times of day.

La Basilica di Santa Croce

To end day 1 in Florence you can make the walk to the La Basilica di Santa Croce.

This church is known for being the burial site for famous artisans and historians such as Michelangelo, Galileo and Machiavelli. Just taking a look at the outside architecture of the church is a highlight within itself.

Day 4 – Florence

During your second day in Florence, you will have the chance to visit some of the world’s best museums as well as some top outdoor attractions within the city. Below are some 6 places to add onto your Florence travel route:

Piazza della Signoria

One of the most famous piazzas in Florence is Piazza della Signoria. A vast plaza that will include numerous statues, one of which is a replica of Michelangelo’s David that you just saw on day 1.

Palazzo Vecchio and/or Uffizi Gallery

Palazzo Vecchuo and the Uffizi Gallery are both rich in history and offer visitors the chance to explore the halls, rooms, and galleries of each one of them.

Depending on preference, you can opt to visit one or both of these museums during your time in the city.

These are both some of the most popular places in the city, so be sure to book those tickets in advance if interested in visiting.

Ponte Vecchio

​After your morning of hitting the museum/s is complete, grab some lunch and then make your way to the most well known bridge around the area – the Ponte Vecchio.

The bridge is known for its amazing viewpoints and picture opportunities as well as all the gold/silver jewelry stores lining it.

Boboli Gardens

Once you make it to the other side of the Arno River you will head to the Boboli Gardens. Since most of the morning will be spent indoors, the afternoon will be spent outdoors.

The Boboli Gardens is a massive area of greenery, sculptures, walkways and fountains. It is really a great way to just get out of the city feel for a bit and take some time to enjoy one of the most vast gardens you will come by.

Piazzale Michelangelo

From the Boboli Gardens, make the walk to the most well known viewpoint of the city at Piazzale Michelangelo.

From the top near the Michelangelo statue, you will be able to see the skyline, rooftops, river and bridges that make up the city of Florence.

For an even more special experience, save the viewpoint for sunset as you get to see the sky’s color changing to end the day.

Day 5 – Siena

While your first two days in Florence will focus in on the city itself, the second two days will be day trips to Siena and Pisa.

This gives you the chance to stay in Florence for a couple extra nights, when you will be able to enjoy the city during the evening times as well.

If you wanted to mix things up a bit too, you could move your days around as you see fit. Whether that is because of personal choice or potentially because of certain attractions not being open on certain days.

​ The first trip I will talk through is a day out to  Siena . Getting to Siena is pretty simple – make your way to the bus station in Florence (which is right next to the train station), and after a 90-minute ride or so you will end up in the city center around Piazza Antonio Gramsci.

There are plenty of busses that make the route and you can buy tickets when you get there or to play it safe head to the bus station the day before to purchase tickets for an exact time.

Once you arrive in Siena you will be greeted by a beautiful walled old city full of hilly winding streets, plazas and home to the famous Palio race (held on July 2nd and August 16th).

If you happen to be in Italy during one of these dates you can definitely check it out, however it will be absolutely packed with people!

The main square (and where the Palio is held) is Piazza del Campo – a unique and historical sloped piazza, where you will find plenty of restaurants and coffee shops in the vicinity.

Sitting at the base of the slope is Palazzo Pubblico , the town hall of Siena. You can visit the museum that sits inside here and also have the chance to climb the Torre del Mangia bell tower .

Climbing the 400 or so steps to the top is quite the experience as well as the amazing view you will get from above.

After taking the bus ride, roaming the streets and plazas, and climbing to the top of the city throughout the morning, you can find a nice restaurant around the area as you enjoy the city around you.

Up next is the Siena Cathedral – an amazing piece of architecture with huge striped columns and arches throughout. You will find detailed mosaics and other types of artwork as you walk around the complex.

Besides for the Cathedral there are some other smaller places to visit right around the area including The Baptistery of San Giovanni ,The Crypt , and The Museo dell’Opera.

You will also want to give yourself some time to just enjoy the city, walk around, and get some shopping in. Once you have had enough time in Siena, take the bus back to Florence and call it a day.

​ Day 6 – Pisa

​ It is time to head outside the city once again on a quick train ride to Pisa . There are plenty of trains that can take you the hour or so to Pisa quickly and efficiently.

Once you arrive at the train station in Pisa, it is a quick 10-minute cab to arrive at the Leaning Tower of Pisa . Once again, it is probably best to buy your tickets in advance to save some time from waiting in line and guarantee your entrance.

Obviously the main attraction here will be the famous leaning tower, however there are a few other attractions around the area that you can check out as well.

It is up to you to decide whether you would just like to check out the tower and then head back to Florence or also add in some additional attractions along the way.

The Baptistery, Camposanto, Sinopie Museum, and Cathedral are the other main places you can check out right around the Piazza.

After checking out the tower and some of the other sites, grab some lunch at one of the local restaurants and take some time browsing the market stalls selling all types of goods. It will also be nice to just walk the city streets, getting a feel for the city and enjoying your time here.

Once you have had enough time in Pisa, take the train back to Florence where you should still have some time to wander around before calling it a day and getting ready for Rome the following day.

Day 7 – Travel to Rome & Vatican City

​ After four days in Florence and its nearby cities it is time to head to the capital of Italy – Rome . There are plenty of trains all throughout the morning that will take you the 90 or so minutes south.

Once again try and get into Rome earlier than later so you will have more time to enjoy the city. After checking into your hotel and grabbing some lunch it is time to already visit another country – Vatican City !

For highly rated hotels with great location & price, check out these for nights 7, 8, & 9 in Rome:

• Rome Life Hotel
• Hotel Colosseum
• Raffaello Hotel
• The Britannia Hotel

The Vatican is notorious for its hours long lines to buy tickets especially during the high summer season. You can however avoid all the waiting and head directly into the museum if you buy tickets ahead of time.

→ If you would like to check out some highly rated third party guide companies feel free to do so as well. All guided tours will include skipping the line.

The main attractions in Vatican City include Saint Peter’s Square, the Vatican Museums, the Sistine Chapel, and Saint Peter’s Basilica. These can all easily be done in a few hours around the area as you enjoy your first day around Rome.

» For an in depth guide about this experience check out the Best Things to Do in Vatican City

Saint Peters Square

As you approach Vatican City, you will probably do so entering Saint Peter’s Square. You can spend some time walking around Saint Peter’s Square first, taking pictures of this column filled oval with various statues throughout.

Vatican Museums

After some time outside make your way first to the Vatican Museums, where you will get to experience a one of a kind art collection. The Museums are filled with so many different pieces of artwork – from The Raphael Rooms to the Gallery of Maps and everything in between.

Sistine Chapel

As you make your walk through the museum you will eventually end up at the Sistine Chapel – a one of a kind piece of art. It took Michelangelo 4 years to complete this detailed masterpiece.

Saint Peter’s Basilica

Up next is Saint Peter’s Basilica. This is not part of the Vatican ticket but is free of charge to get into. It is a massive church with a variety of arches throughout the building.

You will also have the option to climb to the very top of the dome (for an extra fee).

Day 8 – Rome

​ To begin day 8 of your 14 day Italy itinerary you will make your way all around the city of Rome. There is so much to see and explore in the city and this day will be filled with many of its highlights.

» To get a better understanding of everything to do check out the One Day in Rome Itinerary

Feel free to stop by the following main attractions, which are sure to fill up an entire day in Rome:

The Colosseum

The Colosseum is known to be one of the largest amphitheaters in the world and was used for everything from gladiator fights to animal battles. It was a way to bring the people of Rome together and give them different types of entertainment.

The Colosseum is one of the Seven Wonders of the World and for good reason. You can spend hours here admiring the architecture and learning about the history of the site.

​ To book tickets in advance visit the official Colosseum booking website . On the page you can either book a general ticket or have the option to book one of the guided tour options.

General admission tickets include a visit to the Colosseum and the Roman Forum / Palatine Hill area. You must reserve a time slot for the Colosseum and the ticket is then valid for 24 hours (so you can visit Roman Forum / Palatine Hill without a specific time slot).

Roman Forum & Palatine Hill

The Roman forum area is pretty impressive with numerous historical ruins sprawled throughout the surrounding area of the Colosseum.

Just some but not all of the sites include The Arch of Titus, Temple of Saturn, and Temple of Vesta. There are plenty of others that you will pass by along the way.

You can then also make your way to Palatine Hill, which houses some additional ruins. There is also a great view of the Forum from the Hill that makes for a great picture opportunity.

After wandering around the Colosseum area, grab some lunch around the area, and then make the walk to the Pantheon, a former Roman temple.

As of July 2023, there is an entrance ticket needed to visit. Prior to this, the Pantheon was free to enter.

The building itself is basically a huge sphere with an opening for natural light on the very top of the building. You can walk around and spend some time inside before heading out for the Trevi Fountain.

Trevi Fountain

Last up for the day is the Trevi Fountain – one of the most well known fountains in the world. Not only is it a fountain but also a piece of art with many different statues on or around it.

Spanish Steps

The final historical attraction of the day will be the Spanish Steps. From the bottom of the steps at Fontana della Barcaccia to the top, where you will find the Trinita dei Monti church, you will walk up 138 steps.

Day 9 – Rome

​ Your third and final day in Rome will be a bit more laid back as you will have already visited the major landmarks during the previous two days.

Borghese Gallery and Gardens

The first stop will be the Borghese Gallery and Gardens .

As you first arrive at the gallery you will find yourself in front of a beautiful mansion. It used to be a private art collection now open to the public full of different types of painting and sculptures throughout.

» Note that for this museum you must purchase tickets in advance  (FYI closed on Mondays).

After a couple hours exploring the Gallery it is time to stroll around the gardens that surround it. The Gardens are a great way to relax after a few days running around the different attractions in Rome.

The area is filled with winding paths, lakes, fountains, different type of statues and sculptures, and even a zoo, among a variety of other sites. There is also the option to rent a bike around the area in order to see more compared to if you were on foot.

Basilica di San Giovanni in Laterano

Once finished seeing what the Borghese Gallery and Gardens have to offer grab some lunch and then make your way across the city walking and enjoying the streets of Rome to Basilica di San Giovanni in Laterano (also known as Archbasilica of St. John Lateran).

It is known for being the oldest basilica in Rome and houses the Papal seat.

The rest of the day is up to you. This will be your last night before heading off to Pompeii the next day and then onwards to Positano.

Day 10 – Travel to Pompeii & Arrival in the Amalfi Coast

This 2 week Italy itinerary will now take you from Rome to Pompeii and then onwards to the Amalfi Coast .

If you are not interested in heading to Pompeii, then spend the morning of day 10 around Rome, getting in any additional attractions you may want to see. Then head off to the Amalfi Coast via train, bus, or even by ferry .

If you do decide on Pompeii then you will make your way to the train station where you will catch a train to Naples (a ride that should be about a little over an hour).

Once in Naples you will have a couple options – either hop onto the circumvesuviana (local) train line from Naples to Pompeii or you can hop in a cab that will take you there.

Either way you will have your luggage with you. No worries though because you can easily leave your luggage at the lockers at the Pompeii train station, at the entrance of Pompeii, or with your cab driver.

As you make your way down by car or train to Pompeii you will see Mt. Vesuvius to your left – a historic volcano that erupted and covered the entire city of Pompeii and its surroundings in volcanic ash back in the year of 79 AD.

Nearly 1,500 years later, the city was rediscovered as it was preserved over the volcanic ash that covered the city. Now will be your opportunity to visit the archaeological remains of the city and see what life in Pompeii used to be like.

There is just so much to see and learn here. You will pass by the ancient forums, baths, theaters, houses, tombs and much more.

You can go about your day here guiding yourself around the ruins using a map or you can hire a guide to give you some more insight into the ruins. You can spend as much time as you see fit here.

It just depends on your travel plans onwards to Positano later in the day. A good 4-5 hours here will have you seeing a decent portion of the main attractions around the area.

To make it to Positano you can choose from a couple options – local train from Pompeii to Sorrento and then a bus to Positano, or hire a cab to take you the hour or so straight to Positano from Pompeii (more expensive but much easier).

You should most likely be arriving in Positano in the evening, just in time to check into your hotel and have a nice dinner. Your next 3 or so days will be a nice and relaxing way to end your trip.

Day 11 – Positano

Once you wake up the next morning you will get to see the colorful buildings making up the Amalfi Coast hillside.

You can spend some time walking around the city just relaxing and enjoying the surroundings. As you walk the winding roads you are sure to pass by art galleries, fine dining, and a variety of boutiques.

You can then spend some time just laying on the beach and having some well-deserved rest. If you are interested you can also hop on a boat tour or hire a guide to take you around the waters of Amalfi. Spend the rest of the day just enjoying the city of Positano and all it has to offer.

Below are a few top rated hotels options to choose from in Positano for nights 10, 11, 12 & 13:

• Hotel Marincanto
• Hotel Savoia
• Hotel Il Gabbiano
• Hotel Eden Roc Suites

Day 12 – Day Trip to Capri

Now that you have had some time to relax and enjoy Positano, you can make your way to the nearby island of Capri on a one of a kind day trip.

Getting to Capri is nice and easy from Positano as they are located just 30-45 minutes away from one another by ferry.

The first boats leave Positano around 9:00AM and the last boats leave Capri around 6/7:00PM. This should give you plenty of time in between to take advantage of what Capri has to offer.

» The Capri Day Trip guide up on the site will walk through everything to know about the day.

During your time on Capri you can make your way to some beautiful highlights that make up the island. Below is what a potential day could look like depending on your interests.

The Piazzetta

Once you arrive in Capri you can walk, cab or take the funicular up to the Capri Town. The funicular is the probably the best option here as it is quick, cheap and convenient (runs every 15 minutes / 2 Euro).

Once up top in the town of Capri you can spend some time exploring the streets, plazas, restaurants and stores. Nearby you will pass the Piazzetta or Piazza Umberto I.

Augustus Gardens & Faraglioni Rocks

At the Augustus Gardens you can walk through an area filled with a variety of different plants and flowers, as well as take in some spectacular water views of the Faraglioni Rocks out in the distance. It really is just a beautiful place to relax and enjoy.

You can also see Via Krupp down below, a winding pathway down the mountain. Although the road is closed for safety reasons, it still makes for one great picture.

Villa San Michele

After visiting the gardens, you can make your way to the Anacapri side of the island. There are busses and taxis that can take you along the 15 minute drive. Once there you can visit the Villa San Michele. 

Once the home to Swedish physician Axel Munthe, it is now open to the public to explore. You can spend time roaming around the estate, which includes the main villa, gardens, terraces, artwork and some more great views.

Mount Solaro

To finish up the day, head on up to Mount Solaro, the highest point in Capri. To get there you will have to take a single person chairlift up to the top.

While the view from the chairlift are great, the view from up top is even better as you will get to see panoramic views of the entire island.

Day 13 – Positano

​ Your third day in the Amalfi Coast can be spent just relaxing, enjoying the beaches and the town of Positano. You can rent a boat and spend some time out on the water and/or hit the local shops.

As this is your last full day in Italy, it is a a great way to wind down after two weeks of traveling around and seeing all the great sites that Italy has to offer.

Day 14 – Depart to Naples & Head Home

After 14 days of exploring the country, your 2 week Italy itinerary is now coming to an end. The easiest option here is to head to the Naples airport by taxi.

You could also take a bus to Sorrento and then either bus/train to Naples (although longer and a bit less simple to do). 

If your flight is later in the day then you still might have some time to enjoy Positano – either in the city, on the beach, or in the water, before heading back to Naples.

Getting Around Italy

As you can tell, making your way around Italy for 2 weeks will entail some logistics. For the most part though, there should not be too many complexities when making your way between the major cities.

The main mode of transportation in Italy will be the train network . You can take a look at the ItaliaRail train website   which will give you schedules and prices of the various train routes.

Train prices can increase over time as it gets closer to your departure date. Due to this I would recommend booking trains earlier than later to get a cheaper rate and reserve your spot.

The main travel routes to consider for this itinerary in particular will be:

• → Venice to Florence
• → Florence to Rome
• → Rome to Naples

In addition to those particular routes, you will also need to decide on the transport between Naples – Pompeii – Positano, as well as Positano back to Naples.

For the two days trips, you can more easily book a bus to Siena and train to Pisa once you arrive (although you can certainly plan ahead of time as well).

Important note regarding Italy train travel in general:

Many train tickets in Italy must be “validated” before getting onto the train. If you do not validate your ticket, you could receive a fine. So, just be aware of this and get to the train station a bit earlier than expected to validate tickets.

Booking Accommodation

The final topic I wanted to talk through is booking accommodation for your trip to Italy. While there are certainly endless hotel options in the major cities, the highly rated hotels (whether they are mid tier or high tier) will sell out in the peak seasons.

I would highly recommend booking your accommodation well ahead of time once you have your dates all set. This will better guarantee that you will get your choice of hotel and be all set for your trip.

Throughout this itinerary I have mentioned some of the best options to choose from when going about your Italy itinerary.

Feel free to browse through them to see what works best for you. Many of these will have free cancellation options too. So, even if you are not 100% certain just yet, the option to cancel without a fee is a great perk to have.

With all that said, I hope you now have a better sense of what 2 weeks in Italy is all about and how to go about a trip there. If you have any questions or comments, feel free to add them in below.

Also be sure to head over to the Italy itineraries and guides page to check out some more helpful posts. Have fun out there and safe travels!

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2 Weeks In Italy: An Epic 14 Day Italy Itinerary

August 30, 2022 //  by  Follow Me Away //   4 Comments

Are you dreaming of the perfect 2 weeks in Italy itinerary? If so, this article is for you!

Planning your Italy itinerary should be fun and exciting, not stressful, which is why there’s this detailed post to show you how to spend 14 days in Italy!

This itinerary includes some of Italy’s most popular things to do as well as some lesser-known suggestions that may not be recommended by others.

Planning your trip to Italy last minute?

Make sure to book your hotels and tours in Italy in advance to ensure availability! Here are my top picks for your trip!

Tickets you MUST book in advance:

• Vatican Museums And Sistine Chapel (A MUST in advance)
• Colosseum Entry Tickets (Another MUST! Book online in advance!)
• Michelangelo’s David Tickets (Often sells out in Florence)
• Skip-The-Line Uffizi Gallery Tickets (Buy online to save time!)
• Doge’s Palace Entry Ticket (Very busy, can sell out)
• Milan Cathedral And Rooftop Tickets (Sells out and a must-see!)

Top picks for places to stay in Italy:

• Rome: Hotel Relais Dei Papi (Amazing Vatican location)
• Florence: Relais Pizza Signoria (City center location)
• Venice: Hotel Carlton Grand Canal (Grand Canal views!)
• Dolomites: Parkhotel Laurin (Central location with pool!)
• Cinque Terre: Affittacamere Casa Dane’ (Affordable location)
• Milan: Collini Rooms (Just 10 min from Milan airport!)

If you follow this itinerary, you will see the best of what Italy has to offer on your trip. That includes visiting the highlights as well as seeing some seaside villages.

For this 14 days in Italy itinerary, you will be provided with a breakdown of some recommended stops and the best sites to see at each.

There is also a recommendation for how long to stay in each area. Since everyone is different, though, feel free to change this to fit what you would like to see!

Instead of planning out every moment of every day of your 14-day Italy vacation, this itinerary provides you with a structured yet flexible plan to follow for your first trip to Italy itinerary!

If you’re not sure what to pack, check out this list of 10 things to include on your Italy packing list .

Keep reading to learn how to plan a trip to Italy for two weeks!

Read next: 10 Days In Italy Itinerary

Begin Your 2 Weeks in Italy Itinerary by Flying into Naples

When planning an Italy itinerary, most tourists decide on flying into Rome or Milan, as those are the more popular airports. However, it is very possible to fly into smaller airports throughout Italy.

This is great for your 2 week Italy itinerary. To begin your vacation to Italy, you can fly into Naples Capodichino Airport (NAP).

This airport is very convenient, as it is only four miles away from the city center, and is the perfect place to start your 14 days in Italy!

When booking your flight to Naples, an easy way to save money is checking to see if you can switch to a smaller airline.

You will most likely already have a transfer on your way to Italy, so see if switching to a budget airline might make it a lower price tag.

Once you have arrived at Naples Capodichino Airport, it is easy to catch a bus to Napoli Centrale Railway Station or take a taxi to the city center.

Getting Around During Your 2 Weeks In Italy Itinerary

When deciding how to get around during your 14 days in Italy, you have a few options.

The first is by using public transportation during your trip. Italy has some amazing high-speed trains that can get you from city to city quickly and easily.

This is the recommended use of transportation for this Italy sample itinerary, as it will get you to your destinations quicker, leaving more time for sightseeing!

You could also rent a car or a Vespa for this two-week Italian trip. This will definitely be the more expensive option, though.

On top of the normal rental price, you will also be dropping off the vehicle at a different location, which can really drive up the price.

The tolls in Italy can also be pretty high, averaging about $25 a toll. This can add up pretty quickly, so you’ll need to budget at least $200 just for tolls.

Parking can also be hard to find in some of the bigger cities.

Having a car does give you a lot of freedom, though, and you can get from one town to another as quickly or slowly as you would like

There is also the option of hiring a private driver for your 14 days in Italy, but only if it works for your financial position.

Whether you go by car or train, you will love your 2-week Italy road trip!

Read more:  Pros And Cons Of Renting A Car In Italy

Days 1-2: Naples

Whether you want to spend your first couple of days in Italy eating pizza, exploring, or both, Naples is an excellent spot to start your two-week Italian trip!

How long you have in Naples depends on your flight and what time you plan on heading to your next destination.

There is so much to do, so pick what sounds the most interesting to you, and get to exploring!

You will probably be tired once you arrive, but once you take the time to rest, make sure you explore Naples during your 2 weeks in Italy itinerary.

Noteworthy Things To Do In Naples:

Find art at the national archaeological museum of naples.

If you want to see all of the relics from Pompeii and Herculaneum, make sure to stop by the National Archaeological Museum of Naples.

This museum is home to one of the most impressive selections of Roman art and artifacts in the world.

Unfortunately, this museum can be confusing, so it is best to visit with a tour group or a self-guided walking tour from a guidebook.

You don’t want to miss out on any of the artifacts from Pompeii and Herculaneum.

Discover the Church of San Francesco di Paola

Located on the west side of Piazza del Plebiscito is this beautiful 19th-century church.

It is one of the most important pieces of neoclassical architecture in Italy.

This church is actually inspired by the Pantheon in Rome, but you won’t find all of the crowds here.

Tour Palazzo Reale (Royal Palace)

Palazzo Reale is a genuinely spectacular palace that is located in Naples. You should definitely try to make it here during your 2 weeks in Italy!

The palace was initially built in the 1600s as a residence for a Spanish King, who never ended up going to Italy.

It wasn’t used until the 1700s when it became the palace for a Bourbon King.

Since it is also close to the Church of San Francesco di Paola, you can easily see both of them while exploring.

It might not seem like eating pizza should be on this list of what to do in Naples, but it most definitely deserves its spot!

After all, you are in the birthplace of pizza, so finding a restaurant serving up Naple’s signature dish is a must.

If you want to find an authentic Neapolitan pizza, look for a place serving “pizza vera Napoletana.”

If you are interested in trying a more “street food” pizza, then be on the lookout for pizza frittata. It’s fried pizza dough stuffed with cheese and/or meat.

See an Opera at San Carlo Theater

If you can grab a ticket to see the opera at the San Carlo Theater, it is highly suggested.

San Carlo is the oldest theater in Europe and the largest theater in Italy, so it definitely worth seeing during your 14 days in Italy.

If you are not able to snag a ticket to the opera, then take a guided tour so that you can still marvel at the interior.

Buy A Ticket To The Opera

Admire The Veiled Christ

A truly spectacular sight, the Veiled Christ is a must while you are in Naples!

Even if art and sculptures aren’t typically your thing, you will definitely appreciate the Veiled Christ during your 2 weeks in Italy.

The Veiled Christ, which is located in the center of the Sansevero Chapel, was carved in 1753. You should definitely check out the Veiled Christ while in Naples!

Skip The Line By Getting Your Tickets Online

Visit Il Duomo (The Cathedral) 

While you are in Naples, you must visit this 14th-century Cathedral!

This Cathedral is a wonderful mix of periods and art styles, making it fascinating to explore.

It was initially built in the 14th century but was destroyed by an earthquake in the 15th century. There were many repairs and additions made, including the neo-Gothic Facade that was only completed in 1905.

Where To Stay In Naples:

There are so many options for where to stay in Naples.

Whether you’re looking for budget, luxury, or something in the middle, there is an option for you.

The area you want to stay in depends on what you want to do during your time in Naples.

If you want to stay somewhere close to the airport where you still have relatively convenient access to some of the sights, you should stay in the Historic Center.

If you would like to be closer to some of the popular attractions in Naples, you should try to find a hotel in Chiaia. No matter what you’re looking for during your 2 weeks in Italy, Naples will have something for you!

Stay Near Piazza del Plebiscito: Chiaja Hotel de Charm e Check Rates: Booking.com

Mid-Range: Culture Hotel Centro Storico Check Rates: Booking.com

Stay In The historical Center: M Gallery Palazzo Caracciolo Check Rates: Booking.com

Luxury: Grand Hotel Vesuvio Check Rates: Booking.com

How Long To Spend In Naples During Your Italy Itinerary:

How long you spend in Naples will depend on what time your flight arrives and what time you are leaving.

Whatever your schedule, we suggest that you spend at least one night in Naples.

Since it is the beginning of your 14 days in Italy, you will most likely be tired, so this gives you some time to rest before starting to travel again.

While you are in Naples, you should also try to get some sightseeing in, as there are so many incredible places to see!

Days 3-4: Amalfi Coast

The Amalfi Coast is made up of multiple towns set along the mountainous coast of Italy.

It is one of the most popular areas of Italy, and for excellent reasons. It is absolutely stunning and will leave you only wanting more.

There are so many options for which towns to visit during your time at the Amalfi Coast.

Whether you’re looking for the perfect Amalfi beaches , a more authentic (less touristy) town, or the best place for photos, there is a place for you!

Once you decide on which area you want to stay in, then there’s the decision of where to stay. There are so many different hotels and bed and breakfasts to choose from, no matter your budget!

The Amalfi Coast is the perfect place to relax during your 2 weeks in Italy!

You have multiple options for how to get from Naples to the Amalfi Coast.

If you are driving, then it’s a pretty easy drive that should only take you around an hour.

If you are using public transportation, then you have two main options. The first is the train between Naples and Sorrento , as of summer 2019 though, this option is having many delays and cancellations. It is still an option that is very cheap, but recently the service has not been consistent.

Then you have the option of taking the ferry from Naples to Sorrento, which is called Metro del Mare . Taking the ferry is an excellent option for a couple of reasons.

The first is that you have control over which towns you go to. The second is that even if you don’t stop at some of the popular coastal towns, you can still see them and photograph them to your heart’s content!

What To Do At The Amalfi Coast:

Visit the lovely town of sorrento.

This well-known town on the Amalfi Coast is definitely worth a visit during your 2 weeks in Italy.

It’s located in the northern section of the Amalfi Coast and is most popular for its beautiful scenery and the lovely buildings situated along the coast.

While in Sorrento, make sure to check out the gorgeous cathedral that was built in the 11th century.

There are also two different ports in Sorrento that hold fishing and sailing boats.

If you find yourself interested in the history of Sorrento, you can go to two different museums during your time in Sorrento.

Head Out on the Water With This Boat Tour!

Admire The Colorful Positano

Positano is considered one of the most picturesque towns in Italy, and it’s not hard to see why. It is full of colorful houses that are set against the mountainside

If you want an extra-pretty view of Positano, take a boat out so that you can see all of this lovely town.

Full of pretty beaches, cute cafes, and bright buildings, Positano is the perfect spot to relax during your 14 days in Italy.

See Praiano’s Gorgeous Sights

Praiano is located between Positano and Amalfi and is the perfect spot to take in some gorgeous views with fewer crowds.

This town is not as well known as some of its neighbors, but that doesn’t mean that you should skip over Praiano.

It doesn’t matter if you want to stroll through the quiet streets, take a dip in the ocean, or relax on the beach, you will find each to be incredibly enjoyable.

See The Popular Town Of Amalfi

Amalfi is the most popular of all of these coastal towns and is generally packed with tourists.

Don’t be scared of the number of tourists though, Amalfi is still a gorgeous town to visit.

Amalfi even has its own cathedral, which is absolutely magnificent. There are also plenty of shops for you to spend an afternoon exploring.

For The Best Views On The Amalfi Coast, Visit Ravello

While the Amalfi Coast is known for its spectacular views, go to Ravello to see something rather extraordinary.

Unlike the other towns on the Amalfi Coast that are built into the mountainside, Ravello is located at the top of the mountains, giving some breathtaking views.

It is also much more relaxed than some of the other tourist destinations along the coast.

There are also plenty of outdoor terraces where you can enjoy your evening meal taking in the ocean.

Head To Cetara For An Authentic Italian Town

If you want a more authentic experience, head to the town of Cetara.

Unlike most other towns along the Amalfi coast, Cetara remains relatively unspoiled by tourism. It is a great place to head to for a day of relaxing.

Cetara also has the only fishing fleet in this region that is still in operation, so you can see all of the fishermen going about their work.

Tour The Emerald Grotto

If you are feeling up for a bit of an adventure and want to leave the coast, take a tour to the Emerald Grotto, a genuinely spectacular natural occurrence.

The Emerald Grotto is a collection of caves that are bathed in green light. They are only accessible by boat, so I hope you don’t get seasick!

You can take either a car or a bus to get to the facilities along the road, then take an elevator down to the point of departure; it is open from 9:30 a.m. – 4 p.m.

Where To Stay On The Amalfi Coast:

There are so many options for where to stay along the Amalfi Coast, whether or not you are looking for budget or luxury.

Depending on how much you are willing to spend, there are certain areas that will be best for you.

We have an entire post devoted to Where to Stay On The Amalfi Coast in case you are looking for our suggestions in detail! 

Positano and Amalfi are definitely going to be more expensive, so if you are traveling on a budget, these probably aren’t the towns you should spend the night.

Ravello and Cetara would be much more budget-friendly options. If you are planning on staying in luxury though, you will have no lack of gorgeous and unique hotels offering first-class treatment!

Budget In Cetara: Cetara Albergo Diffuso Check Rates: Booking.com

Mid-Range In Ravello: Hotel Parsifal Check Rates: Booking.com

Private Beach In Amalfi: Hotel Miramalfi Check Rates: Booking.com

Luxury In Positano: Hotel Villa Gabrisa Check Rates: Booking.com

How Long To Spend At The Amalfi Coast During Your 14 Days In Italy:

You will probably want to spend 1-2 nights at the Amalfi Coast in order to have a chance to explore or relax.

Because it is more expensive, you might want to spend 2 nights in Naples, then leave early in the morning to head to the Amalfi Coast.

It’s around a 40-minute ferry ride to the Amalfi Coast, so you can spend the day exploring.

This way you only spend one night on the coast but get 2 days of exploring.

If you have found an awesome deal in Naples though, you might even consider staying at a hotel in Naples and taking the ferry both days. I would only deal with this though if you get an awesome hotel in Naples.

Days 5-6: Rome

Next up on your 2 weeks in Italy itinerary is one of the most popular cities in Italy: Rome.

Rome is full of history, art, shopping, and some excellent restaurants! You will have no shortage of things to do during your time in Rome.

Spend time exploring some of Rome’s historical sights, like the Colosseum or Vatican City, or strolling through the picturesque streets and stopping at some of the wonderful little cafes!

You can even find some little hidden gems in Rome !

Driving from the Amalfi Coast to Rome will take you around 4 hours depending on the traffic, and be aware that the traffic in Rome can be pretty awful.

You can also pay for a private driver, but this will come with a higher price tag than some of your other options.

For public transportation, you can take the ferry or train back to Naples, and from there take a train to Rome .

Top Things To Do In Rome:

Throw a coin in the fontana di trevi.

While in Rome during your 14 days in Italy, make sure to stop by the Trevi Fountain and drop a coin in.

Dropping in a coin means that you will return to Rome one day (why not throw in a few more coins for some extra luck on getting back to Rome?).

This is one of the most famous landmarks in Rome, so get there early to beat the crowds!

Explore The Colosseum

No trip to Rome is complete without visiting the Colosseum, so make sure you make it there during your two weeks in Italy!

It is one of the most popular places in Rome, and it will be an experience you’ll never forget!

You won’t be the only one planning on seeing the Colosseum though, so you should look into booking a tour. This way you can skip the lines and guarantee your entrance! 

Skip The Line With This Colosseum Tour!

Explore The Roman Forum

Although not as popular as the Colosseum, the Roman Forum is still an impressive sight, and it’s so close to the Colosseum!

You only have to walk a few steps from the Colosseum, and you’ll be able to imagine how the Roman people used to live.

Book Your Tour For The Colosseum And The Roman Forum Here!

Visit Piazza Navona

If you are looking for a place to spend your afternoon shopping and eating at delicious cafes, head to Piazza Navona!

It is one of Rome’s most popular squares, and for good reason! This square was built in the 15th century and is a beautiful area to explore.

Admire Basilica Di Santa Maria Maggiore

Basilica di Santa Maria Maggiore is known as a Basilica Major, which means it is one of the largest churches in Rome.

It is a truly magnificent structure and is well worth a visit during your 14-day Italy vacation!

The interior is intricately designed with gold, frescos, and detailed paintings on the walls and ceilings.

This is a great place to go during winter in Rome to get out of the cold.

Skip The Line With This Basilica di Santa Maria Maggiore Tour!

Climb The Spanish Steps

What would a visit to Rome be without seeing the famous Spanish Steps?

You’ve probably seen them in a movie or two, as they are one of Rome’s famous landmarks.

If you want to climb the steps (which is highly recommended) make sure to bring your walking shoes, as there are 135 steps.

Gaze Upon Castle Saint Angelo

Castle Saint Angelo, also known as the Mausoleum of Hadrian, is a circular castle that was once the tallest building in Rome!

It was built in 129 AD and was originally intended to be a Mausoleum for the Emporer.

It has now been connected to St. Peter’s Basilica, and if you climb to the top of the castle ramparts, you can see a stunning view of Rome.

Visit The Pantheon

The Pantheon is a former Roman temple that is now a church.

Not only is it one of Rome’s most popular landmarks, but it is also full of interesting history. You should add it to your 2 weeks in Italy itinerary.

Reserve An Affordable Audio Guide To The Pantheon Here!

Wander Through The Vatican City

There is so much to do in Vatican City, that you could easily spend one of your days in Rome just exploring this area.

You’ll definitely want to explore other parts of Rome though, so you should decide on what you really want to do in Vatican City.

The two main things to do in Vatican City are St. Peter’s Basilica and the Vatican Museums.

If you are deciding between the two, we highly suggest touring St. Peter’s Basilica. It will be one of the most memorable experiences of your life!

There are also the Vatican Museums that hold tons of history, and it’s where you will find the famous Sistine Chapel.

The Vatican Museums will take about 3 hours to explore, and St. Peter’s Basilica will take around 1 to 3 hours, depending on how long you want to spend.

Vatican Museum And Sistine Chapel Fast Track Entry

St. Peter’s Basilica: Tour with Dome Climb

Sistine Chapel, Vatican Museums, And St. Peter’s Guided Tour

Where To Stay In Rome:

Staying near Vatican City while in Rome will be your best option, especially when you’re only going to be in Rome for two days during your two weeks in Italy.

This way, you can walk to Vatican Square at night when it is all lit up and it is a peaceful getaway from the hustle and bustle of the city.

We highly recommend taking a look at our detailed guide on Exactly Where To Stay In Rome!  There are also lots of shops around!

If you want to stay at an Airbnb, there are plenty of Airbnb options in Rome from budget to affordable depending on your funds for your best itinerary for Italy. 

Near the Vatican: Vatican Style Suite . Check Rates: Booking.com

Budget: Bed In Roma . Check Rates: Booking.com

Mid-Range: Casa Montani . Check Rates: Booking.com

Upscale:  The Westin Excelsior Rome . Check Rates:  Booking.com

How Long To Spend In Rome During Your 2 Weeks In Italy Itinerary:

For this 2 weeks in Italy Itinerary, we recommend spending 2 days in Rome .

This gives you time to explore Rome, but still gives you plenty of opportunity for the other areas of Italy that you will be visiting.

You can, of course, alter this however you need to. Try not to stay for more than four days though, as this is plenty of time to explore Rome.

If you do choose to stay longer, there are plenty of lovely day trips from Rome to explore!

Days 7-9: Florence and Tuscany

Next up on your 2 weeks in Italy itinerary is Tuscany, specifically its capital: Florence.

Florence is a much more laid-back city than Rome, so it’s a great place to take your time while seeing what Florence has to offer.

It’s also a very walkable city, so you will only need to use public transportation if you want to explore other villages.

There are so many things to do in the Tuscany region !

Getting from Rome to Florence is very easy to do by train, and it will only take you about 1 hour and 30 minutes.

For the best option, take the high-speed train from Roma Termini station to Firenze S M Novella in Florence. This will take 1 hour and 30 minutes. If you choose to drive, it will take you around 3 hours.

Top things to do in Florence:

Explore boboli gardens.

If gardens are your thing, plan a visit to Boboli Gardens !

Whether you want the perfect place for a photo op, or just want to admire the beautiful surroundings, this 16th-century garden is the place for you.

Bring some sturdy shoes though, as Boboli Gardens is up a steep hill.

You should plan on spending around 1-2 hours here, though you could spend less or more depending on your interest.

Boboli Gardens Skip The Line Tour

Visit The Duomo

While in Florence during your 14 days in Italy, make sure to stop by the Duomo. Even if you only set aside one day in Florence, this is a must-see stop!

This Catholic Church towers over Florence and is pretty difficult to miss.

If you plan on going in though, know there is a dress code for women and men; your knees and shoulders must be covered.

You also must be completely silent when visiting the Duomo in Florence .

It is usually very crowded, but you can skip the line by taking a tour.

Skip The Line At The Duomo With This Tour!

Walk Across The Ponte Vecchio

If you are looking for a picture-perfect bridge during your Italy in 2 weeks trip, Florence has you covered!

Ponte Vecchio is a beautiful bridge, and it’s the perfect spot to watch the sunset. You can also enjoy a leisurely stroll and some delicious gelato if you choose!

It is one of the best free things to do in Florence during your trip! 

See David At Galleria dell’Accademia During Your Italy Itinerary

If you are a lover of art, then you definitely want to explore Galleria dell’Accademia.

This museum is home to some of Michaelangelo’s greatest works, including the famous “David” statue.

The museum gets very crowded, and since you don’t want to waste any of your 14 days in Italy, you should consider buying a timed ticket or booking a tour.

Timed Entrance Ticket For Michaelangelo’s David

Marvel At Renaissance Artwork At Palazzo Pitti

Palazzo Pitti is another museum to see if you are an art lover. It’s Florence’s largest art museum, and is full of Renaissance works of art!

There are so many stunning works of art to admire, and it is a wonderful way to spend an afternoon.

Admire The Church Of Santa Maria Novella

If you are arriving in Florence on the train, then you will have no struggle in seeing the Church of Santa Maria Novella, as it is located right in front of the main railway station.

It is a stunning church and is a wonderful example of Renaissance architecture.

Skip The Line And Audio Guide Ticket For The Church Of Santa Maria Novella

Explore The Countryside Of Tuscany

Florence is the capital of Italy’s Tuscany region, but that doesn’t mean there’s nothing else to do.

Tuscany is known for its beautiful countryside full of rolling hills and vineyards. But that isn’t all!

There are many things in Tuscany such as hot springs and magical castles that you are going to want to see, if possible!

Exploring the countryside will be easiest if you are driving, but is possible to take public transportation to some of the villages.

For ideas on what to do in Tuscany, check out this Tuscany road trip .

Where To Stay In Florence:

Florence is much smaller than Rome so if you are staying in the city center there really are no bad places to stay!

We even have an entire post on where to stay in Tuscany which includes Florence!

We also have a complete breakdown of where to stay in Florence .

Hotels in Florence range from affordable to luxury options. You can get a really nice hotel in the city center of Florence for a very reasonable price. 

Affordable:  Hotel Bavaria .  Check Rates:  Booking.com  

Mid-Range:  Globus Urban Hotel .   Check Rates:  Booking.com

Upscale:  Hotel Garibaldi Blu  Check Rates:  Booking.com

How Long To Spend In Florence During Your 14 Days In Italy:

When deciding how long to spend in Florence, it’s important to think about how you want to see Florence.

If you want to wake up early, maybe stay out a little late, and rush through some of the sights, it’s completely possible to see the highlights that Florence has to offer in a day.

If you want to take your time, then two days is the perfect amount of time to stay in Florence.

Days 10-11: Venice

Venice, known as one of the most romantic cities in the world, is next up on your 2 weeks in Italy itinerary.

Venice is the capital of Italy’s Vento Region, and it is made up of over 100 tiny islands!

There is plenty to explore during your 2 days in Venice , and you won’t be disappointed!

If you want to rearrange this itinerary and only spend one day in Venice , that is okay too!

It is so easy to get to Venice from Florence, all you have to do is hop on a train and enjoy the ride!

We even have a full Northern Italy itinerary if you are interested in exploring this region in more detail. We highly suggest it as it is one of the most beautiful spots in Italy! 

Here is a post we wrote on Exactly How To Get From Florence To Venice which explains all of your transport options! 

The best route to go from Florence to Venice is to get on the train at Santa Maria Novela station in Florence and head to Venezia Santa LuciaIf in Venice.

This train trip takes a little over 2 hours and is a nice easy ride. Driving will take you around 3 hours, though this will depend a lot on Rome’s traffic.

What To Do In Venice During Your 2-Week Italy Itinerary

Explore the popular piazza san marco.

Piazza San Marco, also known as Saint Mark’s Square, is the most popular square in Venice, and maybe all of Italy!

It was built during the 12th century and is in the center of the square at St. Mark’s Basilica, which you can tour.

If you are looking to do some bird feeding during your 14 days in Italy, this is the square where everyone feeds the pigeons.

It is also one of the best photo spots in Venice if you are looking for something new for your Instagram! 

St. Mark’s Basilica: Tour with Terrace Access

Climb The Campanile di San Marco Bell Tower

While at St. Mark’s Square, why not climb up the bell tower?

When you reach the top you will have one of the most beautiful views in Venice. The tower itself rises high above the square.

It’s very popular, and you’ve probably seen it in many photos or the replica at Walt Disney World.

This is one of the best things to do in Venice !

Walk Across The Bridge Of Sighs

Legend has it that when criminals were taken away from the palace, over the bridge, they would gaze at Venice for the last time and sigh as they thought about their upcoming punishment, hence the name the Bridge of Sighs.

Who knows how true this is, but it’s something to think about as you cross the bridge on your way to Doge’s Palace.

Go On A Gondola Ride

One of the most popular things to do in Venice is to go for a gondola ride.

Though it will require a bit of a splurge, what could be more fun than riding a gondola through the canals of Venice?

This experience is unlike anything else that you will do on your Italy in 2 weeks itinerary.

Venice: Private Gondola Ride along Canal Grande

Admire The Architecture Of Doge’s Palace

Doge’s Palace is an ornate gothic palace right on the canals of Venice!

It is not only a museum but a showroom, and it is one of the most impressive palaces you will see during your Italy in 14 days itinerary.

Doge’s Palace holds lacework, paintings, sculptures, and more and is a real treat for architecture lovers!

You will definitely enjoy exploring this wonderful palace. If you are visiting Venice during the winter, museums such as this one are the perfect way to stay warm.

Timed Admissions Ticket To Doge’s Palace

Take A Tour Of The Venetian Islands

If you are struggling with deciding which of the Venetian Islands to visit during your two weeks in Italy, why not take a tour?

You will visit the small towns of Murano, Burano, and Torcello, depending on what tour you take.

Since Venice isn’t exactly a walkable city, the best way to see these islands and the lagoon is to take a guided tour.

You will also learn lots of great information about Venice!

Boat Trip: Glimpse of Murano, Torcello & Burano Islands

Walk Over The Rialto Bridge

The Rialto Bridge is an iconic sight that you must see during your two weeks in Italy!

While walking across the bridge is incredible, it is also absolutely beautiful to view it from afar.

It’s the perfect place to get some great photos and is one of the best things to do in Italy during your trip!

Where To Stay In Venice:

When staying in Venice during your 14-day Italy itinerary, we highly recommend staying in the city center!

There is a variety of hotel and Airbnb options in Venice ranging from the budget $70 a night places to luxury $300 a night hotels.

There are plenty of cute, boutique hotels in Venice too if you are looking for something special.

Please don’t forget to check out our VERY detailed guide on Exactly Where To Stay In Venice Italy!

There is something for everyone when planning your stay during your Italy in 14 days trip so choose the accommodation that feels right for you.

We recommend staying near Saint Mark’s Basilica or the Rialto Bridge.

No matter where you decide to stay, you are in Venice and that is something to celebrate!

City Center:  Hotel Casanova . Check Rates:  Booking.com

Affordable: Alberghiera Venezia . Check Rates: Booking.com

4-Star:  Royal San Marco Hotel .   Check Rates:  Booking.com  

How Long To Stay In Venice During Your Italy Itinerary:

Spending 1-2 days in Venice during your 2 weeks in Italy Itinerary should be enough time to experience what the city offers.

The amount of time that you should spend in Venice really depends on how much you want to see, and this Italy itinerary can be easily changed to fit what you desire for your 14 days in Italy.

Days 12-13: Cinque Terre

Cinque Terre is a popular destination for travelers, and it definitely deserves to be explored during your 2 weeks in Italy.

Cinque Terre is split into 5 villages or towns, and that is what the name translates to as “cinque” means 5 and “Terre” means village.

Each of these towns is beautiful and unique, and you should aim to explore each of them during your 14 days in Italy!

Once you have made it to Cinque Terre, getting between the villages is incredibly easy, as there is a train that connects all five.

The journey between villages only lasts a few minutes, so you’ll have plenty of time to explore!

The drive from Venice to Cinque Terre will be around 4 1/2 hours, and you will probably want to use public transportation once you get there, as it can be crazy and expensive to park.

You can also take the train from Venice to Monterosso , which will place you in the perfect spot to explore the surrounding villages.

Top Things To Do In Cinque Terre During Your 14-Day Italy Itinerary

Hike the monterosso footpath.

The Monterosso footpath connects the towns of Monterosso and Vernazza and provides stunning views of the towns!

This hike is a bit challenging as you are going up the coastal cliffs, so plan on at least 1-2 hours to complete it.

The views are worth the effort, but bring plenty of water, especially if you visit during the summer!

Explore The Church of San Francesco

Overlooking the Mediterranean Sea, the Church of San Francesco provides some pretty remarkable views of the dazzling blue water below.

The church was built in the 17th century and is a great place to stop while exploring Cinque Terre during your 2 weeks in Italy.

Visit Parco Nazionale Cinque Terre

This National Park is one of the smallest in Italy at only 15 square miles but it is also one of the most popular and most beautiful!

Parco Nazionale Cinque Terre is one of the most heavily inhabited national parks in Italy and it is easy to see why!

A one-day pass costs $9 per person to enter the National Park. Parco Nazionale Cinque Terre is also a UNESCO World Heritage Site.

Take A Boat Tour Of Cinque Terre During Your Italy Itinerary

If you are short on time during your Italy in 14 days trip, consider taking a boat tour of the Cinque Terre villages.

A boat tour will allow you to see all of the towns with ease and speed and you won’t feel like you missed a thing!

A boat tour is an easy and affordable way to add Cinque Terre to your Italy itinerary even if you are short on time because you can see everything by water!

Cinque Terre: Riomaggiore, Monterosso, Vernazza Boat Cruise

Watch The Sun Set

It doesn’t matter where you do this, but while you are in Cinque Terre you must watch the sunset one evening.

It is absolutely breathtaking, and you won’t regret taking the time to relax and take it in.

This can and should be done from any of the 5 towns in Cinque Terre, so it doesn’t matter where you are staying for the night.

One of the Cinque Terre Beaches is the perfect place for watching the sunset during your trip!

Cinque Terre Sunset Boat Tour 

Where To Stay In Cinque Terre

Which of the 5 towns you decide to stay in during your time in Cinque Terre really depends on what you’re looking for.

Here’s a complete guide to where to stay in Cinque Terre !

You have so many options when staying in Cinque Terre. The hard part will be deciding between all of the beautiful hotels!

Enjoy The Nightlife In Riomaggiore: Locanda Ca Da Iride Check Rates: Booking.com

Stay In Manarola For The Best Views: Olimpo Affittacamere Check Rater: Booking.com

Corniglia Is Where To Stay To Escape The Crowds: Arbanella Check Rates: Booking.com

Stay in Vernazza Near the Beach: Appartamento Margherita . Check Rates: Booking.com

A Room with a View in Monterosso : I Tibei Guesthouse . Check Rates: Booking.com

How Long To Spend In Cinque Terre During Your 14 Days In Italy

Even though there are 5 villages that you can explore during your 14 days in Italy, the simple and quick transportation makes it possible to visit all of them within 1-2 days, depending on how long you spend in each village.

You can adjust this, of course, but try to give yourself enough time to enjoy all Cinque Terre has to offer.

Day 14: Milan And Fly Home

Your final stop on your 14 days in Italy is Milan, and it is where you will fly out.

Milan is home to a very large international airport and many affordable flight options fly in from all over the world.

Beginning your trip in Naples and ending it in Milan is perfect, especially if you want to spend the majority of your Italy itinerary exploring!

For this 2 week Italy itinerary,  you will get the most of your time by buying two one-way tickets.

However, it would be rather easy if you needed to get back to Naples for a roundtrip flight.

All you have to do is book a train or a flight. This could also be done the other way, by flying into Milan and then heading to Naples.

Just because you have only one day in Milan doesn’t mean there aren’t plenty of exciting things to see and do! 

Milan: Bergamo Airport Transfer

Suggested Things To Do In Milan To End Your Italy Itinerary:

Take in the breathtaking milan cathedral.

Even if you are short on time in Milan, you must visit the Milan Cathedral to admire the stunning architecture, even if it’s just for a moment.

You’ve most likely seen pictures of the Milan Cathedral, but it is so much larger and magnificent in person.

Try to make it a priority to see it during your Italian itinerary in 2 weeks!

Milan Cathedral And Rooftop Entrance Tickets

Go Shopping At Galleria Vittorio Emanuele II

If you want to get some shopping done during your 14 days in Italy, you must visit Galleria Vittorio Emanuele II.

It is Italy’s oldest shopping mall, and a very popular place to spend time browsing through all of the fantastic stores.

Even if you don’t want to shop, Galleria Vittorio Emanuele II is incredibly beautiful and deserves a visit just for the 19th-century glass-covered arcade that houses the mall.

Visit Sforza Castle In Milan

Sforza Castle in Milan is a 15th-century castle located right in the city.

It is also home to various artistic works, including those from Leonardo Da Vinci!

If you are looking to add another museum and art gallery to your Italy itinerary, make sure to put Sforza Castle on your list of things to do in Milan.

Explore The City On A Bus Tour

An easy way to explore Milan when you’re short on time is by doing a hop-on-hop-off bus tour!

Even if you aren’t into doing super touristy things, you will still enjoy this bus tour of Milan.

It will provide insider information about some of the most famous sites in Milan and you will easily be able to get off the bus should you want to explore more!

This is perfect if you only have one day to tour Milan.

Milan: 1, 2, or 3-Day Hop-On Hop-Off Bus Ticket

Where To Stay In Milan:

If you are catching your flight out of Milan Airport the next day, we highly recommend spending your last night in Italy somewhere close to Milan Airport.

This will allow you to explore on the last day of your 14-day Italy itinerary without worrying about waking up early and taking a long transfer taxi or bus to the airport to catch your flight the next day.

That being said, we put together this post on exactly where to stay in Milan where we break down the areas so that you can get a feel for what is best for you!

Mid-Range:  Sheraton Milan Airport Hotel.  Check Rates:  Booking.com

Affordable:  First Hotel Malpensa .  Check Rates:  Booking.com

How Long To Spend In Milan On Your 2 Weeks In Italy Itinerary:

You really only need one day in Milan during your 14 days In Italy itinerary at the most.

Compared to other Italian cities on this itinerary, the highlights of Milan can be done very quickly.

If you are looking for how to save time and budget days elsewhere in this 2-week itinerary for Italy, you can shorten the length of your stay in Milan as you can see the city in a short period of time.

Use Milan as your gateway to the airport, stop off and see a thing or two, and then be on your way home!

There is so much to see and do in Italy, that it can be hard to narrow down what you should do during your best itinerary for Italy in 2 weeks.

This itinerary gives you some structure to make some of the big decisions a bit easier.

It is also completely flexible, so you can easily change what it is that you see during your 14 day Italy vacation.

Since not everything has made it onto this list, what are some of your favorite things to do in Italy?

Reader Interactions

August 31, 2019 at 9:28 am

Please send me more info, can we choose our travel dates and expenses. Thank you Andra Cook

June 17, 2022 at 11:23 pm

I am interested in your itinerary. do you have it in a downloadable option?

August 28, 2022 at 1:52 pm

This is a very very nice itinerary. There is no right or wrong answer on where to stay for the 2 weeks. If I was taking my family/friends who have never been to Italy for 2 weeks it would be the following: Fly into Naples early morning and go to Sorrento: 3 nights Sorrento 4 nights Rome 3 nights Tuscany town like Montepulciano 3 nights Florence Fly into Naples and out of Florence. I am in the minority in saying Venice is so over rated and expensive and too far out of the way for an optimal 14 day trip. I think you suggest going all the way North and east to Venice then backtracking from one side to the other to get back to Cinque T. In Sorrento day boat trip to Capri, Day tour Amalfi towns like Positano. Then get a car and stay inside a town such as Montepulciano and drive to see all the towns while coming back to experience spending the evenings/nights in a hillside town. From Florence day trip to Cinque Terre and if yo missed Siena and San Gim. you do that in a Day trip that also includes Pisa. Least amount of backtracking and luggage hauls and checking in/out of hotels. But there is no right itinerary and how did we leave out Sicily or Lake Como, or Dolomites or…..LOL too much to see.

August 28, 2022 at 3:32 pm

Thank you for sharing this!! It sure is hard right!! so many epic things to see!

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Explore Italy like you never thought possible. Revel in the country’s most iconic cities, monuments, and cuisines, while also getting the distinct opportunity to uncover hidden treasures from exploring quaint villages to private tastings at countryside wineries. Discover the beauty of Italy and its many enchantments with a personalized 14-day itinerary from Zicasso.

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Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

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Classic beauty and indelible charm will radiate from ancient ruins, Renaissance artwork, and captivating coastlines during your custom-tailored 2-week tour of Italy. The iconic wonder of Italy will seduce you with panoramas of the rugged Amalfi Coast and the glamour of St. Mark’s interior shimmering with gilded mosaics. The Colosseum reflects remarkable achievement of ancient engineering and the Uffizi Gallery displays the triumphs of spirited expression. Wander along the cherished shores of Lake Como and travel into the past while strolling down the streets of Pompeii. Embrace Italy as an embodiment of culture with classic style and timeless charisma.

Your 14-day Italy honeymoon is remarkable, filled with fine food and fun times, dictated by nothing but the slow circuit of the sun across a cloudless blue sky. It is notable for its uniqueness, taking you to the wonder of Rome and the marvels of Tuscany, the beauty of Florence and the luxuries of the Amalfi Coast for an experience that can only be done in inimitable Italy.

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Open your eyes to the expansive plains of Umbria and vast olive groves of Puglia, the seaside ambiance of Calabria and the flavors of Emilia-Romagna during your personalized Italy tour that will immerse you in the marvels of discovery. Savor the authentic beauty of medieval towns and Baroque cities preserved in time and steeped in tradition. Greek theaters decorate the landscape of Sicily and caves pockmark the soft tufa limestone of Basilicata. Travel from the Adriatic’s turquoise waters to the Tyrrhenian’s azure hues and the Ionian’s sapphire glow uncovering whitewashed homes, pastel-colored cathedrals, and an endless inviting ambiance.

Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the remarkable wines. Engage with the extraordinary local specialties, travel the historical castles, and bask in the majestic landscapes discovered from the Amalfi Coast to Italian Alps.

The sensations of Italy come from traditions ingrained within the soil of the countryside and rising up through the towns and villages. On this 14-day tour through the north and south of the country you will find the most beautiful scenery displayed in Italy’s natural majesty. Climb through medieval villages and find the hidden waterfalls of Umbria, revel in the Tuscan hills and visit the marvelous art of the Renaissance. From natural magnificence to humanity’s endless striving for beatific perfection, you will find, wander, and wonder through it all.

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• How To Spend 14 Days In Italy - 5 Unique Itineraries

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Wonderful Time in Italy We were covered from the moment we landed in Rome. The drivers were great, the connections were flawless, and it was well-planned a...

Frequently topping polls of the most beautiful countries in the world, Italy is a diverse destination that deserves repeat visits. That said, it’s perfectly possible to pack plenty of unforgettable experiences into a 2-week journey. The question is, how to choose where to go? Read on to discover our unique, fully customizable 14 days Italy itineraries.

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Experience the hit TV show 'The White Lotus' in Sicily

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Enchanting Italian Lakes

Experience the picturesque lakes of Northern Italy, including Lake Garda, Como, Lugano and Maggiore; explore the charming Borromean Islands – former favourites of Ernest Hemingway – and stroll the romantic streets of Verona and Milan. All of this, and much more, with this self-drive trip!

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From Venice to Florence: A Grand Tour of Northern Italy

From the atmospheric canals of Venice and the picturesque coastline of Cinque Terre, to the trendy designer boutiques of Milan and the Renaissance-infused streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive trip.

See our 10 days in Italy itineraries below, or get inspired by duration: 5 days - 7-days - 10 days - North Italy - South Italy

Itinerary #1: From Venice to Florence: A Grand Tour of Northern Italy

From the canals of Venice and the coastline of Cinque Terre to the designer boutiques of Milan and the streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive 14-day trip .

On the first day , you will be transferred to your hotel. On the second day , you will be met by a private guide and taken on a beautiful Venice city tour. On the third day , you will embark on a trip to the enchanting islands of Burano and Murano.

The fourth day is reserved for exploration and leisure in Venice. On the fifth day , you will enjoy a journey by train, arriving in Milan. The remainder of the day is yours to explore Milan. Your guide will accompany you on a walking tour of Milan on the sixth day .

Embark on a train journey to Como on the seventh day . Take advantage of the day to soak up the atmosphere of this beautiful region. On the eighth day , you will enjoy a short ride to Lugano, Switzerland. On day nine , treat yourself to a boat trip on Lake Como. Then enjoy a leisurely tenth day .

Your driver will transfer you to the railway station on the eleventh day for your onward journey to Cinque Terre. Embark on an exciting adventure to explore the picturesque villages of Cinque Terre on day twelve .

The thirteenth day is yours to spend at your leisure. On day fourteen , you will be transferred to the airport for your departure flight. Read more .

Gondolas in Venice © Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

• Arrival in Venice
• Overnight in Venice
• Sightseeing tour in Venice
• Murano and Burano boat tour
• Free day in Venice
• Train to Milan, and free time in the city
• Overnight in Milan
• Sightseeing tour in Milan
• Train to Lake Como
• Overnight in Como
• Lugano and Lakeside villages
• Lake Como boat tour
• Free day in Como
• Train to Cinque Terre
• Overnight in La Spezia
• Exploring Cinque Terre and around by train

Day thirteen

• Free day in Cinque Terre

Day fourteen

• Transfer and departure from Florence

Interested? Don't miss the opportunity to book this trip now .

Cinque Terre National Park UNESCO World Heritage Site, Liguria, Italy

Itinerary #2: classic Italy - Rome, Florence & Venice

This 14-day Itinerary is for everyone - learn how to cook pasta in Rome, sample the best gelato in Florence, hike Cinque Terre and explore Venice on your own. This trip is packed with highlights for the whole family.

Rough Guides tip : buy this trip as a Guidebook in our shop .

On day one you'll be transferred to your hotel, and the rest of the day is yours to enjoy at leisure. The second day is dedicated to the Colosseum and Forum Romanum.

Join a small group cooking tour on the third day . On day four you will travel to Florence via high-speed train. Explore Florence leisurely on an e-bike on the fifth day .

Join a cooking class in central Florence on the sixth day of the journey. On day seven you will experience the beauty of Chianti's rolling hills and indulge in its flavours.

Take a regional train from Florence to La Spezia and enjoy the eighth day at leisure. Enjoy a guided hike from Monterosso to Corniglia, experiencing the stunning coastal Blue Trail on day nine .

Day ten is for leisure, exploring and relaxing.

Travel to Venice by train on day eleven and experience a private walking tour of the city. Take advantage of day twelve , and spend it at leisure in Venice. Enjoy day thirteen at leisure, bidding farewell to Italy .

Your final day concludes with a private transfer from your hotel to the airport for your departure flight. Read more .

Colosseum, Rome © Fabregas Hareluya/Shutterstock

• Arrival in Rome
• Overnight in Rome
• Colosseum half-day tour
• Traditional cooking class & market visit
• Transfer to Florence
• Overnight in Florence
• E-bike tour of Florence
• Traditional Pizza & Gelato making
• Chianti wines and olive oil tour
• from Florence to Lerici - La Spezia region
• Overnight in Lerici
• Sentiero Azzurro hiking tour
• Day at leisure at Lerici
• Train to Venice
• Venice walking tour and gondola ride
• Day at leisure
• Transfer to the airport

Feeling curious? Take a step forward and book this trip now .

Uffizi art gallery in Florence, Tuscany, Italy

Itinerary #3: highlights of Italy - Rome, Amalfi Coast, Cinque Terre and more

This 2 week Italy itinerary is nothing short of highlights: spend the first few nights in the capital city of Rome before moving down south to Naples. From here, you will discover the Amalfi Coast before heading to Florence.

On the first day , you will be collected at the airport and transferred to your hotel. Explore the Colosseum and Forum Romanum in a small group tour on the second day .

On the third day , you will discover the Vatican on a half-day tour. Travel to Naples by train and experience the birthplace of Pizza on day four .

On day five you will join a local guide to explore the heart of Naples. Visit Pompeii and Mount Vesuvius on day six .

A journey along the picturesque Amalfi Coast awaits you on day seven . Board a high-speed train to Florence on the eighth day . On day nine embark on a guided tour of Florence.

Travel to La Spezia, and enjoy your tenth day in leisure time. On day eleven , you will join a full-day tour of Cinque Terre with a private guide and a Cinque Terre card.

Days twelve and thirteen a dedicated to Milan. Take a train to Milan and spend the day at leisure. Then explore Milan on a group tour.

Depart from Milan on the last day of your Italian trip with a private transfer to the airport or train station, bidding farewell to Italy. Read more .

Positano, Italy. Amalfi Coast © iacomino FRiMAGES/Shutterstock

• Vatican half-day tour
• Transfer to Naples
• Overnight in Naples
• panoramic tour in Naples
• Pompeii & Vesuvius with wine tasting or pizza lunch
• Sorrento, Positano & Amalfi day trip
• Transfer to La Spezia
• Day at leisure at Cinque Terre
• Exploring Cinque Terre and around
• Transfer to Milan
• Best of Milan walking tour
• Transfer to the airport in Milan

Looking for an unforgettable experience? Don't waste time, book this trip now .

Bridge Naviglio, Milan, Italy @ Shutterstock

Itinerary #4: A delightful family journey through Italy

Embark on a remarkable 14-day family adventure through Italy, immersing yourselves in a world of culinary delights, historical wonders, and breathtaking landscapes.

Arrive in Rome on day one , where you will be transferred to your hotel. On the second day , join a small group tour of the Colosseum and Forum Romanum. Day three promises an exciting culinary experience as you join a small group cooking tour in Rome.

Travel to Florence via train on the fourth day . On day five , embark on an e-bike tour of Florence in a small group. Day six offers a hands-on experience as you join a 3-hour cooking class in central Florence.

Indulge in the beauty of Chianti's rolling hills on day seven with a half-day tour. Take a regional train from Florence to La Spezia, and enjoy the eighth day at your leisure.

On day nine , go on a privately guided hike from Monterosso to Corniglia, traversing the stunning coastal Blue Trail. Day ten invites you to explore and relax at your own pace.

Travel to Venice by train on day eleven and embark on a private walking tour. Make the most of day twelve , spending it at leisure in Venice.

On day thirteen , enjoy a day of leisure, bidding farewell to Italy on your own terms. Conclude your Italian adventure on the final day with a private transfer from your hotel to the airport.

St Peter Cathedral, Vatican, Rome, Italy @ Shutterstock

• Colosseum and Forum Romanum tour
• Traditional cooking tour in Rome
• Traditional Pizza & Gelato cooking class in Florence
• Transfer to Cinque Terre
• Overnight in Cinque Terre
• guided hike from Monterosso to Corniglia
• Venice islands

Cathedral of Saint Mary of the Flower in Florence © Shutterstock

Itinerary #5: Experience the splendours of Northern Italy

Experience a mesmerizing 14-day Italy itinerary through the enchanting region of Northern Italy. Explore its captivating history, breathtaking landscapes, and cultural gems.

On the first day , you will arrive at Venice's Marco Polo Airport, where you will be transferred to your hotel. On the second day , indulge in a delicious breakfast before a private guided tour of Venice.

On the third day , venture out to the captivating islands of Burano and Murano. Take the fourth day to explore Venice at your own pace.

On the fifth day , bid farewell to Venice and go on a comfortable train journey to Milan. Your sixth day begins with a captivating walking tour of Milan.

Journey to the picturesque region of Como on the seventh day . On the eighth day , continue your exploration with a short ride to Lugano, Switzerland, a town nestled on the shores of Lake Lugano.

Day nine presents an opportunity to indulge in a guided boat trip on Lake Como. On the tenth day , enjoy a leisurely pace in one of the world's most beautiful destinations.

Your driver will transfer you to the railway station on the eleventh day, where you will start a scenic train journey to Cinque Terre. Spend the twelfth day exploring the picturesque villages, hiking along the rugged coastline.

On the thirteenth day , enjoy a day of leisure, allowing you to relax, explore more of Cinque Terre. Finish your trip on day fourteen as you are collected and transferred to the airport.

St Mark's Square from the Grand Canal. Venice, Italy © volkova natalia/Shutterstock

• Guided city tour in Venice
• boat trip to Burano and Murano
• Guided city tour in Milan
• Transfer to the Como region
• Lake Lugano
• boat trip on Lake Como
• Day at leisure at Lake Como
• Exploring the Cinque Terre
• Transfer to the airport and departure

Cinque Terre, Italy

You might also want to browse our customisable Italy itineraries or talk to our local Italy experts .

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• Getting around Italy: Transportation Tips
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• Travel Tips Italy for planning and on the go
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• How to spend 7 days In Italy - 8 unique itineraries
• The Best 10-Day Italy Travel Itinerary
• How to get from Rome to Florence

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updated 18.09.2023

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Two Weeks in Italy: A Complete Guide for First Timers

There’s a good reason why Italy tops the bucket list of countless travelers. It has a unique historical significance (even though Italy itself is actually one of the youngest countries in Europe) thanks to the Roman Empire’s escapades, it has a famous food culture (not to mention the wine), and it has gorgeous scenery.

Italy has spent hundreds of years building its brand which has millions of people dreaming of visiting Italy. 

But as we’ve learned over the course of our time in Italy over the past two years (almost two months in total), boiling the entirety of Italy down to just a handful of things it’s famous for means that you’re missing the things that really make Italy special.

Coming from an American perspective, we have a very specific view of what it means to be “Italian” that involves numerous stereotypes including some combination of chicken parmigiana, garlic bread, and talking with your hands (in our experience, only one of those is genuinely found in Italy – which one is it?).

However, after several trips where we’ve been able to go a level deeper than you usually do on that first trip, we’ve come to realize something important. 

Italy is a surprisingly diverse country. 

Not necessarily in terms of race or ethnicity, which is how the word “diversity” often gets translated, but in terms of regional differences that have been formed over thousands of years.  

The regional differences in culture, dialect, and cuisine that come from centuries spent as independent (and often warring) city states are what we love about Italy, and that diversity is what makes Italy a fascinating place to visit.

As you move between regions, you’ll notice that the food and wine menus change drastically, as do the accents and cultural norms. 

With so much to learn, see, eat, and drink in Italy, how do you even go about planning a two week trip to Italy?

In this guide, we’re going to go through what is, in our minds at least, a perfect 14 day Italy itinerary.

It covers Italy’s major cities – Rome, Florence, and Venice – along with some time spent in less heralded places like Bologna that most tourists miss, but we believe is well worth a stop. 

This guide is geared towards first-timers who want to see those main cities, but we also have an entire section below the main itinerary full of ideas on how to modify it, which you might find useful if you’ve done the whole Venice thing before and are looking for something new.

Either way, grab a cup of coffee (or a spritz?) and buckle in for a long one – here’s exactly (and we mean that) how we’d spend two weeks in Italy. 

Disclaimer: Some of the links in this post, like hotel links, are affiliate links, meaning at no additional cost to you, we make a little bit of money if you click through and book. That being said, we would never recommend something to you that we don’t stand behind 100%.

Is 14 Days Enough Time in Italy?

In short, no. Definitely not. However, we do think it’s a good amount of time to see a chunk of the country that will give you a nice overview and help you decide where you want to dive deeper on your next trip.

In this itinerary – which is primarily designed for first timers – we’re going to cover both the main cities (Rome, Florence, and Venice) and some of our favorite places that don’t usually make the list (Bologna and Verona).

P.S. If you have a shorter trip, make sure to check out our guide to 10 days in Italy , which focuses on Rome, Florence (and the surrounding area), and Venice, or our guide to spending a week in Italy , which has five ideas for a week in Italy that you can mix and match to build your own itinerary.

There are two places that you won’t find in this itinerary for various reasons.

First is southern Italy – specifically Napoli, Pompeii, and the Amalfi Coast.

The reason is not that they aren’t beautiful or worth seeing, but that we think your time is better spent in northern Italy, which is our favorite part of the country.

Getting between Napoli and northern Italy is going to take a lot of time that would be better spent exploring!

The second place is the Cinque Terre , and it’s for a similar reason. The Cinque Terre is gorgeous. But it’s not particularly easy to get to.

You’ll need to make multiple connections from Florence, and it’s going to take about three hours each way.

If you do want to add the Cinque Terre, you’ll need at least two full days. We have some ideas on how to add it below the main itinerary.

If you’re interested in visiting Cinque Terre, make sure to read our guides for Cinque Terre.

• The Best Things to Do in Cinque Terre: A Complete Guide
• How to Plan an Amazing 2 Day Cinque Terre Itinerary
• Where to Stay in Cinque Terre: The 4 Best Places to Stay (with Pros and Cons for Each)

Where to Fly In and Out Of?

If you follow the itinerary below as written, which takes you on a tour-de-Italy from Rome to Venice, you’ll want to fly into Rome–Fiumicino International Airport (FCO) and out of Venice Marco Polo Airport (VCE) .

An alternative would be to fly out of Milan (either LIN or MXP – we like LIN better because it’s closer to the city and a newer airport), which generally has more flight options than Venice, but it requires an extra day or two and a train.

Getting Around Italy

The best way to get around Italy is by train. At least for your purposes on the itinerary below It’s going to be cheaper, faster (once you include travel time and security at the airport), and better for the planet than hopping on a short flight.

There are a few things you should know about trains in Italy before we get any further.

First, there are (essentially) two types of trains in Italy – high speed and regional – and they operate differently.

High speed trains are more expensive, significantly faster, and less flexible. To save time since you’ve only got a limited amount of it in Italy, you’ll want to take the high speed trains between cities.

You’ll want to book your ticket as far in advance as possible, which usually will save you some money, but will be less flexible. If you want the flexibility, you’ll have to be prepared to pay a little extra.

Regional trains are slower, cheaper, and more flexible. They’re usually for connecting nearby smaller cities to each other (for example, there’s a regional train between Florence and Pisa).

You can buy these tickets when you arrive at the station, and they’re more flexible. You need to make sure you validate them before boarding.

The best way to book train tickets in Italy is directly through Trenitalia , the company that runs most of the trains in Italy. The only downside is that you’ll need to know the name of the station you want to travel to in Italian. 

We’d take high speed trains between Rome and Florence, Florence and Bologna, Bologna and Verona, and Verona and Venice . For day trips from Florence and Bologna, regional trains will do.

The Itinerary / Route

And now, the itinerary for spending two weeks in Italy. 

One quick note : In general, when you’re moving between cities, we’d recommend taking an afternoon train, which will give you some extra time to explore the city you’re leaving in the morning before heading to the train station.

Here’s how we would plan a trip to see the best of Italy in two weeks, starting in Rome and ending in Venice: 

• Day 1: Arrive in Rome
• Day 2: Rome
• Day 3: Rome
• Day 4: Rome + Train to Florence
• Day 5: Florence
• Day 6: Florence
• Day 7: Florence Day Trip
• Day 8: Train to Bologna
• Day 9: Bologna
• Day 10: Day Trip to Verona
• Day 11: Train to Venice
• Day 12: Venice
• Day 13: Venice
• Day 14: Venice + Fly Home

You’ll notice a couple of different things about the way we’ve structured this itinerary.

First , we’re big fans of spending at least 2-3 days in big cities to avoid feeling like you’re rushing around from sight to sight. That will give you some time to do some exploring to find a new favorite neighborhood, coffee shop, wine bar, or restaurant.

Second , we hate packing and moving accommodations. It sucks. Which is the reason we’re recommending you stay in a place like Florence or Bologna and use it as a home base for exploring the surrounding area.

Third , we’ve included a significant chunk of time in Bologna. Which is our favorite city in Italy not named Rome or Florence (Lucca and Verona are also in the running). 

Here’s why: Bologna is the capital of the best food region in Italy , home to the production of delicious things like Parmesan-Reggiano cheese (we LOVED touring a small producer of Parmigiano-Reggiano with Claudio on this tour ), prosciutto di Parma, mortadella, balsamic vinegar, Lambrusco (a sparkling red wine), tortellini, ragu, and plenty more. 

Not only is the food incredible, but the city – which feels noticeably younger and less “touristy” than most of the cities here – is a nice change of pace from places like Rome, Florence, and Venice.

Bologna also makes an excellent home base for day trips because it is so well connected.

Whatever you do, we’d implore you NOT to cut Bologna. It’s an amazing city, and you won’t regret spending a day or two there.

Fourth, it might seem like a lot of time in Venice at the end. However, it’s really only two and a half days if you take a midday train there, and have an early flight home.

If you have a full 14 days (you’re flying out on day 15, for example), we’d add an extra day either in Florence to do another day trip, or in Rome.

2 Weeks in Italy: A Perfect 14 Day Italy Itinerary for First Timers

And now, on to the detailed itinerary. 

Our intention here is to give you the information we think you need to know to plan an amazing trip to Italy.

We’ll go a little deeper than a short description of each place, giving you some of our favorite things to do, see, eat, and drink that come from our own experiences exploring Italy (and, equally crucially, what not to do – looking at you, Juliet’s House in Verona!). 

We believe those details – like specific wine bars, tours, and coffee shops we loved – are the difference between a good trip and an incredible trip, and hope you’ll find a few places that you wouldn’t have necessarily found on your own. 

The other intention here is to not just give you the same old itinerary that you’ll see in every guidebook.

Of course, we’re going to include Rome, Florence, and Venice, because those are places that are absolutely worth seeing on your first trip to Italy. 

However, we’re also going to include some of our favorite places (like Bologna) that don’t usually make the cut. Rick Steves (who Matt loves – he’s from Seattle too!) doesn’t even include Bologna in his Italy guidebook! What a miss.  

Rome: Days 1-3

I mean, if you’ve never been to Rome before, you’re in for a treat. Rome is one of our favorite cities in Europe, and there’s something special about walking past architecture from over a thousand years ago on your way to a hip natural wine bar in the evening. 

While Rome is famous for its historical sights, it’s also a great city for food and drinks (as we’ll cover below) and as I’m sitting here writing this, I literally made a Roman pasta dish (amatriciana) for dinner last night. 

We’d recommend three days in Rome, at a minimum, which will allow you enough time to see both of the main attractions, dive into the history of Italy’s capital city, and also indulge in some of Rome’s great food and drinks. 

What to Do in Rome

Look, there are two main attractions in Rome that, if it’s your first trip, you probably shouldn’t miss. 

They are, of course, the Vatican and the Colosseum and Roman Forum . They’re popular and “touristy,” but being touristy doesn’t necessarily mean it’s not worth doing. 

However, you should absolutely split them up and avoid doing them on the same day . It will simply be too much information if you try to knock them both out on the same day, and you will be exhausted, which means you won’t get the most out of them.

Do them on different days. Trust us. 

Let’s talk about those two first. However, this is going to be relatively brief.

For a more in-depth version of how we think you should experience them, head over to our guides to the best things to do in Rome , our guide to planning your Rome itinerary, and our review of the Colosseum and Forum tour we did (and, spoiler alert, loved). 

The Colosseum and Roman Forum are perhaps the best example in Rome of the grandeur that the Roman Empire was able to create nearly two millennia ago.

The Colosseum, in particular, is an architectural marvel to us.

The Forum is mostly just stones strewn about at this point, so it’s harder to visualize what it looked like roughly two thousand years ago at the height of Rome’s power. 

Which brings us to an important point: you should definitely do a guided tour of the Colosseum and Roman Forum .  

We have a strong opinion here, mostly informed by the fact that we did an amazing tour of the Colosseum with our favorite Italian tour company (you can read all about it here ) where we learned that some (really, most) of the things we thought we knew about the Colosseum were actually just fairy tales. 

We have personally done (and enjoyed) TakeWalks’ Skip the Line: Premium Colosseum Tour with Roman Forum & Palatine Hill – you can read about our experience here (spoiler: we loved it!). It is a great tour option that includes both the Colosseum and Forum.

Before or after your visit, there’s an excellent view of the Roman Forum from OUTSIDE the boundaries located here .

The Vatican is basically one of the greatest art museums on the planet. Sure, there’s St. Peter’s Basilica, but even that is very much about the art (which at the end of the day is just a way to show that you have money and power).

The Sistine Chapel, in particular, is incredibly moving, especially when you consider how long it took to finish, and how Michaelangelo had to paint it facing the ceiling. 

It’s worth a tour of the Vatican too, if you can afford it. We’d do the “Pristine Sistine” early access tour with Take Walks, which includes early access.

We haven’t done that specific tour ourselves, but we’ve done four separate Take Walks tours now, and all have been excellent because the guides are top notch experts in their fields. 

If you can only do one tour, we’d do the Colosseum and Forum because the added context and historical perspective from a guide is more useful when you’re looking at ruins. 

Since we’ve already rambled so much in this section, here’s a quick hit list of other things to do in Rome. 

The view from the Orange Garden (Giardino degli Aranci) . This is one of our favorite views in the city, and we’re not alone. Head up here around sunset for a treat, but it’s equally gorgeous in the early morning hours (perhaps better, because the sun is generally behind you), and there are far fewer people.

Trastevere in the evening . Our favorite neighborhood in Rome is Trastevere, and it’s not that close. It’s nice in the morning, especially if you visit the open air market that takes place at Piazza de’ Renzi, but the evening is when it comes alive. People spill out of the bars and restaurants into the streets, and the piazzas are full of people drinking and being merry. 

Wine! Enoteca il Piccolo in the Centro Storico ( here it is on Google Maps) is as great as it is popular. The owner came out to the terrace where I tried to explain in my bad Italian what kind of wine I wanted (dry white), and he walked away without a word, and returned with two excellent glasses of exactly what I asked for. If you’re looking for a bottle, Les Vignerons in Trastevere is the place to go (great beer and cider selection, too!). 

Roman cuisine . First, we make the four Roman pastas at home (carbonara, gricia, amatriciana, and cacio e pepe) all the time. Roman food is generally very simple, but delicious. The best way to learn about Roman food is taking a food tour with a local guide, where you’ll not only taste some delicious food, but learn about the history and context behind that food. Which is our favorite part about learning about food cultures of different places. We’d do this tour , which looks truly spectacular and includes a lot of cultural context along with tons of tastings. 

If you’re into good coffee, head straight to Pergamino Caffè near the Vatican, which is home to some of the best baristas in Rome who bring in a bunch of different Italian specialty coffee roasters to brew for you.

It’s my, Matt the coffee snob’s, favorite coffee in Rome. 

Of course, there are tons of other things in the Eternal City that are worth doing, seeing, and eating. For more, head over to our guide to the best things to do in Rome , which has a collection of our favorites. 

Where to Stay in Rome

While there are a bunch of areas you could stay in Rome, we have two strong recommendations for you to help you narrow it down.

We also have an entire, super detailed guide to where to stay in Rome if you want more details to make your decision.

Our overall recommendation is to stay in Trastevere , which is far and away our favorite part of the city.

We stayed there on our last trip, and it’s magical.

It’s a great place to eat and drink, and it really comes alive when the sun goes down, full of lively piazzas and small bars and restaurants that fill up on a nightly basis and spill out into the cobblestone streets.

We stayed at Horti 14 Borgo , a small boutique hotel in Trastevere, and absolutely loved it.

It’s a splurge compared to where we normally stay, but the stylish rooms, comfortable beds, and incredible breakfast buffet were worth it. 

A more affordable (but equally highly rated) option would be Ripagrande a Trastevere , which is essentially right on the River Tiber and within five minutes of everything in Trastevere. 

The only downside to Trastevere is the fact that it’s a little far from the train station, which doesn’t matter as much with three days, but is a little less convenient (you’ll need to take a taxi, most likely).

Which brings us to our second recommendation, which is Rome’s Historic Center (the Centro Storico). 

Stay here if you want to be right in the middle of all the action, within walking distance to just about everything in the city.

It’s the most convenient place to stay, though it will be crowded and potentially loud. Don’t miss an early morning walk from Piazza Navona to the Trevi Fountain and the Spanish Steps!

We stayed for five nights near Piazza Navona at these apartments , which were honestly a perfect location, especially if it’s your first time in Rome.

Coronari Palace and Casa Pietra are two hotels that were also on our list, though we decided we wanted more space and a kitchen for our time in Rome. 

Florence: Days 4-6

Historically, the city of Rome might be the crown jewel of the Roman Empire, but you could make a convincing argument that Florence is the second most important city in the history of the Italian peninsula because of its influence around the birth of the Renaissance. 

On a walking tour in Florence ( this one , which we recommend below because it’s a great introduction to the city), as we were walking through Piazza della Signoria, our guide made a point that I hadn’t really thought about before that moment. 

Florence was one of the richest cities in Europe (if not the world) in the 15th Century and through the Renaissance. 

A lot of people – myself included – might think that wealth came from the amazing art that was produced in Florence leading up to and during the Renaissance.

But the truth is that Florence was already a rich city thanks to silk production, and that wealth is what allowed it to become a cultural icon that thousands of people still flock to five centuries later. 

Walking the streets of Florence, it’s easy to see why so many people fall head over heels in love with it on their visit.

It’s charming. The Duomo is incredible, both because of how imposing it is, and the fact that it’s an architectural miracle. There are two world class museums.

The food and wine are both excellent (definitely get the wild boar if you see it on a menu – pappardelle al cinghiale – which was our favorite discovery on our Tuscany road trip itinerary ). 

I could go on and on about Florence – I’ve spent over a week in Florence between two trips in the past year (at the time of writing) – but let’s leave it there and get into how to make the most of your time in the Tuscan capital. 

In this itinerary, we have you spending two and a half days in Florence itself, and then using it as a home base for a day trip into Tuscany. 

What to Do in Florence

There are two main attractions in Florence that you’ve likely heard of before, and both are well worth your time.

They are the Uffizi Gallery , which is a chronological journey through Renaissance art in Florence, and the Galleria dell’accademia , which is where you’ll find Michaelangelo’s David . 

However, you should definitely try to do them on different days , because it’s too much information to process in a single day.

Believe me, my mom and I tried to do both in a day in Florence on my latest trip to Italy, and it was too much. 

The other thing I would say – and again, I’m speaking from experience here having done both museums with and without a guide – is that you should invest in a guided tour with an art historian if you can .  

After some truly great experiences recently, I’ve decided that I probably won’t do a huge art gallery like the Uffizi or the Louvre without a guide ever again.

The guide is able to add so much in terms of color, context, and storytelling that will give you a deeper connection to just about any museum visit. 

Otherwise, we’d look at the art, say “yeah, that looks pretty,” and move on without really understanding the context behind what we’re looking at.

If you only have the budget for one, make sure to do the guided tour of the Uffizi, where your guide will be able to explain exactly what you’re looking at, and what it says about the changing nature of society and culture during the Renaissance.

We did this guided tour of the Uffizi Gallery , and it was fantastic. 

For what it’s worth, I (Matt) also did this guided tour of the Galleria dell’Accademia on my last visit with my mom, and we also really enjoyed it.

However, like I said above, if you only have time or budget for one tour, you’ll get more out of the Uffizi. 

For more information, including on how to visit both galleries independently , head over to our guides to the best things to do in Florence and our guide to planning your Florence itinerary .  

As we said above, we’d split those two museums up and do one on each of your two full days in Florence. Which, obviously, leaves you with some extra time. Here’s what we’d do with that time. 

Take Andrea’s walking tour . We’re huge fans of walking tours as a way to get an introduction to a new city and connect with a local for tips on what (and where) to eat, drink, and shop. And we loved Andrea’s walking tour , which is a two hour crash course in Florence’s rich history, with all the salacious details about the Medici family (they were essentially royalty in Florence during the 1500’s). He also has a more in-depth version of the tour that adds an hour and includes crossing the river to Oltrarno. 

Climb to Piazzale Michelangelo . On the other side of the river from Florence’s Centro Storico, you’ll find what is arguably the best view of the city at Piazzale Michelangelo. You’ll have a view of the Arno River and Ponte Vecchio (the only bridge in Florence that wasn’t destroyed in World War 2), the Duomo, and the rest of the city. It’s nice at sunset, but it’s busy. Early in the morning is even better, because the sun is behind you and there are basically no crowds. 

Climb Brunneleschi’s Dome . The Duomo in Florence is massive. The best way to experience it, in our opinion, is to climb to the top. Along the way, you’ll get a view of the interior of the dome and the (somewhat creepy) artwork decorating it, then you’ll climb through the area between the interior and exterior dome (which gives you perspective on how it was built 600 years ago, which is mind-boggling) up to the top, where you’ll have a 360-degree view out over Florence. Try to do it first thing in the morning for the fewest people, and book in advance here . 

Dive into Tuscany’s food and drink offerings . We’d strongly encourage you to skip the pizza in Florence, and instead indulge in some of the local specialties. We love Pappardelle al ragu di cinghiale (a pasta with a wild boar sauce that my mom fell in love with), pappa al pomodoro (tomato and bread soup), and the Schiacciata (sort of like a focaccia sandwich, but slightly different). We liked the food at Trattoria da Garibardi . Most of the Florentine cuisine pairs well with the Tuscan reds like Chianti Classico and Brunello, which are a couple of the more prestigious red wines to look for. 

Where to Stay in Florence

Similar to Rome above, we have two recommendations for where to stay in Florence .

Also similar to Rome, your choice is going to be between the coolest neighborhood (in our opinions, anyway) and the most convenient area.

Convenience matters a little more here because you will be taking a day trip, which means you’ll be going to and from the train station.

Our favorite area in Florence is Santa Croce / Sant’Ambrogio , which is a five minute walk east of the Duomo. It has the best food (we think), fewer tourists, and is close to everything in the city.

We stayed at Pietrapiana Boutique Apartments for almost a week, and it was everything we wanted and more: access to a kitchen, a little more space to spread out, a quiet refuge from the hustle and bustle, and a comfortable place to sleep. Highly recommend! 

La Maison du Sage is another good option nearby – it’s more of a traditional hotel than serviced apartments.

The other option, which is best if you want to be super central to everything in Florence, is Florence’s Centro Storico , which is centered around the Piazza del Duomo and nearby Piazza della Signoria (home to the Uffizi Gallery).

It’s crowded, it’s loud, but it’s super convenient. It’s also closer to the train station for your day trip.

Day Trip from Florence (Choose Your Own Adventure): Day 7

Florence is the capital of Tuscany, which might be Italy’s most famous region for its wine and general dolce vita feeling. And, after spending a week in Tuscany, we can definitively say it delivers on both. 

Florence is an excellent base to explore Tuscany from, with most of the highlights accessible within 90 minutes by train. However, the main issue with Tuscany is that you really need a car to be able to see certain things properly.

Here are the three day trips from Florence we’d recommend, and which one you choose totally depends on what you’re interested in. 

If you’re looking to combine San Gimignano, Chianti, and Siena into one day, it’s going to be a long day, but this tour with Take Walks (which, as we’ve already mentioned a few times in this guide, is one of our favorite tour companies on earth), covers San Gimignano, Chianti, and Siena in one action-packed 10 hour day. 

Day Trip 1: Siena for the Cathedral (and the History) 

Siena is a popular day trip from Florence, and it’s a 90 minute train ride south in the heart of Tuscany.

There is, perhaps, no better example of a classic hilltop town than Siena, which is a red city perched on a hill overlooking a lush green valley. 

The cathedral in Siena is incredible, and we say that as people who usually don’t get all that excited about massive opulent churches.

The iconic dark green and white stripes of Siena’s Duomo are just the beginning of what makes it special.

The interior is where the real fun begins, particularly if you’re around when the floors are uncovered (usually in the summer), and the intricate art and tilework on the floors is on full display. 

We recommend climbing up to the Facciatone, which is a viewpoint inside the Museo del Duomo that has an excellent view of both the cathedral and the surrounding landscape. 

The other place not to miss in Siena is Piazza del Campo, which rivals Piazza Maggiore in Bologna (more on that in a second) as our favorite piazza in all of Italy. 

In terms of eating and drinking, head to Torrefazione Fiorella for a morning coffee at a stand-up bar (very Italian), Panificio Il Magnifico to try sweet Sienese specialties like ricciarelli, Du’ Cose Da Berna for traditional sandwiches at lunch (a recommendation from our friendly host at the agroturismo we stayed at outside of Siena), and Ristorante Gallo Nero , which was one of the best meals we had in Tuscany. 

How to get there : There are regional trains between Florence’s Santa Maria Novella (the main station in Florence) and Siena that take about an hour and a half. You can also take bus 131 (or the faster 131R) from the Florence bus station ( here on Google Maps – it’s right next to Santa Maria Novella), which is a similar amount of time. Both are very affordable options.  

Day Trip 2: Chianti for the Wine

Chianti is the place to go for wine. Chianti classico is the name of the game here, which is a Sangiovese-based red wine that follows strict production methods, and is one of the most famous wines that comes out of Italy.

If you don’t like red wine, I have some bad news for you – Tuscany is all about the red wines (except for vernaccia, which is a white wine that comes from San Gimignano!). 

Assuming you don’t have a car, your only option here is to do an organized tour because doing a self-guided tour of Chianti wineries would require both a rental car and a designated driver. 

In terms of guided tours, you have two options.

You can either choose a tour that goes deep on a single winery , usually including a cellar tour and detailed tasting (but you’ll have to make your way out to the winery), or a tour that takes you around to multiple wineries , which is going to be a little less personal, but give you more breadth where you’ll get to see multiple approaches AND usually includes transportation to and from Florence. 

We did this tour of a tiny organic winery and olive farm at the northern end of Chianti, and we loved it.

It was very personal and intimate, and we learned a ton about growing grapes (and olives) in Chianti.

We’d highly recommend it, and the nice part is that it’s easily accessible from Florence (and the hosts will help you figure out how to get there, including a bus station pickup). 

In terms of the other option where you get to visit multiple wineries with transportation to and from Florence, this is a highly rated tour with a sommelier that we considered.

You’ll get to visit three wineries, which are all closed for public visits, which is a good sign that it’s a unique experience because the host clearly has relationships with those specific wineries. 

If you want to see more of Chianti, including the super charming Badia a Passignano, we’d go with this tour . 

Day Trip 3: Lucca For the Views

You might have been expecting to see Pisa somewhere on this list of day trips from Florence, and we’re here to tell you that while, yes, the leaning tower is kind of cool, we would absolutely recommend skipping Pisa (which is crowded beyond belief with people wanting to see the aforementioned leaning tower) and heading to Lucca instead. 

There are a couple of reasons we love Lucca. 

First, the medieval walls are still intact, encircling the entire city. It’s well worth walking the full loop, where you’ll get some nice views of the city and the mountains beyond. 

Second is the tower. Climbing the Guinigi Tower will take you up to what might just be our favorite view in all of Italy.

On a day trip to Lucca, we’d spend your time walking the city walls, climbing the tower, and indulging in some Luccan cuisine for lunch (at Trattoria L’ Angolo Tondo , which is right on the Piazza dell’Anfiteatro where a Roman amphitheater used to be), which is slightly different than the food you’ll find in Florence because of its proximity to the coast, which means more fresh seafood. 

How to get there : There are regional trains between Florence’s Santa Maria Novella (the main station in Florence) and Lucca that take about an hour and a half. They come frequently, and they’re super affordable. 

Bologna: Days 8 & 9

You’re probably a little bit surprised to see Bologna on this itinerary, since it’s not exactly known as one of the “must-see” cities in Italy. However, we’re here to tell you that it absolutely should be on your list, particularly if you love food. 

One of the most interesting parts about traveling to Italy is having our expectations about “Italian” food completely shattered.

Here in the US, Italian food (we now know that Italian–American food is an entirely separate thing) consists of heavy sauces with lots of garlic, garlic bread, and chicken parmigiana. 

The truth is that Italian food culture is vastly different from region to region, and depends a lot on the fresh ingredients available in close proximity.

For example, in Sicily , you’ll find tons of fresh seafood because you’re on an island and are perpetually near the coast. In Tuscany, it’s olives, wild boar, and sheep cheese (pecorino) because those are the ingredients that are readily available. 

If you made us choose our favorite Italian food region, we’d choose Emilia-Romagna, which is where you’ll find Bologna. 

Here’s an exercise: write down your five favorite Italian ingredients (rather than dishes). If you’re anything like us, at least one of the things you wrote down comes from Bologna’s region, Emilia-Romagna. 

There’s a reason the city is known as “La Grassa” (“the fat one”). It’s about as close to heaven for foodies as you can get. 

There are, of course, other things we really like about Bologna. It’s a city of towers that overlook the distinctive red brick buildings (most of them are facades, though).

It’s a University town (one of its other nicknames is “La Dotta” which means “the learned one”) and it has a distinctly younger vibe than just about any other major city in Italy. There are far fewer tourists than any other city you’ll visit.

And it’s well connected to just about every corner of Italy. 

We think you should spend three nights in Bologna, using one of those nights to do a day trip up to Verona, which is another one of our favorite cities in Italy. 

What to Do in Bologna

Here are a few of our favorite things to do in Bologna. For more, head over to our guide to spending a day in Bologna . 

Climb the Asinelli Tower for Excellent Views . We have friends that live in Bologna, and when we visited them on our first ever visit to Bologna, this was the first thing they did with us. It’s a big climb, but you’ll eventually end up on the top of the taller of the Due Torre (“the two towers”), where you’ll have a commanding view out over Bologna. Book here in advance for a timeslot. 

Eat your heart out . Mortadella and filled pastas like tortelloni come from Bologna, but the broader region is home to just about every delicious food we associate with Italy. Parmesan, balsamic vinegar, prosciutto di Parma, lambrusco, and ragu alla bolognese. Go to any of the places in Quadrilatero, which is right off of Piazza Maggiore, to taste and shop. Specifically, we like Tamburini for tagliere (a plate of meats and cheeses) and a glass of wine (lambrusco!), Cremeria la Vecchia Stalla for excellent ice cream (which is NOT the same as gelato), and Vineria Favalli for their excellent Italian wine list.

Take a food tour with a local guide . While you can absolutely get a sense for Bologna’s food offerings on your own, a food tour is going to be the best way to dive a little deeper. This food tour in Bologna was on our list, but after learning they couldn’t accommodate gluten free diets (which, by the way, makes total sense), we decided to skip it. 

Take in Piazza Maggiore and Basilica di San Petronio . Piazza Maggiure is the beating heart of Bologna, and one of Italy’s best piazzas in our opinion (as we noted above, Siena’s Piazza del Campo is a close second). There are events nearly every afternoon and evening, from rallies to concerts, and even when there isn’t an official event, you’ll find some of Bologna’s best musicians out on the square (along with a crowd of admirers). The church is worth going into, but it’s only half finished after they tried to make it outshine the Vatican, who said “you can’t do that.” That’s why part of the church’s facade is exposed brick, which is the unfinished portion, while the other part is covered in marble.  

Make the climb to Santuario Madonna di San Luca . Bologna is known for porticoes, which are essentially just covered walkways, and you can walk through the 666 (someone has a sense of humor) to get up to this church on the hill. For what it’s worth, this the #1 recommendation from our friends that live in Bologna. 

Where to Stay in Bologna

There’s no doubt in our minds – you should stay near Piazza Maggiore while you’re in Bologna . It’s the beating heart of the city, and it’s going to be both the most convenient and the coolest place to stay.

I spent a few days in Bologna solo on my last trip to Italy, and stayed at Bibliò Rooms and Guesthouse . It’s essentially a small B&B that takes up one floor on a residential building about five minutes from Piazza Maggiore.

The rooms are fairly spacious with comfortable beds and private bathrooms, and it’s a good home base for a few nights in Bologna. 

I also stayed at the Social Hub in Bologna , which is a hip, young-feeling hotel in Bolognina up near Bologna Centrale.

While the location is further away from Bologna’s main attractions, it is a gorgeous hotel with all sorts of great amenities (a pool, a nice gym, a bar, an events calendar, and ping pong, to name a few). Plus, it’s about five minutes on foot from the train station, so it’s convenient in that sense. 

If you’re looking for an apartment, look at Canonica Suites , which is where I kind of wish we had stayed. 

We have an entire guide dedicated to helping you figure out where to stay in Bologna with FAR more detail, if you want more of an in-depth look at your options.

Day Trip to Verona: Day 10

On this day, we’d highly recommend leaving your stuff in Bologna and doing a day trip up to Verona, heading back to spend the night in Bologna.

Verona is famous for being the setting for Romeo and Juliet, but it tied with Bologna for our favorite discovery in Italy when we spent six weeks exploring Italy in 2021. 

You might be wondering why we’d do it this way, considering Verona is sort of on the way to Venice (the next stop in this itinerary).

The reason is that we don’t want you to have to worry about juggling your bags, and instead focus on getting an early train from Bologna without the worry of check in times and baggage storage. 

Take the high speed train, which takes about 45 minutes or so (book in advance for cheaper tickets!). 

Rather than go into the details of what to do and see with a day trip up to Verona, we’re going to direct you to a separate blog post where we go through exactly that. Here’s how we’d spend a day in Verona . 

Venice: Days 11-14

Venice is a place that we have mixed feelings about. We’ve both been to Venice, and as we’ve thought about it, we’re truly not sure if we need to go again. 

It’s true that Venice is the best-preserved example of a canal city in Italy, but it’s also true that it’s a beautiful disaster.

There are way, way too many people trying to see Venice for the infrastructure to handle, and cruise ships are a big part of the issue, with huge tour groups coming in for part of a day and contributing very little to the local economy while stressing Venice’s infrastructure. 

Remember in 2020 when the canals were all of a sudden empty and pristine, and the swans came back to Venice? It’s safe to say that’s over now. 

However, it’s not really fair to say that you shouldn’t get to see Venice because too many people go there. 

Instead, we’d recommend that you do go to Venice, but be deliberate about how you do it.

Spend multiple days there so you’re not stressed about the crowds and whether or not you’ll be able to do everything. Eat at local restaurants, and stay in Venice so that your money stays in the local economy. 

The best way to explore Venice is not to spend a day (or less) seeing the main sights and calling it a day.

Venice is at its best in the early morning and evening, when it’s notably less crowded. If you only spend a day in Venice, you’re likely going to miss out on that precious time spent exploring during those hours. 

That’s why we’d strongly recommend two and a half days in Venice, which gives you a couple of mornings and nights to really soak up the atmosphere of Venice when it’s not packed wall-to-wall with people. 

What to Do in Venice

There are a few main sights in Venice that you shouldn’t miss, and two days is more than enough time to see them. Like we said above, part of the fun of exploring Venice is wandering the canals in the early morning and evening. 

Piazza San Marco is the main piazza in Venice, and there are a couple of main sights right on the square. 

First is the Doge’s Palace , which is a big Gothic building (you know because of the pointed arches) on the lagoon. Over its long history, it served as a fort, a prison, and a residence for the most powerful person in Venice, the Doge. 

The version you see today was built in the 1100’s, and has been renovated a few times since as the needs of its inhabitants changed.

It housed the Doge of Venice (sort of like a Duke, but not quite the same) during the Republic of Venice, which lasted for more than 1,000 years starting in the 8th Century and was one of the most powerful city-states in modern day Italy for long stretches because of its position on the water.

The best part about the Doge’s Palace is that it’s an excellent place to learn about Venice’s history. For example, I had no idea that there was a Republic of Venice, let alone how powerful they were.  

You can buy your tickets in advance here . 

The second major attraction on San Marco Square is the church, St. Mark’s Basilica (Basilica di San Marco), which is the biggest church in Venice.

In a surprising (to no one) twist, the church is attached to the Doge’s Palace, showing the relationship between secular and religious power in Venice over the centuries. It’s set on the site of two older churches, which is a story that you hear over and over again at some of Italy’s biggest and most important churches.

Also similar to other churches in Italy, it was built over such a long stretch of time that it’s one big mish mash of architectural styles and art periods. 

It’s an impressive building from the outside, and the interior is special because of the mosaics that cover just about every surface. The Pala d’Oro, which is essentially a big golden altarpiece from the Byzantines, is also pretty cool. 

Information on tickets and opening hours here . 

If you want to see both with a guided tour, we’d (again) recommend doing the St. Mark’s and Doge’s Palace tour with Take Walks , who we’ve done multiple tours with in multiple Italian cities, and love. It’s three hours long, includes both the church and the palace, and will take you a level deeper than just visiting by yourself. 

The islands to the north of Venice – namely Burano and Murano – are well worth a visit, and the vast majority of visitors don’t make it out there.

These tiny islands are known for glassblowing, and they’re relatively easy to reach via water taxi from Venice. From this ferry terminal, it’s a quick 20 minute ride over to Murano, the closer of the two islands (it’s a significantly longer boat ride out to Burano). 

You can read more about what to do in Venice in our guide to spending 2 days in Venice . 

What to Do with More Time in Italy

If you’re blessed with more than 14 days in Italy, we have (lots of) thoughts on what to do with extra time. Whether it’s one or two days or a full extra week, we have ideas for you based on our own explorations. 

Keep in mind that this isn’t an exhaustive list – we haven’t been everywhere in Italy, and it’s hard to recommend something we haven’t experienced ourselves.

For example, the Dolomites and Lake Como are on our list, but we didn’t include them below. Once we make it there, we’ll definitely add them!

You’ll notice that there’s one very popular destination missing from this list that you might be expecting to see: Naples, Pompeii, and the Amalfi Coast.

We contemplated adding it because we know it’s a place that people have seen pictures of and want to visit, but we really wouldn’t do it ourselves due to insane crowds and associated overtourism. 

Just this last summer, we’ve seen about 30 pictures of friends on Instagram who all went to the Amalfi Coast within the same two month period. 

Which, when you take a second to think about it, is pretty crazy. 

We think there are better coastal destinations in Italy (like the Cinque Terre – which has its own over tourism issues – and Sicily ) that we’d recommend way before the Amalfi Coast. You’ll find both of those on the list below. 

Add Another Day Trip from Bologna 

The first thing we’d add if you only have an extra day or two is an extra night in Bologna to explore more of Emilia-Romagna.

Cities like Parma (famous for prosciutto and parmesan-reggiano) and Modena (famous for balsamic vinegar) are an easy train ride away, and are well worth your time. 

We’d highly recommend a day trip that starts with Claudio’s tour of a working parmesan-reggiano dairy, which of course includes a tasting of different ages of parmesan, and a vacuum packed chunk to bring home with you.

It was the highlight of our last trip, and Claudio is friendly, uber-charismatic, and an all around phenomenal host. 

That tour is a morning tour, going until roughly noon. 

We’d then spend the rest of the day in Modena, which is the capital of balsamic vinegar production and is an easy 20 minute ride from the train station in Reggio-Emilia (where you’ll get dropped off by Claudio). That’s what we did. 

We loved tasting small production balsamic vinegar at La Consorteria 1966 (you should know that the tasting costs money unless you buy a bottle afterwards, which are expensive because this is the good stuff). 

We also had multiple people recommend Osteria Francescana , which is a world-famous fine dining experience that you’ll need to book well in advance.

You can also try chef Massimo’s food at nearby Franceschetta58 , which is less expensive and more approachable (you still want a reservation, though!). 

Another great stop is the Mercato Storico Albinelli, which is Modena’s central market. 

Add Another Day Trip from Florence

The second thing we’d add is an additional day trip from Florence. We gave you three options above, and if you took our advice, you’ve already done one of them. Do a second (or third!) one if you have an extra day. 

Cinque Terre (2-3 Days)

For my mom’s 60 th birthday, we took her on a two week Italy trip. Her two must-do experiences were the Cinque Terre and seeing the Last Supper in Milan.

So, we spent a few days exploring the Cinque Terre, and we loved it.

However, we have a major caveat. We would absolutely NOT recommend a day trip to the Cinque Terre, which is what approximately 90% of people seemed to be doing.

The main reason is that it’s a long way from places like Florence and Milan, requiring three hours of travel time.

That means you won’t arrive until mid-morning, which is when all of the other day trippers arrive, and the streets and trails are packed wall-to-wall. It’s no wonder people say it’s too crowded!

The magic of the Cinque Terre is in the early morning and late evening, when the day trippers clear out and it becomes a tranquil, slow paced coastal retreat. That means you’ll need at least one night (two or more is better).

The Cinque Terre, which literally means “Five Towns,” is a series of charming towns tucked between the mountains and the coast in northern Italy.

It’s known for hiking, terraced vineyards, and colorful towns perched on rocky outcroppings above the sea.

You’ll definitely want to hike a section of the Blue Trail (we like the one from Corniglia to Vernazza the most), dive into the wines of Cinque Terre, take in some excellent sunset views, and explore all five towns.

We have a bunch of guides dedicated to helping you plan your Cinque Terre trip. Here are some links for you:

Milan (2 Days)

Milan is a really great city that offers something a little different from other major cities like Rome and Florence.

That’s not to say that it’s not a historic city, but it feels less “Italian” than Rome and Florence mostly because it has been trading hands between the Spanish, French, Italians, and Austrians for centuries.

There is a difference that you’ll notice right off the bat, probably when you exit the train station.

It looks and feels more modern, which is mostly a function of the fact that it’s a major financial hub and home to just about every high end fashion company in the country.

There are two world-class attractions in Milan – the Duomo di Milano which took 600 years to complete and is a mishmash of different styles that somehow still works, and Da Vinci’s Last Supper .

However, it’s worth lingering for an extra day to explore some of Milan’s less famous attractions and the hip food and drink scene.

Wander Parco Sempione and pop into Castelo Sforza, and experience aperitivo in the Navigli District, which is home to some of Milan’s last exposed canals (it used to look like Venice!). 

Where to add it : You could either do Milan after Bologna (there’s a high speed train connecting the two), or after Venice (and fly out of Milan).

We have a bunch of guides dedicated to helping you plan a trip to Milan. Here are some links for you:

• One Day in Milan: The Best of Milan in a Day
• 2 Days in Milan: How to Plan An Incredible Milan Itinerary
• Where to Stay in Milan: A Complete Guide
• The Best Things to Do in Milan
• Where to Find the Best Specialty Coffee in Milan
• Gluten Free Milan: A Complete Guide for Celiacs

Sicily (7 Days)

If you have about a full week of extra time, we’d highly recommend exploring Sicily.

We love Sicily (Alysha’s family is from a small town in southeast Sicily), and spent three weeks on the island in the fall (which somehow was still not enough time). 

However, you should know that Sicily is massive, and it’s impossible to do the entire island in a week.

For that reason, we’d focus on southeastern Sicily (Catania, Mount Etna, and Syracuse) . Unfortunately, that means you’ll miss Palermo, which is an amazing city in northwestern Sicily.

The other reason to focus on southeastern Sicily is that you don’t need to rent a car. The corridor from Taormina to Syracuse is connected by a regional train line, which is something that can’t necessarily be said for the rest of the island.

To get there, you’ll need to fly. The best place to fly into is Catania (Catania–Fontanarossa Airport) .

Definitely don’t miss a day trip from Catania up to Mount Etna, which was among the highlights of our trip (you can read about it in our guide to the best things to do in Catania ) and a trip to the amphitheater in Taormina, which has a spectacular view.

Oh, and eat all of the pistachio and almond granitas you can. 

We have an entire guide dedicated to helping you plan a Sicily itinerary , which has a couple of ideas for how to spend 7 days on the island (P.S. we recently wrote a specific guide for spending 7 days in Sicily , which is even more helpful and specific in this context).

Where to add it : We’d add it after Venice, flying from Venice to Catania (which might require a connection) and flying home from Catania.

What to Do with Less Time in Italy

We’re not going to dive deep into how to spend less time in Italy, mostly because we’ve already done exactly that in some of our other guides. 

We have a guide to 10 days in Italy that’s geared towards first-timers that focuses on Rome, Florence, and Venice, and how to make the most out of your time in those places. 

We also have a guide to spending 7 days in Italy , which is a little different because it gives a bunch of different ways to do a weeklong trip to Italy. 

If you’re looking for ideas for a shorter trip, definitely read those. 

When to Visit Italy

Having spent some time in Italy over two consecutive fall seasons, I’m here to tell you that it’s absolutely my favorite time to be in Italy.

Summer is oppressive for two reasons. One, it’s sweltering. My first ever visit to Italy was late July in Rome, and it was miserable. Two, it’s simultaneously crowded and empty. Crowded with tourists, empty of locals (who all go on vacation in August). Not a great combination. It’s also very expensive, relatively speaking.

Fall is more moderate in both respects. By the end of fall – late October and November – it gets a little chilly, especially further north. But, all in all, September and October are an incredibly pleasant time to be in Italy.

Winter is going to be cooler and grayer, but significantly cheaper. The other thing to watch out for is things – bars, restaurants, shops, tours – closing, especially in smaller, more tourist-centric places like the Cinque Terre and beach towns in Sicily.

Spring is just a hair behind fall in terms of the best time to be in Italy, and anytime between Easter and the end of May would also be an excellent balance of weather and crowds. 

Matt is the founder and main writer behind Wheatless Wanderlust, which he started back in 2018 as a way to share his gluten free travel guides with his fellow Celiac travelers.

Since then, Matt and his wife Alysha have visited 18 national parks, spent three months in Europe and six weeks in Colombia, and have explored every corner of the Pacific Northwest, which is where Matt grew up.

He writes super detailed guides to the places they visit, bringing together personal experience and historical context to help YOU plan an amazing trip.

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2 Weeks in Italy: The Perfect 14 days Italy Itinerary for First Timers

Thinking of planning a trip to Italy? This 2 weeks in Italy itinerary will be a perfect guide to help you plan your Italy trip.

2 weeks in Italy is, in fact, the perfect amount of time to see the major cities of Rome, Florence and Venice along with some introductory visits to the mesmerizing regions of Tuscany, Amalfi Coast and Cinque Terre.

Our own Italy trip and valuable inputs from our Worldwide Wander Community have helped us create this perfect 2 weeks Italy itinerary for first time visitors.

This Italy itinerary shall transport you back to ancient Roman times, make you bask in the Tuscan sun, sail the seas of Amalfi coast, admire the art in Florence, explore the untouched towns of Cinque Terre and traverse the canals of Venice.

All this, while continuously hogging on the best pasta, pizza, Tiramisu, pastries, Aperol Spritz and Limoncello in the world!  

You can follow this 14 days Italy travel guide step by step or simply use it as an inspiration to plan your own trip to Italy!

We’re sure you’ll have an amazing vacation in Italy and shall be planning your return at the end of your first trip itself!

To create the most balanced itinerary for 2 weeks in Italy, follow the outline of our suggested Italy itinerary for 14 days below:

• Day 0: Arrival
• Day 1 – 3: Rome
• Day 4 – 6: Amalfi Coast
• Day 7 – 9: Tuscany
• Day 10: Cinque Terre
• Day 11 – 13: Venice
• Milan 14 – Milan and departure

This article contains affiliate links. This means that we earn a small commission for purchases made through these links at no extra cost to you. Kindly read our full disclosure and privacy policy for more details.

Also, if you refer the following Italy travel blog posts, you can upgrade a good Italy trip to a GREAT Italian Adventure!

• Our Complete 14 Days Italy Itinerary for an amazing first trip to Italy
• 1To Make the most of your time in Rome: A fully Packed 3 Days in Rome Itinerary
• Save Time and Money by following our Cinque Terre Itinerary that allows you to cover all the 5 villages in One Day!
• Absorb culture and beauty of Florence and the surrounding Region of Tuscany by copying our 3 Days Florence Itinerary
• A detailed guide to Venice and its surroundings by following our highly detailed 3 Days in Venice itinerary
• Explore the best of Milan in a single day with this perfectly planned One Day Milan itinerary
• Bring back a piece of Italy with you by shopping from this extensive list of Unique Italy Souvenirs

Quick overview

Day 0: Arrival and Acclimatization

You can start this 2 week Italy itinerary in either Milan or Rome and then follow along the chronology stated above.

In our experience, flight tickets to Rome are the cheapest. Hence, we recommend beginning your Italy trip from here.

However, if you find a great flight deal to Milan, you can follow this itinerary in reverse and it’ll be just as spectacular.

If you’re flying from a country outside Europe, your flight might be landing in Rome by late afternoon or early evening. It shall be impossible to go straight for sight-seeing in Rome considering the fatigue and jet-lag. Hence, use this day to relax, rejuvenate and freshen up for an amazing 3 days in Rome .

If you’re traveling from somewhere nearby, book your tickets in such a way that you reach Rome early in the morning. You can then drop your bags at the hotel, freshen up and start your 3 days in Rome immediately .

2 weeks in Italy Day 1-3 Rome

What better place to start your 2 weeks in Italy itinerary than the Eternal city itself. Rome drips of history from every corner and every cobblestoned street of its medieval infrastructure.

You can plan your Rome trip in the exact same fashion like we have illustrated in our fully packed 3 Days in Rome itinerary . Alternatively, you may take inspiration from it and plan according to your taste and preference.

Either which way, you must include the following must visit attractions and activities in your 3 days in Rome .

Colosseum, Roman Forum and Palatine Hill

The Colosseum is the biggest and the most iconic attraction of Rome. This ancient monument was the symbol of Rome’s grandeur and entertainment. It is the largest amphitheater in the world with a seating capacity of 50,000 spectators when it was operational.

Just beside the Colosseum is the Roman Forum and Palatine Hill. The Roman forum was the center of all social, political, economic and religious life in ancient Rome. On the other side, the Palatine hill is regarded as the birth place of Rome with its own set of ruins and monuments to explore.

It is imperative that you buy a skip the line ticket to the Colosseum to avoid wasting your time in lines during your 3 days in Rome . The ticket includes skip the line entry to the Roman forum and Palatine hill as well .

To enhance your experience 10-fold, we recommend you buy this highly rated guided tour of the Colosseum, Roman Forum and Palatine Hill . The guided tour shall help you optimize your time, click the best pictures for Instagram and leave you a lot more knowledgeable than you were before visiting Rome.

⏰ Recommended Time: 3 Hours

💶 Entry Fee: (queueing required at entrance) Adults: €16 | Youths aged 18-25: €2 | Everyone below 18 gets free entry. This Skip the line ticket is recommended

🧑🏻 Guided Tour: Colosseum Guided Tour with Roman Forum and Palatine Hill (⭐4.7/5 from 25,000 reviews)

Trevi Fountain

The Trevi fountain is the largest and most famous Baroque fountain in the world. It was built in the year 1762 over an ancient aqueduct.

The fountain is always swarming with tourists and crowds are almost impossible to avoid during the day. Hence, visit early in the morning around sunrise to get people free pictures with the beautiful fountain.

Toss a coin in the Trevi fountain with your right hand over your left shoulder. Legend has it that if you do so, you shall be returning to Rome in the near future.

⏰ Recommended Visit Time: Half an Hour

💶 Entry Fee: Absolutely free!

🧑🏻 Guided Tour: Guided tour of the Aqueduct beneath the Trevi Fountain (⭐4.7/5)

The Pantheon is the oldest preserved monument that you’ll come across during your 2 weeks in Italy. It was built in 27 BC by Marcus Agripa, the name you see carved at the entrance of the building.

The architecture of the building is so grand that it was publicly acknowledged by the world-renowned sculptor Michelangelo himself.

Entrance to the Pantheon is free. However, you might have to wait in lines and may not be able to admire the beauty of this masterpiece without a guide.

This highly rated guided tour of Pantheon takes care of both of the above problems!

⏰ Recommended Visit Time: 1 Hour

💶 Entry Fee: €5 from July, 2023. But guided tour is recommended to avoid wasting time in lines.

🧑🏻 Guided Tour: Pantheon Guided tour (⭐4.7/5)

Vatican City and Vatican Museums

Ah! The iconic Vatican City. The smallest country in the world and the residence of the Pope.

The Vatican City houses the famous Vatican museums and Gardens, the Sistine Chapel and St. Peter’s Basilica.

There are REALLY long lines at all of the above spots and buying the skip the line tickets is not only recommended but also insisted.

To better understand the beautiful art of the Vatican museum, get priority access and also get a secret entry to St. Peter’s Basilica, we recommend booking this official guided tour of the Vatican Museums, Sistine Chapel and St. Peter’s Basilica.

If you don’t book the above tour and just buy the skip the line tickets of the Vatican museums, you will still have to wait in long lines to enter St. Peter’s Basilica.

⏰ Recommended Visit Time

🏛 Vatican Museums: 2 Hours

⛪ St. Peter’s Basilica: 1 Hour

💶 Entry Fee

🏛 Vatican Museums: €17 for adults | Youth under 25: €8 | Free for Children under 6 years (queueing is required)

⛪ St. Peter’s Basilica: Free but queueing is required

🧑🏻 Guided Tour: Official guided tour of the Vatican Museums, Sistine Chapel and St. Peter’s Basilica (⭐4.7/5)

We insist you to check out our fully-packed 3 days in Rome Itinerary to get a comprehensive list of all the things to do in Rome in 3 days . The itinerary has a detailed day wise guide and insider tips along with recommended restaurants and budget saving hacks. Also, if you’re a vegetarian like us, you can check out our favorite restaurants to find Vegetarian food in Rome .

2 weeks in Italy Day 4-6 Amalfi Coast

The next stop during your 2 weeks in Italy is the picturesque beach area of the Amalfi coast.

You shall be spending 3 days in this area covering the must visit towns of Sorrento, Positano and the island of Capri.

In order to keep this 2 weeks Italy itinerary convenient, smooth and budget friendly, we recommend basing yourself in Sorrento and then make day trips to Capri and Positano.

For travel between locations in Italy, trains are the cheapest and most efficient modes of transportation. Be sure to book your tickets in advance to get a cheaper rate and also ensure availability.

Another economical option is taking a bus. This is a good option in case you’re traveling between locations that don’t have direct train connections like from Rome to Sorrento.

Find the most competitive Rates for trains, buses and ride sharing in Italy here!

Italy Trip Day 4: Sorrento

As explained above, you need to base yourself in the beach town of Sorrento as it is the most convenient and most affordable of all the places to stay in Amalfi Coast.

How to reach Sorrento from Rome?

There are no direct trains from Rome to Sorrento, so you’ll have to take a train from Rome to Naples and then change for Sorrento. However, that involves a lot of hassle especially when you have heavy luggage with you.

On the other hand, you can do what we did and take the much more convenient option – the bus! It takes about 4 hours but the ride is very comfortable and there are no transfers involved.

Check out ticket prices for your travel dates here!

Things to do in Sorrento

Upon reaching Sorrento, check into your hotel and set out to explore the beautiful beach town.

You can stroll across the Marina Grande and enjoy its boardwalk atmosphere by having lunch at the many sea-facing restaurants.

 Post lunch, explore the vine covered Cloister of San Fresco. Then enjoy a beautiful sunset from Villa Comunale – a park and terrace above Marina Grande, with splendid views of the Gulf of Nalples and Mount Vesuvius .

This town is renowned for its lemons and the various lemon products it makes. Our favorite is the Limoncello, an alcoholic drink made from lemons and it is also one of the best souvenirs to bring from Italy.

Sorrento is the best place to buy Limoncello as the Limoncello here is authentic, locally made and much cheaper than other popular Amalfi Coast tourist towns like Positano and Capri.

Italy Trip Day 5: Positano

On Day 5 of your 14 days Italy itinerary, take the SITA bus from Sorrento to Positano. The ticket costs merely €2 and can be purchased from the tobacconists at the bottom staircase of Sorrento Station .

Make sure that you start early to avoid the crowds in the bus and sit on the right-hand side to enjoy beautiful coastal views of Amalfi during the ride. Starting early is a must because there have been cases where you might have to stand in the bus in case it is overbooked.

❕ Note: Avoid renting a car for your visit to Positano or Amalfi as the roads are a real challenge to drive on and you will have to park the car outside the villages. The parking rates are really steep due to a lack of space and are simply not worth it.

Positano is the most beautiful of the Amalfi coast villages. It still retains its small fishing village vibe unlike the recently well-developed Amalfi.

It has a great collection of cliffside restaurants, an abundant number of private beaches and beautiful nature trails to discover some of the best vantage points.

Explore the narrow cobblestoned lanes of the village, check out the cute boutique shops, try amazing Lemon Gelato and have drink at the many amazing restaurants overlooking the Mediterranean.

If you’re an avid hiker, you can hike the Path of the Gods. It is an 8 km long mule trail that connects the Amalfi villages and provides breathtaking views of the Amalfi Coast.

If you don’t wish to limit this day just to Positano, you can book a chauffeured tour of the entire Amalfi coast like this one that takes you to the beautiful towns of Amalfi, Positano and Ravello.

Return to your hotel in Sorrento before dark to avoid being stranded the last few buses of the day leave around 8 but they get sold out and are often crowded. Buy your return ticket to Sorrento the moment you enter Positano.

Italy Trip Day 6: Capri

Capri is located a mere 20 min. ferry ride from Sorrento.

You can set off early in the morning before the crowds and reach Marina Grande. Book your return ticket in advance to avoid paying premium prices.

Upon reaching Capri, y ou will be heckled by a lot of ferry drivers for boat tours around Capri. These tours are often overpriced and a lot of our friends told us that they were sub-par.

 It’s better to book your excursion around Capri with a reputed company in advance. We booked this amazing Island Boat trip around Capri (⭐4.1/5). No matter who you book with, ensure that your boat trip includes the following stops:

• Punta Carena Lighthouse
• Bagni di Tiberio
• Sea caves of White Grotto and Green Grotto
• Faraglioni Rocks
• An optional visit to the Blue Grotto

❕ Note: The visit to the Blue grotto involves an additional fee of €14 to enter the grotto. Do not skip this. It is a surreal sea cave where the waters glow sapphire blow. The water is the only source of light in the damp, dark cave. It is definitely one of nature’s mysteries and a must visit during any trip to Capri.

⏰ Duration: 2 hours

🧑🏻 Recommended Tour: Capri Island Bat Trip and Blue Grotto Visit (⭐4.1/5)

If you wish swim or snorkel in the amazing blue waters near Capri or if you don’t wish to get into the hassle of taking a ferry to and from Capri, book this highly rated Small group boat tour of Capri from Sorrento (⭐4.8/5).

It includes all the spots mentioned above, a Limoncello tasting, appetizers and two amazing stops for swimming in the Capri waters!

On Capri island itself, explore the Agustus Gardens, ride the scenic chairlift to the top of Monte Solaro and explore the food scene of this tiny, beautiful island!

2 weeks in Italy Day 7-9 Tuscany

On day 7 of your 14 days Italy itinerary, take an early morning bus from Sorrento to Nalples train station . It costs barely €5 and saves a lot of time. You shall reach Naples by 8 AM. Have your breakfast at the convenient but amazing Café Vyta while you wait for your train.

From Naples, take the direct train to Florence and you shall be in the cultural city by noon!

Use the rest of the day to explore the city of Florence as stated below.

2 Weeks in Italy Day 7: Florence

You’ve arrived in noon. So, to make the best of your time, drop your luggage at your hotel and set out to explore Florence. We recommend covering the following locations on your first day.

You can also check out our detailed 3 Days in Florence Itinerary for information on how to get around and best area to stay in Florence, along with other things you can include in the below mentioned itinerary. For vegetarians like us, this detailed guide on finding Vegetarian food in Florence cannot be missed.

Accademia Gallery

You can’t be in Florence and not visit the Accademia! It houses the best sculptures by the renowned Italian Michelangelo, esp. the famous David! The Accademia is also Europe’s first school of drawing. Hence, it boasts of an extensive collection of paintings dating back to the 15 th century.

Book a timed entry ticket to The Accademia so that you don’t have to wait in lines and waste time on the 7 th day of your 14 days Italy itinerary.

As always, a guided tour definitely increases your experience manifold!

⏰ Opening Hours: Tuesday to Sunday | 8:15 AM to 7:15 PM daily. (last entry at 6:15 PM)

💶 Entry Fee: Check out the price for Timed Entry Ticket Here

🧑🏻 Guided Tour: Accademia Gallery and David Guided Tour (⭐4.5/5)

Florence Cathedral

After the Accademia Gallery, walk a mere 500m to the Florence Cathedral. Admire the beauty of this 13 th century Gothic Church with a majestic dome that adorns the city’s skyline!

The dome (Cupola), designed by Filippo Brunelleschi was an inspiration to many architects and artists during the Renaissance period .

Even more impressive is the fresco inside the Dome by Giorgio Vasari, called the Last Judgement.

Marvel at the beauty, intricacy and the grandeur of the architecture of the Florence Cathedral and don’t skip climbing up the dome! You will truly be able to admire the work that went into creating the Cupola and also get an unprecedented view of Florence.

Without skip the line tickets like this one , you shall not be able to visit the Cathedral on Day 7 of your Italy itinerary. So, make sure you book them in advance and witness the Italian sun set over Florence.

⏰Recommended Visit Time

⛪ Cathedral: 1.5 Hours

🛎 Dome: 1 Hour

💶 Entry Fee: Free for Cathedral | Recommended Skip the line Ticket for Dome and Cathedral

🧑🏻 Guided Tour: Duomo Cathedral Guided Tour (⭐4.1/5)

Piazza della Signoria

It’ll be almost sunset by the time you are done visiting the Duomo. Head to Piazza Della Signoria – one of the most artistic, sculpture-laden and happening squares in Florence.

Stroll across the beautiful square and admire the various sculptures like the Neptune Fountain, the replica of David and all other amazing sculptures in the Loggia ( public Sculpture Gallery).

If you have some time left, you can also visit the Pallazo Vechio.

Have dinner in the many amazing nearby restaurants and call in an early night.

2 Weeks in Italy Day 8: Florence and Tuscan Country side in the afternoon

For Day 8 of your two week Italy itinerary, book a tour to Tuscany like this highly rated Chianti Wineries with Food and Wine Tasting . This half day tour begins in the afternoon at about 2:30 PM. As a result, you get a great amount of time in the morning, to visit other epic attractions in Florence.

Start your day at 7 AM and visit the following attractions in the order provided:

Pitti Palace and Boboli Gardens

Be one of the first people to enter Paitti Palace today and book a timed entrance ticket to the Pitti Palace . Witness the grandeur and beauty of the exterior of this lavish palace. Inside the Palace, visit the Galleria Palatina that was used by the Medici family as their residence.

Your ticket also provides you access to the Gallery of Modern Art that houses an exquisite collection of art from the 18 th century to World War 1.

Boboli Gardens are located directly behind the Pitti Palace. These gardens were one of the first examples of Italian landscaping which were later on emulated in many European sites.

The garden has artificial Grottos – stone caves, exquisite fountains, manicured lawns and hedges and marble sculptures throughout its vast landscape. It’s a great place for a picnic too!

⏰ Recommended Visit Time: 3 Hours

💶 Entry Fee: For Pitti Palace | For Boboli Gardens

Ponte Vechio

After spending an amazing morning in the Boboli gardens, take a walk across the Ponte Vechio.

The bridge is a work of spectacular engineering as it was the first segmental arch bride built in the West.

The Ponte Vechio is famous because of two very unique reasons:

• It is the only bridge n Florence that survived the bombing in World War II.
• It is the only bridge in the world where people still have a residence in!

That’s right, people live on this bridge!

Today, this bridge is full of jewelry stores and art dealers. Grab a gelato and make your way to our next stop the Uffizi Gallery

Uffizi Gallery

The Uffizi gallery is one of the oldest museums in Europe and houses one of the largest collections of Renaissance art in the world! You can see works of Michelangelo, Da Vinci, Raffaello and many others. One of the most revered works of art are Boticelli’s Primavera and Birth of Venus .

Apart from the paintings and sculptures, the building of the Uffizi itself is greatly admired as a work of art.

Make sure you book a timed ticket to the Uffizi Gallery in advance as the tickets for your particular time slot generally sell out very fast.

⏰ Recommended Visit Time: 2 Hours

🧑🏻 Guided Tour: Uffizi Gallery Small Group Tour (⭐4.7/5)

You can visit all of the above 3 attractions in reverse order as well depending on what is closer to your hotel. Wither way, your target is to be free by 2 PM as that is when the pick up of you Chianti Vineyards tour is scheduled!

Chianti Wine Tour

You can’t come to the region of Tuscany and not visit the Tuscan countryside ! The region of Tuscany is famous around the world for its vineyards, olive plantations and the products that come from them.

You can easily spend an entire week exploring the little Tuscan villages on a 7 day Tuscany road trip. However, since we are short on time, we suggest booking a half day tour to one of the best vineyards in the region.

This Chianti wine tour includes pick up from Florence, wine tastings in two amazing vineyards, delicious cheeses, breads and cold cuts to pair your wine with a local guide.

If you have an entire day in Florence and wish to cover unique places like Pisa, Siena and San Gimignano along with Chianti, you can opt for this highly-rated Day trip that includes lunch !

The tours are cost effective and is probably the most efficient way to get a taste of Tuscany, so that you can plan an even longer trip later on!

🧑🏻 Guided Tours:

Half Day Chianti Wineries Tour with Food and Wine Tasting (⭐4.6/5)

Full Day Pisa, Siena, Sam Gimignano Day Trip with Lunch (⭐4.4/5)

If you still have time and wish to include more things to do in Florence or want more details on where to live in Florence or how to get around Florence, visit our detailed itinerary on spending 3 days in Florence .

Day 9: Pisa and Transit to La Spezia

Day 9 of your Italy trip involves visiting the beautiful town of Pisa and takes care of logistics to explore the magical area of Cinque Terre. Check out of your Florence hotel and take the train to Florence.

Find the most competitive prices of trains and buses here!

You can drop your luggage in Pisa Centrale station at the storage facility located at the end of Platform 1. The charges are as nominal as €3 for 12 hours.

Once you’ve dropped your luggage, head to the Piazza De Miracoli which houses all the major attractions of Pisa. Take the highly efficient LAM Rossa bus service that runs every 20 minutes .

At Piazza De Miracoli, show your skip the line ticket to the Leaning Tower of Pisa and head straight to the top of the Tower to enjoy unhindered views of the Pisa skyline.

If you arrive early during the day, you shall also be able to take people-free images with the Leaning Tower.

Visit other beautiful monuments in the Piazza De Miracoli like the Duomo (Cathedral), Baptistry di San Giovanni and Camposanto.

The entire trip would take around 3 hours . Post that, you can relax in the gardens or have lunch at a nearby restaurant. We personally loved the food at La Ghiotteria for their authentic Italian cuisine.

Transit to La Spezia

After lunch, collect your luggage at the train station and catch a train to La Spezia. La Spezia shall be your base for exploring the Cinque Terre.

We recommend staying in La Spezia as it is very well connected to all the villages of Cinque Terre by train and you can find better accommodation in La Spezia as compared to the overpriced ones in other Cinque Terre.

Book your hotel near the train station. We stayed at The Poet Hotel , one of the few 4-star hotels in the city very close to the La Spezia Centrale station. It is great value for money as well!

Before leaving the La Spezia Centrale Station collect your Cinque Terre Train Card from the ticket office for the next day.

For €16, this card not only provides unlimited train travel between all the stations but also provides access to ATC bus services, free use of public restrooms in the train stations, WiFi in park hotspots and access to hiking trails! Definitely worth it.

2 weeks in Italy Day 10: Cinque Terre

Spend your Day 10 in Italy exploring the colorful towns of Cinque Terre . You shall be visiting all the five main villages of Cinque Terre in one day by train in the order of your choice. Take the train from the La Spezia Centrale station and use your Cinque Terre train card for hassle free transit.

Each village provides a unique experience with the same cultural and scenic backdrop.

• Manarola: Our favorite town in Cinque Terre. It has exhilarating cliff jumping spots, is great for swimming, has treks to incredible vantage points of the village and amazing cliffside restaurants . A great place for lunch is Nessun Dorma. The Disney movie Luca was based on this little town.
• Corniglia: The town perched up higher than the others in the mountain.  Take the shuttle bus to the town from the station. In the village, grab the best Gelato in Cinque Terre at Alberto Gelateria and explore the narrow back alleys that lead to a breathtaking viewpoint .
• Vernazza: Explore the colorful streets, hike to the Doria tower for unprecedented views of the village, stroll across the jeti and swim in the clear waters in the northern part of the bay . Vernazza exudes a vibe that cannot be described in words.
• Monterosso: The largest of all the villages. It is the only village in Cinque Terre with an amazing sandy beach, ready with sun loungers, umbrellas and a board walk . Relax, get a foot massage and bask in the sun here.
• Riomaggiore: Walk through the tunnels to reach the town from the train station. It has an amazing, stoney jetti that provides post-card perfect views of the village. This is the best town to rent a kayak and go exploring the coast of Cinque Terre!

For a detailed guide and the most perfect way to explore all the towns, check out our detailed guide on visiting Cinque Terre in One Day !

Recommended Guided Day Trips

If you don’t wish to fall into the hassle of all the detailed planning , you can book this supremely convenient Cinque Terre Tour by Train that follows the same route as our 1 day Cinque Terre Itinerary. It also has additional benefits like a local guide and Limoncino tasting!

If you opted for a day trip to Pisa, Siena and San Gimignano on Day 9, you’re probably still in Florence . In that case, you can opt for this extremely highly-rated tour to Cinque Terre from Florence (⭐4.9/5) like a lot of tourists do. It is efficient, cost effective and covers all the highlights!

From La Spezia: Cinque Terre Tour by Train with Limoncino (⭐4.3/5)

From La Spezia: Cinque Terre Sailing Tour by Speedboat (⭐4.8/5)

From Florence: Cinque Terre Day Trip (⭐4.9/5)

❕ Note: Cinque Terre is a hilly town and exploring it requires a lot of walking and a lot of stairs. If you’re someone who has a problem with that, you should substitute these 2 days in Cinque Terre with a visit to Lake Como.

2 weeks in Italy Day 11-13: Venice

On Day 11 of your 2 weeks in Italy, you shall be going to Venice from La Spezia.

You can either make a train trip that involves two transfers or you can opt for a bus that drops you directly at Venice.

Check out the most competitive rates and timings of your bus and train tickets here!

Spend your 3 days in Venice exploring the beautiful city of Venice and enjoy the following attractions and must – do activities in Venice:

St. Mark’s Square, Basilica and Doge’s Palace

St. Mark’s square is the most popular square in Venice. It houses two of the most iconic sights of Venice – St. Mark’s Basilica and Doge’s Palace.

In St. Mark’s Basilica, admire the beautiful golden mosaics covering the high walls and the Pala d’Oro, the spectacular altarpiece made from enamel and gold leaf.

Visit the Doge’s Palace, the seat from which the powerful family ruled the Republic of Venice. Book a skip the line ticket to Doge’s Palace (⭐4.6/5) and stroll across the majestic halls. Marvel at the masterpieces of art, frescoes and the Bridge of Sighs.

To enhance your experience, book this widely loved Doge’s Palace and St. Mark’s Basilica Guided Tour (⭐4.6/5).

The Bridges of Venice

Exploring Venice on foot and getting lost in its alley ways is one of the best things to do in Venice.

What enhances this experience even more is the shear number of unique bridges in Venice.

Some of these bridges are architectural masterpieces, while others have unique story behind them. Explore Venice on foot and cross as many of these bridges.

The following are the best bridges in Venice for an Instagram shot:

• Rialto Bridge
• Ponte dell’Accademia
• Ponte degli Scalzi
• Ponte della Constituzione
• Ponte del Diavolo
• Ponte dei Tre Archi
• Ponte della Paglia

Gondola Ride

Gondola rides in the Grand Canal are so popular that they have become synonymous with a trip to Venice. However, they are a bit too expensive if you buy them on the spot.

During peak seasons, visitors have had to pay upwards of €100 per person for riding the Gondola on a shared basis! In order to avoid paying outrageous amounts of fees on the spot, we recommend booking a ticket in advance.

These are the following, most reasonably priced tickets available:

• For travelers on a budget: Join a group of 5 on this Gondola Ride with App Commentary (⭐4.2/5) to enjoy a Gondola ride at barely 30% of the cost.
• For Couples, groups, families and luxury travelers: Book a Private Gondola ride (⭐4.1/5) which can accommodate a group of 5. This is an ideal set up for couples and families. They can enjoy a Gondola ride privately, at their own pace and without paying the outrageous rates in Venice!

Burano, Murano and Torcello Islands

Ensure that you dedicate one day of your time in Venice to visiting nearby island villages in the lagoon. The villages of Burano, Murano and Torcello are some of the most beautiful and also the most popular!

Burano is a small fishing village that has a string of colorful houses on either side of the lagoon. It is a great spot for exploring hidden gems and getting some amazing shots for Instagram.

Murano is famous all over Italy for its glassware. You can visit a glass factory and see the entire process of crystal-making from scratch!

Torcello is another quaint little town with medieval architecture and a beautiful vibe. One of the main attractions of Torcello are the Venetian-Byzantine Mosaics of Basilica di Santa Maria Assunta. Also interesting is the Throne of Attila. You can easily spend and hour here exploring the beautiful town.

The best way to visit these three villages is by booking this Murano, Burano, Torcello and Glass factory tour (⭐4.4/5). It is, in fact, cheaper than what it would cost if you bought public ferry tickets to all three villages.

🧑🏻Guided Tour: Murano, Burano, Torcello and Glass Factory Tour (⭐4.4/5)

2 Weeks in Italy Day 14: Milan and departure

On the last day of your 2 week Italy itinerary, visit Italy’s design capital – Milan.

Take a direct train or bus from Venice to Milan in the morning.

Plan your day in Milan depending on your flight time. Try to cover as many of the following must visit locations in Milan, before your flight out of Italy:

• Milan Cathedral
• Church of Santa Maria delle Grazie
• Grand Galleria Vittorio Emanuale II
• Castello Sforzesco
• Leonardo Da Vinci Museum of Science and Technology
• The very happening Navigli District
• Tiatro Alla Scala

Don’t be worried in case you think that’s a lot of places to visit in Milan. Most of them are located within walking distance of each other and some even lie between two major attractions.

For example, to reach Tietro Alla Scala (the grand opera house of Milan) from the Milan Cathedral, you need to walk through the Galleria Vittorio. That’s three of the 7 attractions listed above in a matter of 10 minutes!

Refer our dedicated blog post for a more detailed One Day Milan itinerary that explains everything from things to do in Milan, where to store your luggage, how to get around and how to reach the airport!

This shall be the last day of your Italy trip, so make sure you spend it in a way that captures the entire essence of your trip. Eat great food, sip on some Aperol Spritz along the Navigli Canal, marvel at the architecture of the cathedral or admire the works of Leonardo Da Vinci in his museum!

In a Nutshell!

That brings us to the end of our guide to planning a trip to Italy. The beauty of this 2 weeks in Italy itinerary is that you can do the entire trip in reverse.

Rome and Milan are two of the most well-connected transport hubs that offer the best flight rates. And for that we reason, we have kept them at the two ends of our trip to Italy.

We hope this Italy itinerary helps you in planning your own trip to Italy and inspires you to enjoy this beautiful country a little more in a confined amount of time.

Check out our other blogs on Italy or subscribe to our newsletter to be up to date with our new blogs. We have a lot of content lined up to help travelers make the most of their trip to Italy.

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Last Updated on 2 months by Param Vithlani

• My Bucket List

Italy Itinerary: 14 Days in Paradise

From the beautiful Venice on the lake to the historical center of Florence, from the picturesque islands of Cinque Terre to the holy Vatican city, most of the best sights in Italy can be experienced with in 2 weeks. Between stops at notable monuments, we still found time to wander each city endlessly. Below is a list of tips & advice for the cities and towns I’d recommend anyone to visit if they’ve a short stay in the country. I will briefly go over my experience, things to be aware of, and the must-sees for each city. This Italy itinerary 14 days can definitely be adjusted according to your liking!

A Brief Overview of this Italy Itinerary 14 Days

Highlights of spending 2 days and 1 night in Venice:   

Doge’s Palace and Saint Mark’s Basilica in the evening to catch the sunset

Take a gondola or water taxi on the Grand Canal

Highlights of using Florence as a base for 5 days :

Visit the Cattedrale di Santa Maria del Fiore and the open air museum in Piazza Della Signoria

1-2 day hike in Cinque Terre

A morning stroll around Pisa

Highlights of staying in Rome for 4 Days:

Visit the historical Colosseum, Roman Forum, and Palatine Hill. Strolls through the city center and other noted monuments Leave a day for the Vatican City

Highlights and Recommendations for the remaining 3 Days

Best Time To Go To Italy

The best time to visit Italy is in the Spring or during the Fall season. Between May and June, and September and October, the weather in Italy will be picture perfect. Try to avoid school holidays and long weekends for cheaper prices and less tourism.

2 Days and a Night in Venice

Make sure to confirm your hotel/Airbnb address before arriving! Although the location of my Airbnb was shown on Google Maps, it took me some time before figuring out that the address was wrong.

I ended up wandering the streets of Venice with my luggage. Not a fun experience after a flight :'(

Be Aware: Needless to say, the streets of Venice were confusing. On a map, the layout seems straightforward enough. It’s a tiny island with small streets here and there, resembling any other European city. The story is completely different when you are physically there. There were no less than a few thousand intersections and crisscrossing alleyways. Many streets were impossible to locate due to the numbering system ( instead of having different street names, the houses are numbered in accordance with the districts ).

Tips & Advice: It really isn’t an Italy itinerary without Venice! This beautiful town is best experienced by exploring the streets and small shops with a local. Stop by Doge’s Palace and Saint Mark’s Basilica in the evening to catch the sunset. Most spots in the township are easily accessible by foot, but do take a gondola or water taxi on the Grand Canal so you can enjoy the views of Venice from below.

Venice was extremely small and pricey. As such, a day in the town was enough. But to experience the romantic strolls at night, we decided to leave the following afternoon.

5 days in Florence

Use florence as the base for cinque terre  (1-2 day) and pisa (1 day).

Although Florence was crowded with people and traffic, it remains one of my favorite destinations in Europe! Situated 10 minutes away from the spectacular Dome, our Airbnb was only EUR 19 for two beds!

The Cattedrale di Santa Maria del Fiore was breathtaking; the city magnificent, the open air museum in Piazza Della Signoria was extra charming with a saxophone soloist. There is so much to see here. From its beautiful architecture to its art and history, definitely, spend a few nights in this magical city. Piazzale Michelangelo has the best panorama views of the city!

Tips & Advice: To be honest, since the city is small, a day or two is enough to see everything. However, Florence is just charming enough and worth a few more days if you’ve 14 days in Italy! BlablaCar and Airbnb are extremely easy to use in Italy, and much more affordable and flexible in terms of booking. If you have a love for history, take a guided tour of Michelangelo’s David Guided with an art historian.

Italy Itinerary 14 Days: Cinque Terre

An Italy travel itinerary isn’t complete without this beautiful region.

Tips & Advice: Waking up at 6 am, we caught the earliest train at the Florence central station. Cinque Terre is famous for its 5 different villages and their colorful dwellings by the sea. Again, all the trains and associated timetables are available on Itali Rail .

The ticket for these villages as mentioned below are only sold at the station in La Spezia and the front desk of some hotels .

After arriving at Genoa train station (La Spezia), there is a separate train for these villages. The station provides a rather great explanation for what’s to come. They hand out little cards that detail the various trains times between each village, as well as the hiking trails between these little towns.

Experience: Unfortunately, only one of the hiking trails connecting the villages was open, but it was enough for the day. The hike was exhausting, lasting nearly 2 hours. We thought one day was enough for Cinque Terre. If you don’t want the hassle of catching the trains, join an all-inclusive day tour from Florence!

2 Week Italy Itinerary: Pisa

Experience: After returning to Florence for the night, we decided to stop by Pisa the next day. Instead of catching a train, we took a BlablaCar to Pisa. The ride was approximately 1.30 hrs and costed EUR 8 per person. On the way, the driver pointed out the Tuscany Vineyards , which was extremely beautiful.

A day is definitely enough wandering the streets of Pisa, as the space containing all the famous architecture within the city is not too big. Participate in a guided tour of Pisa and its various monuments to better experience this gorgeous city.

Be Aware: A lot of people love bringing food for a picnic on the lawn of the Leaning Tower, but you will likely get hooted off by security.

4 Days in Rome

We spent a few days exploring the streets of Rome and ended up skipping a few tourist attractions due to the number of people. However, if you aren’t exactly keen on going inside the monuments, I found the experience of wandering around town during night-time was much better. There were barely any people and the lights were beautiful!

Tips and Advice: If you only have 14 days in Italy, 3 days was definitely enough for the main tourist attractions in Rome!

• First Day: dedicate 3 hours to the Colosseum , Roman Forum , and Palatine Hill . This includes the wait in line and photo ops. A few hours should be spent walking around the city center, with stops at the Arch of Titus , Piazza Navona , Pantheon, Trevi Fountain and St. Peter’s Basilica . Don’t forget to stop by to get some Gelato and Pizza! This will be a long day, but everything is quite close together!
• Second Day: Visit Trastevere, a quirky little neighbor in the area and explore the streets away from the major tourist attractions. I though Rome can be quite hectic if not planned wisely.
• Third Day: Spend a day at the Vatican! The wait time for the Vatican can be up to an hour or more during the busier seasons

2 Week Italy Itinerary: The Remaining 3 Days

Without a doubt, Italy is so much more than these few cities. There is Milan , one of the fashion capitals of the world. (Visit before or after Venice since it is located in North Italy) . Bologna is yet another great stop located between Florence and Rome. Down south, you have the beautiful waters of the Mediterranean. Visit Naples or the breathtaking Sicily .

This is definitely a very fast-pace and tiring agenda for those who are physically able. However, if you are on a tight schedule yet don’t want to miss any of the spectacular sights, (like myself), this might do!

We spent around CAD 500 for the two of us. This was a pretty expensive trip compared to my usual backpacking journys. But since we opt for nicer Airbnb instead of Couchsurfing , it was quite worth it!

CAD 300 was spent on Airbnb. Aside from the cheaper stay in Florence, Venice and Rome were pretty pricey. The rest were on transportation throughout the country. Trains in Italy were expensive. I didn’t really notice it until going to Cinque Terre due to the lack of BlablaCars in that region. I believe we ended up spending CAD 100 just for the various trains throughout the day.

Nevertheless, this was such a great experience and definitely worth the trip! If you ‘ve any questions about this Italy itinerary 14 days, feel free to email me!

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An Italian Mama's Guide to Italy

14 days Italy itinerary: how to spend two weeks in Italy with kids and see Italy’s highlights

14 days Italy itinerary for families: family-friendly Italy itinerary ideas to spend 14 days in Italy with kids of all ages .

One of the most frequent questions I get about traveling to Italy with kids is what is the best way to plan a 14 days Italy itinerary with children that touches on as many Italy highlights as possible.

Places that top the request are Venice, Florence, the Tuscany countryside, Cinque Terre, Rome, Pompeii and Amalfi Coast.

These are very many places to see in a fortnight and, in many respects, they are too many, once you factor in changing accommodation, packing etc.

That said, it is possible to see pretty much all of them in one form or another, if you are happy to be on the go and chance accommodation often.

With the 14 day Italy itinerary below, I share how this can be done while striking between seeing as much as possible but without getting exhausted.

Is this the best two week italy itinerary?

I believe yes, it is the best two week Italy itinerary for families who want to see many destinations and don’t find changing accommodation too daunting in terms of packijng / uppacking etc.

If your family enjoys a slower place vacation, travels with a lot of luggage, multiple strollers etc, then I recommned you slow it down a notch.

If that’s you, I recommend you look at our 10 day Italy itinerary for families in sad and stay longer in the locations that attact you most.

You can also use the search function at the top of this page to find my guides to specific areas and focus your time on one of those.

I have written it on the basis of my own experience traveling around Italy with my children and I believe they strike a good balance between seeing many things, getting some fun in for the kids and not get overly exhausted.

You can use it are or you can use them as a draft to then tweak them to suit your personal needs and taste.

Please note: this post contains affiliate links. Should you make a purchase though them, we might make a small commission on qualifying purchases.

14 days in Italy with kids: train or car?

The first big decision when planning 14 days in Italy is whether you are happy to drive in Italy or not.

If you are unsure and have heard horror stories about Italy drivers, don’t let them deter you just yet!

First, read our post about driving in Italy and then see if it is for you or train is a better option.

The choice lies with your comfort levels driving abroad and the areas you want to visit.

Some areas are easy by train while in others, the lack of a personal vehicle really limits you.

At a glance:

The train is best to visit the main Italian cities (Rome, Florence, Venice, Milan, Verona, Naples, Bologna), Liguria and Cinque Terre, the Amalfi Coast.

The car is best to visit Tuscany, the Dolomites, Puglia and the South of Italy in general .

If you can, the best way to go about your 14 day Italy itinerary is to mix train and car. In the itinerary below, I will give both options do you can tailor itt your needs at best

14 days Italy itinerary with kids by train and car: stops and tips

Day 1: arrival in venice and settling in.

Your first day will all be about settling in, potentially dealing with jet lag and finding your bearing.

I suggest your spend your first day taking a stroll around Venice, take in the canals, Rialto Bridge and St Mark’s Square, then have an early dinner close to your hotel.

Stay in one of our tried and tested Venice hotels for families or pick your favorite Airbnb in one of these areas >> best area to stay in Venice .

Day 2: Venice

Explore Venice in the morning, allowing yourself to get lost in its pretty center (don’t worry, you won’t stay lost for long as you’ll always find a landmark to get your bearings back!)

If you want to visit the Doge’s palace inside, make sure you get skip the line tickets here .

In the afternoon, take a treasure hunt with Macaco Tour to mix a fun activity for the kids with a chance to explore the city with a guide.

Read our review here to see why we recommend it for kids!

If you have teenagers who may not enjoy a hunt, I recommend instead booking a Street food / Cicchetti tour instead which will get you to taste amazing Venetian food in authentic places

Day 3: Venice islands

Many people will say at this point you are ready to leave Venice; however, I believe that a day visiting the islands is worth it and a great way to slow down an otherwise too busy couple of weeks.

The islands of Murano and Burano and just in front of Venice and while we call it a ‘day trip’, they are so well connected it really is no more tiring than staying in Venice proper.

Murano is famous for its glass-blowing artisan shops.

We like Ferro Toso, which offers glass blowing demonstrations and the option to make your own glass creation (also for kids) at reasonable prices.

In Burano, enjoy the colorful houses and take a tasty break with Buranelli biscuits, a local specialty!

Find here >> our guide to Burano

Head back to Venice for dinner: the lagoon as the sun starts to set is magical!

Day 4: Florence city center and drive to agriturismo

Catch the train to Florence.

If you arrive early enouhg, leave your luggage at the station and have a stroll around Florence city center.

Make sure you pass by the Duomo, Piazza della Signoria and Ponte Vecchio, all very close to one another and to the station.

With small kids, have a stop at the merry go round in PIazza della Repubblica. If in Florence for lunch, have a quiet meal in Nerocarbone.

Head back towards the station and pick up your car rental to head to your agritusimo of choice in Tuscany.

For this first night, I recommend you ask your agriturismo for dinner so you know you can rest and leave the car for the rest of the day.

You can find our selection of favorite agriturismo for families in Tuscany here

Day 5 – Tuscany towns

Spend the day exploring Tuscan towns.

Depending where exaclty your agritirismo is located, you can choose between many pretty towns.

San Gimignano, Monteriggioni, Pienza, Bagno Vignoni are all wonderful but in different areas of the region.

Pick one of two, based on what is closest to you.

Find here >>> the most beautiful small towns in Tuscany

Spend the night at your agriturismo.

Day 6 Tuscany town hopping or agriturismo day

Pick one or two more towns and use the car to exolore a different part of Tuscany from the day before.

If you prefer, you can also spend the day in the agriturismo, maybe taking a cooking class or letting the kids play.

Since the following few days will be of travel, I highly recommend you take this day to relax, take in the views and slow down: Tuscany is ideal for that!

Day 7 Cinque Terre

Drive back to Florence or up to La Spazia to leave the car and then hop on the train to Cinque Terre Area.

Stay in Monterosso or Levanto if you have young kids or pick any of the pretty Cinque terre Towns if you have older kids or teenagers.

Spend the afternoon in your town of choice and enjoy the stunning Cinque Terre sunsets!

Find here >>> our recommendations to visit Cinque Terre with kids

Day 8 Cinque Terre

Spend the day exploring the lovely Cinque Terre towns.

The towns are all connected by train and, in the good season, by local ferries. Famously, they are also connected by hiking trails so you have lots of options on how to explore!

With kids, my favorite way to explore the area is by ferry.

If you have older kids or teenagers, then the trails can be fantastic: make sure you ask the local tourist office which ones are open when you are there.

These are serious nountain traios and are subject to closures for weather conditions and safety.

If you are not sure what towns to see, you can read here >> our introduction to Cinque Terre towns .

Take the train to Rome, then settle in your hotel.

I highly recommend you stay in the center, so you can spend this first day just wandering close to your accommodation while still seeing sight.

If traveling with small kids especially, a fun way to spend the afternoon is by taking a golf cart tour : a great way to see a lot with an experienced guide and without a lot of walking.

A family hotel I love in Rome is the Hilton Double Tree Monti .

If you want more options, I recommend you read here >>> my guide on where to stay with kids in Rome

Hve dinner in Mimi and Coco or Cul de Sac near PIazza Navona. If you are a larger group book in Grappolo d’Oro nearby.

Day 10 Rome

Spend the day in Rome.

Plan your day around one main attraction in the morning, either the Colosseum or the Vatican: make sure you book them in advance as the best value tickets go fast!

The tickets I recommend for families are:

Colsseum (value): Entrance and tour by Coopculture (colosseum direct)

Colosseum (premium): Semi private Express Tour with LivTours

Vatican (value): Vatican Museum Direct Tickets

Vatican (premium): Family Guided Tour of the Vatican with LivTours

In the afternoon, take a strool in the city center: if you’ve visited the Colosseum, it is worth seeing the Vatican from outside and vice versa as they are both scenic areas.

Should tiredness hit, spend the afternoon in the Borghese Gardens: get family bikes for a fun way to explore this last park and make sure you stop at the Pincio Terrace for stunning views over Rome.

Walk back via the Spanish steps and have dinner in Emma Pizzeria in the center or at Tonnarello in Trastevere.

Day 11: Sorrento

Take the train to Sorrento and enjoy your evening in this pretty town.

If you have teenagers and you love food, do not miss taking a food tour with the Gourmet Girls Sorrento who will share with you a wdonerful delicious evening!

If you wantt to visit Pompeii, you can also stop there on the way to Sorrento.

If you do so, make sure you familiarize yourself with the max size of bags allowed into the sight and try get there early enough to secure a luggage storage slot.

With small kids especially, consider getting a Pompeii guide for this wonderful but large site.

In Sorrento, stay in family friendly Sorrento Hilton or Hotel Antiche Mura .

Should bigger rooms be hard to find (often the case in Sorrento) there are many excellent apartments on booking.com .

Since the following days will require taking the ferry, I highly recommned to stay somewhat close or anywhay within easy reach from the port.

Da 12. Amalf coast town hopping

Spend the day on the ferry, town hopping from one to the other: the views from the water are fantastic!

With small kids, I recommend you avoid Positano: while stunning, it is fully vertical and with lots of steps.

If going, have a carrier and make sure your legs are up for it!

You can find here >> our tips for the Amalfi Coast with kids and here >> and overview of the best towns on the Amalfi Coast

Day 13: Capri

Capri is one of the most beautiful islands I have ever seen and while many associate it with glamour, it is also great for kids – if you know what to expect.

You can read here >> our guide to Capri with kids

A lovely way to spend the say here is to divide your time between a boat tour around the island and time in Anacapri.

Both these locations will allow you to lose most of the crowds. On the other hand, Capri town will be perfect for high end shopping.

Head back to Sorrento for a last Italian dinner beafore heading back home!

Day 14 Naples and Fly back

Use this day to get ready for your flight back home. Make sure before you leave Sorrento, you get some authentic italian souvenirs to remind you of your time in Italy.

I hope you enjoyed this itinerary and it helped you plan your family’s Italian adventure!

If you want tips on how to twak this itinerary, join our Italy with kids Facebook Group: it is full of lovely parents with great knowledge if Italy and we will be delighted to hel you plan a perfect vacation for you and your kids (it’s free!)

If you want even more help or you have any questions, please in my FREE Facebook group about traveling to Italy with kids: I will be happy to have you there and the tips from me and the other members are FREE!

How else can you spend 14 days in Italy with kids?

As I mentioned in the opening part of this article, there are so many other ways to spend 14 days in Italy it is simply not possible to suggest an itinerary for each.

Instead, I recommend you read our article ‘ best places to visit in Italy with kids ‘ and ‘ the best things to do in Italy with kids ‘ to get inspired about what you may lie to see, the get in touch via the group above for extra tips.

14 days Italy itinerary for families resources

Best strollers for Italy Travel

Best carriers for Italy travel

Visiting Italy with a baby or toddler

Best shoes for Italy travel

Best luggage for Italy travel

Family packing list for Italy

Marta Correale

Marta Correale is an Italian mama of two. Born and raised in Rome, Marta has a passion for travel and especially enjoys showing off Italy to her kids, who are growing up to love it as much as she does! A classics graduate, teacher of Italian as a second language and family travel blogger, Marta launched Mama Loves Italy as a way to inspire, support and help curious visitors to make the most of a trip to Italy and learn about Italian culture on the way.

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How to plan a perfect 2-week Italy itinerary – 14 unforgettable days in Italy

You’ve been planning a 2 week Italy itinerary for a while and still feel in a stalemate? Don’t worry, you’re not alone. The country is so packed with things to do, wonderful places to visit, and great food to try that anyone traveling to Italy for the first time is bound to feel overwhelmed. Fret not, we’re here to help.

This guide of ours, even though extensive and detailed, will touch the most popular cities you can’t miss in 2 weeks in Italy. Those places you really can’t afford to miss if it’s your first time in this beautiful country. We will squeeze as much as we can into a two-week Italy tour itinerary. It’s not strictly a Rome Florence Venice itinerary, it includes also other places, but it’s pretty classic.

If, on the other hand, you prefer to enjoy the country without the hassle of organizing and planning everything on your own, your best bet is to book a great escorted tour to Italy and relax while the tour leader does everything for you.

Table of Contents

A Perfect 2-Week Italy Itinerary

• Milan, explore northern Italy
• Places to visit in Venice
• Hiking Cinque Terre
• Things to do in Florence
• Things to see in Rome
• What to do in Naples
• Hidden gems and alternative itineraries
• Tips for planning a trip to Italy your own

Planning the best 2 weeks in Italy

Granted, with so much to see, planning your best 2 week Italy itinerary is not easy. Our extensive guide will provide you with the essentials to organize a perfect vacation on your own. If you are visiting for the first time, 2 weeks in Italy are enough to see the main attractions in the main cities.

Planning 14 days in Italy, you will have the time to explore the classics such as Rome, Florence, and Venice. If you want to enjoy a place longer, visit more attractions or take some day trips, you can easily spend 3 weeks in Italy. If you have less time, you can avoid some attractions and spend 10 days in Italy. For sure, we give you the essential tips on how to plan a trip to Italy on your own.

If it’s not your first time or you have more than two weeks in Italy, check out our other guides on specific areas like Sardinia , Sicily in the cities of Catania and Agrigento , and Trentino Alto Adige , both its cities and the Dolomites mountain range.

We will see when is the best time to visit Italy depending on what type of holiday you want, we will suggest the best car rentals in case you want to embark on an Italy road trip, we will tell you what to pack and obviously what to visit to make your holiday smooth and unforgettable.

This guide will empower you to plan a trip to Italy on your own. For each city, we will provide you with the best day tours if you wish to optimize the time of your 2 weeks Italy itinerary and have more in-depth information. At the end of this guide, you will also find a selection of the best tours to Italy in case you want a hassle-free holiday where expert organizers take care of the details and the logistics for you.

Where to go: your itinerary for two weeks in Italy

1. landing in milan and exploring northern italy, first step of your italy trip itinerary – 2 days.

Milan is Italy’s “Wall Street”, a bustling financial hub that attracts businessmen for work or business-oriented travelers. However, with a long history and a good deal of historical landmarks and artistic attractions, Milan has been imposing itself also as an exciting tourist destination for travelers from all over the world. On your 2-week Italy itinerary, we suggest spending 2 days in Milan .

Some of the most important places to visit in Milan are:

• The Duomo. The most popular among Milan’s landmarks, the city’s cathedral is a must. Its Gothic facade never fails to bedazzle visitors and passers-by, the inside is a fascinating journey into Milan’s history and culture, and its rooftop gives you a great view of the city and its architecture.  Click here for Walks of Italy’s Best of Milan Tour that includes a visit to The Last Supper and the Duomo’s rooftop.
• Sforza Castle. Residence of one of Milan’s most prominent families, the Sforza Castle today hosts several exhibitions, both temporary and permanent, as well as being a cultural centre.
• Galleria Vittorio Emanuele II. Known as Milan’s parlour, this long covered gallery is lined with cafes and shops of the most exclusive brands. It’s close to the Duomo’s square, so you can’t miss it!
• Da Vinci’s The Last Supper. Don’t miss the famous mural painting by Leonardo Da Vinci in UNESCO-listed Santa Maria delle Grazie church, beautiful Renaissance building by architect Donato Bramante.
• La Scala Opera House. Milan’s opera house, this is a beautiful Neoclassic building worth a visit even if you are not going to see the performances. You can visit both La Scala and the museum but call first because if there are rehearsals you can’t visit the theatre hall.
• Navigli. Milan’s canals are a great place for a walk both day and night. This is one of the favourite hangouts for aperitivo , dinner or a night out.

READ MORE: Check out our extensive guide to Milan to find out what to do if you have more time .

The next stop in your two-week trip to Italy is La Serenissima, so book your Milan to Venice train and get to one of the world’s most romantic cities. Click here to check timetables and prices with Omio .

2. Venice, the most Serene, the romantic stop in your 2 week Italy itinerary – 2 to 3 Days

One of the most popular destinations in Italy, Venice is as gorgeous as it gets. Unprecedented views, a unique urban landscape, and a long history are the perfect combination for an unforgettable trip. And if you go for the Carnival, the colorful and fascinating masks will add to the charm of the city.

How many days in Venice? We suggest 2 to 3 but it really depends on how much time you have, how much you want to enjoy and explore the city and, last but not least, by your budget.

Some of the things to do in Venice in your two weeks in Italy are:

• Piazza San Marco. One of the key landmarks in Venice that make the city famous is its central Piazza San Marco, the very first place tourists visit. Surrounded by San Marco Basilica and the Doge’s Palace, this piazza is really gorgeous.
• St. Mark’s Basilica. One of the most symbolic buildings in Venice, San Marco Basilica is a gorgeous piece of Oriental-style architecture dating back to the 11th century. Click here to book the exclusive tour of St. Mark’s Basilica after closing time .
• Doge Palace.  Standing exactly where it stood throughout the centuries, the majestic Palazzo Ducale is an important piece of the city’s republican past. Get a VIP entrance to the Doge Palace with Walk of Italy’s Secret Passages tour .
• Jewish Ghetto. Europe’s oldest Jewish ghetto, Venice one was created in 1516 and is now a lovely neighbourhood to stroll around the city’s traditional architecture and eat delicious local treats.
• Canals and Bridges. The beauty of Venice is in its architecture and this is directly related to its unusual layout. Instead of streets, in Venice you have canals and bridges, instead of buses, you will take the boat or if you don’t mind forking out good cash, a gondola. One of the most scenic things to do in Venice is certainly strolling around its bridges, Rialto and the Bridge of Sighs being the most famous. Click here to book Venice Boat Tour to visit the city and its bridges from the water and cruise the Grand Canal .
• Gallerie dell’Accademia. This art gallery hosts the larger collection of Venetian paintings from the Byzantine and Gothic 14th century to the Renaissance.
• Basilica dei Frari. Often neglected by the hasty traveller, this monumental Basilica is 102-meter long and boasts an impressive collection of artwork and 17 altars. It’s also the resting place of several notables, from Antonio Canova to Titian to several Doges.

Unless you are part of an organized tour, from Venice to the Cinque Terre, I definitely suggest you take the train as it’s cheap, comfortable and you can find different times of departure. Click here to book and see the prices on Omio

⇒ Before leaving northern Italy, take a day trip to Bologna and try some of its famous dishes !

3. Cinque Terre, hardly missing in all Italy itineraries – 2 Days

The quaint villages of the Italian Riviera never fail to bedazzle travelers from all over the world. If you want to spend three weeks in Italy, you can stay a bit longer in the Liguria region and explore also cities like Genoa and La Spezia.

Close to La Spezia, the capital of the province, are also beautiful places like Lerici and Tellaro, a sea resort cherished by writers and artists. Being on the coast, you will find great fish restaurants. Alongside the five scenic villages part of the Cinque Terre, La Spezia’s coastline boasts also other towns worth a stop, such as Portovenere, Le Grazie, and Levanto.

The five villages known as Cinque Terre are:

• Monterosso al Mare. It’s the largest of the five towns and boasts also the largest beach of the coastline. Which is why it’s the most popular both day and night for evening parties and entertainment.
• Manarola. Famous for its Nativity Scene set for Christmas, here you can also visit 14th-century San Lorenzo Church and the remains of the local stronghold.
• Vernazza. This is a very scenic village, some consider the most beautiful. It has two beaches and several nice restaurants. You will spend your time wandering up and down its cobbled alleys.
• Corniglia. The smallest and tallest village of the Cinque Terre, here you can visit its famous churches and sanctuaries as well as the remains of old Genoese strongholds.
• Riomaggiore. The closest village to La Spezia city, from its train station you can start the famous Via dell’Amore hiking route and the dock from where to take the ferries for the local tours and cruises.

READ MORE: Check out our complete guide for more info on a Cinque Terre holiday .

From Cinque Terre to Florence, too, you can take the train. First, a regional to get to La Spezia and Genoa, then a high-speed train to Florence. Click here to check timetables and prices with Omio .

4. Florence, a must in your 2 weeks in Italy itinerary – 3 to 4 Days

The birthplace of the Renaissance, Florence is included in most tours, so very likely your Italy travel itinerary will have it, too. Its history was heavily influenced by the rule of the Medici family, and today we can still see much of their legacy. Walking around Florence will fill you with beauty and culture. Enjoy its ancient art and architecture all around the city centre, walk along the Arno river and linger in the Ponte Vecchio bridge for some shopping and photo snapping.

We wrote a full guide to Florence , but here are some of the best things to do:

• Duomo and Giotto’s Bell Tower. Santa Maria del Fiore Cathedral and the adjoining bell tower and gorgeous Baptistery are possibly the most photographed and visited landmarks in Florence and for sure one of the first places travellers head to as soon as they arrive. Click here for a full experience of Florence Duomo and Michelangelo’s David.
• Uffizi Gallery. A huge art collection, at the Uffizi you will find the paintings and statues of some of the world’s most famous artists such as Leonardo Da Vinci, Botticelli, Caravaggio, Raphael, Cimabue and many others. Here the line is very long, so if you want to skip it and optimize your time inside the museum with a guide, check out Walks of Italy’s 3-hour Uffizi Tour comprehensive also of Palazzo Vecchio.
• Santa Maria Novella Basilica. Located near Florence main train station, this beautiful Dominican basilica built with a mix of Gothic and Romanesque styles includes great artwork, paintings, chapels, a big garden and a cloister.
• Pitti Palace. Residence of many of Florence ruling families, Palazzo Pitti today is a large complex of art galleries and royal apartments.
• Boboli’s Gardens. Adjoining to the Pitti Palace, the elegant Giardini di Boboli were built in 1418 when Luca Pitti bought this vast land with the aim to build a mansion (Pitti Palace will be built 40 years later). One of Florence largest parks, Boboli Gardens are one of the most important examples of Italian gardens of the 16th century.
• San Lorenzo Cathedral. The personal cathedral of the powerful Medici family, San Lorenzo huge church also hosts a museum showing the donations received in the centuries, most of them by the same Medicis. Close is also the burial place of the Medicis, known as Cappelle Medicee.

The whole region of Tuscany is amazing, so if you can stretch your holiday a couple more days, you might like to explore also other cities such as Siena and Pisa  and the countryside with a day trip from Florence to the Chianti region and San Gimignano town. Click here to check availability and price .

Florence is not too far from Rome, with Trenitalia’s Frecciarossa or Frecciargento high-speed trains, it takes an hour and a half. Click here to book and see the prices on Omio .

5. Rome, unmissable even if you are on a 1-week Italy itinerary only – 4 to 6 Days

The capital of the ancient Roman empire boasting some 3000 years of history and rich civilization, the places to visit in Rome are endless. From the archaeological sites of the Roman Forum to the quaint neighborhood of Trastevere to the Vatican City, the more you manage to devote to Rome, the better you will experience the city. It goes without saying that Rome is a must-see, especially if it’s your first 2-week or even a 10-day trip to Italy.

Some of the things to do in Rome in your 2 weeks in Italy include:

• Colosseum. Possibly the most famous and photographed landmark in Rome, the Coliseum was built in 70 AD to host fights among gladiators, public shows, animal hunts and even naval battles.
• Roman Forum. Located in the valley between the Palatine and the Capitoline Hills, the Roman Forum was the heart of ancient Rome, where senators and public figures held their speeches, where they organized the city’s markets, court trials and pretty much everything concerning the public life. Click here for the VIP Colosseum and Roman Forum Tour .
• Baths of Caracalla. Gorgeous ancient public baths, these included also a gym, a library, and different rooms for the baths experience and a wellness centre. They are often skipped for lack of time, but if you can make it, they are really beautiful.
• Vatican City. The seat of the Christendom and papal residence for centuries, the Vatican City is packed with sites to visit such as the Sistine Chapel, the Vatican Museums and obviously St. Peter’s Basilica. If you want to fully enjoy the Vatican, the best thing you can do is to skip the lines, especially to the museums and the basilica. In this case, the convenience of booking a tour, apart from VIP access, is that your guide will take you directly to the places you shouldn’t miss. The Vatican is really big!  Click here to see Take Walks’ Private Vatican Tour .
• Trastevere. A gentrified former working-class neighbourhood, Trastevere is the place to go for a good night out. During the day, however, you can also visit the museum of Roman popular traditions that sometimes hosts also temporary exhibitions and Villa Farnesina where are Raphael’s frescoes.
• Hadrian Mausoleum. Built by Emperor Hadrian as his own funerary mausoleum in the 2nd century, this is also known as Castel Sant’Angelo and is located along the Tiber River, giving beautiful views both day and night.
• Pantheon. A very old building, it was a temple devoted to all gods built with an “oculus”, a hole in the big dome to symbolize the direct contact with the divine. Now it’s a Catholic church that hosts several tombs of members of the former royal family and of the famous painter Raphael.
• Piazza Navona. Huge elliptical piazza in the city centre not far from the Pantheon, Piazza Navona has three fountains, the largest being Bernini’s Four Rivers Fountain standing in front of Borromini’s Sant’Agnese church.
• Spanish Steps. Rome’s most famous staircase, the Spanish Steps lead to St. Trinità dei Monti church, ordered by French king Louis XII, while at the bottom you can view Bernini’s sculpture known as La Barcaccia.
• Trevi Fountain. An absolute must, especially if you are visiting Rome for the first time, is Trevi Fountain, the gorgeous baroque fountain built between 1732 and 1762.

READ MORE: Check out our guide to what to do in 4 days in Rome .

Rome is divided into “Rioni”, neighborhoods, and each of them has its own landmarks and personality. From Prati to Trastevere to Testaccio and Ostiense, countless are the things to see in Rome, the restaurants where you can try the traditional food, the park where to run, jog or chill out for an afternoon, the museums, the palaces and more. To get around and see how to best enjoy Rome, check out my full guide of the city , or click here to see what are the best Rome tours if you wish to save some time but still visit the most important sites.

My eBook “ Tasting Rome by Neighbourhood ” suggests five daily Rome itineraries in as many districts, giving you the chance to explore the popular and lesser-known areas of the city stopping to eat in the best restaurants along the way. All the meals of the day are covered, from breakfast to dinner, with some suggestions also for aperitif and gelato.

Your next stop when planning a 2 week trip to Italy for the first time is Naples, the gorgeous capital city of the Campania region not too far from Rome. With Trenitalia high-speed trains you will reach it in a little more than an hour. Click here to book and see the prices on Omio .

READ MORE: Find Rome’s best restaurants with our comprehensive guide to the top places to eat in Rome .

6. Naples to give a delicious touch to your 2-week Italy vacations – 3 Days

Famous for having invented the pizza, alongside delicious cuisine, Naples has a lot to offer to the curious traveler who wants to dig deep into the local history and culture. Walk around its city center, enjoy the view of the Vesuvio volcano and the beach, explore its wonderful coastline and soak in its rich tradition.

Some of the best things to do in Naples in your 2 weeks in Italy include:

• Royal Palace. Naples’ Palazzo Reale is located in Piazza del Plebiscito, an old square that in the Middle Ages was used for public tournaments and shows in the age of the Bourbons. It has been made pedestrian so now it’s the place where locals and tourists like to relax in a historical promenade.
• Archaeological Museum. Launched in 1816, Naples’ Museo Archeologico displays a huge collection of ancient relics, among which you will find relics from Pompeii and others from the Greek-Roman age, Etrurian and Egyptian, and ancient coins from a private collection.
• Duomo.  Naples’ Santa Maria Assunta Cathedral shows the paintings of Luca Giordano and is the place where locals worship San Gennaro, patron of the city. Here you can also see the Treasure of San Gennaro, all the precious donations given by kings, presidents, and leaders of the world for centuries.
• Spaccanapoli. This is the long road built by the Romans to better organize the city, and it runs from the Quartiere degli Spagnoli to Forcella district. Wandering this road you will also wander the city’s history and multifaceted society. Here, in fact, you are going to see old buildings, churches, shops, abusive street vendors and local restaurants that release the unique scent of Napoli’s cuisine.
• Sansevero Chapel and the Veiled Christ. A hidden gem near Spaccanapoli is Cappella Sansevero where you can admire the incredible sculpture of the Veiled Christ (Cristo Velato), a masterpiece by Giuseppe Sanmartino where you will totally mistake the marble veil that covers the body of the Christ for a fine fabric!
• Underground Naples. Beneath the surface, you can visit another Naples, the hidden spots, and nooks that citizens have used for different purposes such as shelter during the bombings, the hideout for the runaway criminals and water spring. Today, you can visit also museums, the relics found after ongoing archaeological diggings, and the Bourbons Gallery.
• Pompeii and Ercolano. I know time is short, but once you are in Naples, we recommend you devote a day to visit the ruins of the ancient cities of Pompei and Ercolano, destroyed by the Vesuvio eruption in 70 AD. They are very easy to reach via a short ride on the Circumvesuviana train and you can spend there the whole day. Book a great Pompeii tour with an archaeologist .

Hidden gems + alternative Italy itineraries

If you like to discover also more offbeat destinations or you can afford a longer holiday, say 3 weeks in Italy, you can really add some interesting places to your Italy itinerary.

For example, you are back in Rome after this two-week Italy trip and you have one extra week? Catch a plane to Sardinia and enjoy a fantastic offbeat destination! To be able to stray off the bigger cities and explore their traditional soul, make sure you rent a car .

If you enjoyed the northern cities and want to explore more of them, a nice alternative is to explore the Trentino Alto Adige region or the beautiful city of Turin .

Alternatively, you can spend more days in some of the cities of our 2 weeks in Italy itinerary and take some day trips. From Florence, you can enjoy a great day trip to Pisa or Siena . From Rome, you can visit Viterbo , Bracciano, Cerveteri or several other towns. From Venice, you can head to Verona and come back in the evening. From Naples, alongside Pompeii, you can take a day trip to Sorrento and the Amalfi Coast.

The possibilities are endless, and soon we’ll be publishing a full northern Italy itinerary and an exciting offbeat Italy itinerary!

Essential tips for two weeks in Italy

1. best time to travel to italy.

Boasting a mild climate and the advantages of four seasons, depending on what your ideal holiday is, any time is good to visit Italy.

Do you like skiing? Explore the beautiful Dolomites in Trentino Alto Adige . Do you prefer chilling out in the sun? Discover the gorgeous beaches in Sardinia in summer.

As far as the main cities go, any month is good to visit. In Rome, Florence and Venice there are so many things to see and do that really any season is good. If you are quite free to choose your holiday time, I would probably avoid July and August as they are very crowded and can be very hot. So not so pleasant to walk around the city center.

Spring and Fall are both great seasons to visit the big cities both to avoid the crowds and to have a more pleasant climate.

2. How to get around Italy

Italy has a great and very widespread railway system, so if you are traveling independently, you can totally rely on Trenitalia or Italo Treno. After each major city, I mentioned the transport you can book to get to your next stop but Italy railway is great to reach also smaller towns and even tiny villages. The perfect way of traveling around Italy for two weeks.

If you are visiting the cities and towns within the railway network, you are covered. But if you are planning on getting off the train route, relying solely on the buses might not be as straightforward. So for example, if you want to visit the Tuscany countryside or some parks outside Rome, I suggest you rent a car. Definitely, the best option when planning a 2-week Italy road trip. Click here for more info and to book a car in Italy.

READ MORE: For more tips, check out our extensive guide to planning a trip to Italy .

3. What to pack for Italy

As Italy has four seasons, you can decide what to pack once you know when you are traveling. Spring is a very popular season thanks to its mild weather, but it can sometimes be tricky as temperatures change all of a sudden.

Avoid annoying online surcharges and nasty surprises by weighing your suitcase with one of the best digital luggage scales .

My advice would be to wear different layers so that you can cover them in the evening when it’s usually colder. If you are planning a 2-week trip to Italy in Spring, make sure you pack some pretty flexible clothes.

The beginning of the Fall in Italy is pretty nice as the summer heat is mostly gone and the winter cold has not arrived yet. Mostly, you can wear light clothes and carry a jacket, a light jumper, and a light scarf for the evening. Make sure you pack an umbrella.

If you are wondering what to pack for Italy for the winter, it’s pretty straightforward: warm clothes, a jacket, a coat, warm trousers, and sweaters. Quite straightforward is also packing for a summer Italy trip: shorts, t-shirts, sandals or summer runners, and obviously a bikini if you are going to the beach!

For some peace of mind, especially on public transport, you might want to wear a security belt. Or the anti-theft clothes of Clever Travel Companion. They have a pretty wide choice of models, colors, and clothes such as scarves, boxers, leggings, tops, t-shirts, women’s underpants, and more. Click here to check models and prices.

READ MORE: Italy packing list: What to pack for Italy season by season

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17 Fun Things To Do In Venice Italy [2 day Itinerary Included]

W e took the train 4 hours from Rome to Venice on our 3 month backpacking trip around Europe and we got 2 gorgeous days with the sun shining! We couldn’t wait to explore this iconic city and to get out on the water. There are so many great things to do in Venice, Italy.

We loved Venice, the vibe, the canals, it is such a beautiful city.

Overview Of Venice

The city is located on 118 islands that are separated by 150 canals. It really does feel like a city on the water! A lot of the islands are connected by 400 footbridges while some of them like Burano and Murano you have to take a boat to get to them in the Venetian Lagoon.

There are no cars in Venice which was amazing. Knox commented how quiet the city was without cars!

You will only find four bridges that cross the Grand Canal. And won’t miss the 400+ gondolas that are floating through the canals all around the city.

Venice is magical. There really isn’t a better way to describe it. I know people have complained about it being too busy or smelly. But when we were there at the end of March/beginning of April it was perfect.

Not busy, not smelly and with the sun out it was perfect weather to be walking around the city.

That being said if you are going to visit Venice when it is busy we definitely recommend you book your tickets in advance and get as many skip the line tickets as you can. The worst thing to be doing in Venice would be standing in line!

Getting To Venice

We took the train into Venice. It was a very easy process and was a beautiful ride coming into the city. Be sure to check your trains stops and make sure you stay on until you reach the actual island.

Once you reach the island you can walk from the train station right across a bridge and into Venice. We purposely picked a vacation rental that was within walking distance to the train station.

That meant we weren’t close to the main attractions but the island isn’t that big so it was no problem walking anywhere we wanted to go.

Things To Do In Venice

Grand canal “tour”.

I have tours in quotes since this wasn’t a paid tour. This was us riding on the Grand Canal public water bus (vaporetto). It was packed with people using it as a bus to get around Venice.

We paid attention and quickly grabbed the seats at the front and got out my phone to open the Rick Steves Grand Tour app on my phone . His tour lasts 45 minutes – starting from the Piazzale Roma and bringing you just past St Marks Square.

It talks about places like the Basilica di Santa Maria Della Salute which is a beautiful church that was built in the 17th century to commemorate the end of a devastating outbreak of the plague that killed thousands of Venetians.

The tour was well done and helped us understand what we were saying as we were riding down the canal. If you don’t want to stay on for the whole tour you can hop on and off at any of the stops the boat makes.

St Marks Square

Next up we headed to St Marks Square (Piazza San Marco). We got our Rick Steves app again and read through some of the highlights of St Marks Square. While we were doing that we noticed all of the people sitting out have a drink in the square. We definitely wanted to try that!

We stopped at Caffè Florian. It was super expensive! But it was an experience so it was worth it. We got overpriced drinks and snacks and looked out over the square as we listed to the orchestra playing from the restaurant.

You could also choose to tour the Doge’s Palace when you are here and see the Ponte dei Sospiri or Bridge of Sighs. We figured with our kids they wouldn’t be into it. But if you like seeing Gothic palaces that were built in the 14th century you should do it!

**Fun Fact: The Bridge of Sighs is a small enclosed bridge that connects the Doge’s Palace to the adjacent prison. Legend has it that the bridge earned its name from the prisoners who, as they crossed it, would sigh at the sight of Venice for the last time before being locked up.

Another option would be to climb to the top of the Campanile di San Marco (bell tower) when you visit Saint Marks square.

Gondola Ride

We of course had to do a gondola ride! They only allow up to 5 people on 1 boat so luckily Nana and Boppa were with us and could take 2 kids!

It was an over priced but fun experience and we are glad we did it! At the time it was $85 for a 35 minute trip for up to 5 people. We tried to see if we could do 6 with the 4 kids but they said no they would lose their license.

I mean you can’t come to Venice and not do the Gondola Ride so be sure you budget for it. Now that we did it we won’t have to do it again but I am glad we did and that the kids got this experience.

It was also fun to explore the canals and see some areas of Venice you can only see on the Gondolas.

Rialto Market

We started the day with a trip to the fish market at the Rialto Market. It was quite the experience. There are all kinds of different fish just sitting out. I mean fish we have never seen before!

Plus there is blood on the ground from the fish and a definite fishy smell! Once of the crazy things is that when the market is done they clean it all up and you could barely tell it was there.

We didn’t buy anything . . . but I have to say I would love to hire someone to bring us to the market and help us pick things out. Then bring us back to our place to cook a delicious meal from the market.

Osteria al Squero

After that we headed to Osteria al Squero to watch the workers fix and build gondolas across the canal at Squero Di San Trovaso.

Scavenger Hunt

If you are traveling with kids you won’t want to miss this scavenger hunt around the city. It was a great way to teach the kids some history of Venice while making it fun and interactive. Plus we visited a couple of places we may not have found on our own during the hunt!

Our guide had a map and clues and split us into 2 teams so we could see who found the clues first and answered the questions correctly.

It was education and fun! And brought to our attention some different things in the city we may not have noticed on our own.

Libreria Acqua Alta

We found this stop on our scavenger hunt and I am so glad we did! It backs up to one of the canals and there is a book staircase you can climb up to look out over the canal.

The store has a gondola in it filled with books and books everywhere. It can get very busy and you may have to wait in line to get in.

Spiderman Movie Spots

If your kids are Spiderman fans they probably remember when Spiderman came to Venice. If that is the case be sure to stop to see the following two spots:

• Santa Maria Formosa Church
• Ponte de l’Arsenal o del Paradiso

The Rialto Bridge

Grab a picture on the famous Rialto Bridge! This is the iconic bridge in Venice that goes over the Grand Canal. If you spend any time in Venice you will most likely catch your self walking over this bridge a few times.

Take note the bridge is called The Ponte di Rialto in Italian.

Learn To Row As A Venetian

This is another activity our friends from Zula Life did when they visited and they said it was a blast! It is one thing to take a gondola ride but to be able to learn how to row that is awesome!

You can learn more about learning how to row as a Venetian here.

Carnival Mask Making

Zula Life also did this activity and said it was a great experience. There are masks stores all over Venice that you can buy masks at. But being able to make your own would be quite an experience!

You can book your own Carnival Mask Making class here.

Teatro la Fenice

If you are into Opera and/or architecture you are going to want to check out this Opera House. You can either do a tour or you can opt to come and see a show here. The Opera House has a long history of being destroyed or damaged by fire and rebuilt.

Burano Island

We only had a little bit of time to see Murano or Burano. We ended up going with Burano because I wanted to see all of the colorful buildings!

To get to the island we had to get on the water bus (vaporetto) at the Fondamenta Nuove stop and took the 45 minute ride over to Burano Island. We didn’t get there until almost 6pm so things were starting to close down. But we were able to grab a quick dinner at Trexento and make a stop in a couple of the shops.

The island’s buildings are painted in bright colors such as pink, blue, green, and purple. The origin of the brightly colored houses is said to be from the fishermen who used to live on the island. They painted their houses in bright colors so they could easily spot them from the sea.

Burano Island is also famous for its traditional lace-making industry. The art of lace-making has been passed down through generations of Burano families, and today it is still possible to see artisans creating delicate lace items by hand. My Mom bought some when we were there.

We definitely wish we had more time on the island! We also really enjoyed seeing the views of Venice from the water on the way here and back.

We didn’t make it To Murano Island on this trip but we ill next time! I just couldn’t resist the colored buildings of Burano so made the choice to go there since we could just go to 1 island. However, getting to Murano from Venice only takes about 10-15 minutes by water taxi (vaporetto).

Murano Island is known for the art of glass making. The skill dates back to the 13th century when the Venetian Republic ordered all glass factories to move to the island to prevent fires in the city. Since then, Murano has been renowned for its exquisite glassware, and the island’s artisans continue to create unique glass objects by hand using traditional techniques.

When you go to Murano you can watch the glass-making process in action by visiting one of the island’s many glass factories and studios. These studios offer guided tours that showcase the intricate and complex process of creating glass objects. You can also see the stunning finished products on display in the studios and purchase them as souvenirs.

Our friends from Zula Life visited Murano Island and did a glass making class and they said they loved it!!

You can see the video of them in the class here.

Where To Eat In Venice

Gelateria il doge.

This Gelato spot is located in Campo Santa Margherita. The kids were able to get their ice cream and they sat by a fountain to eat it while us and my parents found an open table at Fuori Rotta to get a glass of wine.

When the kids came to find us after they were done with their gelato by Dad gave them 20 Euro and said go see what else you can find. That give us a chance to sit for a bit longer and finish our glass or bottle of wine.

Birraria la Corte

We were excited to head to Birraria la Corte to try their pizza! When we walked in they asked if we had a reservation . . . umm no. I guess that meant we might not get a table. Luckily they had some outside seating and since it was a bit cooler not many people wanted to sit out there.

It was actually really nice and we always prefer to eat outside when we can. The drinks were good and the pizza was delicious!

Cip & Ciop

This was a fun little restaurant/bar right by where we stayed. They had these delicious handheld foods like fried mozzarella pocket things and vegetarian tapa’s and other ones filled with meat. I don’t even know the right way to describe them but they were so good!

You just walked up to the counter and they had everything on display in the case so you just asked for what you wanted. We went and ordered and came back and ordered more since it was so good.

I think they are called Cicchetti. Like the Italian version of Spanish Tapas. In any case if you are in Venice ask around about Cicchetti and try all the things!

Cantina Do Spade

Make sure to stop here for a Mozzarella Sandwich. We just stopped in to grab one to go and it was delicious!! While we waited we also got a glass of wine and that was good too.

Where To Stay In Venice

When picking where to stay we picked a place – Residence degli Artisti – that was close to the train station so we could easily walk from there to our vacation rental with our backpacks and bags.

The place we picked wasn’t close to St Mark’s square but we liked that it was tucked away and not in the middle of all the hustle and bustle of Venice.

The place – Residence degli Artisti – was beautiful and we were glad we stayed here.

Venice Itinerary

Here is what we did on our 2 days in Venice. We definitely could have stayed longer. We really fell in love with Venice!!

Venice – Day 1 (day you arrive)

• Head to the Piazzale Roma water bus (Vaporetto) stop. To start the Rick Steves Grand Canale tour at the right place. Check out the water bus schedule here. You can buy your tickets online before you get there.
• Ride the water bus to the St Marks Square stop. If you want more context check out the Rick Steves Tour of St Marks Square on his app. Stop here for a drink in the square.
• Birraria la Corte for dinner.
• Breakfast and Coffee at Cip & Ciop
• 10am – Rialto Market Area – only open until 1pm
• Osteria al Squero to watch the Gondola workshop across the canal (squero di san trovaso).
• Campo Santa Margherita and get gelato at Gelateria il Doge [Dorsoduro 3058/A, Rio Terà Canal]
• Stop at Cantina Do Spade for mozzerella sandwiches.
• Santa Maria Formosa Church – which was in the Spiderman movie.
• Liberia Acqua Alta
• Ponte de l’Arsenal o del Paradiso – which was in the Spiderman movie.
• 2pm – Gondola Ride – 30-45 minutes.
• 3pm – Scavenger Hunt Tour
• 5pm – Head to Burano Island
• Burano Island for dinner at Trexento
• Head back to Venice

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RBC Heritage

Harbour Town Golf Links

Hilton Head Island, South Carolina • USA

Apr 18 - 21, 2024

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I Wore This Viral Lululemon Belt Bag Across Italy for 10 Days, and Now I'll Never Vacation Without It

It has so much space that I could easily fit my passport, wallet, sunglasses, and more.

We independently evaluate all recommended products and services. If you click on links we provide, we may receive compensation. Learn more .

Travel + Leisure / Reese Herrington

Back in 2022 I embarked on a 10-day trek across Italy, and if there was one thing I knew I needed to pick up before the journey, it was the Lululemon Everywhere Belt Bag . At the time, the popular bag — the one you’ve likely seen all over the Internet — was sold out online as well as in most of the other stores across Manhattan, but the very morning of my flight I made a last ditch call to the location near my apartment and was met with nine thrilling words: “We just got them back in stock — but hurry.”

After traveling with my new bag through an airport in Norway on an unexpected layover, to the city streets of Rome, I knew that I would never go on another vacation without my belt bag — and two years later that remains to be true. Plus, right now you don’t have to search high and low for these bags like I did, because the $38 pack is currently fully in stock in 14 stunning colors on the Lululemon site, including new shades like the spring-ready Paradise Green.

Lululemon Everywhere Belt Bag

This versatile bag is everything you could possibly need in a functional travel pack: At 7.5 inches by 2 inches by 5 inches and with a capacity of 1L, it’s spacious enough for my sunglasses, wallet, passport, keys, and phone, and is easily adjustable to fit across my body when wearing just a tank top and even when I'm tucked away in my winter coat. The primary pocket features mesh pouches on either side, which I usually pack my keys and a lip balm into, and an additional slim pocket on the back of the pouch is my favorite way to ensure my passport stays safe and protected.

Water-repellent nylon fabric makes this bag perfect for both rainy days and sweaty adventures, and unlike most bags with adjustable straps that leave one long piece left hanging, this pack is made with a thin piece of elastic that evens out the loop for a more streamlined appearance. It can even be worn as a traditional fanny pack (which I use for running outside), as well as across your body for easy access to your essentials while hurrying through the airport. Thanks to its functional and versatile design, the Everywhere Belt Bag made it onto our list of favorite fanny packs to take hiking .

Travel + Leisure / Merrell Readman

I can get overwhelmed if I have too much to carry while I’m traveling, and this bag has shown me the joys of a hands-free vacation experience. It made it much easier to get through TSA and boarding my flight because my passport was always just a short reach away, and even on outings in Florence and Rome, I was happy to not worry about my purse getting snatched off my shoulder if I were to let my guard down. 

I’m not the only shopper that swears by this versatile fanny pack for travel now, and other Lululemon customers can’t help but rave about this sleek and functional bag. One shopper noted that they “travel a lot” and admitted that the bag is now “indispensable,” adding that it is the “perfect size with convenient compartments to keep well organized without the heavy bulk of a traditional purse.”

Another shopper raved that this pack is “nice if you’re traveling or just doing errands” because “if you have to pull your phone out or your wallet, [they’re] right there instead of digging through your purse to find whatever you need.” 

It’s very rare that an item is actually worth the hype that it has garnered, but in this case the Lululemon Everywhere Belt Bag has earned every ounce of praise it has received. Not only can it fit a frankly impressive amount of essentials (I’m an overpacker), but it’s also comfortable to wear, sleek, and has quickly become one of the most-used bags in my collection. 

Right now, the shopper-loved belt bag is available at Lululemon starting at $38, and is currently in stock in 14 stylish shades. Just don’t wait too long — it’s notorious for selling out quickly.

And if you're looking to elevate your travel style with other comfy and functional essentials, keep reading to find more must-have items to shop at Lululemon.

More Travel Essentials at Lululemon

Chargefeel 2 low women's workout shoe, scuba oversized hoodie, tapered-leg mid-rise 7/8 length luxtreme, restfeel women's slide.

At the time of publishing, the price started at $38. 

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Kygo announces 2024 world tour, check out dates, venues, special guests

“time to bring the music to you part one of my world tour starts this fall with my friends and special guests,” kygo shared with his fans.

Kygo is ready to hit the road again! The Norwegian DJ took to social media on Monday, April 22, to announce the first part of his World Tour. The 32-year-old record producer also revealed that he will joined by his “friends and special guests” Zara Larsson, Sofi Tukker, Gryffin, Sam Feldt, Haylasings, Vandelux, Victoria Nadine, and Klangkarussell.

“Time to bring the music to you!!! Part One of my World Tour starts this fall with my friends and special guests,” he wrote on X, formerly Twitter. Starting this fall, Kygo will embark on the European and North American leg of his 2024 World Tour. You can check out the full list of dates and corresponding venues below:

Full list of dates for Kygo's 2024 World Tour

Saturday, September 7 – Commerce City, CO – DICK'S Sporting Goods Park *+

Thursday, September 12 – Columbia, MD – Merriweather Post Pavilion *+

Friday, September 13 – Brooklyn, NY – Barclays Center *+

Tuesday, September 17 – Boston, MA – TD Garden *+

Friday, September 20 – Montreal, QC – Bell Centre *+

Saturday, September 21 – Toronto, ON – Woodbine Park *+

Wednesday, September 25 – Chicago, IL – Huntington Bank Pavilion at Northerly Island ^~

Saturday, September 28 – Austin, TX – Germania Insurance Amphitheater ^~

Friday, October 4 – San Francisco, CA – Chase Center ^~

Wednesday, October 9 – Seattle, WA – Climate Pledge Arena ^~

Thursday, October 10 – Vancouver, BC – Rogers Arena ^~

Thursday, October 17 – Los Angeles, CA – Hollywood Bowl ^~

Wednesday, November 6 – Copenhagen, Denmark – Royal Arena > =

Friday, November 8 – Oslo, Norway – Telenor Arena > %

Wednesday, November 13 – Stockholm, Sweden – Tele2 Arena >=

Friday, November 15 – Berlin, Germany – Uber Arena >=

Sunday, November 17 – Budapest, Hungary – MVM Dome *=

Thursday, November 21 – Cologne, Germany – Lanxess Arena #=

Saturday, November 23 – Vienna, Austria – Stadthalle #=

Tuesday, November 26 – Amsterdam, Netherlands – Ziggo Dome #=

Friday, November 29 – Milan, Italy – Forum #=

Tuesday, December 3 – Madrid, Spain – Wizink Center #=

Friday, December 6 – Brussels, Belgium – ING Arena #=

Saturday, December 7 – Paris, France – Accor Arena #=

Wednesday, December 11 – London, UK – The O2 #+

Friday, December 13 – Dublin, Ireland – 3Arena #+

Special guests:

• # With SOFI TUKKER
• > With GRYFFIN
• * With Sam Feldt
• ^ With Zara Larsson
• = With Klangkarussell
• + With Hayla
• % With Victoria Nadine
• ~ With Vandelux

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Harley-Davidson HOG Rally, Senigallia, 2024

60019 Senigallia, Province of Ancona, Italy

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About this trip

This is a fully guided tour to the Harley-Davidson rally in Senigallia, Italy.

We have deliberately chosen a route to get to Italy that includes great riding.  The route out to Senigallia includes some wonderful roads in France, Switzerland and Italy, including some amazing high alpine roads in the Alps mountains including Grimsel Pass, Furka Pass and Nufenen Pass.  In Italy, we ride through the Tuscany region and visit wonderful places such as Sienna and Cortona. Check out the route on the map at the bottom of this page.

The tour starts in Folkestone in the UK and we take 7 full days of riding to get to Italy.  We will be staying at 3 and 4 star hotels on route. We arrive in the coastal town of Senegallia on the east coast of Italy on the day the rally opens, Thursday.  We are then at the HOG rally for 3 nights.

The rally site is in the main square of Senigallia and we have two hotels there. The first is a 3-star hotel right on the sandy beach and this hotel is an 8-minute walk to the rally site. The second is a 4-star hotel just a 4-minute walk to the rally site. There is a supplement on the tour price to stay at the 4-star hotel. Both hotels are in terrific locations.

Of course, at the rally site there will be much to do, including bands, the expo, demonstration motorcycle rides, the parade and much more!

Our group sizes normally range from 10 to 14 motorcycles. Due to the likely popularity of this tour, we will run two groups.

With this tour, after the rally you will be riding back to the UK and you have a choice about how you do that. The standard tour includes for riding back over 3 days mainly on motorways through Italy, Switzerland, France, Luxembourg and Belgium.

Alternatively, you can opt to take a 5-day ride back to the UK which includes a stop over in Venice (with a guided tour of the city by Tour1), riding the dramatic San Boldo Pass, riding in the wonderful Dolomite mountains and then riding the spectacular Grossglockner Pass, before getting back on faster motorway roads to Calais. There is a supplement for the tour price if you want to take the 5-day ride back.

Available Packages

Please note, if two riders are sharing a room, you both need to complete one of these booking forms. It is one booking per motorcycle.

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