tuscany travel blog

The Perfect Tuscany Road Trip Itinerary (+ Driving Tips!)

Planning the perfect Tuscany road trip itinerary is no easy feat–but it’s well worth getting right.

If you’re dreaming of delicious Italian food, of romantic sunsets and Tuscan wines, of rolling hills peppered with vineyards as far as the eye can see, of hilltop villages and of Renaissance art, this Tuscany itinerary has you covered.

We’ve put this ultimate guide to planning a Tuscany road trip after spending several months traveling in the region over a period of years, often on road trips.

We’ve explored Tuscany by car, train, and tour, in large multigenerational family groups and as a couple, in tiny towns and in the fabulous cities of Florence and Siena.

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We’ve visited museums, gone horseback riding, zipped along countryside roads on a Vespa, and taken quiet strolls down deserted country lanes. We’ve taken food tours and wine tours, and stopped at more than our fair share of vineyards and restaurants independently, too.

Suffice it to say, we absolutely adore traveling in Tuscany, and this Tuscany itinerary is put together based on our detailed experiences traveling in the region as well as additional research.

We want to help you plan your perfect Tuscany road trip itinerary, especially if it’s your first time in the region.

Here’s what we suggest.

Table of Contents

How We Structured This Tuscany Road Trip Itinerary

How long will this tuscany itinerary take, getting around during your tuscany road trip, will this tuscany itinerary work without a car, the ultimate tuscany road trip itinerary, other destinations to add to your tuscany road trip itinerary, tuscany road trip itinerary map, the best time to visit tuscany, useful travel tips for driving in tuscany, what to pack for your tuscany road trip.

We structured this Tuscany road trip itinerary as a loop beginning and ending in Florence.

It’s designed primarily for first-time visitors to the region who want to soak up the classic Tuscany experience: think rolling hills, golden light, scrumptious wine, picturesque hilltop villages, and some of the best food you’ve ever eaten in your life.

… But that being said, even longtime lovers of Tuscany will find something for them here (just ask our extended family).

With this Tuscany itinerary, you’ll visit some of the most iconic places in the region, while also peppering in stops at smaller towns and attractions that would likely go unnoticed if you stuck to exploring via train.

Is it a cop-out to say that this Tuscany road trip will take as long as you have?

Perhaps, but whether you have 5 days in Tuscany, a week in Tuscany, or a month in Tuscany, this circular route will provide an excellent backbone to your Tuscany road trip.

If your trip is short–say 5 days in Tuscany or less–you’ll be able to shorten your stays in some towns (in a pinch, for example, Pisa and Lucca can be combined into one day), and with a longer trip to Tuscany, you’ll have a chance to adopt a leisurely pace and add in more excursions like wine tasting or days spent at one of Tuscany’s saunas.

Ideally, I would say that this Tuscany road trip would be spread across roughly 10 days to 2 weeks in Tuscany, but of course, that won’t always be possible–especially if you want to see more regions of Italy during your trip!

If you do have a longer trip to Tuscany planned, we recommend taking a look at some of the additional Tuscany road trip destinations that we’ve outlined below the main itinerary and seeing what other spots catch your eye.

For most people, of course, taking a Tuscany road trip will require renting a car.

We’ll cover some tips and tricks for renting a car here below the Tuscany itinerary (or you can use the table of contents section at the bottom of the introduction to this Tuscany travel blog post to navigate there!), but here’s the short version: we recommend renting a small car in Tuscany through Discover Cars , which will allow you to compare prices and inclusions of multiple companies at the same time and choose the best car for you from there.

We also recommend renting your car only after you leave Florence, which we’ll cover a bit more below, so you likely won’t need one for every day of your trip to Tuscany!

Check rates & book your rental car with Discover Cars today!

Short answer? Yes, it can.

Through a combination of trains, buses, and carefully selected guided tours (we recommend several reputable ones in our Things to Do in Florence post ), this Tuscany itinerary can be completed without a car, though the logistics will be challenging in certain places.

That being said, there’s something very special about taking a Tuscany road trip, and by not driving, you will lose out on the charm of seeing some of the smaller towns at night, miss some of the prettiest vistas, and have a little less freedom in planning your trip.

However, we completely understand that not everyone planning a Tuscany itinerary can or would like to drive, and we fully believe you can have a deeply fulfilling trip to Tuscany without a car–we’ve done it several times ourselves.

And, while you will lose some freedom, you’ll also gain a bit of peace of mind, as driving in Tuscany is certainly not the most carefree driving in the world!

Start your Tuscany itinerary in Florence.

As the capital of Tuscany, Cradle of the Renaissance, and home to the biggest airport (and train station) in the region, there’s no better place to start your Tuscany itinerary than in Florence.

Ideally, we recommend a minimum of two full days here, which will give you enough time to explore all of the major sights.

Marvel at the art in the Uffizi Gallery, soak in the views from Piazzale Michelangelo and more, (window)shop for gold jewelry on the Ponte Vecchio, eat your way through Mercato Centrale, stand in awe of the Duomo, and visit Michelangelo’s masterpiece David in the Galleria dell’Accademia.

We’ve created several guides to Florence based on our six weeks or so spent exploring the city, including a one-day itinerary and a two-day itinerary , so be sure to check those out for more detail.

For this Tuscany road trip itinerary in particular, though, we have a crucial piece of advice regarding driving: don’t pick up your rental car until the morning you leave Florence.

Having a rental car while in the city is not only unnecessary, it’s an absolute burden. Driving in Florence’s historic city center is extremely limited, and you’ll save both money and headaches by ditching the car until you’re ready to hit the countryside.

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!

Bargello Guest House  — Located in the heart of Florence, this property is only a short (read: less than 5-minute) walk away from some of Florence’s highlights like the Palazzo Vecchio. Staying here, you’ll be within easy walking distance of the best of what Florence has to offer.

Check rates & book your stay at Bargello Guest House!

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 for one day in Florence!

Check rates & book your stay at Hotel Lungarno!

Start your Tuscany road trip and drive to Lucca.

Laidback and charming, colorful Lucca is the perfect first stop on your Tuscany road trip and an excellent place to grow accustomed to the ins and outs of driving and parking in Tuscan towns.

Lucca is not too big, not too small, and parking is fairly easy to find right outside the city walls.

It also happens to be a gorgeous, relaxing city that is a fantastic place to soak up the ambiance of Tuscany.

While you’re there, be sure to check out the beautiful Piazza dell’Anfiteatro, which, like Siena’s main piazza, is actually an oval rather than a traditional square, and to stroll along the tops of the city’s 16th-century fortifying walls, which are completely accessible to the public.

Don’t miss a climb up Torre Guinigi, either–not only does it boast incredible views of Lucca, but it’s home to several oak trees that are growing in the sky!

Stop by Pisa.

I’ll be perfectly honest: of all the places we recommend or mention in this Tuscany itinerary, Pisa is the one I’m least in a hurry to get back to.

It’s generally far more crowded than most of these other destinations–even the very touristy ones–and outside of Pisa’s famous tower and surrounding historic complex, the town is not exactly known as one of the most beautiful or interesting Tuscan villages.

It is, however, incredibly famous, and the Leaning Tower of Pisa itself more than lives up to expectations. The Leaning Tower of Pisa is truly stunning, and far more opulent and beautiful in person than I expected before laying eyes on it for the first time.

If you’d like to see it, we recommend stopping by for half a day on your Tuscan road trip, checking out the tower itself as well as the nearby Duomo and baptistery, and then moving on.

If you’d like to tour the interior of any of the structures, including climbing to the top of the leaning tower, we absolutely recommend booking skip-the-line tickets in advance .

Book your skip-the-line tickets to visit the Leaning Tower of Pisa now!

Make your way to San Gimignano.

Known for its stunning towers (14 of an original 72 remain), long history of wealth due to its prime location along a Roman trading route, gorgeous city center, beautiful views, and convenient location that is roughly equidistant from Siena and Florence, it’s safe to say that San Gimignano is both incredibly popular and well worth visiting.

We adore this beautiful hilltop town, and highly recommend spending at least one night either in town or nearby if you can, in order to enjoy the city without the crowds of day-trippers that tend to take over the streets during the day.

Don’t forget to make time in your schedule for a scoop (or several scoops, let’s be real) of gelato from the world-famous Gelateria Dondoli: as one of the best-known and most acclaimed gelato shops in Italy, it’s a safe bet that whatever you order is bound to impress.

Head to Siena.

While today Florence is significantly better-known than Siena, that was not always the case: beautiful Siena was once the military rival of Florence, and the history of the Middle Ages in the region is dotted with stories of their back-and-forth battles.

Today, Siena is known for its Palio di Siena horse race that takes place bi-annually in the oval-shaped Piazza del Campo–when you stand in the middle of the piazza, be sure to picture 20 horses running at full-speed around a packed crowd–it’s truly impressive.

Siena is packed full of interesting things to do: it’s home to arguably the most beautiful Duomo in Tuscany (don’t forget to check out the Piccolomini Library while you’re in there!), and we absolutely recommend taking the Porta di Cielo, aka Gate to Heaven, tour of the cathedral’s roof if you can–it’s magnificent.

At least once during your trip, climb to the top of one of Siena’s monuments for an epic view–the Torre del Mangia in Piazza del Campo is a popular choice, but personally, we love that the view from the top of the Opera della Metropolitana includes stunning views of the Piazza del Campo from a bit of a distance.

Spend some time in Val d’Orcia and soak up the Tuscan countryside.

Of all the scenic places in Tuscany, Val d’Orcia might just be the most beautiful of them all.

This UNESCO-recognized valley is home to the Tuscan road trip views of your fantasies, and it truly has to be seen to be believed.

If you have the time in your Tuscany itinerary, we recommend booking at least a couple of nights in a nearby country villa or agriturismo in order to slowly savor the beauty of the region, but if not, even an afternoon drive here is well worth the trip out.

Marvel at the beauty of Montepulciano.

Tiny, gorgeous, and home to arguably some of the best countryside views of all the villages in Tuscany, it’s impossible not to be charmed by stunning Montepulciano–and that’s even before you start sipping its world-famous wine.

While it doesn’t take terribly long to explore a village this size on your Tuscany road trip, Montepulciano has one of those peaceful atmospheres that you just want to savor.

While you’re there, be sure to stop by the beautiful Piazza Grande, admire views of the nearby Church of San Biagio that is located just outside of town, and to taste the local wine, vino nobile di Montepulciano .

Pay a visit to Arezzo.

As you turn back north toward Florence to start to wind down your Tuscany road trip, be sure to check out the beautiful city of Arezzo.

Often overlooked on Tuscany road trips, Arezzo is a delightful city that is well worth the time it takes to visit.

Home to Roman ruins (including the remains of Arezzo’s very own Colosseum), sweeping views of the countryside from the Medici fortress, some impressively well-preserved fifteenth-century frescoes, and a large number of antique shops just waiting to be perused, Arezzo is an excellent addition to any Tuscany itinerary.

Be sure not to miss a chance to climb the clock tower at Palazzo della Fraternita dei Laici right off the main square (Piazza Grande)–the views from the top are absolutely sublime, and it is our personal favorite spot in Arezzo.

Drive back to Florence & say goodbye to Tuscany.

As your Tuscany road trip winds to a close, head back to Florence to drop off your car, say goodbye, and–depending on time–perhaps visit one or two more sights in the Cradle of the Renaissance as well.

While we’ve set up this Tuscany itinerary to act as a loop, if you’re going to be flying out of Italy (or continuing your Italy travels outside of Tuscany) in a different location, you can also consider dropping off your car in Rome, Milan, Bologna, or even Venice–but keep in mind that you will likely incur a one-way drop-off fee for doing so, so be sure to budget for that if needed!

While this Tuscany road trip itinerary gives a solid outline of the region and is a delightful trip all on its own, for those with a bit of extra time in the area (or those who like to move at a very fast pace), there is an unlimited number of additional destinations you could add to your trip, both in Tuscany and in its surrounding regions of Umbria, Emilia-Romagna, and Liguria.

We’ve outlined a few of each here to give you some ideas as you plan your trip to Tuscany!

Within Tuscany

The most famous of all of Tuscany’s hot springs has emerged from comparative obscurity into being a full-blown famous photography location in recent years, but there’s no doubt that it’s still a dream to visit–if you have time during your Tuscany road trip to make the trek out there and you’re a fan of hot springs, it’s definitely worth a visit.

Dating back to the Etruscan period and nestled on a hill high above the sweeping Tuscan landscapes it overlooks, the walled city of Volterra is absolutely worth visiting as part of your Tuscan road trip itinerary.

The ease of accessing it paired with its beauty make this one of the first towns we would recommend if you are looking for additional stops along your road trip in Tuscany.

Cortona is perhaps best known for the famous book/movie that is based there, but even without the fame brought by Under the Tuscan Sun , this tiny Tuscan town is still a fabulous place to visit!

I’ll be honest: a trip to Elba is a bit of a stretch for all but the longest trips to Tuscany, but it bears mentioning simply for the fact that Elba is Tuscany’s very own island–and “Mediterranean island” is just not what you normally associate with a trip to Tuscany.

Whether you want to scuba dive, enjoy delicious seafood, lounge on the beach, or chase down the island’s interesting history (Elba was the first place Napoleon was exiled to, though he escaped a little under a year later), there’s no doubt that Elba makes a unique addition to any Tuscany itinerary.

Easier to access than Elba but equally focused on all things coastal, the seaside city of Livorno is the perfect Tuscany road trip destination for anyone looking to enjoy a little sea and sun as part of their trip to Tuscany.

Best known for its delicious Brunello di Montalcino wine, the hilltop town of Montalcino is a delightful slice of Tuscany that is easy to access from Siena and Val d’Orcia.

Outside of Tuscany

Cinque terre.

Of all destinations outside of Tuscany that people tend to be eager to add onto their Tuscany trip, Cinque Terre almost always falls near the top.

We’ve visited this sensational collection of Ligurian fishing villages twice as part of a Tuscany road trip, as well as on a standalone visit, and we can attest that they are well worth the trouble if you have time in your itinerary.

We absolutely do not recommend driving into the villages, however–instead, drive to the train station at La Spezia or Levanto, park your car, and then take the train into the villages from there.

Known, above all else, for its food, Bologna is the perfect location for foodies to flock to if they’re looking for some truly epic cuisine during their road trip.

Bologna is the capital of Emilia-Romagna, the region that is home to so many of the things us foreigners tend to associate with Italian food: tagliatelle al ragu (aka spaghetti bolognese), mortadella (aka bologna), parmigiano-reggiano , traditional balsamic vinegar, and more.

Once you get done eating, Bologna has plenty of other sights to explore, as well–but the food alone is worth visiting for.

Set on a hilltop overlooking sweeping views of the Umbrian countryside, Orvieto is as historical as it is picturesque: dating back to the Etruscans and once (briefly) the home of the pope, whether you’re looking to dive deep into the history, enjoy the tasty Orvieto Classico wine, or simply admire the magnificent vistas, Orvieto has something to offer.

We adore this little village–be sure to check out the Duomo, the views from the Torre del Moro, and the underground while you’re there, among plenty of other fun things to do.

As the location of the birth, work, and death of St. Francis, Assisi is an enormously popular pilgrim destination among Catholic travelers–but even if you’re not Catholic, this small Umbrian town has plenty of history and beauty to offer.

St. Francis was the founder of the Franciscan Order–a name you’ll see pop up a lot in Italy–and is also one of the patron saints of the country.

In Assisi, you can tour the enormously impressive Basilica of St. Francis while learning about the life and history of the saint.

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.

Ultimately, Tuscany is a beautiful destination year-round, and you can never go wrong with a visit.

Spring in Tuscany brings beautiful flowers but plenty of rain, summer brings lots of tourists but also long days and sunshine.

Fall brings the harvest and temperamental weather, and winter brings cold, gray weather but also low prices and a distinct lack of crowds.

If you ask us, though, our favorite time to take a Tuscany road trip will always be in the fall, particularly late September through mid-October.

True, it’s hardly offseason (in other words, there will be plenty of other tourists around), and there’s a good chance of experiencing a cold and/or rainy day or two–but the changing colors across the countryside, the incredible food that is freshly harvested, and the crisp chill that sweeps through the air each evening as the heat dies down for the year give the region a magical quality that we will never tire of experiencing.

We’ve spent at least part of the last few autumns in Tuscany, and we see no reason to stop that tradition anytime soon.

While driving in Tuscany is not the most difficult driving you’ll encounter in Italy (looking at you, Rome and Sicily), it definitely has its quirks!

Here are a few tips we recommend keeping in mind as you plan your Tuscany road trip itinerary.

Make sure you have access to a GPS for your Tuscany road trip.

This is absolutely imperative, in our opinion, and can make the difference between an insanely stressful Tuscany road trip and a fairly laid-back one: whether you purchase an international cell phone plan through your carrier before leaving for Tuscany or you purchase an Italian SIM card on the ground, you’ll 100% want to make sure you have cell phone data–and therefore GPS–with you as you drive.

Shop around for your rental car.

I’m almost 100% certain that we’ve used a different rental car company every time we’ve rented a car in Italy–that’s how much the prices can vary depending on your time of travel, pickup and dropoff locations, size of the vehicle, and more.

We recommend searching for your car via Discover Car Hire , which will allow you to check out the rates of several different rental car agencies in Tuscany at once and compare prices and inclusions side-by-side.

Shop for your Tuscnay rental car with Discover Car Hire today!

Buy the insurance–you won’t regret it.

Ultimately, this is up to you–I know some people prefer not to buy additional CDW insurance (aka the insurance that covers damages to the actual car you’re driving, as opposed to your liability to anyone else) on trips–but we buy it every. single. time. in Tuscany and have no regrets.

I don’t want to overstate things, because driving in Tuscany isn’t exactly like driving in the Wild West–but let’s just say that the roads are often tiny, the buildings very close, the parking lots cramped, and the other tourists’ rental cars parked nearby are frequently scratched and dinged in a way that while not horrendously damaging, is definitely something a car rental company would love to charge you for if it happened on your watch.

The peace of mind is absolutely worth it to us–you can price it for yourself when shopping on Discover Car Hire , or purchase a travel insurance policy through that includes car rental insurance (but be sure to double-check the policy, because only some policies cover it).

You need an international driving permit to rent a car in Tuscany.

Technically, you always need an international driving permit to rent a car in Italy, and that includes in Tuscany.

You can pick this up before you leave home from AAA, and it’s very easy and cheap to do–just a bit annoying, as it’s one more thing to add to your to-do list before leaving for your Tuscany road trip.

Now, that being said–will your rental agency always ask for it? No. Will the police always ask for it? No.

Is it worth the risk of being refused a rental car or getting a ticket over $25 USD and a bit of hassle? Not in my opinion.

Rent the smallest car possible.

Not only is it cheaper, which is always excellent, but a smaller car in Tuscany is also much easier to drive.

While the highways in Tuscany are pretty standard, this-could-be-anywhere highways, the small country roads, parking lots near villages, and dirt roads leading to vineyards and villas can be incredibly narrow–which, naturally, does not stop them from being used for two-way traffic (you’ll probably end up pulling over to let someone maneuver past you at least a couple of times during your Tuscany road trip).

Be sure to account for how much space you’ll need for luggage, especially if you have three or more people in your group, but other than that–the smaller, the better.

If you get a ticket, you probably won’t know it right away.

Traffic citations in Tuscany are generally captured via camera, so if you get one, you probably won’t know it right away.

Instead, your license plate will be captured, the ticket will be sent to the owner of the car (ie, your rental company), and then your rental company will forward it onto you.

Unfortunately, that means you won’t be 100% sure you didn’t have any infractions during your Tuscany road trip until several weeks after you get home.

You will encounter toll roads in Tuscany–so carry cash.

Most toll roads in Tuscany will accept credit cards, but it’s always best to have small bills/coins of cash on you–just in case you run into a cash-only booth (or you need a last-minute coffee and/or gelato, which are also very important parts of any Tuscany road trip itinerary).

Be prepared to park and then climb up to towns.

Tuscany is known for its delightful hilltop towns, full of winding, narrow streets and plenty of foot traffic.

Combine the above description of Tuscany that we all know and love with the very concept of a Tuscany road trip, and an obvious question emerges: where are the cars?

Usually, they’re in parking garages built literally under the hilltop towns or on the outskirts of historical centers… which means you often have to walk up steep hills in order to reach the center.

Some cities, like Siena, have escalators installed to help alleviate this problem–but in general, be prepared for a little bit of a leg workout when visiting small towns in Tuscany!

Avoid ZTL zones like the plague.

Essentially, ZTL zones are restricted access zones that dot most of Italy’s historic city centers, including in Tuscany.

If you drive into one, even accidentally, you’re risking a big ticket (and we’ve definitely had to call tiny Tuscan police stations to help some of our family members pay them off months after the fact).

Avoid them by parking on the outskirts of historical centers and by doing your research ahead of time, which leads me to…

Whenever possible, figure out where you’re going to park next before leaving.

This is one of our favorite tricks to keeping stress levels down when driving into a new town in Tuscany: know where the public parking lots are and, when heading out for the day, put your directions on for that particular spot rather than just the town.

This will absolutely cut down on the risk of accidentally driving into a ZTL zone (and therefore getting a ticket), and also make the trip into town much less stressful.

Now, in the interest of full disclosure, this doesn’t always work–occasionally the parking lot you have picked out will be full, or you’ll luck out and find street parking along the way–but in general, it will definitely make your life easier during your Tuscany road trip.

Travel Insurance  — We don’t ever suggest traveling without travel insurance–anything can happen, and this is definitely a case of better safe than sorry. We use and recommend  Safety Wing for trips to Tuscany.

International Driving Permit — If you’re coming from outside the EU and plan to rent a car in Tuscany, you’ll need to make sure to acquire an International Driving Permit in your home country, before  coming to Italy.

It is required for all car rentals in Italy, and while the rental company may not ask, it’s not worth the risk of being refused a car once you arrive or getting a fine if you’re pulled over to be without one. Play it safe and if you plan to drive during your trip, add getting an International Driving Permit to your pre-Tuscany planning!

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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.

67 thoughts on “The Perfect Tuscany Road Trip Itinerary (+ Driving Tips!)”

I love this website It has convinced my husband and me to go on a driving tour of italy! I actually have a question. How do you know or find out where is the ZTL zones so you can avoid them? Thanks! Ilene

So glad to hear that, Ilene! Hope you guys have a great time!

Your GPS can help you avoid the ZTL zones, but the biggest thing is paying very close attention to the signs, as they’ll be marked there. As a general rule, historic centers of cities are ZTL zones, so it’s safest to avoid those entirely and park outside the center before walking into the town!

Hi Kate, Do you have any recommendations for accommodations on the Tuscan itinerary? We would be going in Sept 2022.

Hi Sabrina!

Yes, absolutely. We have several properties linked in this post, but if you’re looking for specific towns/cities, we also have recommendations in each of our independent city guides.

Hello, You guys look like you have a great life! My husband and I are older than you but have retired a bit early so we can travel while we are still able to move about. We have traveled quite a bit independently throughout the years so we are comfortable going to new places. Your blog is great and has so much useful information. Thank you for putting all of your knowledge out there. I know it’s a lot of work to do so. If you don’t mind me asking…we were told you have to have a permanent address at least 6 months out of the year for tax purposes. How do you get around that? Don’t mean to overstep. Thanks!

Thank you so much, Joanne! We really appreciate it. 🙂 Residency requirements vary by state, but we maintain a technical permanent address in our home state of Oklahoma where we pay our taxes, maintain our businesses, keep our driver’s licenses up to date, etc. Most nomadic travelers have a similar setup for logistical purposes!

Hello, thanks so much for this post. It’s so helpful! My partner and I are going to copy this for our holiday in June this year. I was just wondering if you could tell me which towns you stayed overnight in? Grazie, Olivia

So glad it was helpful, Olivia! Where to spend the night really depends on your specific taste, but from this itinerary, we’ve stayed overnight in Florence, Siena, and Arezzo. We’ve also stayed in countryside villas near the Val d’Orcia and Lucca.

Since you’ll be driving, we 100% recommend staying in the country at least once–Tuscan villas and agriturismos are absolutely amazing. For staying in the towns themselves, make sure your hotels have parking, but other than that, any and all of them make a great place to spend the night.

My daughter and I just booked a rental car for our trip to Tuscany this summer thanks to your post. I was nervous about driving but you laid it all out perfectly, thank you. We’re going for her graduation present and it’ll be the first time in Italy for us both. Bookmarking your site now for when the trip gets closer. Thanks again!

That’s amazing to hear, thank you Susan! Comments like this never fail to make my day, we are ALL about making sure your trip goes perfectly! Hope you guys have a fantastic time, and congratulations to your daughter on her graduation!

Hey, this has been quite useful. Im planning my road trip, but im going clockwise on this route. Since i live in The Netherlands, i will drive in from the north, Florence and start here and after Pisa-Lucca, the last stop instead of heading back to Florence is Cinque Terre, to enjoy a bit of the coast. I will take the advice of leaving the car in La Spezia, but if you had to choose to spend a night in Cinque Terre, which woudl you guys recommend, Vernazza or Manarola?

Glad to hear it, thanks Rodolfo!

Which village is best for spending the night in Cinque Terre is definitely a matter of preference, and Vernazza and Manarola happen to be two of my top 3 favorites (the other is Riomaggiore). You can’t go wrong with either, but I’d recommend Vernazza if you’re looking for something smaller, and Manarola if you want to have access to a wider variety of shops and restaurants. Manarola is a more popular (read: crowded) sunset spot, but both places will quiet down considerably once the day trippers head home.

Wonderful, informative article! I am so glad I found your website. We are hoping to be able to visit Tuscany in summer 2022. Italy is our favourite country, but we haven’t been to Tuscany or Cinque Terre, so I really appreciate the wealth of information on your website!

Thank you so much, Cheryl! So glad to hear that. 🙂 Hope you guys have an amazing trip to Tuscany and Cinque Terre!

Hi! I just came upon your site when doing a search for info on an upcoming trip. My husband and I are planning a trip for the end of Oct. We will be renting a car in Florence, spending about two days driving through Tuscany and returning the rental in Rome. I know that’s way too short to do Tuscany justice, but we have a commitment in Venice prior to Florence, and are bookended with a fixed return date from Rome. Where in Florence would be our best choice to rent a car so we can get on the road to Tuscany easily? Same question for returning rental in Rome without having to deal with city driving. Lastly, we are doing some basic research in Tuscany in order to maybe get a place there down the road. Should we consider spending our two nights there in Lucca? Thanks so much and I will definitely be following your adventures!

Hi Rohini! There are so many places to rent cars in both cities it’s really impossible to say–I’d keep an eye out for the best deal and then look carefully at the directions. Unfortunately, some city driving is probably unavoidable if you want to make it all the way from Florence to Rome, but you can limit it based on your schedule.

If you’re just going to relax, Lucca is a great choice! If you want to compare possible areas to own a property in Tuscany though, I’d probably recommend one night there and one night in the Val d’Orcia area. You may also want to consider a look at Siena, depending on whether you want to be close to a city or not.

Hi Kate. Thanks for your quick response! This is very helpful info. I had read somewhere that Tiburtina station in Rome is a good spot for rental return since it would not involve going into the city to return. Would you say that is the case? Once again, thank you for your help!

Hi guys, I imagine you’ve had some ups and downs in your travel in the last 2 years because of Covid. I really hope you’ve been able to stay safe and still continue some of your adventures. I found your site and am really keen to follow your path around Tuscany when my husband and I go this year. I looked up your destinations and would really encourage you to look into coming to Australia and New Zealand some time if you can. Down Under is a wonderful place and New Zealand has just about everything you could ever want to see in a really small country! Thank you for your really helpful and informative site. Take care.

Yes, there have been many ups and downs over the last couple of years for sure, but luckily things are mostly up right now! We’ve decided to base ourselves in Portugal for the next little bit to enjoy lots of Europe throughout 2022. 🙂 Knock on wood, but hopefully our next Tuscan road trip is just around the corner!

We’d love to head down to Aus and New Zealand one day! No plans at the moment, but you never know. 🙂

Hope you guys have a wonderful trip!

Such a great and helpful Itinerary, thank you!

We’re planning to visit late September and I am nervous about the driving portion – what location would you recommend for pick up, outside of Florence? We’re hoping to get a drive to our first destination (open to anywhere) and then pick up a car – appreciate any extra tips you might have! I was surprised to not see any mention of Greve as a stop, have you been? This was what I thought was my main stop in Tuscany but I am now rethinking everything! 😀 We have 5 nights in Tuscany (counted Florence separately as a stop when we head North) and prefer to not spend too much time in the city and want to visit many wineries and enjoy the local food! If you have any very specific favorite wineries to stay at or places to dine, I would love to hear about them!

Thanks again for such a detailed post! I have a lot to consider 🙂

Thanks so much, Cait!

There’s never enough time for all the towns, lol, but if you want to swap in Greve you absolutely can! We haven’t been ourselves yet but generally speaking there’s no such thing as a “wrong” Tuscan town to visit. 😉

If you want to pick up a car outside of Florence, I’d recommend taking a look at Siena. By the time you get into the very small hilltop towns like San Gimignano, etc, there may not be car rental agencies available (or if they are, it’ll just be an office and they’ll need to drive the car itself to you from a bigger city–which often comes with a fee).

Have an amazing trip!

Hi, I am planning a vacation trip to Rome (5 days) and from there a road trip (5 days) to the Tuscan area. I’ve been already to Florence and Pisa. I will like to know cities or towns with good food and scenery off the beaten path. Thanks so much for your time and sharing your knowledge.

It depends on how you define off the beaten path, but just about everywhere in Tuscany is further off the path than Florence and Pisa! And virtually everywhere in Tuscany has great food. 🙂

Arezzo, Volterra, Pienza, Montepulciano are all delightful, some more commonly visited than others. Montalcino is tiny but beautiful.

We also love Lucca, it’s much quieter in many ways than Florence or Siena.

A common theme is that if you spend the night in any of these places, they will get much more peaceful and quiet if you spend the night, as the day-trippers will head home.

Some of the spa towns other than Saturnia can feel off the beaten path, such as Bagno Vignoni. They’re popular, but more catered to tourists from nearby.

Wonderful article – thanks!

Planning Sept trip – 4 days Rome, 2 days Florence, 3 days Venice (as of now)

Considering adding a Tuscany component but limited to time. Any suggestions to condensing to 2-3 days as a loop or feasibility of starting in Florence and ending in Venice?

Any input greatly appreciated.

Happy to help, Richard!

With a 2-3 day driving loop from Florence, I’d recommend driving to either the Val d’Orcia (so towns like Montalcino and Pienza) or a nearby base like Montepulciano, and then basing yourself there for a couple of days. You can drive between a handful of close-together towns, see the landscape, enjoy an agriturismo, do some wine tastings, etc, all within a close distance.

Driving from Florence to Venice isn’t a go-to suggestion of mine since you don’t need a car in either city, but we’ve actually made the drive ourselves as part of a family trip and it was lovely! Bologna, Ferrara, and/or Padua are easy stops right along the route.

If you wanted to take a couple of days between the two cities, a loop through Parma, Modena, Reggio-Emilio and Bologna would put you in the heart of Emilia-Romagna, which is the origin of some of the most beloved Italian foods (traditional balsamic, parmigiano-reggiano, etc).

It’s not the most efficient way to get from Florence to Venice of course (that’d be the high-speed train), but if you want to make a trip of it, you’ll have fun!

If you do want to consider renting a car in Florence and dropping it off in Venice, though, be sure to ask your rental company if they allow it and what fees they would charge before making any plans.

One of my stops is in Luca and the hotel and parking garage are in the Atlantic. How do I get a permit to drive through it.

I think you may have a typo in there, but I’m assuming you mean you have a hotel booked in the historic center of Lucca? If the hotel offers private parking on-site, you can give them your license plate number and they’ll be able to make arrangements for you.

If they don’t have parking, you’ll likely need to park outside the walls and walk into the center to reach your hotel.

Hope that helps!

The parking os not on-site but within the walls.

So you are saying that all I need to do is call either the garage or hotel with my rental car license number and they would be able to get me a permit to drive inside the walled city to get to the hotel and garage?

In your case, I’d contact the hotel and ask where they recommend you park, and then if you head to the garage inside the walls, look at the map to confirm the directions to access it.

Essentially, your goal is to avoid the ZTL zones, which trigger an automatic ticket (and technically two–one for entering the zone and one for leaving it). Unfortunately, since all of the traffic controls are done by camera, you’ll have no sure way of knowing at the time you park if you’ve crossed the boundary.

The public parking within the walls should have a way to access it without passing through a ZTL zone, the concern is taking a wrong turn, etc. If you do need to pass through a ZTL zone (generally speaking in Italy), hotels within the walls can get access for their guests but I’m not sure if yours can since they don’t have on-site parking. These rules also vary from city to city in Italy.

Generally speaking, in the case that you do get access to a ZTL zone to access hotel parking (I know yours doesn’t have it, but just generally), you won’t get a paper permit or anything like that. It’s all done by license plate and camera.

Hi Kate! What an insightful article. I am planning a trip to Itlay in August for 12 days with a girlfriend who has never been to Italy. We are landing in Rome, spending 3 days there, and making our way to Florence by train. We will have 6 days in the Tuscany region and plan to rent a car after reading your article. This is what I am planning for our road trip and what your feedback. Would love to know if you can recommend an amazing winery with meals and wine tasting at one of our stops. I have taken suggestions from your blog on places to see and things to do at each stop:) Am I packing in too much? Day 1 – Florence to Lucca to San Gimignano spend the night here Day 2 – San Gimignano to Siena to Val D’Orcia spend 1 or 2 nights here Day 3 or 4 – Val d’orcia to Montepulciano to Montalcino (not sure about Montalcino) Day 4 – Drive to Saturnia from the last destination and head back to Florence

Hi Gira! All of the places you have mentioned are wonderful, but yes, I’d highly recommend cutting a few places from your list in order to savor the others more!

Driving, parking, walking into historic centers, etc, all eat up quite a bit of time.

I’m assuming you’re planning a couple of days in Florence on days 5-6. Ideally, I’d recommend only changing your “base” one other time. Montepulciano is a convenient spot as you can reach the Val d’Orcia, Montalcino, etc, from there. Siena is another fantastic option, but it’s definitely a small city, not a tiny town.

Saturnia is pretty far out of the way from everything else on your list, so unless it’s your dream destination in Florence, I’d consider trimming that. 🙂

Hi, Your article is very informative. Thanks. One question, I understand that leaving anything in the car in Italy is not a good idea as it can be stolen. What about these small towns in Tuscany? Is it risky to leave luggage in the trunk when parking there, too? Thanks

That’s essentially down to your personal risk tolerance. Many people leave luggage in the car when they have no other good option if it is kept out of sight in a locked trunk.

Obviously, there’s always a small risk with that, but it’s a fairly common practice.

The most important thing is to make sure nothing visible is left behind.

Thank you for such a insightful article, it has definitely helped to make a road trip through Tuscany feel less daunting!

Are there are places on your list that are more or less English friendly? We will obviously try to learn what we can in Italian, but it is always helpful to know 🙂

My husband and I previously visited Florence and did a day trip to Pisa, Siena, and San Gimignano. The scenery was so breathtaking it quickly made a road trip through Tuscany a MUST on our bucket list! Having already visited those places (wouldn’t mind visiting San Gimignano again!), what would be your top picks for 5-6 nights (not including Florence but starting from there)? I would love to make a stop at Saturnia if time allowed. Thank you SO much for your suggestions!

Hi Samantha,

Thank you so much! Glad we can help. 🙂

Unless you go exceptionally off the beaten path, you won’t have any problem using English (plus body language/hand signs/etc) in Tuscany, so don’t worry! Definitely learn what Italian you can, but Tuscans are very friendly and exceptionally used to foreigners.

Since you guys have already done quite a bit in the northern part of Tuscany, I recommend heading to the southern part! Montepulciano, the Val d’Orcia (including towns like Pienza and Montalcino), Cortona, and Saturnia, make a great loop.

You might also look at taking a day trip to Civita di Bagnoregio, Orvieto, Perugia, or Assisi. Those places aren’t in Tuscany but are wonderful, and depending on your itinerary might make fun additions.

This is so helpful Kate, THANK YOU!!!! This will be my first time in Italy, I’m traveling solo, and I’ve never driven outside of the U.S. before, so I’m thinking I’ll stick to trains to get around this time (which I know will limit how much flexibility I have). Are any of these towns easily accessible by train from Florence (and/or each other)?

Happy to help, Tara!

Yes, Lucca, Pisa, Arezzo, and Siena are all easy to get to by train.

The smaller hilltop towns are generally harder to access without a car, and many don’t have train stations. You can technically get to Montepulciano by train, but the station is outside of town and you’ll need to catch a bus or taxi to get all the way there.

If you want to visit a few of the tiny hilltop towns, I’d recommend signing up for a day trip one day–we link a some popular ones in this post: https://www.ourescapeclause.com/best-day-trips-from-florence-italy/

Generally from Florence, you can find either day trips that focus on the north (San Gimignano is a common stop) or the southern Val d’Orcia towns. They’re a great way to see harder-to-access spots while letting someone else deal with the driving and parking!

Thanks so much for responding and for the additional tips! <3

Hi Kate! Thank you, thank you, thank you for the wealth of information. Very helpful for our upcoming visit!

Any possibility of emailing you directly with a few more questions?

Thanks, Lori and Steve, USA, coming in October for our 60th birthday’s!!!!

Yes, of course!

We’re not travel agents and don’t plan/book trips for people, but we’re always happy to answer a few questions and point travelers in the right direction. 🙂

Happy early birthdays!

Hello again, We will only have about 4 (3 full) days and nights to explore Florence and Tuscany. We hear that Florence is not terribly large and is very walkable? Would it be practical and safe to utilize motor scooters to do so? The countryside is a PRIORITY, but we are considering not venturing too far from the city to limit travel time. We’d like to spend at least one night in the city, and at least one in the country. And we very much want to explore a couple of very small villages. Suggestions?

Would you recommend purchasing train tickets in advance, or is it really not necessary? Likewise for renting a car, and making hotel reservations (First week of October).

For the train tickets–it depends. For high-speed trains across long distances, like from Florence to Venice, yes, absolutely book in advance. The prices increase dramatically as you get closer to your dates.

For regional/slow trains, like taking a day trip from Florence to Lucca, there’s no need to book in advance.

What gets a bit confusing is that some lines, like between Rome and Florence, have both high-speed trains (essential if you’re making a day trip, as it takes under 2 hours), and regional/slow trains, which depending on the exact timetable can take anywhere from 3-5 hours or so.

If you want an overview of what’s available, we recommend using Omio to search for tickets and compare prices/timetables.

For hotels and a rental car, yes, you’ll want to book in advance. It’s not as urgent as in, say, July, but to get maximum availability it’s best to be prepared, especially if you have special requirements for your rental car such as wanting to rent an automatic.

I hope that helps and that you guys have a great time! October is our favorite month to be in Tuscany. 🙂

My daughter & I will have 5 days in Tuscany, have a rental car & want to visit mostly hill towns. Our hotel is outside Florence. We’d like to drive to Cortona then to for wine tasting, then to Monticchiello for a 7:30 dinner at Daria & spend night. Is this possible? Where do I find city maps?

I think you mean you plan to spend the night in Monticchiello? If so, yes, that will probably work well. Cortona is a bit out of the way as far as Tuscan hill towns go, but it’s very popular!

For city maps, your hotel will usually offer one, especially if you ask. For towns that you just take a day trip to, the easiest way to find them is to head to the tourism office (there’s virtually always a well-marked office in the town center).

Some tourism offices do charge a nominal fee for maps, so it’s a good idea to have a few Euros in small coins/bills on you when you go.

Totally loved it!!! Would you recommend doing this roadtrip with a child? I really want my 5year old daughter to witness new cultures and enjoy some holidays with mum and dad!

Of course it depends on the child, etc, but it’s definitely possible! Italy is considered to be very kid-friendly, and kids are adored and welcome just about everywhere.

The distances in this road trip are also fairly short, so no extremely long car days to contend with.

I don’t see your 2 night Tuscany itinerary?

Hi Lorraine,

I’m not sure what you mean–maybe you’re looking for our 2 day Florence itinerary? Here it is: https://www.ourescapeclause.com/2-days-in-florence-itinerary/

I don’t have anything on spending 3 days/2 nights in Tuscany specifically, but for most visitors, I’d recommend spending 2 days in Florence and then taking a day trip to the countryside on the 3rd day.

Hope that answers your question!

Thank you very much for your article, it was very helpful to consider the cities/town to visit in La Toscana. What would you recommend me for a 10-day trip (honeymoon 🙂 ) by arriving to Rome? For sure, I want to rent a car and do all by car. Would it be better to take a train all over to Florence and from there do the trip all over to Rome? Is it a big deal if I do not have an international license? Thank you for your help.

You can definitely structure this trip as a road trip from Rome to Florence, touring Tuscany by road trip along the way instead if you prefer. For that version, you’ll likely want to start at Montepulciano and then make sort of a “V” shape ending in Florence. Keep in mind that you’ll probably have a one-way car rental fee if you do it this way.

In that case, you may want to add on a stop in Orvieto along the way as well–it’s in Umbria, and a beautiful place: https://www.ourescapeclause.com/things-to-do-in-orvieto-italy/

Having an international driving permit is required for non-EU drivers in Italy. It’s not often asked for, so you can choose to take the risk, but your rental company can refuse to rent to you and of course, you can have issues if you get into an accident, etc, if you don’t have one as well. They’re not complicated to get, so it’s much better to acquire one before going to Italy!

Hi! Thank you so much for this wonderful site – it is so informative!! We are planning 2-3 days traveling from Florence to Rome and wonder if there are private drivers for hire in Tuscany. Is that an option? And, if so, do you have a sense of how we would locate good drivers? Our concept is that it may be easier on us if we just left the driving to a trained professional local… your thoughts? Thanks again! Paul

We’ve never hired a private driver in Tuscany, so I can’t speak to that personally! I know that some private drivers and tours advertise through Get Your Guide. Other than that, I’d recommend asking your hotel concierge, they’ll no doubt know of someone.

However, if your goal is to travel between Rome and Florence, you could also easily take the train. If you’d rather take 2-3 days to do the journey and sightsee along the way, Orvieto and Siena are both stops to consider on the way.

If you’re confident drivers, though, that route is fairly simple–lots of highway driving, etc. If you’re considering the option of driving yourselves, I’d say there’s no real reason not to.

Hi Thank you for putting together all this info, it has filled me with excitement thinking about our trip this year. My husband and I are hoping to fulfil my dream of travelling to Tuscany this year at the start of April. We will be driving from the UK and stopping off in Normandy then driving across to Italy and Tuscany. The first large city we will enter is Turin before moving towards Tuscany. We have 7 days in Italy but we thought a circular road trip would be great made up of countryside, wine, food and wandering around towns and markets. I love the road trip based around Florence but given our route and our starting point, would you be able to recommend anywhere we should visit/stay/avoid that starts further north and drops into Tuscany. I don’t want to disappoint myself by making poor choices in destinations so any help would be much appreciated. Thank you

Sounds like a wonderful trip! We’ve driven from Portugal to Italy and/or France (and back) several times ourselves, so we’re very familiar with the breadth of the drive you’re taking on.

The Langhe region of Piedmont, located close-ish to Turin, is fantastic: think small towns, gorgeous views, delicious wine, and fewer crowds than Tuscany. You may want to consider a stop there before heading further south! We loved La Morra in particular, but there is lots to see around there, including Alba, Barolo, etc.

Depending on what route you take in, you may pass through Emilia-Romagna as well, one of our favorite foodie regions in Italy. There are a million places to fall in love with there, but Parma might be right along your drive: https://www.ourescapeclause.com/best-things-to-do-in-parma-italy/

Hope you guys have a fantastic trip!

Hi, I loved your article. My husband and I are planning to head to Tuscany in September. My thought is to arrive in Florence from the states and stay for 3 nights. Originally I was planning to head to Greve and stay at Borgo de Cabrea. for 5 nights and just do day trips from there. (The pictures of the hotel views blew me away). However after doing some more research, I’m thinking that I would leave Florence and head down to the Val d’ Orcia region for two nights, do some day trips from there, then head back up to the hotel in Greve for my remaining 3 nights. I don’t want to short change my experience in southern Tuscany. Looking for advice on where to stop on the way down, and the way up versus day trips from where we are staying. I’m thinking of stopping in Sienna on our way back up since it’s closer to Greve then we can avoid a day trip back down. Where do you think is good place to stop on the way down vs. places that would be better as day trips? Also any advise on where to stay in Val d’ Orcia region? Thanks for the advise on the cars. The site you suggested is much cheaper than the one I was originally looking at.

Those hotel views do look incredible!

With the caveat that you can’t make a very wrong decision in Tuscany, I’d recommend spending 3 nights in the Val d’Orcia area and 2 around Greve. Definitely check out the tiny town of Montefioralle when you’re in the Greve area, too: https://www.ourescapeclause.com/montefioralle-italy/

Siena is a decent-sized city rather than a hilltop town, so I’d spend more time there than you can–but if a couple of hours is all you can spare, visiting the Piazza del Campo + the Duomo + visiting one of the viewpoints to see the city from above will make for a memorable stop.

As for where to stay in the Val d’Orcia, we’re partial to Montepulciano as a base. It’s not in the Val d’Orcia, but nearby, well-connected, and beautiful. Pienza also makes an excellent base and has some hotels whose views I think you’ll also love: https://www.ourescapeclause.com/pienza-italy/

Depending on which route you take down from Florence, you may pass Monteriggioni, if so, that’d be a lovely stop during your drive.

Thank You so much for your response. After doing some of my own research and keeping your advise in mind, we booked a hotel in Montepulciano. I have another question for you. We are renting a car and tried discover cars. The prices for renting a compact car through Noleggiare are significantly cheaper than any other company. We need an automatic so it can get pricey. The reviews are mediocre and I was wondering if you had any experience with them. Thanks!

I don’t think we’ve ever used them in particular, but in general, we’ve never had any issues with a car rental in Italy and have zero brand loyalty with rental cars there. We tend to go with whoever is most affordable, as the prices can vary so much. We do buy rental insurance, though–for us, it’s worth the peace of mind.

Hi Planning on driving from Rome to Florence, taking our time. Where would you rent the car? And can you drop off a car in Florence if you rent in Rome. Thanks

Hi Sebastiano,

Personally, we’d rent the car in Rome wherever we could find the best deal–we’re not particularly loyal to any one car rental company.

You can definitely rent a car in Rome and drop it off in Florence, however, you’ll likely incur a one-way rental fee. These can vary dramatically, but are usually pretty reasonable if you’re picking up and dropping off the car in the same country (driving from Italy to Switzerland, for example, would be a different story).

Hi! I liked your insights very much, I hope to go visit Tuscany soon with my family. Though you didn’t really mention seaside areas – I guess it’s because people don’t tend to visit Tuscany region because of beaches, but still, there IS some seaside (judging from map sorry), and I would like to know more, either if you had any experience, or from locals or friends. I clinged to the one photo of a beach at Livorno. I was wondering, if it is worth seeing the seaside as well, if there are any beaches, maybe areas where swimming is not recommended, dangerous tides, sharks… or are there nice places as well, worth visiting. Is the shore easily accessible? The shoreline area is more flat I guess, less hills there as I assume again, from maps…

You’re right, I didn’t include seaside areas because typically, that’s not what non-Italian travelers are looking for from the Tuscany region. You’re right that it has a lovely coastline, though!

A few popular beach towns in Tuscany include Viareggio and Forte dei Marmi. Livorno is a popular cruise ship stop, and has a historic fort right on the water. Don’t miss the view from Terrazza Mascagni if you go!

If you want to go further off the beaten path, the Tuscan island of Elba (where Napoleon was once banished to) is beautiful.

If you’re in a beach town, you’ll definitely have access to the sea!

Will be in Tuscany for four days and thinking one day each in Pisa, Florence and Montepulciano (or combine a couple (like Pisa/Florence). Can you suggest a good home base area? We will have a car – any suggestions for a couple of one day road trips (if we can combine P, F or M) to visit wineries, different towns, etc? So many things to see it’s hard to decide and are hoping you can help us out. Thank you so much!!!

Hi Collette,

If you plan to have a car, I’d recommend staying outside a city center and enjoying the countryside a bit. That’s the advantage of having a car in Tuscany!

I’d also recommend combining Lucca with Pisa–Pisa doesn’t take long to see, but Florence definitely takes a full day at a minimum assuming you want to go inside a museum, up a viewpoint, etc.

On the route from Florence to Montepulciano, Monteriggioni and Siena are great options (depending on which route you take). The Chianti area is also between the two, though it’s a bit more out of the way to access!

San Gimignano and/or Volterra would also make a great day, and would be enhanced by having a car.

Deciding where to stay can be fairly flexible, as all of those places can be visited as a day-trip from the others, but I’d choose based on your priorities, as you’ll have some long drives round-trip. The Siena area makes a great base if your priority is Montepulciano and towns like the Val d’Orcia. The Lucca area or Chianti area is lovely for accessing northern Tuscany (Florence, Pisa, San Gimignano, etc).

Ciao! Thank you so much for writing so much about Italy! It’s been very helpful while planning our upcoming Tuscany road trip. We’re planning to rent a car from Florence and are seeing a lot of negative reviews on all the cheaper Discover Cars rental companies. What rental companies have you used in the past and would you recommend them? Also, are there any we should stay away from? Trying to be budget friendly but also do not want hit with a bunch of fees after the fact. Thank you so much for your help!

Hi Natalie,

Happy to help!

Honestly, I could not even remember all the rental companies we’ve used in Italy, let alone in Europe. We’re not picky–we’ve used everything from big brands like Hertz and Sixt all the way to tiny local outfits that we spot on the ground. We’ve never been charged for damage, but we do take precautions.

Specifically, we ALWAYS thoroughly photograph and video (a full 360 video) the vehicle when picking it up, and we tend to buy the additional insurance as well. If you want to ensure there’s a 0% chance of being charged for anything, most companies offer a $0 deductible (in Europe, a deductible is called excess) policy. It’s an increase in the upfront budget, but offers a lot of peace of mind if it’s something you’re worried about!

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Tuscany Itinerary: See the Best Places in One Week (+Map & Tips)

By Author Jurga

Posted on Last updated: July 4, 2023

Planning a trip to Tuscany and not sure where to start and what’s the best Tuscany itinerary?

In our previous post, you could read about some of the most beautiful towns in Tuscany . In this article, you can read how to combine all those beautiful places (and some more) and create the perfect Tuscany trip itinerary that allows you to experience the very best of this picturesque region in one week.

How many days do you need in Tuscany

While you can see the main cities in 3-4 days, I recommend at least one week for Tuscany . This will allow you to see not just all the highlights of the best towns of Tuscany, but also to get a glimpse of the beautiful Tuscan countryside.

Below, you can find our suggested Tuscany itinerary that shows you where to go and what to see if you have one week in Tuscany. Read on!

How to see the best of Tuscany in one week

This Tuscany itinerary starts and ends in Florence. However, you can start and end in other towns and combine this trip with a visit to the other regions (e.g. Cinque Terre or Bologna ). This is really just meant to show you what’s possible and how to plan your time in Tuscany.

In order to see the very best of Tuscany and to experience some of its stunning landscapes, it’s best to visit the region by car. On the other hand, you don’t really need a car in the cities. Train connections between major towns in Italy are really good. So if you want to, you can visit some of the most beautiful towns using public transport only.

While this Tuscany itinerary is made assuming that you have a car, you can easily adapt it to your needs and your way of traveling. Just use this itinerary as a guide to the best places in Tuscany, how much time you need at each place, and how to best plan your trip.

At the bottom of the article, you can also find a map indicating all the places mentioned in this Tuscan itinerary. Read on!

One Week Tuscany Itinerary

Day 1 – florence.

Florence is one of the most beautiful cities in Italy and is not to be missed in any Tuscany itinerary.

One full day is the minimum that you need in order to see the main highlights of Florence . You can find more information, tips, and advice for visiting Florence in some of the more detailed guides to the city on our blog.

Not to be missed in Florence is the Cathedral (you can climb the dome of the Duomo as well), Ponte Vecchio, Accademia Gallery, Uffizi Gallery, and Palazzo Vecchio. If you have just one day in Florence, stroll the old town, check out the market, and walk to Piazzale Michelangelo for the best sunset view in Florence. Alternatively, have a drink at one of the best rooftop bars in Florence .

Stay in Florence for at least one night, in order to take full advantage of your time here. If you are traveling by train, I recommend a hotel close to the railway station. We recently stayed at Hotel Croce di Malta , an excellent mid-budget 4*hotel with a lovely rooftop terrace. If traveling by car, keep in mind that parking in the city is very expensive.

TIP: If you only have limited time and want to see the best of Florence in one day, be sure to book priority tickets for ALL the places you absolutely want to visit inside.

LEARN MORE: One Day in Florence

Day 2 – Florence to Siena

Leave Florence early in the morning and drive to Siena. Via Chiantigiana road SR 222 from Florence to Siena is very scenic, so you may want to take this road rather than a highway.

Spend the rest of the day exploring the beautiful town of Siena. Must-see in Siena is Piazza del Campo with its Palazzo Pubblico and the Mangia Tower, Siena Duomo (Cathedral), and the picturesque streets of the Old Town. 

TIP: Stay in Siena for 1 or 2 nights. Albergo Chiusarelli is one of the best picks in towns in terms of price/location/quality.

LEARN MORE: Best Things to Do in Siena

Day 3 – Val d’Orcia – Tuscan countryside

Here is a scenic road trip suggestion through the picture-perfect Tuscan countryside – Val d’Orcia – that you can take as a day trip from Siena.

If you have the time, you may want to spend a couple of days in this area, but one day is sufficient to drive through the scenic Tuscan countryside.

From Siena take the road SR2 to San Quirico d’Orcia. From here continue East along the SR146 in the direction of Montepulciano. This is the most scenic road in Tuscany – the one with the typical Tuscan landscapes you see in travel magazines and on postcards. 

Take your time to explore Val d’Orcia and visit at least a couple of charming little towns in the area: Pienza , Montepulciano , San Quirico d’Orcia , Monticchiello , Montalcino … Also the Abbey of Sant’Antimo is worth a visit.

With just one day in this region, I think I’d focus on Montepulciano, Pienza, and the countryside of Val d’Orcia.

TIP: If you are in Siena without a car, the best way to explore the Tuscan countryside is by taking an organized tour, e.g. this wine tour that brings you to Montalcino, Pienza, and Montepulciano from Siena .

READ ALSO: Best Things to Do in Montepulciano

Day 4 – San Gimignano and Volterra

San Gimignano and Volterra are both relatively small towns and their proximity to each other means that you can easily visit them in one day. 

San Gimignano , famous for its fourteen medieval towers has a tiny but very picturesque Old Town. It can get extremely busy during the day, so I recommend going there first thing in the morning.

One of the main places to see is Piazza della Cisterna. You can also climb to the top of the Torre Grossa.

Volterra has a great atmosphere in the evening, so it’s best to visit it later in the day. It’s a charming medieval town and it’s nice to just stroll the streets, check out some souvenir shops, and have a nice Tuscan dinner.

In my previous post, you can read more about what to see and do in San Gimignano and in Volterra .

TIP: One of the nicest and good price/quality hotels in Volterra is Hotel La Locanda . If you are on a tighter budget but want something really special, stay in Chiostro Delle Monache Hostel Volterra . It’s located in the 15th-century Franciscan monastery, has a great location, and free parking.

Day 5 – Pisa

Take your time to explore Pisa . Don’t limit your visit to the leaning tower of Pisa only! In fact, the leaning tower of Pisa is just one of the many monuments of Miracle’s Square. The Cathedral and the Baptistery are very impressive as well.

Pisa town center has no crowds and is very picturesque as well. Stroll the Arno River promenade and check out the Borgo Stretto, an old shopping arcade with many restaurants, cafés, and shops.

TIP: If you are touring around Tuscany by car, I’d advise not to stay in Pisa. Instead, drive to Lucca after you visited Pisa and stay there for two nights. Lucca has such a great atmosphere and several really nice hotels. They are located inside the city walls and so parking is not free (but possible). Check out  Hotel Palazzo Alexander or  Hotel Alla Corte degli Angeli .

Day 6 – Lucca

Lucca is our favorite town in Tuscany. You can see the main highlights in just one day, but you definitely won’t regret it if you choose to stay a bit longer. 

The main landmark is the city walls of Lucca which you can explore on foot or by bike. In fact, the best way to see Lucca is by taking a self-guided bike tour .

Piazza dell’Anfiteatro is another must-see in Lucca. Make sure also to climb at least one of the towers -Torre Guinigi or Torre Delle Ore for the best views in town. Here you can read more about what to see and do in Lucca .

TIP:  Take a food tour in Lucca – it’s a great way to explore the town and taste some of the typical local specialties.

Day 7 – Collodi, Pistoia, Prato, or the outskirts of Florence

There are several nice towns that you could visit between Lucca and Florence. Collodi, Pistoia, and Prato are all worth a detour.

We liked exploring the outskirts of Florence as well. You’re hardly out of the city, but the scenery is amazing. Take a road from Florence to Fiesole for stunning views and a beautiful Tuscan landscape.

Alternatively, you could easily visit Bologna. It’s located in the nearby Emilia Romagna region (so not in Tuscany), but is more than worth a visit if you find yourself in this part of Italy.

READ ALSO: Florence to Bologna Travel Info & Itinerary + Best Things to Do in Bologna

Where to stay for this Tuscany itinerary

Many people ask what’s the best area to stay in Tuscany . The answer really depends on what kind of trip you are planning.

If you are thinking of making a road trip in Tuscany , you can find my suggestions for hotels in each town in the day-to-day Tuscany itinerary above.

If, however, you don’t like changing hotels and packing your bags every day, you can also stay at one central location in the Tuscan countryside and take day trips from there. Sometimes you’ll need to drive an hour, sometimes two, so it’s not perfect, but it might still be easier and more relaxing, especially if you are traveling with kids.

TIP: If you want to stay in just one place for sightseeing, the best place to stay for exploring Tuscany would be the area close to Volterra or San Gimignano. It is very centrally located in Tuscany and is therefore ideal if you are looking to stay at just one hotel and explore the region by taking day trips. Here you can find the best deals for accommodation in Volterra and hotels in the San Gimignano area .

In fact, a few years ago we did just that when we were visiting Tuscany with our kids. We stayed at just one hotel in the Montaione area for 12 days and combined relaxing days by the pool with sightseeing. It worked well for us. You can read more in our best of Tuscany – itinerary from one central location post.

On our most recent trip to Tuscany, we were focusing on the area around Siena and Val d’Orcia, plus a few other places in Umbria too. For that, we opted to stay at this beautiful country house in Bettole.

There’s really not one ‘best’ spot to stay- Tuscany is way too big for that. So it all depends on which places you decide to visit.

Without a car: If you are not renting a car, the best places to stay for exploring Tuscany are either Florence or Siena. They both have good railway connections to the bigger towns and also a big choice of organized tours to the smaller villages in the countryside.

One week Tuscany trip itinerary map

Below, you can see an overview of this suggested Tuscany itinerary on the map.

Start in Florence, drive down to Siena, then on to San Gimignano and Volterra. Continue your trip towards Pisa and Lucca, and end in Florence.

Alternatively, continue to Cinque Terre, which is just a short ride from Pisa. Here you can find more information about how to see the best of Cinque Terre in one day .

Best Time to Visit Tuscany

Tuscany is a beautiful destination that has something to offer at any time of the year. That being said, the best time to visit Tuscany is in late spring or in early autumn. The very best months for sightseeing in Tuscany are May and September.

In the summer months, it’s very hot here. So if you are visiting in July or August, you may want to concentrate on the Tuscan countryside. A popular thing to do is rent a villa with a pool and make an occasional day trip to one of the smaller towns in the area.

Whereas the weather in late fall, in winter, and in early spring is more suitable for visiting the big cities rather than touring the countryside.

READ ALSO: Best Time to Visit Europe

So, this is our suggested Tuscany itinerary for up to one week. If you are planning a trip to Italy, make sure to check our Italy travel guide for more tips and travel advice for a big variety of popular destinations in Italy.

Alternatively, check our selection of articles below for more tips for a variety of destinations in Italy.

More tips for some of the most visited destinations in Italy:

• Best Things to Do in Rome
• Best Things to Do in Venice
• Best Things to Do in Milan
• Best Things to Do in Naples
• 2 days in Rome
• 1 day in Milan
• 1 day in Venice
• 1 day in Cinque Terre
• Tips for Visiting Rome
• Best Things to Do at Lake Como
• Bellagio, Lake Como
• Best of Lake Garda
• Best of the Italian Dolomites
• Emilia Romagna Region
• Hiking in the Dolomites
• Tips for Visiting Cinque Terre
• Amalfi Coast Itinerary
• Italian Riviera
• Best Day Trips from Naples

READ ALSO: Best Places to Visit in Italy

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Monday 26th of February 2024

What a fantastic blog! This has really inspired me! I am thinking to visit Florence and Tuscany for a week in mid-June.

After 2 nights in Florence, and having a car, what town would you recommend to stay as a base and then do day trips? In terms of day trips, a must visit for us are Sienna, Lucca and Volterra. And definitely a winery but without driving to it. Advice very welcome!

Tuesday 27th of February 2024

Hi Teddy, if you want to visit Sienna, Lucca, and Voltera, you could stay somewhere in the middle between all these towns and make sure there's a winery nearby. I quickly checked something for you in the San Gimignano area which is very central and fits your criteria. There are several wineries that you can visit in that region and many accommodations, so you can find places to stay within walking distance to one or the other winery if you like. For example, this agriturismo (Capanna 1826) is just near this vineayrd. From what I read in the reviews of this accommodation, they even include a visit to their vineyard for free if you stay there. But there are many more options. You just have to do a bit more research and see what's available for your travel dates. If you don't mind taking a taxi to one or the other vineyard, then it will be easier. Just pick a hotel you like and then see what wineries there are nearby. Also, the San Gimignano area is just one of the many, so it's just a suggestion based on the info you gave. If you are traveling in June, I'd book your accommodations asap.

Ann Marie Pugliese

Friday 6th of October 2023

Hello, this blog seems very helpful. I am traveling to Italy for the first time with 9 family members for 2 weeks in June. We were trying to fit in so much, but don't think it's feasible with so many people. Was hoping to visit Venice, Tuscany, Rome and The Amalfi Coast. Also, we are planning to stay in Air bnb's along the way. Just not sure if we should travel to each area and stay for 3 days or find 2 central hubs and take day trips? Any insight you can offer would be greatly appreciated. Thanks!

Monday 9th of October 2023

@Jurga, THANK YOU SO MUCH!! Greatly appreciate the information!!

Sunday 8th of October 2023

Hi Ann Marie, since these areas are located quite far from each other and each has so much to offer, I think that staying in each place for a few nights is indeed better than looking for two base locations. You could start with 4-5 days in Sorrento (from where you can easily visit Amalfi Coast, Capri Island, Naples, Pompeii, etc.), then move on to Rome for 3-4 days. From there, take a train to Florence which is a good base for Tuscany, Cinque Terre, and also Bologna. Depending on what you want to see, you could stay here for 4-5 days. And finally, take a train to Venice and stay there for 2-3 nights. You can find lots of information for all these destinations on our blog. See an overview of all articles on our Italy travel page. This 2-week Italy itinerary might also be helpful - just to see what's possible and how you could structure your time at some places. For Amalfi Coast, take a look at this guide. Good luck with the planning!

Sunday 18th of June 2023

Hi, I am considering a 3 night stay in Florence next Summer followed by a week in self catering accomodation somewhere on the coast (we will not be driving, therefore, will be making use of public transport when we transfer from Florence to our second destination). We love Sorrento, Taormina and the Lake Garda towns and are wondering where on the coast (quite manageable by train from Florence), would have a similar vibe / buzz (i.e lively atmosphere) to these places? We would obviously fly into Florence but would be happy to go home from a different airport.

My other option is to follow on from Florence with a week in self catering accomodation (definitely with a pool to cool off), within walking distance of one of the cities / towns in the region - but I'm having difficulty deciding between Siena. Lucca and San Gimignano (or somewhere else with a Sorrento type 'feel' to it!!).

Any suggestions / advice would be gratefully received

Many thanks, Becs

Tuesday 20th of June 2023

Hi Becs, as you can imagine, there are too many options for me to give you any kind of reasonable suggestion. :) Also, there are two coasts - with places like Rimini or Ravenna to the east or the Cinque Terre area, Ligurian towns, etc. to the west. I assume you mean west? Without a car, by the sea, you could split your stay between the Cinque Terre area and Italian Riviera (e.g. Portovenere or Monterosso al Mare for a few days followed by a few days in Rapallo or St Margherita Ligure. If you are looking for a bigger city - check out Genoa. If you rather stay in central Tuscany, then Siena is definitely a lot better than San Gimignano - in terms of transport, things to do, etc. San Gimignano is a tiny village. Lucca is also very nice but not as centrally located as Florence or Siena for all the most popular places. Bologna is amazing too, btw! You can also just stay in Florence the whole time and make day trips. It also depends so much on what exactly you want to see. Good luck! Whatever you choose, you can't really go wrong - the whole area has so much to offer.

Kim Hendrickx

Monday 17th of April 2023

We are a family of 5 and we will be going on a week trip to Tuscany at the end of this month, We will be staying in a country guesthouse in Montaione. This will be our base to see different places in Tuscany, as we have a car. Could you recommend which cities are best to visit to get a real feel of Tuscany. We also want to do some wine tasting in Chianti and Montepulciano, so any tips on nice wineries to visit would be much appreciated. Thank you.

Hi Kim, you can find all the suggestions in this article and you may also want to take a look at this guide to some of the best towns in Tuscany. This is by no means a complete list and there are dozens of amazing places. But if this is your first time, you'll probably not want to miss the main cities such as Florence or Siena, so you need at least 2-3 days for that. The rest really depends on your interest and preferences. Of the smaller ones, San Gimignano is really nice, also Volterra, Montepulciano, and Pienza. If you have even more time, you may want to check out Montalcino and Cortona, also San Quirico d'Orcia. A week will fly by! As for the wineries, we really enjoyed a very unique wine cave visit in Montepulciano last summer. You can find more details in our Montepulciano guide. And this is a really nice winery that you can visit in Chianti. The problem with winery visits is that it's not really something you can do (and enjoy wine) if you have to drive afterward. So ideally, you have a dedicated driver, find a winery close to your accommodation and take a taxi, or book a tour (but those are usually only available departing from big towns so not ideal unless you stay in Florence or Siena). But definitely check out the wine cellar in Montepulciano if you go there! You can also taste just a bit of wine and buy some to take with you to enjoy at your accommodation. Enjoy your trip!

Tuesday 21st of March 2023

Looking for some advice on my trip to Italy in Aug/Sept. Flying into Venice and staying for 3 days then headed to Florence/Tuscany region for 5 nights. We don't want to rent a car but want to go wine tasting and check out the countryside and maybe the hill towns. After the 5 nights we head to Sorrento for 4 nights and finish off in Rome. Looking for advice on where I should stay in Florence/Tuscany area. Should I stay a few nights in both places or stay in one place and do day trips by train? Where do I take the train from to end up in Amalfi? Any advise appreciated.

Hi Rosemary, some of the best places to stay in Tuscany when traveling by train are Florence and Siena. You can find plenty of Tuscan countryside/wine tours from any of these towns (see here for tours from Florence and here - from Siena). If you don't mind changing hotels, you can spend a few nights at each of these; otherwise, I would recommend staying in Florence. There are many nice hotels close to the station (just in the center too), and it's very easy to explore the city or plan day trips. At the bottom of this guide of the best places to see in Florence, you can find some hotel recommendations for this area. For the Amalfi Coast, you'll have to take a train to Naples (there are high-speed trains from Florence to Naples - see here for train schedules and to prebook your tickets). Here you can find our guide on how to get to the Amalfi Coast from Naples. Have a great trip!

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Tuscany travel blog — the fullest tuscany travel guide for first-timers.

Those who have been to Florence, definitely must have heard of the poetic countrysides of Tuscany (Toscana in Italian), Italy. Cycling around Chianti, enjoying premium wine, or visit the vast countrysides of Siena. But actually, the most beautiful countrysides in Italy are located quite deep below, they are Val d’Orcia and San Quirico d’Orcia which are always covered with a endless green color of meadows, vineyards and beautiful farms on highlands and in valleys. So, what to do and how to plan a perfect budget trip to the dreamland and paradise of Tuscany for the first-time? Let’s check out our Tuscany travel blog (Tuscany blog) with the fullest Tuscany travel guide (Tuscany guide, Tuscany tourist guide) from how to get there, best time to come, where to stay, best places to visit and top things to do to find out the answer!

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I never intended to go to Tuscany when knowing this is just the central Italian countryside, until I accidentally came to Florence and got lost in the scenes of villages, medieval towns, vineyards, olives groves with wineries, lush green vegetation. Tuscany instantly captivated me so that the first days of summer were surprisingly beautiful.

Tuscany travel blog: Overview of Tuscany

I have known Tuscany since I was a landscape photographer. That’s when I got to see the amazing photos of Val D’Orcia and San Quirico D’Orcia. If the natural beauty of Switzerland with mountains and rivers, then in Tuscany, it is majestic, poetic countryside, immense grasslands. The natural picture here is green in one color, gentle, tranquil and liberal, enough to inspire any lover or dreamer when coming here.

Tuscany blog: When to visit?

There are two beautiful times to consider for a roadtrip in Tuscany, which is from late April to mid-May, and autumn in Europe. In spring, flowers bloom everywhere in Tuscany, which is perfect for visiting the farms or large gardens. If you go in the fall and want to see the vast green prairies, you should go in early August, because at this time, local people will start cutting the grass and harvesting grapes. Then the hills will appear with a dry yellow color and not smooth.

• If you want to see sunflower fields, you must go after June and before September. From early September onwards farmers have already harvested seeds to make oil.
• The most beautiful time with green fields is around June and July. From August onwards, it has started to dry. From September onwards, the scenery have turned to yellow but romantic. However, July and August are the hottest months in Italy. You must bring sunglasses, hat and sunscreen. In the summer, even though it’s really hot, it will get colder in the evening. Especially if you go higher areas.
• In addition to summer, traveling to Tuscany from March to May is also okay, very green. However, it is still cold and there are no flowers at all.

Tuscany travel blog: Where to go, what to do?

To start exploring Tuscany, Florence is a must-visit destination. The capital of Tuscany in central Italy, Florence owns everything to be voted by many prestigious travel magazines as the most wonderful city in Europe. The whole city is a giant architectural style with pastel colors of walls and terracotta roof tiles of houses, each street corner seems to be a museum with untold stories. Florence deserves many fine words. If you’ve been here, you can’t help but visit the Florence Cathedral Duomo(Cathedral of Santa Maria del Fiore), the legendary Ponte di Vecchio, the Galleria dell’Accademia, and the Piazzale Michelangelo square.

From Florence, you can travel by train to many ancient cities and towns in Tuscany, or just 30 minutes by car, you can visit a nearest olive grove and vineyard. If your time is tight to make an itinerary, as Tuscany’s most developed tourist city, Florence offers you everything with countless day tours to pick and explore all of Tuscany.

Siena used to be a large city in the Middle Ages, so the architecture of Siena is still keep intact. In the middle of the city is the town hall with the horse racing square, every year the small districts in the city will bring their horses here to race to win glory for themself. If you go to Siena on Saint Catherine’s Day on April 29 every year, or the horse racing day, the districts of the city will hang their own flags. I was lucky enough to come to Siena on the occasion of St. Catherine’s day, so I saw countless flags hanging along streets, alleys, feeling like I was watching Game of Thrones.

Things to do in Siena include tasting the region’s famous Chianti wine, visiting Piazza di Campo square, Siena’s church which made entirely of marble and don’t forget to go inside the church to explore the Piccolomini library which is built by Pope Pius II. The architecture inside is overwhelming and for me this is the most beautiful church I’ve been visited in Europe.

San Gimignano

A medieval town with 14 towering stone towers. In medieval times, San Gimignano was likened to today’s Manhattan in terms of prosperity. San Gimignano is quite small so you can explore in an afternoon. But don’t forget to climb a tower for a panoramic view of Tuscany to the horizon.

To explore Siena & San Gimignano, you can book a tour in Florence, or book a tour through KLOOK , I found that when buying from KLOOK the price is cheaper, so just book it and the service is very good.

Located in Umbria, Assisi is a beautiful hill town. When hearing about a place that has existed since the Middle Ages, surely many tourists will think of a town forgotten by time, not very developed with narrow winding streets, narrow alleys, houses with stone walls and old painted wooden doors. However, unlike the imagination above, Assisi is one of the largest Christian centers in the world with beautiful churches. In which Basilica of San Francesco d’Assisi (Basilica di San Francesco d’Assisi) is the most famous cathedral in Assisi.

This ancient city is also known as a student city because there are many universities and colleges with many different disciplines. The most prominent is the University of Perugia, built in 1308, the University for Foreigners of Perugia and many other colleges such as the Academy of Fine Arts Pietro Vannucci.

Perugia is also famous as a cultural and artistic center of Italy with many festivals taking place all year round such as EuroChocolate festival, Umbria Jazz Festival, International Journalism Festival, …

Lake Trasimeno

When you come to Trasimeno, you can rent a house on a farm and experience the feeling of waking up in the sunrise of the Italian countryside. Make yourself a cup of hot coffee and make a delicious and light breakfast while enjoying the poetic beauty of Lake Trasimeno.

After that, you’ll have a full day of exploring and boating on the lake. If you go in a large group, you can also organize a picnic with dishes made from fresh ingredients at the farm.

Montepulciano

Although Montepulciano is a small town, the scenery here is extremely poetic and beautiful with brilliant sunflower fields. In addition, wine is also a famous specialty here. If you have stopped by Montepulciano, then come and enjoy wine at the bars here.

Like the Italian style itself, Lucca has a beauty that blends the modern and the antiquity of the time with fashion boutiques interspersed between immaculate ancient structures.

Lucca is also home to many famous composers such as Giacomo Puccini (with famous works of La Bohème and Madama Butterfly), Nicalao Dorati, Francesco Geminiani, Gioseffo Guami. With such a history, it is not surprising that the annual Lucca Summer festival is one of the most popular musical events in Tuscany.

In addition, Lucca is also the host city for the Lucca Comics & Games Festival, the biggest festival for comics, movies and games in Europe, attracting hundreds of thousands of fans to attend each year.

Pisa is a port city in the lower reaches of the Arno River. In Renaissance Period, Pisa was the second richest city after Florence. Today Pisa is a small city but has a unique artistic style and owns a unique architectural symbol in the world: the Leaning Tower of Pisa. From Florence, you take the 50-minutes train to get to Pisa. Then follow the flow of people to the Leaning tower of Pisa to visit.

The Leaning Tower of Pisa itself is so famous but it is only part of Pisa’s Central square. Visitors come here mainly just to take hundreds of pictures from the simple to the weird with the Leaning Tower. Personally, I like architecture, so I wandered around to see this small, sparsely populated city to understand more about the most important port city in Tuscany.

Not all of Tuscany’s hills and vineyards have the stunning coastline below. But Punta Ala is a great stop on the coastal area known as La Maremma.

Island of Elba

Elba Island (Isola d’Elba) is a romantic tourist island, located off the coast of Tirreno Sea, in the famous Tuscany country. Looking at Elba from above, you will have the feeling that the island looks like a small goldfish swimming in the sea.

Portoferraio – the main port town and also the capital of Elba – looks cute and gentle with its small houses painted in soothing pastel colors. The streets here are narrow, on both sides of the roads there are many colorful flower pots swaying in the wind, only the slopes are more pleasant than other central Italian cities such as Perugia, Siena, Assisi or Spoleto.

Enjoy Tuscan wine and olives

The Tuscan countryside can be seen from car, but to get a real taste of it, visit a winery and sample its fine wines. I stopped by Tenuta Torciano Winery and not only enjoyed more than 7 types of red to white wines but also used delicious vinegar and olive oil. These farms are not open to a single tourist, so you can book a tour in Florence to visit during the day, definitely a true Italian experience. There are two famous and savory Tuscan wines you should try called Sangiovese and Super Tuscan.

To experience this, you can buy a day tour in Florence, or book online through KLOOK to explore both San Gimignano and Siena.

Buonconvento

Buonconvento is a small town, just about 2-2.5 hours drive from Florence, this town is extremely peaceful, few people but has a lot of interesting things. It takes about 10 minutes to drive from Silvia’s farm (where I stayed) to the town center. Everything here is as peaceful as countrysides around it.

Another interesting thing not to be missed in this beautiful little town of Buonconvento is the delicious Gelato ice cream that we discovered located right next to Da Mario restaurant. Not only has delicious ice cream, but the salesman is also very cute, giving customers a lot of ice cream, the best Gelato I have ever tasted in Europe, the price is also cheaper than in other regions.

More things to do in Tuscany

In addition to visiting the Tuscany lush green prairies, there are many other places here that you cannot miss. It could be touring the small towns of the region, or going to the vineyards to enjoy fine wines.

Another route that you should refer to when traveling from Siena to Buonconvento is going through Asciano (please see on the map). On this road, the scenery on both sides is also extremely beautiful. The day I went, the grass here was almost cut, so the color could not be as beautiful as in the southern region. Alternatively, on the way from Buonconvento to Asciano, you can visit the Abbazia di Monte Oliveto Maggiore monastery. This is a monastery located on a high mountain with a beautiful view.

Another very beautiful place that you might consider visiting is La Foce garden located in Val D’Orcia. Entering this garden, you will feel like walking in a large royal garden of a palace, like a mix of Versailles palace and Tuileries Garden. In La Foce, the owner also has villas for rent, but the price will be quite high and require a minimum stay of 2 nights for each booking.

In general, with a travel time of only 2-3 days, it is difficult to fully enjoy the vast Tuscany region. If given the opportunity and conditions, I would love to stay longer than about 1 week. This place is extremely suitable for those who come with family, a fresh air and spacious space for everyone to experience together. Simply rent a large enough SUV, free to explore each road, small villages but hidden full of interesting things in this Tuscany region.

Tuscany travel blog: What and where to eat?

Enjoying pasta, pizza and wine as well as Tuscan cuisine is a fascinating experience you can’t miss! Like Italian cuisine in general, Tuscan cuisine is based on the use of the freshest and simplest ingredients of season including a variety of beans, cheeses, vegetables and fruits. And here are some suggestions for you:

• Crostini Toscani: The word crostini literally means bread, similar to a baguette, served with chopped chicken liver sauce.
• Panzanella (Tuscan-Style Tomato and Bread Salad) is a cold bread salad with the main ingredients including unsalted bread, tomatoes, red onion, basil, olive oil, vinegar, and salt.
• Lardo di Colonnata: This dish is actually pork lard produced in the town of Colonnata.
• Ribollita: Ribollita soup is one of the most popular winter dishes in Tuscany containing different types of cabbage, beans, onions, and carrots.
• Castagnaccio: It is a traditional Tuscan chestnut cake made with chestnut flour, very popular in the Apennine mountain region of Tuscany.

Tuscany blog: Suggested 2-day Tuscany roadtrip and how to get from Florence

As mentioned above, you can take the train to the countryside in Tuscany, but it will be quite inconvenient and take a long time. The most convenient is to rent a car in Florence and then self-drive to the south, through Siena and visit its beautiful countrysides. Rentingg a private car to drive can both be proactive in the schedule while you can go and admire the scenery on the roadside, stop whenever you like.

Details of my 2 day Tuscany itinerary:

Day 1: Took the car from Florence and drove down to Buonconvento, where I booked an overnight stay at a local farm. The itinerary will have to go through Siena so you can choose to go straight on the highway to Buonconvento because my main purpose is to visit Val D’Orcia. If you have time, you may not choose the highway but follow the SR222 road to visit more Panzano or Chianti. Dinner in town and overnight in Buonconvento.

Day 2: Early morning drive to visit two regions Val D’Orcia and San Quirico D’Orcia, which have the most beautiful scenery in Tuscany (in my opinion). Then come back, resting and exploring the farm Podere Salicotto that I chose as a place to stay. On the drive back to Florence I took the route from Buonconvento through Asciano and back to Siena to access the highway to return to Florence.

The route from Florence to Buonconvento has many stops to admire the beautiful scenery on both sides of the road. If your time is tight, you should choose the highway to go for faster, the traveling time for a 150km distance is only about 2.5 hours, the highway is very beautiful and the speed is stable.

After picking up my car from Locauto rental company I started driving out from the center of Florence. The street was not too crowded and easy to go, so you can rest assured, just go according to the law. Follow Google Maps and get out of the city to access the highway. From here running straight to Siena and continue to Buonconvento. One thing to note is that if you want to be fast, you should only take the highway, and you need to pay attention to the road because it is easy to go wrong on roads in town, make the speed will be slow a lot because these roads have many traffic lights, many cars make you cannot go as fast as on the highway.

Tuscany blog: Where to stay in Tuscany?

However, coming to Tuscany, you must stay at a beautiful farm in this region.

Along the romantic swath of Tuscany are vast countrysides known for its rolling hills, cypress trees, charming old towns, stone castles and along with numerous private farms. Each farm with hectare area with quite similar architecture. Houses are built of red bricks or can be called separate villas. It took me a whole week to choose for myself the best place to stay, which is Podere Salicotto’s farm.

I had a very detailed review of this property here , it’s very wonderful, you can also refer to and book via Agoda.com or Booking.com .

The capital of Tuscany is Florence, so it has the largest number of rooms of all types and vary prices as well as making it easy for you to travel to many cities, towns nearby, choose the right day tours to explore beautiful Tuscany. Plus, if you want to try the local experience, it’s also easier to rent an Airbnb in Florence when you’re sharing a house with a local.

But if you like the feeling of waking up in the countryside, Siena is the better choice because the city is small and located among the vast fields of Tuscany.

You can find more, check rates, availability & book for hotels in this city on Agoda.com or Booking.com .

Tuscany travel guide: Getting to Tuscany

You should go to Florence first because it offers many choices of hotel rooms and also convenient to travel to its surrounding areas. Florence’s services are also easy to find and relatively inexpensive. Buses can be booked at GoEuro.com and train tickets can be purchased at booths at the central station, choose Treinitali or Italo train.

Take a day tour from Florence

I recommend taking a tour to Siena because the cost is quite cheap but there are many interesting experiences for only 44 euros. In addition, you can book a tour to Cinque Terre to explore the equally wonderful Liguria region.

Tuscany blog: What to buy as a gift in Tuscany?

Florence is very famous for its leather goods, you just go to the ancient bridge, there are many leather goods shop with hundreds of years old to buy. In addition, Chianti red wine is also a popular choice.

Souvenirs such as statue of David or the leaning tower of Pisa are also things that tourists often buy as gifts.

Some best day tours, trips, activities and transfer services, tickets in, from and to Florence you can refer to

• Duomo Monumental Complex Direct Access Ticket in Florence with Guided Visit
• Florence Duomo, Baptistery, and Museum Tour
• Small Guided Tour with Fast Track Entry to Duomo and the Secret Terraces
• Florence Duomo Skip-the-Line Tour with Balcony & Dome Access
• Uffizi Gallery Guided Tour with Fast Track Entry
• Accademia Gallery Skip-the-Line Ticket in Florence
• Val d’Orcia Tour from Florence
• Pisa Half Day Tour from Florence
• Florence Bike Tour with Food Tasting Experience
• Florence City Sightseeing Hop-On Hop-Off Tour (Open Top) and Leonardo da Vinci Museum Skip-the-Line Ticket
• Tuscany Day Tour with Lunch and Wine Tasting from Florence
• Rome to Florence Day Tour
• Chianti Afternoon Tour from Florence
• Excursion to Pisa through the Tuscan Countryside from Florence
• Florence Dome Tour with Skip-the-Line Ticket + Free Souvenir Old Polaroid Photo
• Florence Accademia Gallery Skip-the-Line Ticket with Tour

Are you looking for more top things to do in Florence: Tours, activities, attractions and other things? Let’s check it out here . And Italy travel guide here .

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How to Experience the Best of Tuscany: 12 Travel Tips for Italy’s Heartland

I love Italy. (Who doesn’t?) And after years of traveling all up and down “The Boot,” one area in particular keeps drawing me back: Tuscany, Italy’s heartland. In this country notorious for its challenging idiosyncrasies, Tuscany is the one place where everything is in perfect, serene harmony. What’s not to love? Amazing art — check. Gregarious locals — check. Epic history — check. Stunning landscapes — check. Incredible food — check. Entertaining cities — check. Gelato — super-check.

Six months ago, as I was plotting out my summer travels, I volunteered to do some guidebook-updating work in Italy: Orvieto, Assisi, and, oh, I don’t know, maybe a few other places… like, say… Tuscany?

Jennifer Madison Davis, the managing editor who keeps our guidebook production schedule humming like a finely tuned machine, eyed me suspiciously. “ Tuscany , eh?” She remembers all too well that the last time I went to Tuscany on a guidebook-updating expedition, I came home with a chapter twice as long as the one I left with…including a nine-page, fresco-by-fresco, self-guided tour of an obscure monastery tucked deep in the Tuscan hills. “Now, why might you want to go to Tuscany?”

I cut to the chase: “Look, I just want to go. I promise that I won’t get carried away. I’ll just update what’s already there. Honest!”

She went for it. And now I’m back in one of my favorite places on earth.

When I’m in the bucolic heart of Tuscany, I have trouble getting to sleep. I’m amped up, like I’m a toy-crazy little kid and every night is Christmas Eve. My head spins with the sublime experiences of the day that just ended, and my pulse quickens thinking about what tomorrow will bring. It’s like I’m on some sort of globetrotting drug…freebasing the essence of peak travel. And when I get home, it all feels like some sort of surreal fever dream. (Or maybe it’s just all the pecorino and truffles.)

Our tour company just announced a brand-new Best of Tuscany Tour for 2020. Impeccably designed by Heather Lawless and other experts and guides in our Tour Operations department, it weaves together 12 days of vivid Tuscan experiences. Comparing notes with Heather as she’s put this tour together, I’m both gratified to see many of my personal favorites on the list…and impressed by how many entirely new-to-me experiences Heather has sniffed out. I’ve led many Rick Steves’ Europe Tours, but I’ve never been on one just for fun. That’s about to change — my wife and I are signing up to be tour members on the Best of Tuscany in 2020.

Why is Tuscany my first choice for a European vacation? I think it’s because it’s so experience-rich. And, after years of visits, I’ve assembled this “best of” list — a running tally of the intensely pleasurable experiences that put Tuscany in travel’s all-time hall of fame. Here my top dozen things to do in Tuscany — whether you’re going with a tour, or on your own.

Bask in Stunning Scenery

One of Tuscany’s calling cards is its mind-bending scenery: Sumptuous, extravagantly green, undulating farm fields that look like a painting. Hillsides grooved with twisty rural roads and lined with pointy cypress trees. Stately churches, humble chapels, rustic farmhouses, and circles of trees perched just so in resplendent tableaus. But it’s not just the landscape. Beauty is in the DNA of Tuscans. One Siena native recently told me that Tuscans consider themselves the inheritors and stewards of a centuries-long legacy of beauty. Every tree that’s planted, every farmhouse that’s restored, every road that’s re-routed — it’s all carefully considered not only on practical or economic merits, but also on aesthetics.

Here’s a list of the best viewpoints in Tuscany — where you can snap postcard-worthy photos of your own. 

Have a “Zero-Kilometer” Meal on a Farm

“Farm-to-table” was a thing in Tuscany centuries before it became trendy among 21st-century American foodies. Tuscans have always been keenly aware that the same produce can taste very different, depending on the specific conditions in which it’s grown — soil, sun exposure, micro-climate, and so on. Many Tuscan farms invite visitors to learn about how they make their wine, olive oil, and prosciutto. You can walk through the vineyards, check out the olive press, and step into the hut where giant ham hocks hang on racks, slowly curing in the dry air. The ultimate farm experience is having a “zero-kilometer” meal — meaning that all of the ingredients are sourced from within less than a kilometer of where they’re eaten. A meal like this is an interplay of earthy flavors, where the taste of each item enhances, and is enhanced by, the taste of every other item. At a zero-kilometer meal, you’re not just eating food. You are, in effect, eating a very specific place .

Read about a zero-kilometer meal you can experience just outside of Montalcino.

Ogle Great Art in a Forgotten Church

During the 1400s and 1500s, the Tuscan art world had a very, very, very deep bench: Michelangelo. Da Vinci. Raphael. Donatello. And many others (Botticelli, Brunelleschi, Giotto, Vasari, Fra Angelico) who don’t share their names with radioactive turtles. But many of my favorite works don’t hang in famous Florence museums; they’re hidden away in off-the-beaten-path towns and overlooked countryside churches. Two examples stick out in my mind: In Arezzo, you can step into the Technicolor apse of the town church to see luscious frescoes by Piero della Francesca. And deep in the Tuscan countryside, at the abbey of Monte Oliveto Maggiore, the cloister is gloriously frescoed with fascinating works by Luca Signorelli and Il Sodoma — offering both a lesson in the life of St. Benedict, and countless examples of two dueling artists whose egos ran amuck 600 years ago. Best of all, because 99 percent of travelers have never heard of these sights, they’re all yours.

Read more about these two overlooked Tuscan masterpieces…and why Il Sodoma may be the quirkiest character in art history. 

Meet a Real-Life Artisan

Because of their deep dedication to beauty, many Tuscans have devoted their lives to mastering a craft — creating something with care and precision, while carrying on a proud aesthetic tradition going back centuries. If you take the time to slow down and seek out these modern-day masters, you’re left with indelible memories: Roberto the alabaster sculptor. Cesare the coppersmith. Adamo the vintner. Giulio the steak maestro. Nicola the gelato artist. (All of these craftspeople — and others — are recommended in our Rick Steves Florence & Tuscany  guidebook ). If you want something done just right, with precision artistry and care…find yourself a Tuscan.

Here are four Tuscan artisans you can get to know in Montepulciano.

Sleep (and Eat) at an Agriturismo

Italy has more than 20,000 agriturismi : farms that are subsidized by the government to introduce travelers to a unique pastoral lifestyle. Agriturismi  are required to be working farms (that is, they must actually produce something) while also offering accommodations, restaurants, educational activities, or all of the above. Settling into an agriturismo , you meet fascinating locals and feel close to the earth. It’s like summer camp for grownups. We recommend our favorites in the  Rick Steves Florence & Tuscany  guidebook , and you can also find a comprehensive list at Agriturismo.it .

Read more about one of our favorite agriturismi : Cretaiole, just outside of Pienza.

Play “King of the Castle” atop a Fortified Tower

Tuscany is crazy about its towers — whether it’s the turreted townhouse of a wealthy local bigwig in San Gimignano, the fancy facade of a humble town hall in  Montepulciano or Volterra, the towering City Hall of Siena, or the famously tipsy bell tower at Pisa’s Field of Miracles . Tuscany’s towers date from a time long before there was an “Italy” — when this area was a loose collection of city-states and wealthy families, all vying for the upper hand. Towers both served a defensive purpose and stood as status symbols for proud communities. That architectural legacy is a boon for today’s travelers, who enjoy climbing to the tops of these towers for views over the rooftops and rolling hills of Tuscany.

Learn more about the roots of Tuscany’s obsession with towers. 

Lick Artisanal Gelato

My favorite gelato artist in Tuscany, Nicola Sgarbi, is a perfectionist…a total gelato snob. He makes several batches fresh every morning, so they’re not even available until mid-day. And then, in the late afternoon, when they’re gone — they’re gone. But if you’re lucky enough to hit his shop when he’s all stocked up, you’ll enjoy his explosively flavorful creations. Nicola goes all-in on seasonal flavors (creamy basil), surprising combinations (carrot-ginger, kiwi-spinach), and top quality. Nicola’s gelaterie — in Pienza and in Montepulciano — are just two of many great places to try top-quality gelato in Tuscany.

Get to know my favorite gelato artist, Nicola. Or study up on how to sniff out the best gelato wherever you go, anywhere in Italy.

Get to Know the Etruscans

Hold on! Stick with me. Don’t let your eyes glaze over. I know — when compared to things like gelato and Michelangelo and pappardelle alla bolognese , it’s hard to get excited about the people who lived in Tuscany 3,000 years ago. But the Etruscans may well be the most fascinating prehistoric people you’ve never even thought about. Not only did their advanced culture lay a foundation for the ancient Romans, and ultimately for all of Western Civilization. Not only did they warn Julius Caesar about the Ides of March and give their name to the region of Tuscany. But, despite all of this, the Etruscans left virtually nothing tangible behind — shrouding their distant civilization in mystery. A few tragically under-visited museums around Tuscany display what does survive, including delicate artwork (like the hauntingly beautiful statue called The Evening Shadow, or L’Ombra della Sera) and evocative funerary urns, showing Etruscans with big personalities lounging at an eternal banquet for the gods. Give the Etruscans a little bit of your touristic attention…and you may just find yourself entranced by the stories they have to tell.

Here are a few of Tuscany’s top Etruscan artifacts, and where to find them.

Sail Away to Elba for an Island Getaway

So much of the traveler’s Tuscany is rolling farm fields, world-class art, stony hill towns, and hearty, meaty cuisine. For a change of pace, consider hopping a ferry for the one-hour crossing to the little isle of Elba. I went there earlier this summer (researching a new chapter for the upcoming 18th edition of our  Rick Steves Florence & Tuscany  guidebook ) and was totally charmed by the place. Elba is synonymous with Napoleon, who was exiled here for 10 months after his bitter defeat. Today, touring his now-shabby residences is poignant. But there’s much more to this rocky little island: pebbly beaches, hardworking harbors, seafood dinners, and a truly terrifying gondola ride. Elba makes for a relaxing island escape from a busy Tuscan itinerary.

If you’re intrigued by the idea of splicing a little Tuscan seaside into your trip, check out my full report on Elba.

Take a Cooking Class

“Tuscan cooking classes” are an entire subgenre of travel. I’ve blogged more about that subject than I have about entire countries. That’s because this region has an outrageously appealing food culture — ranging from big, sloppy plates of pasta to refined high cuisine. And there’s a cooking class for every taste: hand-rolling pasta in a casual, family-friendly setting; going to the private residence of a talented home chef to assemble a seasonal feast; hanging out in the kitchen of a Michelin-star chef ; and everything in between. Also remember to look beyond the kitchen. While not technically a “cooking class,” going on a truffle hunt in a Tuscan forest — chasing after a smart-as-a-whip dog who has the scent of those precious deposits — gives you a whole new appreciation for a plate of truffle pasta.

For inspiration, here’s a rundown of my all-time-favorite Tuscan cooking classes.

Linger on a Convivial Piazza and Join the Passeggiata

Tuscany is all about community. And there’s no better place to commune with the Tuscans than on the piazza, or main square — particularly in the late afternoon, when families are out strolling…doing those aimless laps that they call the passeggiata. Each Tuscan town’s piazza has its own special character: Florence’s is in the shadow of the towering Palazzo Vecchio. Pienza’s is a perfect Renaissance cube. Lucca’s follows the footprint of an old Roman amphitheater. And Siena’s — the best of them all — is a vast, slanted, brick-paved oblong that hosts a twice-yearly horse race. These are places where it’s actually worth paying way too much for a fancy aperitivo for the privilege of just hanging out at an al fresco table and getting serious about people-watching. Then, hop out of your chair and join the informal people parade as it promenades through the traffic-free town center. Become a temporary Tuscan. Come to understand the local saying, il dolce far niente — “the sweetness of doing nothing.”

Looking for the ultimate Tuscan piazza? Check out this “best of” list.

Visit Off-Season — and Have the Place to Yourself

Tuscany — like other popular European destinations — can be extremely crowded. Fortunately, the region remains entertaining off-season, when things are much quieter. One of my all-time favorite trips to Tuscany came in late November . It was chilly but not cold, a crop of winter wheat blanketed the hillsides with a green vibrancy, seasonal ingredients (like chestnuts, persimmons, and truffles) infused each meal with autumnal flavors, and — best of all — we could simply show up spontaneously at museums and restaurants that would have been mobbed a few months before. While off-season travel comes with its downsides (cooler weather, earlier closing times, fewer daylight hours), visiting Tuscany outside of peak season can be a great plan for flexible travelers.

Here’s what to expect in off-season Tuscany.

There’s so much more that I haven’t covered here — cycling around Lucca’s ramparts , taking a dip in the Roman-era hot springs of Bagno Vignoni, doing a tasting of high-end “Super Tuscan” wines at a Florentine enoteca — but hopefully this is enough to stoke your wanderlust for your next trip to Tuscany.

What have I forgotten? What are some of your favorite Tuscan experiences?

This roundup is designed to inspire you to pack your trip with quintessential Tuscan experiences. For all of the details on everything described here, check out our Rick Steves Florence & Tuscany  guidebook .

Or…let someone else do all that planning. My inspiration for this piece is the arrival of our just-announced Best of Tuscany in 12 Days Tour , which weaves together, in some form or another, virtually all of the experiences I’ve described here. I’ve already signed up for one of the 2020 departures — just for fun (no work this time, I promise). Maybe I’ll see you there.

21 Replies to “How to Experience the Best of Tuscany: 12 Travel Tips for Italy’s Heartland”

Cameron, Just wondering if you, Sarah Corfield, or any of the guides (including Rick) have been to ‘Basco della Ragnaia’, just outside the village of San Giovanni D’Asso? It’s an interesting art garden of an eccentric (U.S., I think) artist, open to the public. I thought the village was fun, also.

It’s a great garden. The story behind that garden is very special. We had one of our most memorable lunch up at the castle restaurant in town.

Hi, Rick. Yes, I have been to that lovely garden! It is, as you describe, somewhat eccentric and an enjoyable place for a little walk. In fact, I went there once after a truffle hunt (with the hunter and his dog), simply to learn about the garden. Suddenly the dog got excited, started digging, and discovered a truffle right in the middle of a pathway through the park. San Giovanni d’Asso itself is a nice little town (and very striking from afar, since it perches on a little plateau). Many great truffle-focused eateries there…

My trip was in 2005, Loved it, wish I could live the there, did almost everything you suggested except cooking class, not enough time.

We stayed in an Agriturismo outside of Orvieto and had the most amazing farm to table communal meals there with guests from all over the world. Highly recommend!!

What was the name of the place you stayed? It sounds lovely. Thanks

What was the name of that farm to table? We are looking close to Orvieto!

Touring Tuscany in May 2016 was a dream…I was lucky to have a seasoned traveler to Italy with me……..trying hard to pack in Florence, Cinque Terre, followed by a leisurely week in Lucca ( followed by 5 days in Montepulciano )where we rented a lovely apartment and got to know the local baker and the veg &fruit lady…… we rented bikes and rode the rampart surrounding the town…..but the very best experience was a live concert of Puccini arias in a lovely old church ( since Puccini spent some time in Lucca….the town has claimed him as their own… with concerts one evening a week pretty much throughout the year…..front row….we could most reach out and touch the performers…..breathtakingly beautiful ! 4+ stars !

We attended that same opera while visiting Lucca. Then went on to have one of our most outstanding dinners while in Italy. It was one of our best memories of that trip.

We love Tuscany…have been to Cesare’s workshop where he made a gift for us. We stayed at a marvelous B &B in Montalcino. And a wonderful Agriturismo just outside Assisi….we had a glorious view of Assisi and could easily hear the church bells pealing. As an added bonus we were able to throw open our shuttered windows….it was April and the nights were cool…and one of the resident cats hopped through the windows and spent the night in bed with us!

I’m so excited cuz I’m booked on the September departure of the Tuscany tour. Thank you for this new tour and thanks so very, very much for all the wonderful experiences I’ve had with your tours. You have changed my life in such a wonderful way that I can’t even express. Happy Travels!!!

I want to move there! Looking into it…

Hi Steve, your Italy book recommended one of my favourite little towns, “civita di bagnoregio” if someone wants to travel off the beaten path. I found it a magical place to visit.

My wife, Sandy, and I have been to Italy several times and Tuscany is our favorite. Our last visit was in April, 2017 and we stayed two weeks in a condo located in the serene countryside near Assisi. We rented a little Fiat 500 and enjoyed day trips from our home base, buzzing along the narrow country roads throughout Tuscany and Umbria. We chose one destination per day, soaking in the scenery and ambience of each, visiting farmers markets and vineyards, and enjoying an inexpensive lunch (usually per Rick’s recommendations). Of course, we always indulged in a mid-afternoon gelato, too! During each day’s jaunt, we loved speaking with the locals in our limited Italian and they seemed to love (and get a kick out of) our attempts to do so! We usually returned late to our little condo and I cooked up the fresh veggies and pasta that we purchased for a few Euros along our journey, enjoying it with a little Tuscan vino and fragrant bread. Over dinner, we discussed our plans for the next day’s adventure. This was our favorite visit to Italy and our takeaways were: 1) spend a couple of weeks in one homebase location (if possible); 2) rent a vehicle for sightseeing in Tuscany; 3) Learn a little Italian and speak to the people you meet; 4) Try doing some of your own cooking with the amazing, fresh Tuscan produce; 5) Enjoy a daily glass of Tuscan wine and, of course, a gelato!

My wife and I have been to Siena three times, but the most memorable visit included two days before and after the New Year, especially because of the magnificent 360-degree video projection in the palazzo leading up to the New Year countdown. As fate–and the surprising Italian planning would have it–the video was completely Beatles themed, if I recall correctly. Everyone in attendance sang along to the group’s many hits and without a hint of an Italian accent. The thing that made the night most memorable, however, was that in the two or three hours before the celebration, a steady rain had been falling and we had waffled on whether to go to the party. We’ve always been glad that we decided to go. However, I’m still upset with the local guy who kissed my wife at the stroke of midnight before I did. (I just checked my records, and the end of this year will mark the tenth anniversary of that visit.)

PS: We don’t go to Europe without a Rick Steves’ book to guide us.

We have been to Cretaiole several times and it is our favorite place on earth. Isabella taught us to make pici. One visit was at Halloween, a fabulous time of year to go! The harvests and cooler air, the scent of roast chestnuts in Pienza, the warm uncrowded waters of Saturnia were unforgettable.

Tuscany and the Cinque Terre are our favorites. One night in Vernazza, we sat on the cliffs with a view of the full moon over the Mediterranean! And fireflies (none where we live) just added to the magic.

Ugh, five weeks from today I was heading to Italy to start the new Tuscany tour. Oh well. Hope to do it in the future!

Looking for recommendations for moving about Tuscany in Oct 2021. We are a group of 6 and we would like to spend 2-3 nights in area as we move from Cinque Terre to Florence. We think we’d like a driver/ vehicle so we could travel about together. To rent our own van doesn’t make sense. Also favorite lodging is appreciated.

Hello Cameron, Thank you for this delightful article. We all know how 2020 turned out but thankfully there is 2022 coming up and we signed up for this tour. I’ll be scouring more through the links you posted so we can maximize our time in Tuscany next year. Can’t wait!

Thank you Cameron..love all the information. Our 7th Rick Steves tour coming up! We just signed up for Best of Tuscany in May, 2022. We’ve been on the wait list..got in..so excited..celebrating my 71st B’day!

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Tuscany Road Trip: Bucket-List Tuscany Itinerary

September 2, 2022 //  by  Follow Me Away //   4 Comments

If you are writing a Tuscany road trip itinerary, you are in for a real treat!

Tuscany is one of the most famous and beautiful regions of Italy, for a good reason.

Whether you have been to Italy multiple times or this is your first visit, the Tuscany region will take your breath away.

Planning your trip to Tuscany at the last minute?

Make sure to book your hotels and tours in Tuscany in advance to ensure availability. Things sell out as your dates get closer! Here are our top picks for Tuscany:

Top Tours And Tickets To Book In Advance:

• Uffizi Gallery Skip-The Line Ticket (Likely to sell out!)
• Chianti Wineries Tour (Includes food and wine tasting)
• Pisa/Siena/San Gimignano Tour (Includes lunch)
• Leaning Tower Of Pisa Ticket (Skip the line!)

Top Picks For Places to Stay In Tuscany:

• Hotel Palazzo San Lorenzo & Spa (Breakfast included!)
• Villa Nottola (Budget option in Italian villa)
• Relais Piazza Signoria (Sweeing Florence views)
• Hotel Art Atelier (Florence city center)

From cute, ancient cities and good food, to magically remote hot springs and rolling fields of green, Tuscany has something to offer everyone.

One of the best things to do in Tuscany is to take a road trip to see it all!

For this itinerary for Tuscany, we are not specifying an amount of time so you can make the drive as time allows in your schedule.

Driving this route straight through would take you 8 hours, which really isn’t that long, all things considered!

If you only have a few days in Tuscany, then modify this road trip route to fit that length of time.

If you have a week, consider spending a few days in each location to really take in what each area of Tuscany has to offer.

No matter what amount of time you choose to explore this magical region of Italy, your Tuscany trip will not disappoint!

Don’t forget to check out our Detailed Road Trip Packing List so you don’t forget any essentials for your trip!

Get ready to plan the best itinerary for Tuscany!

Table of Contents

Getting To Tuscany

Florence is the birthplace of the Renaissance and the perfect place to begin your Tuscany road trip!

To get to Florence, we recommend flying into one of the large nearby international airports in either Venice, Rome, or Milan.

Remember to  check out Skyscanner to find the best and most affordable flights into Italy. We use this tool to discover the best flights for our trip because you can easily compare rates. 

From whichever city you fly into, you can simply take the high-speed train to Florence. This is where you will begin your road trip.

Alternatively, you can rent a car in the city you flew into and then drive to Florence. 

Whether you are spending 10 days in Italy , have a little more time like 2 weeks , or are renting a car and planning an Italy road trip , all of our itineraries include a stop in Tuscany!

We highly recommend spending time exploring this beautiful region, even if it means planning another trip!

This is one of the BEST ROAD TRIPS IN EUROPE so you are in for a real treat and a memorable experience!

Getting Around During Your Tuscany Road Trip

Since this is indeed a road trip, you will be renting a car or the set of wheels of your choice for driving in Tuscany.

If you are only traveling with a backpack or if you are making Florence your home base, you may even choose to take a motorbike instead of a car.

We recommend a car as it is easy to store your belongings during the trip and makes for a more enjoyable ride.

You can rent your car in a large nearby city, or wait until you are in Florence.

It may be cheaper to rent in larger cities such as Rome and then drive to Florence for the start of your Tuscany road trip.

Keep in mind that renting a manual transmission will usually always be cheaper than an automatic one when renting in Europe.

It is the law to use your headlights at all times when driving in Italy. Make sure to have them switched on before you leave.

Finally, some of the roads you may drive on during your time in Tuscany will be toll roads.

Make sure to come prepared with extra money for the tolls. Tolls in Italy can add up quickly so we want you to be prepared!

We always book our vehicles through Auto Europe . We find Auto Europe is often the best and most comprehensive booking engine when we plan our European trips, including Tuscany road trips.

Is it Difficult to Drive Around Tuscany?

Driving in Tuscany is NOT difficult! As long as you know the rules of the road, drive safely, and pay attention, you will be fine.

Be prepared for roundabouts, narrow streets, toll roads, and speed cameras.

Pay attention to speed limits to avoid getting a ticket. In towns, the speed limit is 50 km/h, or about 30 mph.

Outside of town, it goes up to 70-90 km/h, or about 43-55 mph. On the Autostrade motorway, it can get up to 130 km/h, or 80 mph.

It is best not to drive in towns. Instead, park your car and walk.

In most towns, driving in the historic center is banned. Look for “Zona Traffico Limitato” or ZTL signs to avoid fines.

Lastly, do not forget to include a GPS with your car rental, or bring your own. This will save you headaches later!

The Ultimate Tuscany Road Trip Itinerary

Stop 1: spend time in florence to begin your tuscany trip.

You will begin and end your Tuscany road trip in Florence.

This city is so beautiful and relaxed when compared to other larger cities in Italy such as Rome, Milan, and Venice.

You will feel welcome the moment you arrive. Even if you only set aside one day in Florence , you are going to love it! 

While you are in Florence, make sure to check out the famous “David” statue at Galleria dell’Accademia.

You are going to want to buy tickets ahead of time to beat the lines.

Next, we highly recommend checking out Boboli Gardens which is a beautiful ancient garden overlooking the city.

Click here to check out our photoshoot in Boboli Gardens! 

You should make time to visit the Duomo which is the large Basilica in the center of town.

You can’t miss it and the outside is so beautifully done. It is one of the best things to do in Florence .

Make sure to wear modest clothing if you want to go inside.

Finally, spend time walking the Florentine bridges such as Ponte Vecchio. Relax with some gelato as you watch the sunset.

You can spend anywhere from 1-3 days exploring Florence at either the beginning or end of your Tuscany road trip itinerary.

We highly recommend booking your tickets in advance to beat the lines and save money:

Book Here:  Boboli Gardens Skip The Line Tour

Tickets Here:  Duomo Skip The Line Tickets And Dome Tour

Book Here:  Timed Entrance Ticket For Michaelangelo’s David

Stop 2: Visit Poppi For Your First Wine Tasting

Located around an hour and a half outside of Florence, Poppi is a stunning little gem of a city. This is your first taste of Tuscan wine culture.

We all know you are going on a Tuscany road trip for the beautiful views, quaint towns, and of course, wine, so why not kick off the itinerary with all three in one place?

Be sure to stop at Brancaia Winery for a tasting and tour. This is a great afternoon activity, especially if you leave a bit earlier on your Tuscany road trip from Florence.

You will be able to tour the winery and taste some delicious wine, before heading off for dinner.

We even have an entire post on the Best Tours In Tuscany if you want more suggestions! 

The town of Poppi also features a remarkably well-preserved 13th-century castle that towers over the entire city.

Be sure to visit the Castle of Counts Guidi during your time in Poppi. Then marvel at the many small churches that sit in and around the town as well.

There are many fantastic castles in Tuscany that you should see and this is one of them!

If you drive out into the distance and stop and look back, you will see rolling green hills and the town in the background.

This is the perfect photo point if you are looking to capture some of the romance of Tuscany!

It is also one of the best places to visit in Tuscany by car!

Where to stay in Poppi

Parc Hotel . Check Prices On Booking.com

Stop 3: Get Cultured In Arezzo

Just 45 minutes from Poppi, Arezzo is a wonderful stop on your Tuscany road trip because there is so much to see and do!

The city is home to so many monuments, churches, monasteries, and viewpoints that you would have to spend a month just to see them all!

It is also the wealthiest city in Tuscany due to its history in gold smithery!

Arezzo is a larger town than Poppi, so plan on spending a bit more time here.

It is also easier to find hotels if you are looking for where to stay in Tuscany!

If you are looking for the best viewpoints, we highly recommend visiting the beautiful hilltop Arezzo Cathedral.

If you are a photographer, this is a great vantage point to shoot from!

The Basilica di San Domenico contains the 13th-century “Crucifix” painted by Cimabue which is still in fantastic condition and a wonderful work of art to see.

Every Wednesday and Sunday, from April to October,  I Giorni del Vino Winery opens the doors to the public. If you are a wino, you will be able to visit and see the behind-the-scenes of this working Tuscan winery.

Arezzo provides many options for fun during your Tuscany road trip so there is something for everyone!

You will agree this is one of the best driving in Tuscany locations!

Book An Arezzo Wine Tasting Tour

Book An Arezzo Cooking Class

Where To Stay In Arezzo:

Budget: AC Hotel Arezzo, a Marriott Hotel . Check Rates On Booking.com

City Center: Graziella Patio Hotel . Check Rates On Booking.com

Stop 4: Experience Siena, A UNESCO World Heritage Site

Victoria grew up going to a Catholic Church called “Saint Catherine Of Siena.”  Of course, the famous Catholic Saint is actually from Siena, Italy!

She petitioned for peace and was instrumental in persuading the Pope in Avignon to return to Rome back in the 1300s.

Siena is a GREAT place to make your “base” as you explore a few of the below stops on your Tuscany itinerary.

The next 3-4 stops are all within 30-60 minutes from Siena. This is the perfect day trip distance, and you can really see some great sites.

Our suggestion is to stay a bit outside of the Siena downtown if you are using it as a base as parking in Siena is a massive pain if you are staying in the heart of the city! 

DO NOT make the mistake we did and drive into Siena. You can get fined, and you are NOT allowed.

You are not allowed to drive in downtown Siena, aka the old town, but your GPS does not know this and will take you anyway!

Keep an eye out for signs in Italian which look like red stop signs.

They are not big and this is intentional as we have been told this is an “easy” way for the city to make money off unsuspecting tourists.

If you have been to any famous museums, you have probably seen multiple paintings featuring Saint Catherine which makes your visit to Siena even more meaningful!

Siena is a relaxing stop on your road trip through Tuscany, and it is just an hour away from Arezzo so the drive is quick and easy.

This is also a lovely base for spending your honeymoon in Tuscany and the city really comes alive at night!

During your time in Siena, we highly recommend exploring the historic city center which is a UNESCO World Heritage Site.

If you found Florence too crowded, then you are going to love Siena.

The Duomo, also known as the Siena Cathedral, is a must-see and not easy to miss.

If you love palaces, Palazzo Chigi-Saracini is the place to be.

And if you are looking for more history on Saint Catherine Of Siena, the Piccolomini Library is home to frescos depicting her.

Book Your Siena Walking Tour Here!

Get Fast Entry Into The Siena Duomo!

Book Your Sunset Tour of Siena!

Where To Stay In Siena Italy:

There are many great places to stay in Siena.

Whether you want to stay in the heart of downtown within walking distance of all the historical sites, or you would prefer to stay on the outskirts to have easy access to other day trips!

Check out some quick suggestions below! 

Affordable: Villa Piccola Siena . Check Rates On Booking.com

Mid-Range: Hotel Athena . Check Rates On Booking.com

Luxury: Grand Hotel Continental Siena . Check Rates On Booking.com

Stop 5: Visit Famous Photography Spots Near Asciano

Asciano is about a 30-45 minute drive south from Siena and it is a teeny tiny town. The town isn’t really the best stop, although it is typically Tuscan!

The best thing to see in Asciano is the nearby Tuscan villas and manors that are beautiful and stunning.

You probably have seen them all over Instagram or in travel guidebooks as well!

As you are heading south out of Asciano, you will see the tree-lined roads appear higher up on a hill to your right.

Type in the GPS coordinates below and you will be well on your way to seeing one of the best photography spots in all of Tuscany! 

There is no official parking spot for this fabulous view. That being said, you can easily pull over on the side of the road.

The side of the road is well-worn from all the other people who have pulled off. While this is a “popular” spot it is in no way famous or as well-known as other views on this Tuscany road trip itinerary! 

The best time to stop here is during the sunset as the views are incredible! 

GPS Coordinates: 43.20083 11.58947

Google Maps Location

Stop 6: Drive Through The Stunning Val d’Orcia Countryside

This is the best of the best Tuscan countryside that you do NOT want to miss!

Val d’Orcia is an incredible place to visit, and you can do it on a day trip from Asciano or Siena if you don’t want to spend multiple days down here.

If you do, that is okay too and it is the best place to visit in the entire region!

There are many stops you can make in Val d’Orcia on your Tuscany road trip itinerary, and we are going to break down the best ones for you!

Even if you don’t want to have “a plan” that is okay! You can simply drive around and enjoy the gorgeous countryside!

Don’t forget to add this place to your Tuscan countryside itinerary!

Tuscany Groves

While you are in this region, you will pass by these very unique and interesting shaped trees.

They are the traditional cypress trees but they are planted in a circle.

This almost looks as if it had been planted for an ancient ritual of some sort and has become a lovely place for people to visit when they are driving through this part of the country! 

These unique trees are located just south of the small town of Torrenieri so make sure to put in the GPS coordinates below and then keep an eye out for them when you pass through this town! 

GPS COORDINATES: 43.06401  11.55827

The Chapel of the Madonna di Vitaleta

The Chapel of the Madonna di Vitaleta is another wonderful stop in this region of Tuscany!

Once you are finished with the circular trees, head to this tiny chapel located among the rolling hills.

This is one of our favorite stops on your road trip through Tuscany because it is so unique, and you don’t see it on the top of many itineraries. 

If you really want to catch a wonderful sunset, this is the perfect place to do it!

It was built in 1533 and two rows of Cypress trees flank it.

It is located in this UNESCO World Heritage region and although small, makes for a striking and memorable stop while you are in Tuscany. 

Stop 7: Monteriggioni Is A Quick But Beautiful Stop

Monteriggioni is one of the quicker stops on your Tuscany road trip, but worth the visit as you head along to your next stop.

Depending on how much time you have in Tuscany, you can choose to visit Monteriggioni as a day trip from Siena as the small town is only 25 minutes away.

This is why we think Siena is a good base to visit both Asciano and the Tuscan countryside as well as the northern parts of Tuscany as well!

Everything is within 30-60 minutes which is the perfect driving distance! 

You can also choose to hit Monteriggioni on your way to your next stop and just get out and walk around for a few minutes or a few hours.

If you have more time to spend and love cute, Tuscan villages, you can even choose to spend the night here and escape the larger cities!

There are also tons of lovely Tuscan villas that you can rent out to spend the night for a very affordable rate!

Monteriggioni is a walled castle city that overlooks the region.

Stop and explore the watchtowers and walls before heading to Chianti Sculpture Park for some modern art.

The way Monteriggioni blends the ancient with the modern is what makes it such a unique stop on your Tuscany road trip itinerary!

If you are a photographer, you are going to love this location as it looks like it is out of a postcard.

It is one of the most beautiful Tuscany scenic drives!

Where To Stay In Monteriggioni:

Mid-Range: Romantik Hotel Monteriggioni . Check Rates On Booking.com

Stop 8: Explore Colle Di Val D’Elsa And Day Trip To San Gimignano

Colle Di Val D’Elsa is a beautiful city in the province of Siena and just a short drive away from Monteriggioni.

Colle Di Val D’Elsa is a truly medieval hilltop town in Italy and it is very well preserved.

If you are looking to shorten your Tuscany road trip, Colle Di Val D’Elsa is just 30 minutes away from Siena and 45 minutes away from Florence.

If you are in either city and want a quick Tuscany getaway, Colle Di Val D’Elsa is the perfect place to visit!

While you are in Colle Di Val D’Elsa, we recommend taking a short day trip or driving up to San Gimignano.

It is just 25 minutes away from Colle Di Val D’Elsa, but a little off the main road that the rest of your Tuscany road trip itinerary will be following.

San Gimignano is one of the most visited towns in all of Florence and is also known as “The Town Of Fine Towers.”

There are 14 towers that remain out of the 72 that were built in the 12th century and they are a beautiful sight to behold.

If you are looking for something a bit different, you could visit the Museo della Tortura which showcases all sorts of historical facts about medieval torture!

Explore San Gimignano & Taste Some Wine On This Tour!

Book Your Sunset Tour of San Gimignano

Where To Stay In Colle Di Val D’Elsa:

Affordable: Hotel Palazzo San Lorenzo & Spa . Check Rates On Booking.com

Stop 9: Visit Volterra For An Authentic Tuscan Experience

To visit Volterra on your Tuscany road trip, you will continue down SR68 from Colle Di Val D’Elsa.

If you put these three cities in the map, you will see why it makes sense for San Gimignano to be a day trip from Colle Di Val D’Elsa.

You can continue straight from Colle Di Val D’Elsa to Volterra during your road trip in Tuscany.

Not that all towns in Tuscany aren’t authentic, but Volterra really provides the romantic feel you are looking for in the region.

Volterra is actually one of the oldest cities in Europe, dating from the 7th century!

It is very well preserved and enclosed in an ancient city wall that dates back to the 4th century.

Not much has changed since the town was built, which is why we recommend stopping at Volterra during your Tuscany road trip if you are looking for a truly authentic and ancient Italian experience.

Make sure to spend some time exploring the Medicean Fortress and the great Roman Theater.

If you are a foodie, make sure to try Zuppa di Volterra which is a delicious local dish! You won’t regret adding it to your itinerary for Tuscany!

Book Your Volterra Tour Here!

Where To Stay In Volterra:

Budget: Casa Mosaico . Check Rates On Booking.com

Good Location: Hotel La Locanda . Check Rates On Booking.com

Stop 10: Experience The Ligurian Coast In Livorno

We don’t know about you, but we  love the water and the Ligurian Coast is some of our favorite stretches of coastline in the world.

The Ligurian Coast is set right on the Mediterranean, and you are in for a real treat when you come to this part of your Tuscany road trip itinerary.

After days of seeing fields of green, ancient cities, and wineries, the refreshing breeze of the sea will prepare you to finish out your Tuscany vacation!

Livorno is a port town with a medieval fortress, like most other towns in Tuscany.

We highly recommend visiting the Terrazza Mascagni which is a seaside waterfront terrace, similar to a boardwalk, that overlooks the Mediterranean.

This is the best place to watch the sunset during your Tuscany road trip and you really should take advantage.

If you are looking to step away from history for a moment, you could visit the lovely Livorno Aquarium for a change of pace.

This is also a great stop if you are completing this Tuscany road trip itinerary with small children.

Finally, if you are looking to head to the beach, Cala del Leone is the place to stop for a picnic or a swim if the weather is warm.

Book Here To Tour The Majestic Views of The Ligurian Coast! 

Where To Stay In Livorno:

Affordable And Nice: MAX Hotel Livorno . Check Rates On Booking.com

Great Reviews: Grand Hotel Palazzo Livorno . Check Rates On Booking.com

Stop 11: Visit Famous Places And Hidden Gems In Pisa

No Tuscany road trip itinerary is complete without a stop in Pisa!

You would be living under a rock if you haven’t heard about the famous Leaning Tower Of Pisa, and since you are road-tripping Tuscany, you just have to stop.

This famous tower is one of the best things to do in Italy !

Now, of course, you can’t stop at the Leaning Tower Of Pisa without taking a tourist-filled cheesy photo so just get it over and done with from the start.

We promise we won’t judge you!

You are going to want to book your entrance to the Leaning Tower Of Pisa in advance so you beat the lines, especially if you are visiting during the summer months!

Besides the Leaning Tower Of Pisa, there are so many other things to see and do in Pisa which makes it a worthwhile stop on your Tuscany road trip, even if you hate tourist traps.

Make sure to stop at Pisa Cathedral, Piza Baptistery, and Knight’s Square at a minimum during your time in the city.

You can see Pisa in a day, so relax in Livorno and then take on the crowds in Pisa in one day.

Skip The Line With This Ticket To The Leaning Tower of Pisa!

Book Your Pisa Tour Here!

Visit Tunnel Di Pini

After you run around the Leaning Tower Of Pisa, you may want to head out into nature.

Tunnel Di Pini is the most fantastic tree tunnel in the WORLD!

We have been to pretty much all of the ‘famous’ tree tunnels on Instagram, from the Dark Hedges (wasn’t a fan!) to the one in Point Reyes (love it!) but this one TAKES THE WIN! It is better than any tree tunnel ever! ⁣ ⁣ Tunnel Di Pini is located literally 5 min drive from the Leaning Tower Of Pisa in Parco Regionale Migliarino – San Rossore!

When you arrive at the park, there are three roads.

Take the road that is straight in front of you and leads directly to the ocean. Peek at your GPS if you aren’t sure which way the ocean is!⁣ ⁣ Eventually, the road will close and you have arrived! Pullover and park!

The road for the tree tunnel is VERY, VERY long, probably over a mile!

We found better photography was near the beginning of the road as the trees were fuller.

You can walk the whole thing if you want some exercise and time in nature!

This national park is a must-see stop on your Tuscany road trip while you are in Pisa that many people don’t think about!

Why not see this Italy hidden gem with your own eyes?

Where To Stay In Pisa:

Affordable Luxury: Allegroitalia Pisa . Check Prices On Booking.com

Budget Option: AwesHome Hanging Gardens . Check Prices On Booking.com

Stop 12: Get Off-The-Beaten-Path In Pistoia

As you drive from Pisa to Pistoia on your Tuscany road trip, feel free to stop along the way at any cute village or shop that catches your eye.

Pistoia is one of the least visited towns in Tuscany. It is a great way to wrap up your Tuscany road trip after the hustle and bustle of Pisa.

Pistoia is famous for its world-renowned chocolatiers. The city isn’t touristy  at all so you will have the chocolate all to yourself.

Make sure to stop for a glass of delicious wine to go with it and enjoy an authentic Pistoian snack!

The Cathedral of St. Zeno is located in the center of town and was built in the 12th century.

The bell tower and colorful facade make for a stunning architectural design. San Giovanni Fuorcivitas is one of the prettiest buildings in Pistoia and you shouldn’t miss the exterior design.

It is actually quite similar to the Duomo in Florence so when you visit, see if you recognize the design.

This building is made out of brick while the Duomo is constructed out of different materials on the outside, but it is still quite similar and striking.

Pistoia is a wonderfully relaxing way to end your itinerary for Tuscany without the noise and crowds of larger cities.

Book Your Private Walking Tour of Pistoia

Where To Stay In Pistoia:

Great Reviews: Hotel Patria . Check Rates On Booking.com

Affordable But Nice: Hotel Piccolo Ritz . Check Rates On Booking.com

Where To Stay In Tuscany

As you can imagine, Tuscany is actually a HUGE region of Italy!

We have provided you with multiple places to stay at almost every stop on this Tuscany itinerary!

Some stops, such as Siena or Florence, may be better to use as a “base.” Then you can take day trips to other locations.

If you prefer “slow travel,” you may want to stay the night in many towns around Tuscany as you drive only for a little bit each day.

This will allow you to enjoy your stay even more and spread out the time that you have to spend! 

We have an entire article on Where To Stay In Tuscany if you are looking for specific recommendations for each region or want to go into more detail.

We also have a post on the Best Tuscany Villas including tips on how to book your villa in Tuscany.

Villas in Tuscany are actually way more affordable than they seem so you are in for a real treat!

Packing Tips For Your Trip To Tuscany:

Here are some of our favorite items you should consider packing for your trip to Tuscany!

These are essential travel items we use and love, and you should make sure to consider them for your travels. 

A  concealed travel pouch  may be one of the most important items you bring with you! This  unisex RFID-blocking concealed travel pouch is  lightweight and comes in several colors.

It has lots of organization to give you peace of mind. You can keep your most valuable documents safe and secure next to your body.

If you have a pouch already you may not want to or need to invest in a new one. If it does not come with RFID protection , these  RFID  sleeves  would be handy to prevent identity theft.

This configuration comes with enough passport and credit card sleeves that the entire family would be protected.

They are slim too, so they will easily fit into your current pouch or wallet. These are the kind our family uses not only when traveling but at home as well.

If you have a camera on your packing list, you need to add additional  memory cards  to your list as well.

Unless you are packing a computer for your trip, you will not be able to upload photos and clear your existing memory card.

Purchasing additional memory cards   cost under $20  and take up no space in your luggage.

Having a backup can have the potential to save you a lot of heartache if something goes awry!

There is nothing worse than coming across that perfect moment and then finding out you don’t have enough space to capture it on your camera!

Similarly, if you are planning to capture your trip on a smartphone, we beg you to bring some way to back up your memories.

The best way to do this is with a portable smartphone flash drive. A flash drive is a small storage device you can connect to your smartphone and then safely and easily download the photos onto this device. 

If you are planning on taking a lot of pictures with your phone, you will definitely want to consider an  external charging battery .

This  Anker high-speed phone charging battery  is the exact one we carry with us on all of our trips .

It can be used on a variety of phones, not just an iPhone like we have. And wow is it fast!

We like that it holds its charging capabilities for several uses so we do not have to worry about it while out and about.

And if we forget to recharge it at night, it will still be good to go the next day.

My mom was never a fan of  packing cubes  until she tried them out! Now she is sold .

These Bagail packing cubes   are  the exact ones she uses whenever she travels and she travels a lot.

She cannot believe how much more organized she is now! And she will never leave without them anymore.

We never leave home on a trip without our  Bobble filtration bottle.

The 18.5-ounce size is perfect for travel. It will fit nicely in the pocket of a backpack or your purse.

Also when filled with water, it is not too heavy to carry. And the Bobble carbon  filter  ensures fresh clean water whenever and wherever you fill the Bobble. You can find  filter replacements here. 

Perhaps you are traveling a long distance and packing space is at a premium.

Then this  set of collapsible silicone foldable water bottles  would work well for you. They don’t take up much space in your suitcase at all.

You will want to bring a  backpack or daypack  with you to store snacks, your water bottle, phone, extra clothes, etc.

This   foldable water-resistant backpack  would be great. It is very affordable and is available in many color options for you to choose from.

The fact that it folds down into a zippered pouch will make it easy to pack.

Perhaps you need a more substantial  backpack  for your international travel.

This  antitheft backpack   has a charging port, is water-resistant, and can comfortably carry up to a 15.6″ laptop.

It comes in a range of colors to choose from, and it is inexpensive as well. 

We all need to  protect our eyes  from the sun’s harmful UVA/UVB rays.

These  unisex polarized sunglasses   come in a lot of lens colors and frame designs and are extremely affordable too.

If you are fond of the  aviator-style of sunglasses  these polarized aviators may interest you.

We like polarized sunglasses because they remove the glare of the water and help you to see things more clearly. 

Don’t forget to bring along a  universal power adapter  if you are traveling abroad.

This  worldwide   power plug  is a great example and will charge your phone at the end of your busy days.

And this  world traveler adapter kit   can charge several devices at the same time.

This is what you will need when there are several people traveling in your group or if you bring several electronic devices on your trip that require charging at the same time.

Tuscany Road Trip Map

Sometimes, seeing a route visually is much easier! That is why we put together this Tuscany road trip itinerary map just for you!

This way, you can see where each Tuscany itinerary stop is located around the map.

We recommend downloading this map “offline” to the Google Maps app on your phone before you leave on your Tuscany road trip.

This makes it very easy for you when you are in Italy and your phone service may not be great.

You can simply go to your map which will work the same way as if you had internet.

We love using Google Maps offline and it was very helpful during our own Tuscany road trip itinerary!

Click Here For Google Map Of Tuscany Road Trip Driving Map

If you are looking for a breakdown of the individual stops, you can check out the map below as well!

Within the article, if there was something that was difficult to find, we included the Google Map location as well as GPS coordinates to make it easier for you to find! 

Click Here For Google Map Of Tuscany Road Trip Stops

Planning a Tuscany road trip doesn’t have to be stressful.

We hope with our guide, you will have a wonderful Tuscany vacation you will remember for a lifetime.

Keep in mind you can choose any and all of these Tuscany itinerary stops depending on the amount of time that you have to spend.

The entire route takes about 9 hours. You could do the entire thing in 2-3 days if necessary if you don’t spend a ton of time in each location.

You could also spend a week completing this route. Either way, we know you are going to love this driving itinerary for Tuscany during your trip to Italy.

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Reader Interactions

March 10, 2019 at 6:53 pm

Hi V & T, So nice to find your site. I will be driving from Rome to San Gimignano next month w/my daughters . Is this itinerary realistic? Any additions or suggestions for things to do or places to eat are appreciated. Leave Rome on Thursday am , stop in Tarquinia or Porto Santo Stefano for lunch. Continue to San Gimignano. Sleep in SG. Tour the town Friday am. Drive to Livorno tour the town return to SG. Saturday drive to Pistoia tour the town. Leisurely drive back to Rome. Thank you Carol

August 4, 2019 at 3:21 pm

Thank you for the tips, can you share the exact location where the last picture was taken?

August 4, 2019 at 6:18 pm

It is the Cathedral of Saint Zeno in Pistoia!

August 30, 2019 at 6:27 am

I have one day in Livorno and would like to travel obrigada those small roads tjat we see on the movies Is it there ? And also where is the picture before the last? Thankyou

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Tuscany road trip | across cypress roads and vineyards

Imagine a picture-book perfect countryside with cypress avenues, olive trees, and vineyards wherever you look. While you cruise around, you let down the window and feel the warm wind dancing up your nose, carrying a scent of orange blossom. On your Tuscany road trip you dive into the sweet Italian life. As the sun slowly lowers, those soft-colored hills, dotted with old villas and medieval towns, gleam as pretty as postcard motives. Time for a glass of wine!

Table of contents

Which places to visit on your Tuscany road trip?

Northern tuscany, firenze (florence).

To do in Florence:

• Walk across Ponte Vecchio – the iconic bridge with houses on it
• Walk up to or take an e-bike tour to Piazzale di Michelangelo for the best view across the city, especially for sunset when it’s tinted in orange light
• Join a free walking tour – to learn more about the historic place
• Visit the cathedral Santa Maria del Fiore – one of the most beautiful cathedrals in Italy
• Visit the Uffizi – the famous gallery showing many of Da Vinci’s stunning pieces of art
• Join a Chianti wine tour and tasting  – to try some of the best Italian wines in the gorgeous Chianti hills
• Learn how to make Pizza and Gelato – a unique experience at a farmhouse outside of Florence

Hotel recommendation for Florence: Liberty House Firenze

In Manuela’s small hotel, you’re in the best hands. She takes great care of her little gem and her guests and it’s just a 20-minute walk to the center of Florence. You can feel the warmth of her place the minute you arrive. Also, her homemade breakfast is amazing!

• Visit Torre Guinigi – this tower gives you the perfect panoramic view across Lucca with several old oak trees on top
• Walk across the ancient city walls “Mura di Lucca” – You don’t have to do the entire 4 km. And you don’t even have to walk. You can rent bikes or just take a seat close to one of the gates.
• Stroll through the old, cobblestoned alleys to Piazza dell’Anfiteatro – as you enter the oval-shaped piazza you get a hint of the feeling it must have been entering the Roman theater
• Acquedotto del Nottolini – Take a short walk outside of town and admire this old aqueduct that used to carry water to the town. The perfect photo spot!

Hotel recommendation in Lucca: L’Iris B&B in Terrazza

You will love this wonderful rooftop terrace where you can enjoy your breakfast on top of a lovely little Tuscan house. It’s in a perfect location just within the city walls, so you can easily explore Lucca on foot. You can even rent bikes.

• Take a stroll – Explore the steep alleys by strolling around
• Walk up to the castle Castello dei Conti Guidi – to enjoy the view on the stunning countryside
• Visit the Leonardo da Vinci Museum  – What would be a visit to da Vinci’s birthplace without learning something about him?

Agriturismo recommendation close to Vinci: Agriturismo Spazzavento

This beautiful Tuscan house just a few kilometers from Vinci is the perfect stopover on your road trip around Tuscany. Here, you stay with a lovely family who produce their own wine and olive oil. Don’t miss the wine tour with Daniele. And afterwards, you can cool down in their wonderful pool.

• The Tower – Make sure to get a Skip-The-Line ticket for the Leaning Tower
• The historic center – Don’t miss lingering through the winding alleys of the historic center
• The river – Take a walk along the river Arno
• Outside of Pisa – Stop by the Via del Gombo in Parco San Rossore, a beautiful cypress avenue

B&B recommendation close to Pisa: Vecchio Granaio

A wonderful small, family-run Bed & Breakfast with a large green garden and a pool. Here you’re a bit further from the touristy hot spots of Pisa, so you can recharge after exploring all the surrounding highlights of Tuscany.

Central & southern Tuscany

San Gimignano

• Climb up Torre Grosso – A true highlight is the view across the town and its surrounding landscape from this tower.
• Take the effort to queue at Gelateria Dondoli – to try the world-famous and awarded ice cream
• Vino – Try the Tuscan white wine Vernaccia di San Gimignano & stop by the closeby Vineyard Teruzzi & Puthod.

B&B recommendation in San Gimignano: Terra d’Ombra Bed&Breakfast

The breakfast view of the Tuscan landscape on top of this lovely terrace is probably unbeatable. Although this B&B is set in a beautiful historic building, the rooms are modern and bright. You can walk into the center of San Gimignano in just a few minutes, but you can also use this B&B as a great base to explore more of Tuscany.

• Climb up the 400 stairs of Torre del Mangia – for a panoramic view across the city
• Allow yourself to get lost – to take some time to look at the small details on the historic monuments, such as the animals marking which district you’re in
• Take the marvelous “Porta di Cielo” tour of the dome’s roof
• Visit the Piazza del Campo – a busy fan-shaped square where both locals and tourists like to spend time
• Enjoy dinner in the Chianti vineyards

Hotel recommendation in Siena: Podere Il Pero

Set in a beautiful historic Tuscan house, the lovely hosts of this small hotel will make you feel right at home. It’s decorated with much love for detail and you can enjoy the wonderful garden anytime you want. From here, it’s also just a 20-minute walk into Siena’s center, but you can park for free.

Montepulciano

• Visit the underground city – to see its caves and tunnels
• Stop by the lovely Piazza Grande – the town’s main square
• Join a Vino Nobile wine tasting – such as the free tour and tasting by Azienda Agricola Ercolani

B&B recommendation in Montepulciano / Val d’Orcia: CUGUSI BnB

A wonderful rural house with a scenic view of Montepulciano. Tiziana, the host is extremely helpful and has lots of recommendations for the surrounding area. There’s also a small shop where they sell local products such as wine and cheese.

Val d’Orcia & Asciano

• Drive around – It’s all about the landscape over here, so take some time to drive from one cute village to another and stop on the side of the road whenever you catch a special view.
• Montalcino – Visit the cute hilltop town
• Try the delicious Brunello di Montalcino wine – to get a true taste of the area
• Visit the Cipressi di San Quirico – where the traditional cypress trees are planted in a circle

Tuscan beach time

Hidden gems in Tuscany

Hidden gems in northern tuscany.

Apartment recommendation in Pistoia: Il CortilettoPistoia

A beautifully decorated apartment just outside of Pistoia’s center, where you can park for free on the calm street. You can feel the host Elisa’s love for details in this beautiful apartment, the perfect base to enjoy this hidden gem in Tuscany.

Greve in Chianti

Apartment recommendation in Poppi: Podere La Casaccia

This is a true calm little oasis just a 10-minute drive from Poppi. You can use the lovely pool to cool down after a day of exploring the area’s highlights and recharge in the garden.

Time for wine tastings

Hidden gems in central & southern Tuscany

Agriturismo recommendation near Bolgheri: Tra gli Ulivi, Chiappini

A family-run Agriturismo with a vineyard where you can also join a wine tasting. The Tuscan flair spreads all across the site. The pool is awesome but so is the love for every single detail in this stunning house. And the breakfast is a dream come true.

B&B recommendation in Arezzo: Il Piccolo Cavour Charming House

A small but pretty hotel with four lovingly and modernly furnished rooms with a balcony and a view of the old town of Arezzo. The breakfast is great and you can park nearby (for a fee).

Monteriggioni

Colle di val d’elsa, tuscany itineraries, enjoy the road.

Enjoying the landscape in Tuscany

Tuscany Itinerary 7 days

7 days round trip starting and ending in florence (suggestion 1):, florence (2 nights)  ⇨ vinci ⇨ lucca (1 night) ⇨ pisa ⇨ montepulciano (1 night) ⇨ val d’orcia / asciano ⇨ siena (2 nights) ⇨ san gimignano ⇨ back to florence.

• Florence: The capital of Tuscany is a great start for your trip, especially if you arrive by plane. After 2 days in Florence, you can pick up your rental car.
• Florence ⇨ Vinci Start your Tuscany road trip with a short distance and a day trip to Vinci.
• Vinci ⇨ Lucca After a morning/afternoon in Vinci, head on to Lucca where you can enjoy dinner, spend the night, and use the next morning to explore.
• Lucca ⇨ Pisa In case you feel like seeing this tourist magnet, you can stop in Pisa, as it’s quite close to Lucca.
• Lucca/Pisa ⇨ Bolgheri After spending your morning in Pisa, be ready for a longer drive down the E80 along the coast. Feel free to spontaneously stop wherever you feel like. A great stop is Bolgheri. Don’t take the highway, because the idyllic E80 is so much more fun.
• Bolgheri ⇨ Montepulciano Once you turn inland after your stop in Bolgheri, it’s time for the typical Tuscan countryside. This route is one of the most beautiful parts of your Tuscany itinerary.
• Montepulciano ⇨ Siena Spend the night and a relaxed day in Montepulciano, before driving to Siena. I’d suggest driving through Val d’Orcia, Val d’Asso or Asciano, as this area is extremely beautiful. Then, spend two nights in Siena, as there’s so much to see.
• Siena ⇨ San Gimignano On your way back north, San Gimignano is the perfect stop, as it’s a small town.
• San Gimignano ⇨ back to Florence In case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car. You could add a stop in Greve in Chianti, if you’d like to. If you came all the way with your own car, why not add another few stops such as Volterra or Arezzo on your way back north?

Map of 7-day Tuscany itinerary suggestion 1 (click for interactive map)

7 days round trip starting and ending in Florence (suggestion 2):

Florence (2 nights)  ⇨ greve in chianti ⇨ arezzo (1 night) ⇨ montepulciano ⇨ val d’orcia (1 night) ⇨ montalcino ⇨ siena (2 nights) ⇨ colle di val d’elsa ⇨ san gimignano (1 night) ⇨ back to florence.

• Florence: Just as in the first suggestion, start your Tuscany itinerary with two days in beautiful Florence.
• Florence ⇨ Greve in Chianti Pick up your rental car and drive down 45 minutes to the wine region Greve in Chianti.
• Greve in Chianti ⇨ Arezzo After spending your morning or afternoon in Greve, head on to Arezzo where you can enjoy dinner, spend the night, and use the next morning to explore.
• Arezzo ⇨ Montepulciano Now, it’s time to head further south with a stop in Montepulciano.
• Montepulciano ⇨ Val d’Orcia After a morning or afternoon in Montepulciano, dive deep into the Tuscan landscape around Val d’Orcia where you spend another night with stunning surroundings.
• Val d’Orcia ⇨ Montalcino Beautiful Montalcino is the perfect stop-over to spend a few hours before driving to Siena.
• Montepulciano ⇨ Siena Spend two nights in gorgeous Siena, and soak up this beautiful gem.
• Siena ⇨ San Gimignano On your way back north, the small town San Gimignano is the perfect stop.
• San Gimignano ⇨ back to Florence In case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car. If you came all the way with your own car, you could add another stop such as Volterra or even Lucca on your way back north.

Map of 7-day Tuscany itinerary suggestion 2 (click for interactive map)

Tuscany Itinerary 10 days

10 days round trip starting and ending in florence:.

Florence (2 nights)  ⇨ Vinci ⇨ Lucca (1 night) ⇨ Pisa ⇨ add Bolgheri & a beach stop (1 night) ⇨ Montepulciano (1 night) ⇨ add Val d’Orcia (1 night) ⇨ Siena (2 nights) ⇨ add Monteriggioni or Colle di Val’dElsa ⇨ San Gimignano (1 night) ⇨ back to Florence

Florence (2 nights)  ⇨ Greve in Chianti ⇨ Arezzo (1 night) ⇨ Montepulciano ⇨ Val d’Orcia (1 night) ⇨ Montalcino ⇨ Siena (2 nights) ⇨ Colle di Val d’Elsa ⇨ San Gimignano (1 night) ⇨ add Bolgheri (1 night)  ⇨ add Pisa ⇨ Lucca (1 night) ⇨ add Vinci or Pistoia ⇨ back to Florence

Florence (2 nights) ⇨ Poppi ⇨ Arezzo (1 night) ⇨ Montepulciano (1 night) ⇨ Val d’Orcia/Asciano (1 night) ⇨ Siena (2 nights) ⇨ Monteriggioni ⇨ San Gimignano (1 night) ⇨ Volterra ⇨ Lucca (1 night) ⇨ back to Florence

Tuscany itinerary with one base

Good to know

What’s the best time to visit tuscany, how to get around tuscany, how much time do you need for a tuscany road trip.

Where to start your Tuscany road trip?

Where to stay in tuscany, what to be aware of, sustainable travel in tuscany.

That brings us to the next part. When you eat out or buy products at a local market, and cook yourself, you support the locals . That’s awesome because your money goes right to the Tuscans instead of international companies.

Also, try to avoid unnecessary waste by bringing your own tote bag for shopping and a food container , and your own   cutlery for your snacks. In case you buy something that causes litter, make sure to take it with you when you leave and properly ditch it into bins where you can separate the trash . This way, you can make sure that it gets properly recycled. Many parking areas along the beaches in Tuscany have trash bins with waste separation.

One of the largest polluters is bottled water. So avoid buying plastic bottles . Instead, bring your own water bottle. There are many public water refill stations in Tuscany. Just search for “Casa Dell’Acqua” or “drinking water fountain” in Google Maps. Those are stations where you get free filtered water or sometimes for 5 cent/liter.

Besides, you can also bring your own water purifier , such as a Grayl water bottle . This way, you can take water from any tap and filter it yourself.

Interested in getting a water bottle with a filter?

More about reducing waste during your trip, tuscany – a wrap-up.

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Great guide with lots of details! It made me want to visit Tuscany! Saving it for when I will plan my own road trip in the region!

Hi Elina, I’m so glad to hear that my post made you want to visit Tuscany. Thanks so much for your kind words!

Tuscany is a region I am dying to explore. You’ve convinced me to book a trip next summer. I also love your itinerary suggestions. I will need to do more research to choose which one to copy. In the meantime, I will dream of being there through your photos. Thanks for sharing the great post.

Thanks for your lovely comment, Mayi. All the itineraries include amazing places, so the choice is hard, I know. But one thing is for sure: You will fall in love with Tuscany, no matter where you go!

[…] While many of the windows were no longer used in the following years, and some even got bricked off, the wine windows celebrated a revival in recent history. They’ve become such an important part of Tuscan culture and travelers love to try the experience of ordering a glass of wine from a window when they’re on a Tuscany road trip.  […]

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Tuscany Road Trip: The Perfect 5 Day Tuscany Itinerary

Rolling hills with perfect rows of manicured vineyards, hilltop towns with medieval architecture, and some of the best food you’ll find in all of Italy: these are just three of the reasons to take a Tuscany road trip.

While you can go on day trips to Tuscany from Florence , the best way to explore the scenic Tuscan countryside is to rent a car and drive through it yourself!

A Tuscany road trip will take you through some of the most beautiful villages and medieval towns in Italy, with lovely historical centers, beautiful churches, and spectacular castles.

Whatever season you visit Tuscany in, this picturesque region will reward you with spectacular views and unforgettable experiences.

To help you ensure you won’t miss any must-see sights, I put together an itinerary with some of the best spots to visit on this road trip through Tuscany.

In just 5 days in Tuscany , you’ll be driving through the region’s most beautiful cities and villages, tasting great local wines, and — perhaps most importantly — enjoying delicious food!

All you need to do is book your flights and rent your car, and you’re ready to fall in love with Italy’s most charming region — I’ve done all the legwork for you!

Table of Contents

What to Know Before Planning your Tuscany Road Trip

Before getting into this Tuscany road trip itinerary, it’s worth covering a few practical details you should be aware of.

Driving in Italy is not without its quirks, so here are the most important things to keep in mind before driving through Tuscany!

Hopefully, these tips will help you plan the Tuscan road trip of your dreams.

We also suggest reading this guide to renting a car in Tuscany before your trip, as it gives helpful driving tips for the region.

Best Time for a Tuscany Road Trip

Tuscany is beautiful any time of the year but the ideal time for a road trip is either late spring or autumn.

Although in summer the region is also beautiful, the months of July and August are also the busiest, so you’ll risk finding many places crowded and everything pricier.

Plus, everything is hot, hot, hot, and most of the joys of a trip in Tuscany is spending time outdoors.

Whether it’s sitting on patios that overlook vineyards sipping local Chianti or wandering through an ancient city street…. none of that is fun when the temperatures are so high you feel like you’re melting!

Spring is a great season to enjoy beautiful landscapes, with flowers blooming and the typical Tuscan hills covered in all shades of green.

The temperatures are also pleasant if you visit in late April and May, and as long as you prioritize the early part of June, June is still a good month to visit.

Since Tuscany is famous for its wines, autumn is also a great time to visit the countryside and enjoy wine tasting in Tuscany while admiring the hard work that goes into getting ready for the harvest season.

Best of all, the temperatures are still pleasant from mid-September to late October, and the crowds get smaller, so the season is perfect for a road trip!

If you’re wondering whether you could do a road trip in winter, the answer is yes.

However, it can get quite cold, the landscape is not nearly as pretty, and you’ll also find some restaurants and museums closed for the season.

On the bright side, you’ll find lower prices and no crowds — it may be worth it, but I don’t think it’s the best time of year.

Driving in Tuscany

Driving through the Tuscan countryside doesn’t pose any particular issue.

Even as a foreigner, you should have no problem getting around — as long as you have an international driving permit (IDP).

You’ll mostly be driving along regional roads, but from time to time, you may take the highway, which has tolls.

You shouldn’t expect to pay much, but having some coins always with you can be handy.

Most tollbooths take credit or debit cards too, but sometimes you may not have this option, so don’t get caught off guard!

Even if you visit Tuscany in winter, which is not a popular season for road trips, you shouldn’t worry.

Temperatures rarely go below 0°C (32°F), and snowfall is uncommon, so there are no particular hazards when it comes to driving in Tuscany in winter.

Wine Tasting and Driving in Tuscany

No trip to Tuscany would be complete without some wine tasting, of course!

But if you’re road tripping in Tuscany, you need to be aware of both laws regarding alcohol consumption and driving and, of course, your safety (and the safety of others on the road with you!)

According to Italian law, you can drive with a maximum blood alcohol content (BAC) of 0.05% if you are over 21. Younger drivers are not allowed any alcohol if driving.

While the BAC depends on various factors, from your gender to your weight and whether you drink on a full or empty stomach, a good rule of thumb is to minimize your alcohol consumption as much as possible.

Here are some charts that help you calculate your BAC , so you can know how many glasses of wine you can safely consume before driving.

The bottom line is, while alcohol is always better avoided before driving, by law, you can have a glass or two of wine with your meal and drive, depending on a variety of factors.

If you’re traveling with a partner or group of friends, this is ideal as you can take turns for who can wine taste and who is the designated driver throughout the trip.

Where to Begin Your Tuscany Road Trip

The best place to start your road trip around Tuscany is the region’s capital and biggest city, Florence — plus, it’s just a marvelous city to visit as well, home to sites like the Statue of David and the Florence Duomo.

Be sure to dedicate at least one day in Florence before exploring Tuscany, unless you’ve been there before and feel like you’ve already covered the city!

The international airport Firenze-Peretola has flights to and from many European cities, making it a great place to start your road trip.

Furthermore, you’ll find plenty of high-speed trains going to Florence from all the other big cities in Italy.

A train ride from Milan only takes two hours, while Rome is just over one hour and a half away.

While you could base yourself in Florence and just do several day trips , a Tuscany road trip allows for far more freedom and way less back-and-forth trips.

How Many Days for a Tuscany Road Trip?

You could easily spend two weeks driving around Tuscany, and you’ll still come across new, wonderful places — that’s the marvel of this region.

On the other hand, you could potentially cut this road trip significantly, and you could even condense this itinerary down to a three-day road trip to see some of the main sights.

However, anywhere between five and seven days for a Tuscany road trip is a good option.

This way, you don’t have to rush and you still get to see the most important places.

As written, this Tuscany itinerary takes five or six days, depending on whether you spend one or two nights in Siena — a city so marvelous it deserves a little extra time.

You can combine this itinerary with a two or three-night stay in Florence before or after the road trip.

You may also want to spend a few nights in a Tuscany villa with a private pool , perhaps at the end of your Tuscany road trip, to really soak up some relaxation before you leave!

I won’t cover any attractions or activities in Florence in this article, but you can find a dedicated post about the best landmarks in Florence and a three-day itinerary to discover the Tuscan capital.

You can combine them in any way that makes sense for your trip!

Day 1: Florence to San Gimignano

Leave florence, with an optional stop at castello di poppiano..

Start your trip around the gorgeous Tuscan countryside in the morning, bright and early so that you don’t miss out on any of this trip’s glory!

The first day of your road trip in Tuscany is dedicated to exploring the picturesque Via Chiantigiana .

This scenic road unfolds through the undulating hills and vineyards known for producing the grapes for the famous Chianti wine, and it’s an exquisite start to your road trip.

As you drive out of Florence, you can have an optional stop, but it requires a prior reservation, so be sure to look into it before starting your trip. Check the website here .

Roughly 45 minutes from the center of Florence, Castello di Poppiano is a medieval castle belonging to the Guicciardini family since the late 12th century.

Amazingly, the family still owns the castle, passed down through the generations, and now they run guided tours with wine and olive oil tastings — delicious.

If you wish to join a tour of Castello di Poppiano, make a reservation at least two days before.

You can choose between a shorter one-hour tour and a longer two-hour one that includes access to the tower terrace and a bigger tasting with wine, oil, and food.

I do suggest the two-hour tour if you can make it work, but if you don’t have time, one hour is okay, or you can skip this stop entirely.

Head to Greve in Chianti.

After your visit to Castello di Poppiano, make your way to Strada in Chianti , where you’ll join the Via Chiantigiana (SR222) .

Drive south along the picturesque road for about 15 minutes to reach your next stop, Greve in Chianti .

A popular stop along the Via Chiantigiana, Greve in Chianti is a cute town where you can stop for a walk around, and enjoy a delicious lunch.

Where do I recommend? Depends on what you want, but Ristorante Pizzeria La Cantina is a popular stop for tasty pizza or traditional Tuscan dishes served with a glass of Chianti.

Move on to Castellina in Chianti.

After lunch, continue driving south to the next town on Via Chiantigiana, Castellina in Chianti.

In the small historic center, visit the lovely Church of Saint Salvador and the Archaeological Museum of the Chianti Area .

Note that the museum is closed between January and March and only opens on certain days in November and December.

The area around Florence in winter does shut down a bit, so keep that in mind if planning an off-season road trip to Tuscany.

Make a brief stop in charming Poggibonsi.

Your next stop before your final destination for the day is the town of Poggibonsi , less than half an hour from Castellina in Chianti.

The town is an important stop along the Via Francigena pilgrimage route and has a rich history dating back to the Neolithic period.

Stroll around the old town, check out the medieval Castello della Magione , and visit the Fortezza di Poggio Imperiale .

The town is small but charming, so you only need about one hour — that’s enough to check out the main sights before moving on to your final destination of the day, and settling in for some well-deserved rest at your hotel.

End the day in lovely San Gimignano.

Finally, drive to San Gimignano , one of the most picturesque towns in Tuscany.

This town is known for its wine production and charming streets, but it’s even better known for its many towers — 72, if I want to be precise.

Aim to arrive before sunset so you can climb one of the towers and enjoy a spectacular view from above!

Torre Grossa is the tallest in the town, but the effort to climb its many stairs will reward you with the best views.

For a different, less crowded option, you could alternately pay a visit to the twin towers, Torri dei Salvucci .

Other popular landmarks in San Gimignano are the iconic squares Piazza della Cisterna and Piazza del Duomo , great people watching spots in town.

In terms of landmarks, make time to visit the Duomo Collegiata di Santa Maria Assunta as well as the history museum, Tower and Casa Campatelli .

Visit all the attractions you can in the afternoon before heading for dinner: I recommend Ristorante Bel Soggiorno or Ristorante San Martino 26 .

Since you’ll be sleeping in San Gimignano, you may leave some things for the following morning, before continuing your road trip.

Day 2: San Gimignano to Siena

Finish up in san gimignano and (optionally) make a visit to certaldo..

Spend the morning of your second day exploring the sights you didn’t get to see in San Gimignano.

However, be sure you leave a few hours before lunchtime so that you’ll have enough time for this jam-packed day ahead.

For the first stop of the day, the town of Certaldo , you’ll need to backtrack north for roughly 20 minutes… but I promise it’s worth it!

If you’d rather spend more time in San Gimignano, you can skip this stage and start driving later to the next attraction, Volterra .

If you choose to visit Certaldo, you’ll be rewarded with the picturesque sights of its medieval center, located in the upper town.

Catch the funicular to reach the upper town, and visit the main landmarks, including Palazzo Pretorio and Chiesa dei Santi Jacopo e Filippo .

The medieval town of Certaldo is also home to Boccaccio’s house , the birthplace of Giovanni Boccaccio, famed author of the Decameron.

The house is now a museum and offers lovely views of the Tuscan countryside.

Head to Volterra for lunch.

Whether you visited Certaldo or chose to spend extra time in San Gimignano, either way, next we’ll head to the town of Volterra .

The hilltop Tuscan town features well-preserved Etruscan walls around its gorgeous medieval center.

The landmarks you shouldn’t miss are the Cathedral of Santa Maria Assunta , the 13th-century Palazzo dei Priori , and the Roman Theatre .

Wander around Volterra’s picturesque alleys and charming squares and stop for lunch.

Try delicious sandwiches at La Sosta del Priore or enjoy a traditional Tuscan meal at La Taverna della Terra di Mezzo .

Head to Chiusdino and its famous abbey.

After lunch, drive to Chiusdino, another delightful Tuscan village with a compact but beautiful medieval town.

Explore the small village and visit the Church of San Michele before continuing your drive toward Siena.

An optional stop just outside Chiusdino is the Abbey of Saint Galgano .

This Gothic-style 13th-century abbey stands roofless in the middle of the Tuscan countryside. The abbey is close to the road, so it’s easy to stop by for a short visit.

Head to Siena to end the day.

Finally, drive to Siena, where you can spend one or two nights, depending on how much time you have reserved for this Tuscany itinerary.

The city is full of amazing landmarks, so you can easily spend more than one day exploring its main sights.

Nevertheless, if you’re short on time, you can check out the most important landmarks in just half a day, if you have to.

Keeping this as just a half-day stop would keep this as a 5-day Tuscany itinerary, but if you spend another day in Siena, that will make this a 6-day road trip.

If time is short, spend the rest of your afternoon and evening exploring the historic center of Siena, revolving around the iconic Piazza del Campo .

The imposing Gothic-style Palazzo Pubblico and the iconic Torre del Mangia tower over Piazza del Campo, and both are must-visits even if you have a short time in Siena.

Just a few minutes away, in Piazza del Duomo , you’ll find the Romanesque-Gothic Duomo di Siena known for its striped marble façade — one of the most beautiful churches in Italy, which is high praise.

End your evening in Siena with a traditional dinner at Osteria Il Carroccio or Osteria degli Svitati , both serving delicious Tuscan dishes.

(Optional) Additional Day: Siena

Explore the town of siena, on your own or with a tour..

If you decide to spend a second day in Siena, there are plenty of landmarks to explore and activities to do.

You can take advantage of the fact that you won’t be driving and go on a wine-tasting tour.

Choose between staying in Siena and joining a local tour like this Siena: Food and Wine Walking Tour or exploring the nearby countryside on this half-day Educational “Vine, Wine, & Life” Tour & Tasting .

Spend the rest of the day exploring Siena and visiting more beautiful landmarks.

In Piazza del Campo , climb to the top of the Tower of Mangia for sweeping views of Siena’s historic center.

The climb up the 87-meter tower can be challenging, but the view is one of the best in town.

Another cool observation point is the so-called Facciatone .

You’ll climb on top of the façade of what was supposed to be an additional nave to the Duomo di Siena but was never completed.

The incomplete project is now known by its literal term, Facciatone, meaning big façade.

Outside the historic center, visit the 16th-century Fortezza Medicea to enjoy the view of Siena from a distance.

Not far from the fortress, the Basilica Cateriniana San Domenico houses several relics of Saint Catherine of Siena, the patron saint of Italy, together with Francis of Assisi.

The most important relic is the saint’s mummified head — creepy but very cool, as long as you don’t mind a little macabre sightseeing!

These landmarks and activities should keep you busy for a whole day in Siena, but if you have extra time and you enjoy visiting museums, you can check out the museum of Santa Maria della Scala , housed in a former hospital.

For your last dinner in Siena, check out the scenic SaporDivino Restaurant or the beautiful terrace of Ristorante Tar-Tufo .

Spend one more night in Siena before you continue your Tuscany road trip.

Day 3: Montalcino to Montepulciano

Make your way to montalcino..

From Siena, start driving south toward the small town of Montalcino , better known for its signature wine, Brunello di Montalcino.

On the way, you’ll pass through Buonconvento , another lovely town with a small but charming historic center.

Park the car and go for a short walk along the few narrow streets that make up the little town.

Roughly 20 minutes south of Buonconvento, you’ll reach Montalcino.

The hilltop town offers panoramic views of the surrounding Tuscan countryside, one of the best views you’ll see on this Tuscany road trip.

The best views are from the Fortress of Montalcino , a 14th-century fortress at the highest point in town.

You can walk all around the fortress walls for a small fee and even check out a wine shop inside.

The small medieval center of Montalcino has other beautiful viewpoints and a few more landmarks worth visiting, including the Palazzo dei Priori and the Cathedral of the Holy Savior.

If you’re looking to buy a bottle of Brunello di Montalcino, you’ll find many wineries and wine shops in town to bring home this delicious Tuscan souvenir!

Make a stop at the Val d’Orcia Scenic Spot.

From Montalcino, you’ll head to Pienza… but not without making a stop at one of the most famous photo spots of Tuscany!

You’ll need to drive for about half an hour to the east to reach Pienza , one of the most beautiful towns of the Val d’Orcia, and your stop for lunch.

But first, plug in Val d’Orcia Scenic Spot to your Maps app or navigation device — this is where you’ll want to stop for that iconic photo of Tuscany that may have inspired this trip in the first place!

Head onwards to Pienza.

Once you reach Pienza , it’s time for lunch — your stomach is probably growling at this point.

In the charming Piazza di Spagna , the cozy osteria Sette Di Vino serves heartwarming dishes in an old-fashioned setting.

After lunch, explore the small historic center of Pienza and visit the Pienza Cathedral (Duomo di Santa Maria Assunta) and the beautiful Palazzo Piccolomini .

Near the cathedral, you’ll also find a few viewpoints to admire the rolling Tuscan hills stretching in the distance.

End the day in Montepulciano.

Finally, drive to your last stop for the day, Montepulciano .

Like many towns in the region, Montepulciano also gives its name to a wine variety, so a wine tasting is in order!

Once you reach Montepulciano, you’ll be done driving for the day, so you can relax, explore the town, and check out one of the many wineries.

De’ Ricci Cantine Storiche is smack in the historic center of Montepulciano and offers great tours of their cave cellars, along with wine tasting. You can join the wine tasting before or after exploring the town.

A few sights you shouldn’t miss are the gorgeous Fortezza Medicea and the Piazza Grande .

The famous piazza is encircled by impressive buildings like the Palazzo Nobili-Tarugi , Palazzo del Capitano del Popolo , and the Cathedral Saint Mary of The Assumption — all worthy of a stop!

End the day with a delicious dinner in Montepulciano before heading to your hotel for a good night’s sleep.

I recommend Rosso Rubino Trattoria and La Pentolaccia : two great options for genuine local dishes that use the flavors and ingredients of the region.

Day 4: Chianciano Terme to Arezzo

Make a brief stop at the sanctuary of the madonna..

Start your second to last day of the Tuscany road trip by visiting the Sanctuary of the Madonna di San Biagio , just outside Montepulciano.

A gorgeous example of Renaissance art, the sanctuary is a must-see for anyone passing by Montepulciano.

For a small fee, you can admire the beautiful artwork inside the church and get an audio guide.

Head to Tuscany’s beloved thermal baths.

Next, drive to Chianciano Terme for a relaxing time at the stunning thermal baths in town.

The Theia Thermal Baths feature four outdoor pools and three indoor ones with thermal water coming from the Sillene spring, so long known for its beneficial properties that it’s been used since the Etruscan times!

Reserve your access to the thermal baths in advance and enjoy a few hours in the pools overlooking the Tuscan countryside, relax in the sauna, and maybe get a massage in the wellness center.

You can stay for lunch at the on-site restaurant or drive to your next destination.

Make your next stop in Cortona.

Less than one hour north of Chianciano Terme, Cortona is another delightful town known for its Etruscan heritage.

If you’re a history geek, the Accademia Etrusca is a great spot to learn about the town’s history and admire Etruscan artifacts.

The historic town of Cortona is full of beautiful churches, including the Cortona Cathedral and the small Church of St. Nicholas , jam-packed with beautiful paintings.

Around the main town square, Piazza della Repubblica , you’ll find charming historic buildings and many restaurants.

If you didn’t eat at the springs, you can stop here for lunch at the cozy Osteria del Teatro , a place I highly recommend.

End the day in Arezzo.

After exploring Cortona, it’s time to drive to Arezzo , where you’ll be spending the last night of your road trip around Tuscany.

On a hill in the eastern part of Tuscany close to its neighboring region of Umbria, Arezzo was an important city for the Etruscan civilizatio, until it was later conquered by the Romans.

The city is best-known for its medieval churches and buildings and the ever-present Medicean Fortress .

The top sights in Arezzo are the medieval Arezzo Cathedral and San Francesco Basilica , two must-visit religious sites.

If you want to keep exploring, visit the National Museum of Medieval and Modern Art , people-watch on the gorgeous Piazza Grande , and of course spend some time enjoying the Fortezza Medicea with its surrounding park.

To end a full day of activities and exploring, enjoy a tasty dinner at Teorema del Gusto or Il Covo dei Briganti , then spend the night in Arezzo.

Day 5: Arezzo to Florence

Stop at the little town of anghiari..

On your last day exploring Tuscany, it’s time to drive back to Florence, but not before exploring two more gorgeous Tuscan towns on the way.

Your first stop is the charming town of Anghiari , only half an hour from Arezzo.

Anghiari is famous for being the location of an important battle between Florentine and Milanese troops in 1440, back when Italy was divided into several states.

The battle was later meant to be depicted on a mural in the Palazzo Vecchio in Florence by Leonardo da Vinci, but he never completed it.

You can learn more about the battle and the town’s history at the local museum, Museo della Battaglia e di Anghiari .

Wander for a while around the small medieval center and along the old town walls (N’tra Le Mura D’Anghiari) to enjoy beautiful views and check out the charming squares, medieval buildings, and beautiful little churches.

Make a final stop in Poppi before returning to Florence.

After visiting Anghiari, drive for around one hour north to reach the last town on this Tuscany itinerary, the picturesque Poppi.

The town is home to the medieval Castle of the Earls Guidi , the beautiful Church of San Fedele , and the Monastery of Camaldoli .

If you choose to have lunch in Poppi, you should try the delicious, heartwarming cuisine of La Taverna del Castello , right in the town center.

After lunch, start driving back to Florence, roughly one hour and a half from Poppi.

In Florence, you can leave your rental car and, if you have extra time, spend a few more days visiting the many landmarks and museums of the Tuscan capital.

Roxana is a Romanian-born freelance travel writer who has lived in Italy for over 15 years. She has a Master’s in Journalism and a Bachelor’s in Film Studies, and she studied at Università degli Studi di Roma Tre. Besides her native Romania, Roxana has lived in Rome, Lisbon, and Berlin, and she has traveled through much of Europe in search of hidden gems, history, and culture.

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An Italian Mama's Guide to Italy

5 days in Tuscany: beautiful Tuscany road trip itinerary + map

5 days in Tuscany road trip: an easy to follow itinerary to see the most beautiful destinations in Tuscany and travel tips for each.

Tuscany is one of the most beautiful regions in Italy and a destinations many have on their Italy bucket list, and rightly so!

The areas is blessed with pretty much anything a visitor can ask for.

Beautiful countryside, historical hilltop villages, the art powerhouse of Florence, thermal baths, wonderful food: this and much more you can experience in Tuscany.

But with so much to see, how can you make sure you pick the best destinations ans truly see the best of Tuscany?

I recommend you follow this itinerary!

We visit Tuscany very often and have overtime refined an itinerary for 5 days in Tuscany that I believe is perfect for a first visit and will allow you to see the best scenery and villages in Tuscany at a reasonable pace.

This is a Tuscany road trip itinerary so you will need a car. however, we have kept the driving time to a minimum for each day so you can spend the time exploring and not behind the wheel!

5 days in Tuscany itinerary at a glance

When planning your 5 days in Tuscany, the main thing you need to decide is if you want to include Florence in your itinerary or leave it for a different trip.

For this itinerary, I am leaving it out however, it is possible to replace any of these days with one in Florence .

If you do so, my recommendation is to start your holiday in Florence and finish in San Quirico d’Orcia.

• Day 1: San Gimignano and Monteriggioni

Day 2: Siena and Bagno Vignoni

• Day 3: Pienza and Monticchiello
• Day 4: Montepulciano and San Quirico

Day 5: Pitigliano and Saturnia

Tuscany road trip itinerary map.

Our 5 days in Tuscany road trip recommended itinerary

Day 1: monteriggioni and san gimignano.

Tuscany is famous for wonderful hilltop villages so what better way to start a road trip in this wonderful region that with two of the most scenic of all?

The two villages for this first day are Monteriggioni and San Gimignano, both located in the countryside between Florence and Siena and easily reached by car from either city.

San Gimignano is a wonderful hilltop town, enlisted as UNESCO World heritage Site for its beautify and peculiar history.

The town thrived during the Middle Ages and the Renaissance and the wealth and power of its most important families gave the town the characteristic that still makes is stand out from the rest: an incredibly high number of towers!

San Gimignano can be visited in a matter of hours and it is a wonderful day for a morning and early afternoon.

Find our guide with what to see and travel tips for San Gimignano here.

After what I am sure will be a delightful lunch in San Gimignano, I recommend you make your way to Siena and stop in Monteriggioni for a couple of hours.

Monteriggioni is a tiny hilltop village still entirely surrounded by medieval walls and offering sweeping views over the countryside below.

The village is tiny and I should probably call it a ‘castle’, rather than a town however, the word castle can evoke elegant interiors and regal chambers, which is not what Monteriggioni is about

Monteriggioni is a castle in the sense that it is a fortified village with a central piazza still entirely surrounded by mighty walls.

Entering the village is like stepping back in time to the Middle Ages.

Take your time to have a snack in the piazza and explore its picturesque alleys and take in its small yet perfectly formed beauty: even better, spend the night so you can truly enjoy the slow pace and views of this gorgeous town.

You can find our guide to Monteriggioni here

I recommend you spend your second day road tripping in Tuscany visiting Siena and then relaxing in the nearby thermal village of Bagno Vignoni,

Siena is one of the mos beautiful small towns in Tuscany and Italy in general and has such impressive vestiges of its important history it entered the list of UNESCO world heritage sites in the mid 1990s.

You can visit Siena in a day or a little less: Piazza del Campo and the Duomo will be unforgettable!

You can find our guide to a day in Siena here .

After the beautiful yet busy town of Siena i recommend you take the short dive to nearby Bagno Vignoni.

Bagno Vignoni is a tiny, delightful village famous for natural hot springs and a central town square with a hot pool!

The town is a little more than a congregation of houses but it is a perfect place for an afternoon and a nigh under many accounts

Here you have lovely thermal resorts (some budget friendly), a picturesque central square and also the chance to taste the food and wine of this area, famous for world renowned wines such as Rosso, Brunello di Montalcino and Morellino di Scanasano

Staying in the village for the night it a great way to experience this slow pace village and to go wine tasting without having to drive.

You can find our guide to Bagno Vignoni and recommended hotels here .

If you prefer a bigger center and do not care for thermal baths, then Montalcino can be a great option too, also perfect for wine lovers.

Day 3 Val d’Orcia: Pienza and Monticchiello

On this day, you get into the heart of Val d’Orcia , one of the most scenic areas of Tuscany.

I recommend you start your thirds day in Tuscany visiting Pienza, a stunning hilltop village often refereed to as the ‘ideal city’.

The nickname is not a modern marketing hack but rather taps into the peculiar history of Pienza.

Originally a village like many others in the vicinity, in the XVI century the town as entirely redesigned by will of Pius II, who decided to turn his native town into the perfect example of the ‘Humanistic ideal town’

The result is wonderful!

Pienza is a delight and a beautiful place to explore for one morning.

You can find our guide to Pienza here

After Pienza, I recommend you take the short drive to Monticchiello, an off the beaten path, beautiful village in the middle of the Tuscan countryside.

Monticchielllo is a small gem of a place and a beautiful preserved medieval village with something special: in simmer, the town turns itself into a stage and host theater performances widely acclaimed n the arts world!

Monticchiello is along a dust road yet well kept road and the drive and village are north worth the effort.

I recommend you stop here in the afternoon and either spend the night in the village (find our guide to Monticchiello here ) or, before dark, head to a nearby Terre di Nano and spend the night there: this is an agriturismo and winery so beautiful, it is a destination in itself and easily will stay as a highlight of your Tuscany road trip!

Day 4: Montepulciano and San Quirico d’Orcia

A short drive from Monticchiello lies the wonderful hilltop town of Montepulciano, maybe my most favorite of all!

Montepulciano is a historical medieval and renaissance town perched on top of a hill in between two of the most beautiful areas in Tuscany: Val D’Orcia and Val di Chiana.

The town develops vertically and it crowned by a stunning piazza, Piazza Grande, with beautiful palazzi and an unforgettable historical well.

The town is a delight to visit for a day and has some lovely food and wine worth trying.

I recommend you have lunch at Cafe Poliziano before heading to our next stop: San Quirico d’Orcia.

San Quirico d’Orcia is a tiny village with wonderful Romanesque churches and a delightful central piazza.

Small and scenic, this is a lovely town to spend a couple of hours and a great place to call home for the night while tasting the delicacies of the area.

You can find our guide to San Quirico d’Orcia here .

If you have not included Florence in your itinerary, then I recommend you spend this last day heading a little farther South and exploring the stunning area of Maremma, in the south of Tuscany.

The first place I recommend you to see here is Pitigliano.

This is a wonderful hilltop village very different from the others in this list and possibly form anywhere else you have seen in Italy.

The town is perched on top of rock of tufo (a local stone) and blends in with the scenery so well, it looks as if it emerges from the ground itself!

The first glimpse of Pitigliano from the road is unforgettable however, the town itself is also worth exploring.

Home for centuries to the local Jewish community, it has a fabulous Jewish Quarter and Synagogue that is now open to the public and very interesting to visit and is a pretty village with scenic views, worth of your time.

Find our guide to Pitigliano here .

After Pitigliano, I recommend you go visit one of the most photographed places in the whole of Tuscany: Saturnia!

Satrunia is a locality known for thermal waters and while this has been a popular destination for decades, it seems to have only lately gotten international acclaim thanks to aerial shots of its wonderful Cascate del Mulino , a free thermal bathing area.

Indeed, the cascate are wonderful and one of the best thermal spring destinations in Tuscany.

They are a stretch of land where the hot water of the spring creates small waterfall and bathing pools with a white pearly color, where people can bathe for free.

They are a busy yet beautiful place to visit and a great locality to relax for awhile before saying good bye to Tuscany on your way back to Florence or nearby Rome.

You can find our guide to Saturnia hot springs here.

Tips for a Tuscany road trip

No matter what season you are planning this road trip for, I highly recommend you book your rental car and accommodation in advance.

If renting a car, remember that in Italy we drive on the right and that car seats for children are compulsory.

Please find our tips for traveling in Italy safely here .

Remember that motorways in Italy are tolled. This itinerary keep you on non-paying roads most of the time however, you are likely to be on the motorway when close to Siena.

Always be prepared for tool booths with cash and cards.

Do not drink and drive: if planning wine tasting, make sure you select a place that allows you to stay the night, walk home or that can arrange a driver for you.

Do not drive at night: while the roads are well kept, many of the roads on this itinerary are country roads and can be dangerous in the dark

I hope you enjoyed this recommended itinerary for 5 days in Tuscany and that you will have a wonderful time. Safe travel planning!

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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Privacy overview.

Tuscany Road Trip Guide: Tips for Visiting the Tuscan Countryside

Planning a road trip through Tuscany is no small task. There are so many tiny hillside towns, cypress-lined roads, fields of sunflowers, and gorgeous churches, how can you possibly see them all? It’s easy to get a perfect mental image of how the trip is going to turn out, but a different thing altogether to plan one that is going to work.

For starters, there is so much more research to do when you’re trying to find out which are the best towns in Tucsany. Each town has something special, plus there is less information online about lesser known towns – so you really have to dig for the inside scoop. Plus there are the additional logistics involved in driving a car in a foreign country!

That said, touring Tuscany by car is so worth it! Here are my top picks for places to visit the next time you’re in Italy, tips for a stress-free road trip, and my own Tuscany itinerary for 7 days!

“Life is a combination of magic and pasta.” — Federico Fellini Tweet this

Before you go to Tuscany

Renting a car – Whatever you do, MAKE SURE you get additional insurance for your car when driving in Italy. This applies to anywhere to drive in Italy whatsoever. Italians are known for bumping other cars in order to parallel park as tighly as possible, you don’t want to get dinged (ha!) for damage at the end of your trip.

We always rent our cars through DiscoverCars , and I definitely recommend them for finding the best price for your car rental.

What to pack – If you’re going to be staying outside of major cities, bring insect repellant if you’ll be traveling during the summer months. Besides that, sunscreen, hat, and sunglasses are no-brainers you’ll need to withstand the Italian sunshine. My favorite sunscreen of all time is this Biore SPF 50 sunscreen – it’s Japanese so you know it’s the absolute best.

Recommended Accommodation – Agriturismo La Dogana is a farm stay on Lake Trasimeno, complete with a swimming pool on a hill of olive trees overlooking the lake. Dreamy location and a great value, if you are looking for a home base to explore the area. Not only that, but when we went to a nearby restaurant, they gave us a bottle of wine to take home when they heard we were staying at La Dogana!

If you’re looking for a little relaxation, it doesn’t get better than this view at La Dogana.

Where to go in Tuscany on a road trip in 7 days

Here’s a high-level look at all these spots on the map! As you can see, everywhere is pretty close together, and driving from one city to the next doesn’t make more than two hours at most (that is, so long as the road isn’t under construction!)

• Day 1 : Florence
• Day 2 : Florence and Lago Trasimeno
• Day 3 : Assisi and Perugia
• Day 4 : Lago Trasimeno
• Day 5 : Montepulciano
• Day 6 : Siena
• Day 7 : Lucca

We stayed on the border to Umbria, so we visited places in both Tuscany and Umbria. That said, even if Umbria is less famous than Tuscany, it still has gorgeous towns which will be included in the list!

Best towns in Tuscany and Umbria

Here are all of the best towns we visited in Tuscany, Italy. At the end I’ll also list towns we did not visit, but are also worth checking out if you have the time or the drive (ha!) to see even more.

Montepulciano

Lago trasimeno, san gimignano.

Ponte Vecchio, the most famous bridge in Florence, Italy

First stop on the roadtrip was Florence – no trip to Tuscany would be complete without it, and after going, I understand why: Florence is beautiful, colorful, and delicious. Florence is especially known for Bistecca alla Florentina , the local way to prepare a T-Bone steak. In short, you get 1-1.5kg of meat, cooked rare, and served up all for you. If you’re not carnivorous, Florence is also famous for gelato within Italy .

Even though food is probably the number one thing on my mind when going to any new city ( especially an Italian city), Florence has some of the most recognizable art of all time, such as the statue of David and the Birth of Venus. I’d argue that the city itself is just as much a piece of art with people living in it. Do not miss Florence on your Italian roadtrip!

Photo taken from the Tower of Palazzo Vecchio

Things to do in Florence

• Il Duomo – The Florence Cathedral is easily the most famous sight the whole city! There can be a MASSIVE queue to enter the cathedral, so be prepared for that (but at least it’s free). Don’t miss climbing to the top of the Duomo for incredible views over Florence. Ladies, be sure to have a way to cover knees/ankles because traditional Italian churches don’t allow you to waltz in with a ton of skin showing. I used a jacket to make it work.
• Uffuzi Gallery – Probably the most famous art museum in Florence, this gallery is home to Botticelli’s “Birth of Venus”, Carvaggio’s “Medusa”, plus works by Da Vinci and Michelangelo among many others. One of Europe’s oldest museums!
• Accademia – This where you can see the famous statue of David by Michelangelo.
• Tower of Palazzo Vecchio – One of the best places for views of the Duomo and Ponte Vecchio! This tower has multiple levels you can use to take photos of the city and see famous locations from the air. Be aware, there a a whole lotta stairs to climb to get to the top but the view is worth it.
• Ponte Vecchio – Walk across this bridge, which has a bunch of shops on it. Come early in the morning if you want a little more space, it’s a pretty popular spot in Florence!
• Santa Croce – Probably the second most famous cathedral after the Duomo, there’s a big square in front of it where you can enjoy a coffee and people (or piegon) watch.
• Piazzale Michelangelo – Come here for one of the best views over Florence, which is completely free to access! Just cross one of Florence’s bridges to the other side of the river and start the climb. Be prepared, there are many stairs 😉
• San Lorenzo Leather Market – Florence is famous for its leather, but do watch out for shady deals .

Tower of Palazzo Vecchio , where you can get some of the best views over Florence

Where to eat in Florence

Cafe Zaza claims to have been the birthplace of Bistecca alla Florentina , the famous Florentine Steak that weighs a kilo and takes a small army to complete. Here you can order this famous dish, or a ton of other mouth-watering options. At the end, wash it all down with some tasty limoncello as the locals do.

Apparently Assisi is known amongst Italians, because everyone I told that we planned to go there gave me their congratulations. It’s easy to see why: this small town is one of the most impressive as you approach it from the road. High, white walls make it look like the city is meant to withstand siege, meanwhile the only thing threatening to breach its walls are fields of sunflowers.

This place has the highest concentration of real-life monks and nuns that I’ve ever seen – as well as tour groups. Luckily it only takes a little walking up the hill to escape them into Assisi’s charming stone alleys.

Basilica of San Francesco d’Assisi

Things to do in Assisi

• Basilica of San Francesco d’Assisi – St. Francis is buried in the lower cathedral, though both are beautiful. Again, like the other churches in Italy, you need to be prepared to cover your knees and shoulders.
• Rocca Maggiore – There’s also an old fortress above Assisi, climb up here for the best views over umbria’s rolling hills.
• Drink some wine – You can do this at just about any village in Tuscany, but there are some popular wineries here you can visit for a taste of local drink!

We went to Montepulciano with a single mission: wine. But on our way to the enoteca (wine bar), there were so many side streets that captured our attention that it took us almost an hour to get there, dispite how small Montepulciano actually is. Of everywhere we went in central Italy, this one had by far the most impressive views.

If you are looking for scenic drives through Tuscany , the ones leading to Montepulciano are just your ticket. You’ll pass fields of sunflowers, vineyards, country homes, cypress trees, and have plenty of fun winding roads to traverse on the way.

If you want to come to Montepulciano for wine-tasting, it’s important that you make a reservation if you want to combine the wine-tasting with lunch or dinner. If you just want to taste wine and perhaps nibble on small snacks, it’s usually possible to do that without a reservation. Italians tend to eat dinner around 8pm, so show up earlier to ensure you get a spot.

Things to do in Montepulciano

• La Bottega del Nobile – If you want to do wine-tasting in Montepulciano , check this place out. Here you can help yourself to a wide selection of local wines dispensed through a cool card system that keeps track of what you’ve tasted.
• Val d’Orcia – This ultra-famous valley is home some of the best views over the Tuscan countryside, and is wonderfully seen from Montepulciano.

While exploring Tuscany, we made Tuoro sul Trasimeno our homebase and visited the rest of the area on day trips by car. Possibly the most amazing part of this arrangement was the fact that our farm stay was so inexpensive while most of the surrounding restaurants were so expensive . Luckily, staying in a house means that you can DIY your breakfast and morning coffee with a beautiful view of the lake, so it ended up being a good deal anyways.

Take a boat ride to the island in the middle of the lake for some hiking and lounging on the beaches.

My number one tip for visiting Italy has to be: bring insect repellant . Everyone in our party ended up with numerous bites, with the poorest of all easily reaching double digits. This is especially bad when you’re staying in a foresty area or near a lake (both of which, of course, we were doing).

Where to eat on Lago Trasimeno

• Il Vecchio Mulino – A favorite of locals, and very affordable spot for pizza and pasta. The prices were a relief compared to many places throughout the area!
• La Badiaccia – Menu only in Italian, but the staff was super kind in helping us to understand what our options are. Food and wine was fabulous and we were even given a bottle to take home!

Yet another hillside town with hopelessly narrow streets – thankfully we weren’t driving an American-sized car or there’s no way we’d have mode it out. There were times when we had mere inches on either side of our rental car, and it was probably dumb luck that we didn’t get any scratches on it! It’s really clear that these cities were not designed with automobiles in mind.

Perugia is special not only for its tiny streets, but the fact that the entire city seems to be made out of stone. There are delicate arches linking buildings together throughout the town, it’s amazing that it’s all still stuck together after the stone has been worn so smooth.

Things to do in Perugia

• Piazza IV Novembre – the main square, you simply can’t miss it!
• Perugia Cathdral – Perugia’s most prominent cathedral

It’s no surprise that Siena was the one city where the number of tourists was still noticable during the shoulder season – its church is OUTSTANDING. I’m not one to care about any ole Italian cathedral, and am the first to admit that they all look pretty similar once you enter the second half of a roadtrip through Italy. But the one in Siena was seriously awesome – known as The Beetlejuice Church , Siena’s cathedral is one of the few that actually takes its stripey pattern seriously enough to apply it to the interior.

Things to do in Siena

• Piazza del Campo – unique central square, shaped like a scallop
• Cathedral Santa Maria Assunta – hands down the most memorable church in Tuscany!
• Facciatone – climb for panoramic views of the tower and the main sqaure
• Lots of shopping on Banchi di Sopra – Siena’s main shopping street

The smooth cobblestone streets shone in the rain and reflected buildings that still managed to be bright and vivid in spite of heavy grey skies. Every shop looked like the platonic Italian market. And of course, high fashion shops mixed seemlessly with the local ones. Lucca, like Italian style, is a mesh of effortless beauty and timelessness. The city’s cohesive color scheme was meant to be immoralized in photos – and you bet I obliged.

Come to Lucca for some of the most quintessentially Italian vibes of the entire trip.

Things to do in Lucca

• Torre Guinigi – Centuries-old oak trees crown this tower, offering lovely views of the city. This tower is probably the most famous sight in the whole city and well worth spending a couple of euros to get to the top.
• Museo Villa Puccini – Puccini is the most famous resident of Lucca, as a renowned Italian composer, he has both a statue in public as well as a dedicated museum.
• Santa Christina – Cute and quirky cafe and enoteca, where I’d definitely recommend popping in for lunch! Lots of nice wine options and decent prices.

Check out my article on more things to do in Lucca, Italy if you’ll have more time in this ultra cute Italian town.

Naturally, you know all about the Leaning Tower of Pisa , possibly the most recognizable building in all of Italy. Pisa has this and more to offer, and is a really popular stop right next to Lucca. Unfortunately I’ve only been to Pisa on a layover, so no pretty photos, but I’d love to go back and do this town justice. Don’t forget it if you’re planning a trip through Tuscany!

Besides Montepulciano, San Gimignano is another popular place to go for wine-tasting in Tuscany. Like many towns in Tuscany, San Gimignano is perched on a hill and has old, medieval houses all throughout its city limits. You can visit its tower, Torre Grossa or enter its most famous church, Duomo di San Gimignano .

Again, somewhere I didn’t get to spend any time but belongs on my next Tuscany Iterary for certain!

Seven tips for a stress-free road trip in Italy

• Get the insurance on your rental car. Italians are known for having a less “gentle” relationship with cars. Get the insurance, at least on the exterior of the car.
• Speed limits don’t matter until they do. Italians often surpass the speed limit and though the fines are high, they’re rarely enforced.
• Save some cash at the pump. Use a self-service station to avoid paying to have someone pump your gas for you.
• Beware of toll roads and closures , both of which are common in Italy – especially if you need to make a deadline in another town, you may face unexpected traffic. Take this into account while planning.
• Getting into small Italian towns by car is tricky. Look for parking before you approach town. Often parking is only available outside the city walls. Parking prices vary greatly depending on where you are.
• Balance your time between small and large towns. Even the touristy spots in Tuscany are well-visited for a reason – don’t pass up the big cities like Florence and Pisa just because you’re worried about fighting the crowds. At the same time, small towns can get repetitive, as each is just as charming as the last. Keep things fresh by mixing and matching!
• Schedule wine tastings in advance. If you’re looking to combine a wine tasting with a meal, booking ahead is absolutely necessary. Without a meal, many wine shops offer less formal tasting (and therefore, don’t necessarily require a reservation).

Have you been to Tuscany or Umbria? If you could pick any of these idyllic towns to visit, which would you pick?

Share your experiences and tips in the comments, I’d love to hear advice on what to do next time!

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About the author

Hi there! I'm Monica, an American expat living in Germany for over six years and using every opportunity to explore the world from my homebase in Berlin. My goal is to capture my memories in photos and posts that show how easy it is to start from scratch and travel the world by working abroad.

Follow along on Instagram , Twitter , Bloglovin , & Facebook .

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The Tuscany Itinerary You Should Steal

By Helene Sula

It's clear why Tuscany has been the backdrop of many movies, books, plays, and novels. The cascading cobblestone streets, rolling green hills dotted with poppies, and the promise of delicious pasta and gelato make for the perfect escape. But there are so many cute little towns – how can you ever choose?! This guide is going to help you to see the best of Tuscany, the can't miss spots, and give you a full Tuscany Itinerary you'll want to steal. And you're welcome to do just that.

For the purpose of ease, I'm calling this post a one week Tuscany itinerary. But I also focused on cities outside of Tuscany, in the regions of Umbria – such as cities like Perugia and Assisi, Terni and Lazio. If that's confusing, just know that these regions of Italy are right next to each other so it made sense to go to all of them.

Below you can find a map of all the places discussed in this post:

In order to see the best of Tuscany you need a plan and most likely, a car. There are so many spots along the way you'll want to stop and gawk at or snap a photo of. There is public transportation, but to get to all the small, charming towns, a car is really best. This itinerary will be particularly helpful if you have a car. Luckily, renting a car in Europe is relatively inexpensive. I suggest checking rates with companies like Sixt where you can find great deals no matter where you're traveling.

The only problem with driving is finding parking. You MUST be careful where you park in Italy. You could wind up in a very interesting situation. I'll elaborate more down below!

I tend to be a go, go, go vacationer. But I had recently torn my ACL while skiing in the alps and this trip to Tuscany was actually the perfect speed. It's nice to slow down the pace and enjoy the countryside and everything the region has to offer.

How much time to spend in Tuscany

You can easily stay under the Tuscan sun for months, years, even. But since we don't always have that much time I created a one week itinerary for Tuscany. I suggest 4-7 days in Tuscany to really see it all. Florence is a big city with lots of sights, so I suggest 1-3 days here alone. I've done trips that were 10 days in Italy and also spent 5 days just in Tuscany. This blog post is going to focus on other cities outside of Florence since you can read my guide for that city here .

How to get to Tuscany

If you're only spending time in Tuscany or want to fly directly, I suggest flying into Florence or Perugia. For this particular trip, I'd already been to Florence, so I wanted to focus on more of the countryside of Tuscany and the tiny villages that lie between the countless vineyards.

If you're coming from places like Rome or Venice, you can easily take the train directly to Montepulciano or Florence. I personally use GoEuro to book all of my train tickets in Europe. It's just the easiest, and it will give you a vast number of times, options, and prices.

Where to stay in Tuscany

For our home base, we chose Montepulciano. You know how when you lay eyes on somewhere new and immediately fall in love? That's how I felt at Sant'Antonio Country Resort in Montepulciano. Driving here was one of the most scenic roads I've had the pleasure to ride shotgun on. You'll see the typical Tuscan landscapes with rows and rows of vineyards and lush green hills.

We drove up from the train station in Perugia to one of the most picturesque scenes: miles of rolling hills, olive trees galore, and a 800-year-old former monastery turned hotel. We stayed in a large private villa that included a kitchen, large bedroom, bathroom, and my favorite part, a living room complete with a fireplace. Upon arrival, we cracked open a bottle of red wine and watched the fireplace flicker. It was the perfect start to our Tuscany trip.

Sant'Antonio was the perfect location to easily get from place to place, along with ample parking. The furniture is original seventeenth and eighteenth century and made for a cozy oasis in the hills. The rooms are stocked with local wines from the area along with water, beer, and soft drinks. There's even a swimming pool, a running path, and lovely garden.

The ambiance is peaceful and provides the perfect respite after a day of touring around Tuscany. I felt like I had my own moment of “Under the Tuscan Sun” in our lovely villa. We'd open up the windows and look out to see the gorgeous countryside. The owner is also one of the most dynamic people I've met and makes you feel right at home. I highly recommend Sant'Antonio .

Day 1 – 3 Florence

There is so much to see in Florence , so I suggest spending a good 2-3 days here. The architecture incredible, scenery captivating, and the museums are world renown. I suggest touring the Duomo , visiting the Uffizi and Galileo Museum , seeing Pitti Palace , and walking on the Ponte Vecchio .

If you have extra time, I suggest making a day trip to Pisa when you're in Florence. It's an easy half-day trip, and you can hop on a train to get there and see the leaning tower. You can read my guide to Florence and Pisa here . This post is going to focus on more of the Tuscan hillside towns and the scenic places you can see along the way.

Day 3 – Assisi and Perugia in Umbria

Technically, Assisi and Perugia are in Umbria, just after the border for Tuscany in Italy. We started the day by driving from Montepulciano to Assisi . The drive is about an hour and a half and is full of plenty beautiful sites along the way and bright reddish-orange poppies dotting the paved roads.

I was excited to see Assisi, as I grew up Catholic, I knew this was a hot spot for one of our most famous and important saints, St. Francis, and a UNESCO heritage site. The city is situated upon a hill and it rose out of the fog in the distance in front of us. We drove up to the city and found some free parking just before the pedestrian zone in the town.

As we walked into town I marveled at the beautiful stone of the homes and buildings. Fist, we went to Basilica of San Francesco d' Assisi . This is the burial place of St. Francis of Assisi and it's absolutely stunning inside. You'll find that St. Francis himself is buried in the church. Surprisingly, Assisi and the basilica have suffered a number of earthquakes. There has been extensive work to rebuild from the damage.

This well preserved city has a maze of cobblestone streets and you'll find a panini stand on nearly every corner. Eager to try some food, we picked up a toasted sandwich made with delicious cured meat and a glass of wine for an additional Euro. In all of the towns in this area each one has a myriad of flags, all different from town to town. We always stopped to take note of the city's new flag.

After getting a good view of Umbria from Rocca Maggiore , we headed on to our next destination: Perugia.

The drive from Assisi is heading back towards Tuscany and only about a half hour. I read online to park near the train station and take the Mini Metro up to the town. DO NOT DO THIS. There is plenty of parking in the old part of the town and I wish we had listened to our guts and not parked in the garage. I'll explain why shortly!

The Mini Metro is a hilariously small tram that takes you up to the hilltop and old part of Perugia. After taking the Mini Metro up, you take various escalators up to reach the top of the town. We walked around the town and stumbled into chocolate shops. Perugia is famous for its chocolate and Baci Perugina-  chocolate filled with hazelnut. You can go to the Perugina House of Chocolate to try all the different flavors and learn how it's made. My favorite was the delicious dark chocolate balls.

Since my sweet tooth wasn't satisfied yet, I opted for gelato at Gelateria Gambrinus . I'm telling y'all, this was one of my favorite gelatos I've had in Italy. And I've had a LOT of gelato.

We made our way to the main square, Piazza IV Novembre , with the gorgeous fountain, Fontana Maggiore . The medieval fountain dates back to 1275 and marks the end of the former Roman aqueducts for that area. Behind the fountain is the medieval cathedral, Cattedrale di San Lorenzo .

We walked over to the aqueduct after which is surprisingly uncrowded and offers one of the prettiest views in the area. Just a few minutes from this spot, we found a great place for dinner, Tozza e Bocconi . We were told a few places to check out and they all looked too touristy. Sometimes just wandering and finding a place is best.

A couple of bottles of wine later, we decided to go back. But on our way back to the metro, we stumbled upon a spot claiming, called Il Birrino, to be the “3rd smallest bar in the world.” I've come to find this is definitely false, upon various Google searches for, “smallest bar Perugia,” I've come up short.

Why you shouldn't park your car in a garage in Italy

Later than expected, we headed to the Mini Metro, only to find that it closes at 9 pm. Tired and weak (remember, I'm on crutches), we go to the bus stop. We called a cab as well, but they told us it would take 20 minutes which was the same time we'd have to wait for the bus. When we got down to the train station we walked to the garage. Curiously, no lights were on. And worse still, there was a metal grate locking in all the cars.

Puzzled, we walked around trying to find answers. We looked at all the signs posted at the entrance of the parking garage and nothing mentioned anything about closing times. We even asked police officers nearby and after they tried to help with no success, we looked online and found that the garage closed at 10 pm.

We were sleeping in Perugia that night.

Luckily, we found a really nice hotel that I'd actually recommend if you wanted to stay in Perugia or the Umbria region! Hotel La Rosetta was surprisingly nice and came with a great breakfast.

It was an unfortunate and somewhat hilarious situation. I've been told parking can be tricky in Italy, and now I won't be parking in a garage in Italy any time soon. Typically, if you want to park, the blue lines mean you need to “pay and display.” So, pay at the meter and display that you've paid with the receipt in the window. White lines typically mean free parking. As for garage parking, read the signs. If there are none, skip it.

Day 4 – Orvieto and Civita di Bagnoregio

After our hiccup the day before, we were ready to hit the road and explore more. We headed from Montepulciano to Orvieto , about an hour long drive. Orvieto is in the Province of Terni and holds one of the most incredible cathedrals, Cathedral of Orvieto . This small city dates back to 1290 and was once the center of Etruscan civilization. There's also the archaeological museum that features many artifacts from the Etruscan period.

This tiny town was easy to meander around and was pretty quiet compared to some of the other towns we visited. While the cathedral was impressive, I was most taken with the food. We ate at Trattoria Del Moro and before walking in, we talked to a guy outside who raved about his meal. “Best in Italy,” he gushed. He wasn't lying.

I had the most decadent four cheese ravioli. It was so simple but so divine. Michael ordered something called “nidi” which was pasta filled with pecorino cheese and drizzled with honey. If it sounds weird, it doesn't matter, because it tasted delightful.

After seeing the cathedral, it started raining, so we opted for gelato just beside the cathedral at Gelato at di Pasqualetti . Another good option in case it rains, or just in general, is the Posso dell Cava , an underground city. You'll find Etruscan homes and underground routes and tombs, textile workshops and more 36 meters deep!

Escaping the rain, we got in the car and went to Civita di Bagnoregio in the Lazio region. I had no preconceived notions about this place, but I can tell you it's worth it to see this incredible city. This beautiful hilltop top town is perched high above the valley, dramatically rising into the sky. The long bridge leads up to the city and is only wide enough for a moped or tiny vehicle.

The city truly looks like a painting and we stopped and stared before making the trek up. Again, this spot was relatively quiet. So much so, I was able to grab some pictures without anyone else in them!

Civita di Bagnoregio is known as the “dying city” as there isn't much life here and the erosion of the soft volcanic rock has put the place in danger. By the time we got there, the few restaurants there were already closed. There are a couple places to stay here, but it's mostly quiet. I highly recommend seeing this place as little has changed since it was built in the 6th century. The cobblestone streets and vine-covered villas are like walking into a fairy tale, complete with friendly cats who follow you as you make your way through the tiny village.

For dinner that night, we headed to the grocery store and picked up Italy's finest wines, cheeses, meats, and bread and went back to our sweet Sant'Antonio Resort in Montepulciano. I absolutely adore having a meal like this. It's cheaper and often very tasty. Another reason why I loved our stay in Montepulciano, was the ability to have a real dinner since we had a kitchen. We couldn't help having a fireplace and savoring the red wine from the region.

Day 5 – Pienza and Montalcino

Today, we focused on Tuscany with our first stop in Pienza , just twenty minutes from Montepulciano. This town was such a treat and felt like the perfect representation of true a Tuscan town. The gem of the city is a UNESCO world heritage site in the Val d'Orcia area of Tuscany. The Piazza Pio II is the main square which is flanked by the lovely cathedral, St Mary's , which is stunning inside. You'll also find great views behind the church.

We also found a wonderful gelato shop with a chef who came back to Italy to share his passion at Buongusto . He makes unique flavors based on the different seasons and the strawberry with rosemary flavor was surprisingly delicious.

Next, we headed to our much anticipated wine tasting and tour in Montalcino . We went to gorgeous Poggio Rubino for our wine tasting. For only $15 per person you get a tour of the winery (ours was even a private tour!) and you get to try various wines along with cheese, meat, bread, and olive oil and balsamic vinegar. This is one of the highlights of the trip for me. The Brunello red wine was exceptional and satisfying.

All of the wines, olive oils, and grappas are made with the highest quality ingredients. We even took some grappa to take home with us. Although, it didn't quite make it since we drank it all. I'd highly recommend this tour because it helps you have more of an appreciation for wine, it's a great price, and the wine was delicious.

To cap off the day, we went to hot springs of Bagni San Filippo . Tuscany has many hot springs which are thought to help cure and purify. The hot springs are free, and a different way to experience Tuscany. The water gets pretty hot, so no matter the season you can comfortably dip in.

Day 6 – Montepulciano and Siena

For our last day, we stuck around our home base and explored Montepulciano – a true Renaissance style town with a breathtaking view. The winding streets are car-free and allow you to meander from shop to shop. This city is known for the wine produced in the area, and they proudly offer a great selection.

We walked about the Piazza Grande , the main square of Montepulciano. It might look familiar, it's the scene from the Twilight saga, “New Moon.” We also peaked into the Chiesa di San Biagio , a beautiful Renaissance church. Then we opted for the phenomenal views while sipping cappuccinos and eating croissants.

If you have time, check out a wine bar with a terrace where you can watch the sunset. A good choice is E Lucevan Le Stelle .

From here, you can head an hour away to Siena for one of the most incredible churches: Cathedral Santa Maria Assunta . Also, climb up the Facciatone for panoramic views of the tower and the main square. You can also go shopping on Banchi di Sopra, the main shopping street.

Other towns of note in Tuscany are: Lucca, Chianti, Cortona, San Gimignano, and Volterra. If you'd like to round out your trip, you can do 7 days in Tuscany and hit up all these places!

If you have more time, head down to the Amalfi Coast (Capri, Positano, Amalfi, and Ravello) for an exquisite stay by the sea. See my full guide here .

In Tuscany, you can't go wrong. All of the towns are so lovely and each is a bit different and charming than the next. I'm sure the Tuscan hill towns will beckon you back again and again. Whether it's the delicious food, wine, or cypress-lined driveways, you'll find a reason to come back. Italy always seems to do that to us.

MEET THE AUTHOR

Helene Sula

I believe that one trip can change your life. It did for me. I'm a self proclaimed home body that quit her job, moved abroad, and more often than not, lives out of a carry-on bag. If I'm not traveling, I'm most likely re-reading Harry Potter or watching "Midnight in Paris" while snuggling my dogs. I'm a digital marketing expert who turned my love of travel into a full-time career. And I help others do it too.

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Road Trip in Tuscany: Itinerary & Our Tips for the Most Beautiful Destinations

Ciao Toscana! Hello beautiful Tuscany! It’s no secret that we fell in love with this region instantly, it was love at first sight . Tuscany has this unique combination of Italian lifestyle and holiday flair. Our road trip through Tuscany was one of our best trips and most memorable trips (not just because we got to spend it with family).

In this travel guide, we share with you our itinerary and which places we visited on our Tuscan road trip. As always, we have included our personal tips as well. All the destinations on our road trip can be found at the end of the article on an interactive map.

• 1. Tuscany Road Trip: What is Tuscany like? 

2. Itinerary through Tuscany: The Stops of our Road Trip

3. map: overview of our road trip through tuscany, 4. extra travel tips for your tuscany road trip, 1. tuscany road trip: what is tuscany like  .

Olive groves and vineyards as far as the eye can see, rolling hills and picturesque towns: Tuscany is home to some places that are too beautiful to be true, with incredible photo opportunities all around.

In the heart of Tuscany, you’ll find beautiful, romantic cities , such as Florence with its stunning cathedral. But the smaller cities are the ones that really captivated us. We were particularly taken by the small charming town of Lucca, with its well-preserved medieval city wall.

However, Tuscany would not be Tuscany without its characteristic landscapes: the gentle, rolling hills are mesmerising in the golden hours – as are the lovely cypress trees and olive groves.

Mornings are best spent with breakfast from local places, and the evenings are best spent enjoying sunset out in the countryside – you can’t get more Tuscan than that! You’ll find it easier to switch-off and be more in the present – life slows down here, just enough that it’s therapeutic.  

Florence is the ideal starting point for a road trip through Tuscany because being the capital of Tuscany, it is home to one of the largest airports in the region.

With almost 400,000 inhabitants, Florence is not a huge city, but certainly larger than expected. It’s also very touristy with large crowds, especially in the centre. Nowhere else in Tuscany was coffee more expensive than in Florence.

The most famous sight in Florence is the Uffizi Gallery – a complex of buildings that has now become one of the most famous art museums in the world. Therefore, it might be a good idea to get your tickets in advance. One of the highlights was the stunning cathedral of Florence called Santa Maria del Fiore . We were speechless at the sight of it, this is one of the most beautiful cathedrals we have ever seen.

Our tip: enjoy a magical sunset overlooking Florence from the Piazzale di Michelangelo . This is far from a secret, but the view from up here is simply incredible.

Our hotel tip for Florence: Corte Calzaiuoli Elegant Suites Beautiful, very stylish, small boutique hotel right in the centre of florence. Great location, very good breakfast – one of the best accommodation on our road trip.

Of all the destinations we visited on our road trip in Tuscany, we found Lucca particularly charming and would highly recommend you to see this place for yourself. The architecture style has a very medieval feel and the city of Lucca is actually surrounded by an excellently preserved medieval city wall , which you can walk or bike around its entire 4 kilometre length.

One of the most famous sights in Lucca is Piazza dell’Anfiteatro . As the name implies, this square was built on the ruins of a Roman amphitheater, which is where it gets its characteristic oval shape from.

Our tip: do not miss the view from the Torre Guinigi (Guinigi Tower). From up here you have a beautiful panoramic view over Lucca.

Our detailed blog article: Lucca Travel Guide

Our hotel tip for Lucca: Il Pozzo di Santa Zita Very nice boutique hotel in a historic house with individually decorated rooms. It has a fantastic location in the centre of Lucca.

Welcome to the city that is home to the most famous attraction in Tuscany: the Leaning Tower of Pisa . The Leaning Tower of Pisa is one of Italy’s most well-known landmarks. No wonder the crowd was even bigger than we expected.

Of course it’s great to see the tower with your own eyes, but we have to admit that there are definitely more impressive and charming places than the grassy areas of Piazza dei Miracoli around the Leaning Tower of Pisa. During peak summer season, this place is swarmed by tour groups .

Right next to the Leaning Tower of Pisa is the Duomo of Pisa (Cathedral of Santa Maria Assunta).   Overall, we found the centre of Pisa less impressive than that of Lucca.

Our hotel tip for Pisa: B & B Di Camilla Lovely accommodation with a unique country house style. The location is central, but nice and quiet.

Upon arrival, we already had a good first impression of Volterra: The medieval city is perched on a hill and visible from a distance. Volterra’s twisting labyrinth of narrow streets had the potential to be one of our favourite places in Tuscany, if it wasn’t so crowded.

Nevertheless, Volterra is definitely worth a stop. Fun fact: Volterra is also called the alabaster city , as it was well known for its mining and processing of alabaster. That’s why you’ll find countless shops selling alabaster products in the city centre – most of them are your typical souvenir shops.

Our accommodation tip: Villa Loghino Very stylish accommodation in an old country house with a pool. It’s located outside the centre of Volterra and it’s very nice and quiet.

San Gimignano

The next city on our Tuscany road trip is San Gimignano. San Gimignano is one of the most impressive cities in Tuscany and also known as the “Medieval Manhattan” . If you approach San Gimignano, then you immediately see why: 15 medieval towers reach up towards the sky, giving the city its strikingly unique appearance.

One of the highlights is the view over San Gimignano from the towers. Perhaps the most famous one is the lookout point from Torre Grosso . Although most of the information you see on the Internet says that this is the only accessible tower, we actually found ourselves on another tower. However, in our particular case, this alternative tower was actually home to an apartment. Therefore, mostly likely only accessible if the apartment is not currently rented out. Either way: San Gimignano from above is a must-see.

Our tip: There is a lovely winery near San Gimignano called Teruzzi & Puthod , where we stopped to look around. If you want to buy a bottle of wine or two, then this is the place for you. One of the classics from this particular winery is the Tuscan white wine – Vernaccia di San Gimignano.

Our detailed blog article: San Gimignano Travel Guide

Our hotel tip for San Gimignano: Podere Sant’Elena Very nice accommodation in a restored country house with pool and large garden. Just outside San Gimignano, but very idyllic.

For two things, the small, charming place is particularly well-known: Firstly, you will find plenty of wineries in and around Bolgheri. And on the other hand, the journey to Bolgheri is very special: you drive through the famous cypress avenue , the so-called Viale dei Cipressi. Centuries-old cypress trees line this street.

Bolgheri itself is a charming little town that is explored fairly quickly. Worth seeing is the castle of Bolgheri , through whose gate you also drive when you come to Bolgheri. Otherwise, you can pass the time in one of the wine bars – there are some in Bolgheri.

Another must on a Tuscany road trip: Siena. Siena, located in the heart of Tuscany, is considered one of the most beautiful and charming cities in Italy . Not for nothing is the old town Siena UNESCO World Heritage Site.

The best way to start your city tour is in the most important square of Siena, Piazza del Campo . This sprawling, shell-shaped space is a popular meeting place for locals and tourists at any time of the day.

From the tower of the Palazzo Pubblico , the Torre del Mangia, you have a magnificent view over Siena. More than 400 steps have to be overcome before you can enjoy the panoramic view over Siena. He is really breathtaking!

Our detailed blog article: Siena Travel Guide

Hotel tip for Siena: Casatorre dei Leoni Beautiful and very tasteful accommodation in a historic house right in the center.

Val d’Orcia

One of the most iconic destinations on our Tuscany road trip is the beautiful Val d’Orcia, located south of Siena. Here all the Tuscany clichés that you have in your head become reality.

You can look forward to beautiful, medieval towns surrounded by a picturesque, gently rolling landscape. We particularly liked Pienza, Montalcino and Montepulciano.

For wine lovers, the Val d’Orcia is also a must on a road trip in Tuscany. The Val d’Orcia is home of the famous Brunello di Montalcino.

Our detailed blog article: Val d’Orcia Travel Guide

Hotel tip for the Val d’Orcia: Borgo Canalicchio Di Sopra Relais A wonderful hotel in a quiet location surrounded by vineyards and olive groves. This is how you imagine the perfect vacation in Tuscany!

To give you a better idea of ​​where all these locations are, we’ve mapped out all our Road Trip Destinations through Tuscany in this interactive map below.

Transport in Tuscany: Car Rental Tips

If you are not planning on travelling Tuscany with your own car, then we can highly recommend you book a rental car. In Tuscany, getting around by bus can be rather difficult, especially when it comes to smaller towns. If you have a car, then you can be much more flexible with your travels, which is a very important aspect for many people (like us).  

We always book our rental cars via Sunny Cars , who act as an intermediary. On their website, you’ll find an overview of the cheapest rental car offers from different companies such as Hertz or Europcar.

The biggest advantage of Sunny Cars is that you have full comprehensive insurance . So in the case of an accident, you will also be reimbursed the excess or deductible. The type of car is also important (eg. an SUV is perhaps a little unnecessary for Tuscany). We would say a mid-range car is a good ballpoint.  

You can search for cheap rental cars here: Sunny Cars

What is the best Season for a Road Trip through Tuscany?

Spring and autumn are most ideal for a road trip through Tuscany. The best months are perhaps May and June for Spring, as well as September and October for Autumn. The climate is usually pleasantly warm during these months and not too hot. Bonus: not so many tourists during these months as you would get in the peak summer months of July and August.

Tip: If possible, avoid the peak summer months (especially July and August). We have experienced what it’s like to travel Tuscany in August and can confirm that some places were just hopelessly overrun during this period. Especially places of historically significant sites, such as San Gimignano and Volterra. However, if you want to combine your Tuscan trip with a beach getaway on the coast, then perhaps you might prefer the warmer summer months.

How much Time should I plan for a Road Trip through Tuscany?

Difficult question as it really depends on the individual. We ourselves only spent one week in Tuscany, but at the same time, we could have easily filled in two weeks with beautiful destinations.

If you prefer a slower style of travelling, then we would recommend you allow two weeks , which will also give you enough time to explore a few places off the beaten path.

The distances between destinations should not be underestimated either because the Tuscany region is quite extensive : There are actually nine provinces, which theoretically would take several hours to cover them all. Although Tuscany does not seem as big on the map, you should also keep in mind that some of the roads are not perfect. You might find yourself driving on the country roads, which often take longer than you might have originally planned for.

Day Trips from Base vs Staying in Multiple Places

You have two options here: either you have a fixed base with just one accommodation and do day trips from there. Or you hop around and stay in several places along the way. Both have their advantages and disadvantages.

1) Day Trips from Base: If you’re going with this option, then it makes sense to find a good base, preferably somewhere in the centre of Tuscany (such as Pisa or Siena), as this should help minimise the amount of travel time. The good thing is, you just need to pack what you need for the day. But you will end up spending more time on travel than the other option. We stayed in a historic estate in the province of Livorno and it was great being so close to the sea. Our tip: Before you book your accommodation, just check (via Google Maps) how long it will take to get to each of your planned destinations. That way, you can plan your day trips better and thus, make the most of your day.

2) Staying in Multiple Places: If you want to stay overnight in several places on your road trip, then you have the luxury of being a little more flexible. However, this also means you have to travel with all your luggage and you’re constantly having to pack and unpack your belongings. A good starting point would be Florence, where they have lots of international connections.

Disclaimer: Affiliate Links

This travel guide contains our personal recommendations in the form of affiliate links. If you book or buy something through these links, we will receive a small commission from the company. But this does not alter the price for you at all. A million thanks from the both of us!

Have you ever done a road trip through Tuscany? Perhaps you have extra tips? We look forward to reading your experiences!

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2 responses.

Thanks so much for all these amazing tips! I love how charming all the places look and now can’t wait for my trip to Tuscany this year 😍

you’re welcome! Have a wonderful trip to Tuscany. :)

Thank you for your message & safe travels, Kathi & Romeo

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A Local’s Guide to Travel in Tuscany

Tuscany, the most famed region in Italy and a place visited by millions of people every year, really needs no introduction. Featured in countless films and often used as the postcard image of quintessential Italy, Tuscany is squarely on the tourist map for just about everyone.

And that’s for good reason; because this is a truly spectacular region!

Tuscany has just about everything that you could ask for from a vacation destination: majestic UNESCO world heritage cities and towns, a to-die-for countryside, lovely mountains and fabulous beaches, and globally-renowned culinary and enological traditions. Simply put, we’ve got it all here!

And when it comes to culture, Tuscany is a fabulous part of Italy to discover. Tuscan, the region’s dialect, is very similar to Latin, and today’s standard Italian language was born from it. This is largely thanks to the writings of local artists like Dante Alighieri, Francesco Petrarca, and Niccolò Machiavelli.

On top of that, this was also the cradle of the Italian Renaissance, with Florence having been the epicenter. If you’re interested in art and history, few places in Italy can beat Tuscany.

So, if you’re looking to sample great food and wine, enjoy beautiful scenery, walk through history in medieval towns, and maybe even hit the beach for a bit, Tuscany has got you covered. No matter your tastes, travel style, or interests, Tuscany has something to offer.

More Tuscany travel info:

For more info on travel in Tuscany and Italy, check out our 7-day Tuscany itinerary and our guide to the Chianti wine region .

If you could use some one-on-one help planning your itinerary, consider scheduling an Italy travel consultation with one of our Local Experts!

Guide to the Val d’Orcia

Citu guide to Florence

City guide to Siena

City guide to Montepulciano

City guide to Lucca

City guide to Cortona

City guide to Pisa

Day trips around Tuscany with Stefano

Table of contents

Where is tuscany, best time to visit, how long to spend here, how to get to tuscany, where to stay in tuscany - best bases.

Transportation and how to get around

Is Tuscany expensive? Average travel costs

Paying for things and using credit cards, what to do in tuscany.

Best places to visit in Tuscany

Tuscany itineraries - from 5 days to 2 weeks

Local help with your planning

In the article below we’ve shared lots of advice and many tips on how to plan a trip to Tuscany. But it’s impossible to mention everything that you might want to know in just one article. Also, no two travelers are alike so not everything we’ve mentioned will be the right fit for everyone.

So if you’ll be planning your trip independently but could use some help sorting through all your options, consider scheduling a Tuscany travel consultation with one of our Local Experts!

These are one-hour Zoom calls where you can chat with a Tuscany-based travel pro about the trip you’re planning and they’ll share their tips and advice, answer your travel questions, and help you perfect your itinerary.

Tuscany is located in central Italy, about a 2-hour drive north of Rome at its southernmost point, and an hour south of Bologna in the region’s north. It is bordered to the northwest by Liguria, to the north by Emilia-Romagna, to the east by Marche and Umbria , and to the south by Lazio (where Rome is).

The western edge of Tuscany, runs all along the coast, from the Tyrrhenian Sea in the south to the Ligurian Sea in the north. Along much of the region’s northern border, you will find the Tuscan-Emilian Apennine Mountains, along with the Apuan Alps in the northeast.

Tuscany is a fairly big region for Italy (about 8,900 square miles), which means that there is a lot to see and do, and there is much more to it than just its (beautiful) countryside and the (magnificent) city of Florence.

Scattered all throughout Tuscany you will find fortified hilltop towns, mid-sized cities, beaches and coves, mountains, parks, and hot springs. Ready to start discovering it? Then keep reading!

The best time to visit Tuscany is indisputably late spring or early fall, especially the months of May and September. These are the periods when traveling in Italy is most enjoyable, and Tuscany is no exception.

Visiting in late spring and early fall

In late spring, the temperatures are already warm but not excessively hot, so it’s perfect for visiting historic towns, the countryside, and also the coast.

Besides Florence, which is crowded all year round, late spring isn’t packed with tourists, so you will surely enjoy your time there. Italians are still at work/school, so prices for accommodation and other attractions haven’t yet skyrocketed. Plus, most restaurants on the coast and less touristy areas/towns will already be open since they usually open up right after Easter (which is in late March or until mid-April).

Similarly, September also has great weather, lower prices, and less crowds. On top of that, seasonal venues (beach clubs, for instance) are still open and going full swing, before things die down toward the end of the season and everyone closes up shop for the winter.

If you can swing it, there’s no question that late spring or early fall are the perfect times to travel in Tuscany.

Visiting in summer

In summer, the weather is roasting hot in the cities and towns, while the coast overflows with vacationing Italians and foreign tourists. This is especially true from mid-July to the end of August.

Prices are incredibly high and availability is limited pretty much everywhere, so you need to reserve way in advance for hotels, rental cars, restaurants, and even entrance tickets to popular museums and historical sites.

Now, if summer is the only time you can come to Tuscany, don’t despair! While it’s not the ideal time to visit, it’s not as if every town, beach, or vineyard is going to be permanently packed.

You can always find hidden places that the masses have yet to discover, and if you visit popular locations early in the day or later in the evening (before the day trippers have arrived or after they’ve left), you can still enjoy beautiful places in Tuscany without being constantly shoulder to shoulder with others.

If visiting in summer, you just need to plan ahead, make reservations in advance, and visit the right places at the right time.

Visiting in winter

Visiting Tuscany in winter isn’t an outright bad idea either. While entrance tickets for museums and monuments are the same all year long, hotels and car rentals are much more affordable than at other times of year. If you’re looking to save money, this is the ideal time to travel in Tuscany.

November, January, and February are the least busy times to visit the region, which all makes it the ideal time to travel through the beautiful hilltop and art towns, which are packed throughout much of the rest of the year.

However, just be aware that it’s pretty chilly at this time of year, the weather is unpredictable and can often be grey and rainy, and trips out to the countryside or coast aren’t especially pleasant.

There is much more to see in Tuscany than just Florence and the Chianti hills. Tuscany is rather big, and it’s home to many historic sites and art towns (which are towns of great artistic/historic importance). The Tuscan coast is also stunning, with not one but two beautiful islands that you can travel to.

For the most part, it’s also quite easy to get from one place to another since the distances are pretty manageable by train or car, and there are good public transit connections for major destinations. Thankfully, you will never have to sacrifice entire days to travel, and will instead be on the road for at most a few hours before reaching your intended destination.

Even so, to appreciate Tuscany properly and to really get a feel for the region, you will need to slow down and take your time. This is especially true if your itinerary includes Florence, as that will take up a minimum of two days.

5 days - for a decent introduction

You need at least 5 days in Tuscany in order to appreciate the region and see a bit of what it has to offer. Remember, this is a region filled with beautiful hilltop towns, renaissance cities, coastline, mountains, and world-renowned wine country, so it has a lot to offer you.

While many people come in to Florence for 2 days, and then tack on a day trip out to the Val d’Orcia or Chianti area and call it a day, that’s not recommended - you’d simply be missing too much of what makes this region special.

To do things the right way, dedicate 5 days to Tuscany, and spend 2 of them discovering the renaissance jewel of Florence, then venture out to the Chianti countryside to visit wineries, thermal baths, or the coast, and give yourself a day or two to road trip between a few of the region’s beautiful hilltop towns.

Doing all of that in 5 days won’t be especially relaxing, but it will allow you to actually see Tuscany and begin to understand what the region is all about. 7 days would be better, as that would give you time to slow down and enjoy yourself a bit more, while having an extra day for Tuscany’s natural areas and another one to visit more of the historic towns dotting the entire region.

7 days - enough time for a solid itinerary

A 7-day trip to Tuscany gives you enough time to check off many of the highlights, while also spending some time enjoying the region’s gorgeous countryside. It’s not enough days to see the entire region, but it will let you beyond just the surface.

With 7 days, you could spend a pair in Florence, go wine tasting in Chianti, enjoy Siena, and then hop around the hilltop towns of the Val d’Orcia before finishing your trip in Pisa.

Depending on what your interests are, you could trade out a day in the Val d’Orcia for a day spent visiting places closer to Florence like San Gimignano and Monteriggioni. For your final day, if Pisa doesn’t appeal you could consider Lucca or Cortona instead. With 7 days, you have some good options.

For a detailed one week plan, check out our 7-day Tuscany itinerary .

10 days - the ideal visit

With 10 days in Tuscany, you can fully experience the region and see it in all its glory. This is the perfect amount of time to spend here. With a week and a half, you can do everything mentioned above, visiting art towns to your heart’s delight, making a trip to the gorgeous city of Siena, spending plenty of time in Florence, and then heading out into the countryside for a few days discovering the hills and wineries of the Chianti or Val d’Orcia regions.

You’ll likely even have time to spend a coupe of days beach hopping along the Tuscan coast, visiting seaside cities like Livorno, and quiet coves lined with pine trees.

To really mix things up, you could shorten your time visiting the hilltop towns or cities of the region, and add on visits to the islands of Elba or Giglio.

With 10 days, you can thoroughly discover this region. There are countless ways to spend a week and a half in Tuscany, and the beauty of this is that you will never run short of things to do and places to visit. Your only challenge will be deciding where you want to spend most of your time!

Connect with Tuscany travel expert Stefano for help perfecting your itinerary, answers to all your travel questions, and fabulous local tips for a better visit!

Tuscany has two cities with international airports: Florence and Pisa.

Florence’s airport is called “Amerigo Vespucci Airport” (FLR), and it’s located about 10 kilometers northwest of the city. This airport is small but efficient and hosts flights from cities around Italy and Europe. If you are traveling from the US or elsewhere in the world, you will probably need to fly into Rome or Milan instead.

From Florence’'s airport, you can take a tram into the city, and then from the central Santa Maria Novella train station you can transfer to virtually anywhere in Italy, with high-speed connections to Milan, Rome, Bologna, Naples, La Spezia, and other destinations.

Pisa International Airport’s (PSA) official name is Galileo Galilei Airport, and its distance is only 6 kilometers from the town center. Flights here depart to/from other Italian cities and some European destinations.

From the Pisa airport, you can easily arrive into the city center with the Pisa Mover, a high-speed monorail train that gets you into the city in just 5 minutes. Then, from the Pisa train station, you can catch trains to many other destinations in Tuscany, including Florence.

Arriving by train

Tuscany’s major towns are incredibly well-connected by trains with other parts of the country. You can easily arrive into many different cities and towns in Tuscany from Rome, Bologna, Milan, Turin, La Spezia, etc. Many of these routes are served by high-speed trains. You can also travel to and throughout the region by Intercity and Regional trains, which are slower but cheaper.

Of course, the central hub for all of Tuscany is the city of Florence , which has high-speed train connections with almost every other major city in Italy. In many cases, if you’re traveling to Tuscany from elsewhere in Italy, you will probably first arrive to Florence’s central Santa Maria Novella train station, and then catch a connecting train on to your final destination in the region.

You’ll usually find multiple daily departures from Florence to many other Tuscan cities and towns. For information on trains and timetables, check the Trenitalia and ItaloTreno websites.

Most trains in Italy are operated by the national rail service, Trenitalia . However, depending on where you’re coming from, the private train company Italo , which exclusively operates high-speed trains on Italy’s most heavily used routes, may also be an option.

Taking a ferry

For those of you who are coming from Sardinia, Sicily, or Corsica, you can also arrive to Tuscany by ferry, into Livorno, the largest port in the region. From Livorno, it’s an easy train ride on to other destinations in Tuscany.

Where to buy train and bus tickets

In general, we recommend booking your public transport tickets directly with the service provider. That said, when you’re trying to see all your options and compare routes and prices, it can be a real hassle to have to look up each individual company.

Omio is an aggregator that shows options for public transport routes all over the world. When you do a search, you’ll be able to see all your options for trains, buses, flights, and even ferries along with a host of different companies that provide the services. Comparing prices is easy, the site has a great design, and you can keep all your bookings in one place. It costs a little bit more than booking direct, but it’s really convenient.

If you’re planning to stay in Tuscany for anything more than 3 days, you should split your time between a few different bases, so that you can see different areas of the region and minimize time spent driving or taking the train out to places of interest.

For stays of 3 days or less, however, and especially if this is your first time in Tuscany, you should almost certainly base yourself in Florence. More on that below.

Florence , the birthplace of the renaissance, is a gorgeous city and a must-visit for anyone traveling to Tuscany. Florence is iconic, and the city is filled with more world-class museums, galleries, churches, gardens, and gorgeous buildings than you could possibly visit in a single trip.

Is it touristy? Yes. Is it still worth visiting? Absolutely yes! As long as you know what to expect and have a good plan for your visit, you will have a great time in Florence. Millions of people come here for a reason!

Florence is also an ideal base because being Tuscany’s biggest city, it offers a huge selection in terms of accommodation, restaurants, tours/experiences, nightlife, and cultural offerings.

From a purely practical standpoint, Florence is centrally located within the region, it’s extremely accessible without a car, and it’s the central train hub for all of Tuscany, meaning that you can get almost anywhere else you want to go quickly and easily from there.

One quick transport note: if you plan to rent a car for your trip, wait to get it until you’re done visiting Florence, or drop it off before you arrive in the city (if you’ll visit Florence at the end of your trip) as parking in the city is an absolute nightmare.

Staying in Siena is a great idea if you want to be in a city, but close enough to the Chianti and Val d’Orcia regions to easily visit them as day trips. Siena is also a beautiful city in its own right, and is well worth a full day’s exploration. A bustling university town, it’s got plenty of great restaurants and bars where you can enjoy a fun night out.

Siena is also known for its many antique shops and a weekly market, the Mercato delle Merci, which is one of the largest in Tuscany.

The city isn’t especially big (only about 50,000 residents), so you won’t find quite as many hotel options as in Florence, but there should still be plenty of places to choose from at all price levels.

One important thing to know is that the towns and countryside outside of Siena (Val d’Orcia, Chianti, etc.) are not very well served by public transportation, so you will really need to have a car if you choose to stay here and want to visit the surrounding area.

Monteriggioni/the province of Siena

Now, if you’re interested in staying in the countryside amongst the smalls towns of rural Tuscany, the province of Siena is your best option. This area is gorgeous, it’s got tons of wineries, and is bursting with “agriturismi” (elegant farmhouses converted into hotels, many with pools and excellent on-site restaurants), which are wonderful accommodation options.

The town of Monteriggioni is one excellent countryside base. Here, you can visit the local castle, admire stunning views, do all sorts of outdoor activities (from horseback riding to e-biking), and quickly travel to Siena and other points of interest.

The Maremma Coast

On the Maremma coast, which begins a bit south of the city of Livorno and continues down into the region of Lazio, you can stay in charming towns like Grosseto, Orbetello, Follonica, or Porto Santo Stefano.

Porto Santo Stefano is a particularly beautiful town, beloved by the rich and famous, which boasts a bubbly atmosphere in a Mediterranean setting. The town doesn’t offer cultural attractions, but it has stunning beaches and coves. The surrounding area is especially verdant, so it’s also a great place to enjoy scenic walks in nature.

Since the main attractions in this area are the beautiful beaches, many of which are not served by public transporation, you will need to have your own car in order to really experience what makes the Maremma Coast so special.

Transportation and how to get around in Tuscany

A “Regionale” train. Photo: CAPTAIN RAJU , CC BY-SA 4.0 , via Wikimedia Commons

When it comes to traveling within Tuscany, you can easily bounce between the major cities of the region by train. If you intend to only visit big cities like Florence, Siena, and Pisa, there’s no need to have a car, and it would actually probably be inconvenient to get one.

However, if you plan to visit the countryside, the coast, or smaller towns, you will very likely find that having a car is the most convenient option. Public transportation does not cover rural areas and it’s very slow and indirect for many art/hilltop towns, so unless you want to spend a lot of time waiting around on buses, you’re really better off renting a car.

Renting a car and driving in Tuscany

Renting a car in Tuscany is extremely straightforward. You’ll find rental car offices in major cities like Florence, Siena, and Pisa, as well as at the airports. All of the major international rental car companies can be found here, along with a few local options, and you can pre-book your car online and pick it up when you arrive.

The price per-day for renting a manual-transmission compact car is usually around €30.

Now, regarding driving in Tuscany, Italy is somewhat infamously known for having aggressive drivers, so you might be intimidated by the thought of driving here.

However, Tuscany's peaceful landscapes (which is where you’ll likely be doing most of your driving) are lightly trafficked and the locals in those rural areas usually drive quite reasonably. Driving in the Val d'Orcia or Chianti hills is largely a stress-free experience.

If you are visiting the Argentario Coast during the peak of summer, you will certainly find traffic, but drivers will be mostly laid-back and in no rush, as the area is heavily frequented by people on vacation.

Driving within the cities or in the narrow winding roads of the hill towns can be a bit more stressful, but there’s really no need to use your car within a city or town, so once you park it, you won’t have to worry about repeated trips into heavy, impatient traffic.

Where to find a car rental

For the largest selection of cars and agencies, you should plan on renting in either Florence or Pisa. This is where Tuscany’s two main airports are, so you have the most cars and usually also the best prices.

In Florence, you can rent directly at the airport, at Santa Maria Novella train station, or in a few downtown locations. In Pisa, all the rental agencies are at the airport.

You also have a few rental agencies in Siena, a couple in Arezzo, and a few in Chiusi (near to Montepulciano). If you’re coming off of a cruise ship or ferry, the port city of Livorno also has lots of car rental agencies.

To check prices and book, I recommend using the following two car rental websites:

DiscoverCars includes offerings from all the major international rental companies as well as lots of smaller local agencies, which often have much better pricing. You can often find great deals.

RentalCars is very similar, although they tend to list mostly larger companies. It’s now owned by Booking.com, so is backed by a familiar and reputable brand. Their prices are good too.

Road conditions

Most secondary roads in the region are two-lane country roads, and they might not always be perfectly paved.

Medieval towns and villages have tiny and tight roads inside the centers. Mostly uphill, these streets are challenging to navigate. They are usually one-way roads, but this isn’t always true, so you might have to stop, pull over, and let the a passing car go by before you can drive on.

Manual transmission cars

In Italy, it is still popular to drive manual transmissions cars, so if you are not used to it, make sure to select a car with an automatic transmission when booking your rental car (just note that the price might be higher).

ZTLs - traffic limited areas

Some town centers, especially historic ones, have ZTL (Limited Traffic Zone) areas that only residents can drive through. If you drive into a ZTL area, you will almost certainly receive a fine, so always be on the lookout for the signs alerting you to them.

You will see a “no traffic” or ZTL sign at the entrance(s) to the town, so you will know when you can’t proceed with the car.

Finding parking in small towns is often quite difficult, so it’s can be more convenient to leave the car outside the center of Medieval towns and then walk in.

Usually, there will be municipal parking lots right outside of the medieval walls. Many of these are metered, so you’ll need to pay a small fee.

When parking on the street , you will see different strip colors on the curb. White strips mean that the park is free (unless differently specified on street signs), blue strips mean you have to pay, and yellow strips mean you can’t park there.

To pay for parking, you will need to look for parking meters along the curb.

International Driving Permit

An International Driving Permit (IDP) is legally mandated in Italy. Online sources will tell you that it’s not necessary and that you won’t be asked for it when renting a car.

While they are right that rental agencies rarely request to see it, some do, and the police can fine you if you don’t have it.

Train travel in Tuscany

Tuscany is overall well-connected by public transit. Trains and buses operate all over the region, but trains mainly link art cities and the centers along the coast. Regional and local trains are operated by the national rail service, Trenitalia .

In the countryside, you will need to take public buses or taxis to get around if you don't have a car.

Train travel in Tuscany is affordable and efficient, and the major cities and towns are quite well connected. The biggest downside is that many small towns that you may be interested in (like San Gimignano), don't have train stations. Instead, they will need to be reached by bus, or a combination of bus and train.

While most of the main cities/towns have a train station directly in the city center, the hill towns represent an exception to this: they usually don’t have train stations at all, but even when they do have a dedicated station, it will often be located a couple of kilometers outside of the town center.

This is because you can’t run train tracks up hills that steep! In these cases, you’ll have to catch a local bus or get a taxi to take you into the center of town from the train station.

Schedules and frequency of train departures

For routes between popular destinations and big cities, trains depart more or less every hour, with more frequent departures during the peak hours. The frequency of departures varies significantly from one destination to the next, but generally speaking, trains depart as early as 7 am and as late as 11 pm.

Types of trains

In Italy, there are three types of trains:

Trenitalia Frecce fleet - these are high-speed trains that make very few stops between their starting and ending destinations

Intercity , which travel between the country's major cities and towns, making more stops than the high-speed trains, but still not too many

Regionale - slower trains that make a high number of stops within a region

Intercity and Frecce trains assign a specific seat with your ticket, and for popular journeys and/or during busy periods, it’s not uncommon for them to sell out. So, you should always reserve tickets in advance if possible. This will also usually be cheaper than buying at the last minute.

Regionale trains, on the other hand, don’t assign you a specific seat with their ticket (which means you can sit where you prefer or find an empty seat), and as such, never sell out. The certainly can get packed though!

For traveling between the cities and towns within Tuscany, you will likely mostly be relying on Regionale trains, and since they don’t sell out, you can always buy those tickets directly at the train station shortly before your train’s departure. Tickets are also available on the official Trenitalia website/app though.

You also have a company named Italo Treno that runs a network of high-speed trains (similar to Trenitalia’s Frecciarossa fleet) on some of Italy’s most heavily traveled routes.

Validating tickets

If you purchase a physical ticket at the train station, you will need to validate it before boarding the train. There are dedicated machines where you can do this at the station and along the platforms, but if you can’t find them, ask the personnel at the ticket office. If you don’t validate your ticket, you may get ahttps://trainline.tp.st/HluOWC3ghefty fine.

There is no need to validate website-purchased tickets; just show the ticket on your phone to the “capotreno” (train conductor) when asked and you will be all set.

Cost of tickets and booking in advance

Trenitalia train tickets can cost as little as 3€ for local travel, and 50€+ for longer-distance, high-speed train rides. Keep in mind that if you book your long-distance train tickets well in advance, they will be cheaper.

For short routes, there really isn’t a need to buy in advance as the price doesn’t change much. On holidays or at exceptionally busy times of year, you should reserve in advance though just to make sure you get a seat.

Bus travel in Tuscany

In Tuscany, public buses fill the gap that the trains don’t cover, connecting the cities to smaller towns and rural villages. Buses are even cheaper than trains, with tickets costing as little as 1,20€. Bus tickets can be purchased in local kiosks/shops (called "tabacchi" in Italian), inside train stations, and directly onboard from the driver (although they don't always have tickets up for sale).

To validate your ticket, there is a dedicated machine inside the bus, usually in the front, where the driver is.

Bus companies and schedules

The main bus companies in Tuscany are Autolinee Toscane , Sitabus , and Tiemme . You also have Flixbus .

Bus schedules change throughout the year, and it might be challenging to find the updated one, so if you can’t find good information online, it’s best to go to Tourist Infopoints or ask at the "tabacchi" where you are purchasing the ticket. Google Maps is usually quite accurate with bus schedules as well.

In general, the first bus ride from any regularly-serviced destination usually departs around 6 am, and the last trip will be between 10 pm and midnight (depending on how frequented that bus line is, of course). Buses travel between towns on many different frequencies, and you can find them as often as every 10 minutes, or only every couple of hours.

Where to book train and bus tickets

For local buses, you can buy tickets at any bus station, at “ Tabacchi ” (little shops that sell miscellaneous goods, newspapers, and tobacco products - you’ll find them in every Italian town and city). sometimes at bars/cafe, and often aboard the bus.

For longer distance buses and trains, it’s ideal to book directly with the service provider, but the website/app Omio is also very convenient to use.

Taking ferries on the coast

To reach the islands of Giglio and Elba, you’ll need to take a ferry. Elba's ferries depart daily from the towns of Piombino and Livorno. The companies that operate the route are Toremar and Moby. Tickets cost around 20€ one-way and without a vehicle on board.

The ferries to Giglio Island depart daily from the town of Porto Santo Stefano. This route is operated by the Toremar and Maregiglio companies, and a one-way ticket costs around 15€, again, without a car.

Speaking of cars, non-residents cannot bring theirs onto the island during high season, so be aware of this if you’re considering taking your car with you.

Taxis and ride-sharing apps

Ride-sharing apps are illegal in Italy, so these are never an option here. As such, taxis are your only choice. You will find taxis lined up in dedicated locations at airports and train stations, and will usually need to wait in line to take one.

Otherwise, you can google "taxi" followed by the city/town you are in to find the local taxi company that services that town/area. To book a ride, you will usually need to call the company directly.

Compared to other regions in Italy, Tuscany is rather pricey. This shouldn’t be a much of a surprise though, as this is a premier tourist destination that welcomes millions of visitors every year.

Here are some rough prices for typical expenses:

A night at a hotel: 80€ to 150€  

An average meal: 15€ for daily lunch specials (typically a main dish, a drink, and coffee or dessert), and 20 to 50 euros for dinner, depending on how fancy the place is and whether you want wine and multiple courses.

A glass of wine: 3€ to 9€

A coffee: 1-2 euros for an espresso or cappuccino at a non-touristy bar/cafe

Renting a car: 30€ per day (potentially much more in the high-season, or if you need an automatic)

A taxi ride within a city/town: 10€ to 25€

Short-distance bus/train ticket: 3€ to 10€

Long distance bus/train ticket (but still within the region): 10€ to 25€

Entrance tickets: 0€ to 25€

There is a wide range of costs here. Local museums or lesser monuments and attractions will usually not cost more than 10 euros, while visiting places like the Accademia Gallery, Uffizi, Siena Duomo Complex, and other premier destinations can cost around 20 euros.

Wine tastings at a winery: 10-20 euros (this usually includes multiple tastings and some light snacks)

Bike/E-bike rental in the countryside: 50 to 100 euros for the day

Guided tours (private and group):

Half-day private guided tour: approximately 250 euros

Full-day private tour: 400-600 euros.

Small group tours: 40-80 euros per person.

Credit cards

When in Italy, you can pay with both debit/credit card and cash. You can use your card to pay in most places in Tuscany. Just note that some smaller bars can ask you to pay cash if you are consuming a meal that costs less than 5€.

So it is advisable always to have some euros in your wallet. You will find ATMs in every town, but the withdrawal of money might apply some fee. 

Tipping is not customary in Italy. However, it is sort of expected by foreigners (and especially from North Americans), and it is appreciated by those working in hospitality.

You can only tip in cash, and how much to tip really depends on you. In general, you should tip a few euros for a short and/or undemanding service (like a drink at a bar). In this case, you usually leave the change if you pay cash. You should tip more for ongoing services (like a week-long cleaning service).

Tuscany is best known for Florence, wineries, and its lovely Renaissance towns where famous artists and scientists lived, from Leonardo Da Vinci to Michelangelo. This is a big region though, and there’s much more to it than just that, so there’s a lot to see and do here!

Here, architectural wonders and artistic masterpieces mingle with beautiful landscapes made up of green hills, cypress trees, vineyards, and olive groves.

An agricultural powerhouse, Tuscany produces excellent-quality olive oil and wines, both which are key-ingredients of the many delicious local dishes made here. As such, food and wine tasting are very popular here.

For scenic drives, rolling hills, and bucolic countryside, the Chianti region and the Val D’Orcia (a UNESCO heritage site) are simply unbeatable.

Heading toward the coast, idyllic beaches with crystal-clear waters backed by coastal plains, such as in the Maremma region, are perfect for snorkeling, boat tours, and other water sports.

And last but not least, Tuscany has two incredible islands that should be on everyone’s bucket list: Elba and Giglio.

For some more ideas, here’s a quick list of some interesting things to see and do when visiting the region:

Visit charming hilltop towns like Cortona , San Gimignano, Montepulciano , and Lucca  

Hit the beach - the Argentario area is the best one, also for snorkeling

Go for a wine or olive oil tastings in the Chianti region

Hike in the Apennines, Monte Capanne, or Monte Capanne

Explore the heart of the renaissance: Florence , Pisa , and Siena are the best places to do it

Go truffle hunting in San Miniato

Ride e-bikes through the hills in the Val d’Orcia

Tour Fortezza delle Verrucole (a scenic castle in Garfagnana)

Relax in nature in Parco Naturale della Maremma

Join a food tour in Florence

Take a pasta cooking class. Everyone does it for a reason - it’s good fun!

Ride a Vespa through the countryside - Toursity? Yes. A blast? Also yes.

Learn about marble in Carrara

Go bird-watching at the Laguna di Orbetello

Best Places to Visit in Tuscany

Tuscany is truly blessed with an abundance of wonderful places to visit and things to do. With an incredible number of beautiful towns, great beaches, lovely countryside, and pristine nature, you could spend weeks here and still not see everything.

So, we could easily list 100 “best places to visit”, without exaggerating. However, no one has unlimited vacation time (or money), so you probably won’t be able to see all those places. As such, below is a list of 20 destinations that we think are well-worth visiting whether this is your first time in the region or your tenth.

1. Florence

One of the most visited cities in the world, Florence is packed with astonishing artworks and architecture dating back to the Renaissance. Lying on the Arno River, Florence was home to incredible artists of the likes of Da Vinci, Michelangelo, and Botticelli, who worked to make the city a renowned art capital.

Elegant palaces, incredible museums, and centuries-old churches are not all you will find in Florence. The city is also popular for its culinary traditions and cutting-edge shopping opportunities.

This picturesque town, founded by the Etruscans over two millennia ago, lies 70 km south of Florence. Siena might be small but is full of cultural landmarks and architectural marvels.

From the famous shell-shaped Piazza del Campo to the black-and-white-marbled Duomo, Siena is mainly known for the horse race called “Palio di Siena”, which is held twice a year (in June and August).

Worldwide known for the iconic Leaning Tower, Pisa boasts many other artistic and architectural treasures. One of the richest cities during the Middle Ages, here you can marvel at Romanesque buildings, Gothic churches, and Renaissance squares - with Piazza dei Miracoli being particularly beautiful.

Pisa is also a university town, so it has a lively vibe and hosts great bars, cafes, and cultural events.

Lying very close to Pisa, Lucca has among the best-preserved city walls in Italy. Surrounded by green hills, the walls have been turned into a pedestrian promenade that you can walk to circle this enchanting Tuscan town.

Besides the city walls, Lucca is home to elegant squares, centuries-old churches, and a couple of still-standing lofty towers.

The town is popular in Italy for hosting the Lucca Comics & Games, the country’s biggest comic event held annually between October and November.

5. San Gimignano

You will spot San Gimignano from a distance: the hilltop town is characterized by 14 tall medieval towers that create a unique skyline. Once in number 72, the towers were commissioned by powerful families to show off their wealth.

Climb the towers for breathtaking views of Tuscany hills. The “Town of Fine Towers”, as San Gimignano is called, also has a couple of excellent museums and Gothic and Romanesque buildings lining the streets and main square.

6. Val d’Orcia

Tuscany is beloved for its rolling hills, and the Val d’Orcia is quintessentially Tuscan in this sense. This fertile area extends from the hills south of Siena to Mount Amiata.

Visiting pretty medieval towns like Pienza, Montalcino, and Castiglione d’Orcia are just a few things you can do in the valley. And of course, visiting the wineries is an ever-popular activity.

Relaxing walks among olive groves, tall cypresses, and vines make the area perfect for discovering Tuscan nature.

The dreamy landscapes of the Val d’Orcia have been used for shooting scenes in many movies (like “Gladiator” and “A Midsummer Night’s Dream”, just to name a few).

Sitting on a sloping hillside, Arezzo was once one of the 12 towns of the Etruscan League. With a long and rich history, the city delights visitors with many churches and archeological museums.

Among the city’s highlights is the central Piazza Grande with the Vasari Loggia, the Palazzo della Fraternita dei Laici, Arezzo Cathedral, and Corso Italia, lined with boutiques and shops selling antiques.

Many scenes of the award-winning movie “La Vita è Bella” were shot in Arezzo’s historic center.

8. Parco Naturale Migliarino San Rossore Massaciuccoli

A little inlet on Lake Massaciuccoli. Photo: Albarubescens , CC BY-SA 4.0 , via Wikimedia Commons

The Migliarino Nature Park is a protected area that stretches from Pisa to Lucca. It covers 230 square kilometers and encompasses many habitats, including pine forests, wetlands, and coastal dunes.

The Migliarino Nature Park is perfect for discovering Tuscany’s natural beauty and biodiversity. The area also boasts the lovely Lake Massaciuccoli, which can be explored by bike or walking.

Located in the Province of Arezzo, Cortona is set atop a hill full of Medieval and Renaissance buildings. Cortona’s main draw is the surrounding countryside, where the popular movie “Under the Tuscan Sun” was shot. 

Besides the stunning landscape, Cortona has a rich history and heritage that can be discovered by visiting the Museum of the Etruscan Academy, as the town was once part of the Etruscan League.

10. Hot Springs

The Terme di Saturnia

Tuscany has many natural hot springs, some of which are pretty popular (and busy), while others are still under-the-radars. You will find both hot springs enclosed in spa centers and beautiful outdoor hot springs, which are free to visit.

The most famous hot spring in the region is the Terme di Saturnia, which has become pretty busy. If you prefer a less-frequented but just as scenic, head to the Bagni San Filippo, in the namesake village. Here, the small thermal pool is hidden within the forest, and it is characterized by candid-white rocks that create a snow-like covered landscape.

A gorgeous beach on the island

The town of Portoferraio in Elba.

Elba is an island surrounded by the sparkling Tyrrhenian Sea. Famed for being the place of Napoleon’s exile, the island is much more than sun-kissed shores, beautiful beaches, and coves for a beach getaway.

Elba’s coastline is dotted with lovely towns where you can delve into the island’s cultural heritage, such as Portoferraio and Porto Azzurro.

The inner part of the island is home to fertile vineyards, and Monte Capanne, with a height of 1,018 meters, makes for an ideal hiking spot.

12. San Miniato

Photo: I, Sailko , CC BY-SA 3.0 , via Wikimedia Commons. Cropped from original

A quaint village in the province of Pisa, San Miniato is the place to be to taste one of the food products you can find in Tuscany: the rare white truffle. To this incredible food is dedicated a whole cultural event, the “Mostra Mercato di Tartufi”, hosted every November. In San Miniato, you can do truffle tastings and also participate in truffle hunting.

The village is also lovely to explore by foot, and its most stand-out feature is the medieval Piazza del Seminario.

But there’s more: San Miniato is one of the stops of the historic Via Francigena.

13. Chianti Region

Gorgeous scenery in Radda in Chianti

Another unmissable area of Tuscany for any food lover is the Chianti region . Kilometers of rolling hills with fertile vineyards create not just a wonderful landscape to discover by bike or motorbike, but it is also where the world-famous Chianti wine comes from.

Having a wine tasting in the Chianti hills while sampling local foods and meeting local winemakers is a must-do experience in the area.

14. Porto Santo Stefano

Located in the Argentario Peninsula, Porto Santo Stefano is a semi-island tied to the mainland. All around Porto Santo Stefano are striking coves that will be the joy of beach dwellers. Some coves are private, while others can only be reached by boat or with a short hike. One of the best coves is Cala Gesso, which is a perfect snorkeling spot.

The town is also one of the main seaports of the area, with a bubbly atmosphere and daily transfers to reach Giglio Island.

15. Giglio Island

Giglio Island lies within the Arcipelago Toscano National Park, just 16 km from Porto Santo Stefano.

This Mediterranean island offers visitors natural beauty and rich history. The narrow streets of the main town of Giglio Porto are lined with artisan stores and outdoor restaurants.

The island is home to stunning beaches for swimming and snorkeling - don't miss Campese Beach and Cannelle Beach.

Another highlight of Giglio Island is the town of Giglio Castello, on the island's highest point, where you can visit the medieval fortress Rocca Aldobrandesca to marvel at 360-degree landscape views.

16. Volterra

Volterra is one of the larger hill towns in Tuscany. Located between the Era and Cecina valleys, Volterra is enclosed by double walls of Etruscan and Medieval times. If you like narrow streets, ancient walls, and a towering fortress, you will surely love this town.

Volterra is particularly known for the craftsmanship of alabaster, and you can purchase decorative objects in the many artisan shops in town or visit the interesting Ecomuseum of Alabaster.

17. Monteriggioni

Photo: Maurizio Moro5153 , CC BY-SA 4.0 , via Wikimedia Commons. Cropped from original

Another walled town in Tuscany, Monteriggioni's main feature is the 13th-century castle that overlooks the entire landscape. You can walk on the medieval walls that are part of the castle to have a bird's eye view of the Chianti countryside. The town also has 15 still-standing medieval towers, two impressive doorways, and charming little streets. 

Monteriggioni is located along the pilgrimage route known as Via Francigena, and it was featured in two famous movies, "The English Patient" and "The Gladiator".

18. Orbetello

Orbetello is a seaside town in the Argentario, with a lovely center with shops, restaurants, and a lively weekly market selling local food products. But Orbetello is much more: the town boasts a lagoon, which makes the area geographically unique. The Laguna di Orbetello is rich in fauna of all kinds, which is protected by the WWF.  

The lagoon is surrounded by a cycle-pedestrian path that you can go through to admire pink flamingos, white herons, and flocks of coots.

19. Livorno

Livorno is an important port town in Italy, where ferries depart for many other parts of Italy, including the Elba Island in Tuscany.

Embellished during the Renaissance by the Medici family, in Livorno, you can visit many attractions like a castle (the Fortezza Nuova), the beautiful Terrazza Mascagni (a sea view terrace), and the Nuova Venezia (the streets surrounding the castle, which are lined with canals).

20. The Tarot Garden

Tuscany has an unusual attraction, The Tarot Garden. This artistic garden is located right outside the village of Capalbio, and it was created by the mind of artist Niki de Saint Phalle.

The park houses installations representing the 22 major arcana of the divinatory tarot, which are made of iridescent mosaic tiles and metal. The artist took almost 20 years to complete this project, and this magical attraction is open from the beginning of April through mid-October.

5-day itinerary - Art towns

Days 1-2: Florence

Day 3: Pisa and Lucca (day trip from Florence)

Day 4: Siena

Day 5: San Gimignano, Monteriggioni, Colle di Val d’Elsa (day trip from Siena)

7-day itinerary - Art towns and the Chianti area

Day 6: Chianti region

Day 7: Arezzo and/or Cortona

10-day itinerary - Art towns, the countryside (Chianti and Val d’Orcia), and the coast (Argentario and Giglio Island)

Day 5: Chianti region

Day 6: Val d’Orcia with Montepulciano

Day 8: Terme di Saturnia

Day 9: Argentario (Porto Santo Stefano and Porto Ercole)

Day 10: Giglio Island

2-week itinerary - The best of Tuscany (art towns, islands, Argentario, hot springs, and the countryside)

Day 4: San Miniato

Day 5: Elba Island (ferry from Livorno)

Days 5-6: Porto Santo Stefano & Porto Ercole

Day 7: Giglio Island

Day 8: Bagni San Filippo

Days 9-10: Val d’Orcia with Montepulciano

Day 11: Cortona or Arezzo

Day 12: Siena

Days 13-14: Chianti region

At Go Ask A Local we connect independent travelers with in-destination Local Experts for personalized travel planning that goes way beyond the highlights. Whether you’re planning a DIY trip and just want some expert advice on your plan or are looking for a fully tailor-made trip, our Local Experts can help you plan better!

One-week Serbia Road Trip Itinerary - By A Local

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The Perfect Tuscany, Italy Road Trip Itinerary: Florence, Montepulciano, Chianti And More

• Last Updated On: September 8, 2023

Tuscany, the land of wine lovers is an ideal Italian road trip adventure. After traveling through much of the country including road trips through Sicily , Puglia , the Dolomites in the north, the Amalfi Coast , Lake Como , and more, it was time to focus on the ultimate wine region in Tuscany.

Tuscany is probably one of Italy’s most well known areas and has been endlessly referenced in pop culture by movies like Under The Tuscan Sun. It’s not hard to see why. The picturesque rolling hills, beautiful vineyards, and impossibly cute hillside towns make this a bucket list adventure for many travelers.

I spent a week driving through Tuscany drinking my way from north to south. I visited a seemingly endless list of beautiful villages, ate delicious Tuscan cuisine, and watched countless sunsets. This is how I structured my trip and the places I visited. If you’re also planning a trip through Tuscany and are overwhelmed with which villages to visit/stay, and which wineries to drink at, hopefully this guide will help you out!

Where I went in Tuscany

I had one week to spend in the Tuscany province of Italy. I think one week is actually a decent amount of time to explore Tuscany. This includes a stay in Florence, its capital city as well as many nights through its iconic wine regions.

There is not much distance to travel on this trip especially if you start and end your trip in Florence. The wine region is all within a two hour drive from Florence. However, if you plan on visiting many of the smaller towns and wineries, you will spend a lot of time driving just because of the small roads.

When did I visit Tuscany?

I visited Tuscany in the summer season. Summer (July and August) is the high season for a reason as you can expect warm weather throughout the day and lush vines at the wineries. It’s definitely a picturesque time to visit the Tuscany region. However, I visited in 2021 during COVID so the tourism was not even close to what it would be like in normal times.

Having spoken to many Italians working in the region, normal summers pre-COVID are absolute insanity. Entourages of huge tour buses drop off tourists by the hundreds in small towns like Montalcino and San Gimignano. Restaurants and wineries are fully booked weeks in advance so you don’t stand a chance being spontaneous.

These are the places I visited in Tuscany:

• Montepulciano
• Chianti Region including Siena, San Gimignano
• San Quirica D’Orcia
• Wineries all day, everyday, everywhere

If these places ring a bell and sound like the places you want to visit, this is the perfect itinerary for you! Note that there are SO MANY more villages to visit in Tuscany but these were the ones I saw with the time I had. You don’t need much time in each town so if you want to spend less time wine tasting, and more time village hopping, this is also a possibility!

How to get around Tuscany

Unlike other parts of Italy where you can get around by public transportation, you really need to have a car to explore Tuscany. If you’re just planning to visit the main towns like Florence, Siena, Montepulciano etc, then the bus system will suffice. However, if you want to explore the countryside and really immerse yourself in it all, you will need to rent a car.

There are no buses that will drop you off at the Brunello wineries in Montalcino for example. There are no Ubers to speak of in Tuscany and taxis are both expensive and elusive. Essentially, you won’t get much wine tasting in if you don’t rent a car which is probably the main reason you want to come here!

Driving in Tuscany

Driving in Tuscany is both simple and beautiful. The Tuscan landscape is famous for its rolling hills that contrast wheat fields, Cyprus trees, and lush green vineyards. It’s a view you won’t tire of while driving.

The driving is quite easy and the roads are perfectly fine. The distances between places might seem short but make sure to budget more time because you won’t drive more than 70km/hr at most points. Gas is abundant and easily found all along the way.

Where to stay in Tuscany?

I wrestled with where to stay in Tuscany for a long time. Tuscany is not a big province per se but the roads are small so it takes a long time to get anywhere.

I couldn’t decide whether to stay in Chianti and Montepulciano or just stay in one of the two and make day trips.

Ultimately, I settled on doing day trips from Montepulciano which seemed like a central and livelier town. I only had four nights in the wine region so it would feel a bit rushed to do two nights in one place and then have to drive somewhere else.

I don’t regret my decision and found Montepulciano to be a great central point to explore the region.

Wine tasting in Tuscany

Wine tasting in Tuscany is one of the main events you’ll be doing. Tuscan wine is perhaps the most popular wine in Italy and certainly one of the most popular wines in the world. Even when I was drinking boxed wine as a college kid, somehow I had even heard of Tuscany being this magical wine region in Italy that had high end wine that a kid of my stature should definitely not be drinking at the time.

Fast forward a decade later, and here I am drinking my way through Tuscany. And drink I did. I spent five days in the Tuscany area, and each day I would visit two or three different wineries.

How does wine tasting work in Tuscany

Then you go to places like France or Germany where most wineries are smaller shops without a wine tasting infrastructure set up. The bigger wineries require reservations in advance and always include a tour of the cellars that I could care less about.

Some wineries have the whole package which includes the wine tasting, tour of the cellars and property, and bread/cheese. Some of them you could just pay to drink wine. I’m definitely a proponent of the latter because I could care less about touring cellars. I’ve done this countless times already and you just end up forgetting everything anyway.

Cost of wine tasting in Tuscany

Tuscany is not a cheap area to travel. In Italy, it is probably one of the most expensive wine regions simply because of the quality of its wine and the name recognition it enjoys.

Having just visited the Douro Valley in Portugal the week before, it was a bit of a shock to see the prices in Tuscany. Wine tastings are definitely pricier. I was paying €15 or more for tastings of three wines. The quality of the wine tastings are quite good however. There was ample amounts of explanations and information however so I was mostly satisfied.

Some of the fancier wineries definitely exude a sense of arrogance and entitlement whereas most of the wineries I went to were on the more relaxed side with very friendly people (as it should be). I really enjoyed my conversations with some of the people about the wine and just about the culture in the area.

Tuscan Wine Summary

Tuscan wines specialize in the San Giovesse grape. This grape is found all over Italy but its most cultivated in Tuscany. Tuscany wineries mostly grow the San Giovesse grapes along with numerous other varieties. The wines in Tuscany mostly focus on this grape.

The biggest regions in Tuscany are

Each region produces wines with the San Giovesse grape but each region has different standards and requirements for the higher end versions of their wines. There are too many rules and requirements to speak of so I will just list some of the most interesting ones:

• Nobilo Di Montepulciano : The wineries here make Nobilo which is 85% San Giovesse minimum, and has to be aged for two years
• Brunello di Montalcino : The most famous wine in the region is without a doubt Brunello. These have to be 100% San Giovesse, hand picked, and must be aged for five years. Yes,  5 years. 
• Chianti Classico : The highest grade of Chianti requires 80% Sangiovese grape, and must be aged for a minimum of 12 months. Reservas must be aged 24 months.

Full Tuscany Trip Itinerary

Of course, if you have not been to Rome before and have closer to two weeks to spare, then I would definitely recommend visiting Rome for at least 3-4 nights.

From Rome, I rented a car and drove north through Umbria and into the province of Toscana (Tuscany). On the first day, I stopped in the town of Orvieto for a few hours before arriving at my destination for the next four nights in Montepulciano.

From Montepulciano, I spent one full day exploring the wine around the area including which produces Rosso Di Montepulciano and Nobile wines. In the same day, I drove west to Montalcino (30 minutes or so) and sampled the famous Brunello di Montalcino wines. These were amazing.

The next day, I spent the entire day exploring the Chianti region in the north. I stopped at a few wineries and visited the towns of Siena and San Gimignano. Definitely need to start early for this one.

From Florence, I flew back home as this was the end of the trip. If I had more time, I would have definitely continued on to Cinque Terre as that is just a short train ride away.

Day 1: Orvieto and Montepulciano

The trip starts in Rome. Again, I only flew into Rome to start the trip as it was the best international flight option.

Had I not been to Rome before, I would definitely spend at least 3 nights here to see the endless sights and history the city has to offer. Nevertheless, the Tuscany adventures must go on.

From Rome, I picked up my rental car from  Noleggiare car rental and was on my way northward. The first destination is Montepulciano but as I arrived in the morning, I had most of the day to explore. I stopped in the town of Orvieto as I had heard many good things about this historical town. It’s actually not in the Tuscany province but rather that of Umbria.

Orvieto Town

Orvieto is home to incredibly beautiful and quaint Italian architecture. With its picturesque buildings and cobblestone streets, simply walk around the town and get lost in its little alleyways. Before you know it, you’ve come across the stunning and large Duomo that dominates the town. This Duomo is definitely one of the more stunning cathedrals in Italy. The detailing and murals in its facade are breathtaking.

The cathedral is over 800 years old and as you’d expect in Italy, is in as great of condition as ever. It costs €4 to enter and well worth the visit.

Visit the Belltower of Orvieto

No Italian town is complete without a bell tower. Make your way back onto Corso Cavour to head to  Torre del Moro . This tower offers the most breathtaking 360-degree views of Orvieto and is absolutely worth the €2.80 entrance fee. The best part? There is an elevator that takes you half way up so you don’t have to walk like a chump, and then you climb the last stretch of stairs to get to the viewing platform.

Arriving in Montepulciano

After having lunch in Orvieto, it was time to drive towards Montepulciano. If I wasn’t so tired, I would have probably just visited Pilignano on this day and checked it off the list. Instead, I saved that for a few days later in the trip.

Montepulciano is probably the biggest village/town in Tuscany. I consider Siena and Florence to be cities but among the cute must see traditional villages, Montepulciano is the biggest.

Montepulciano is one of many hilltop towns in Tuscany. Its beautiful Medieval buildings located on the top of a hill makes it incredible to look at from afar. While in the town, there are beautiful street after beautiful street for you to walk through.

Make sure to make a reservation at Osteria Acquacheta which is famous around the region and serves a delicious Bistecca Florentina. The pastas are also incredible here so make sure to try the pasta with tartufa (Truffles).

Day 2: Montepulciano and MOntalcino

The day is long so make sure to have an early start. Wineries open between 9:30 and 10:00am on most days.

Wine tasting at Bindella Winery

The first stop is the Bindella winery which came highly recommended from my Airbnb host. This winery is one of the biggest and grandest wineries in the Montepulciano region. It is modern, spacious, and has absolutely spectacular views of the Tuscan landscape with a beautiful tasting room overlooking it.

We just showed up without a reservation and had our first of many tastings of Tuscan wines. Being in Montepulciano, I learned all about the wine production here and about the Sangiovese grape. I tasted a basic Rosso Di Montepulciano from Bindella, as well as their higher end Nobilo wines.

Delicious, and beautiful views without a doubt. The tastings are a bit pricey however at 21 euros.

Lunch around Pienza

One of the best places to try Pecorino is at the Cugusi Silvana farm. Located right outside of the town, this farm produces pecorino and has an onsite shop that provides tastings as well as the ability to create your own picnic basket. Once you’ve selected your cheese and meats (I’d recommend tasting the more aged pecorinos), you can take it and enjoy it on their properties which have stunning views of the Tuscan landscape.

This is every Italian lovers dream. Eating outside on the rolling hills of Tuscany enjoying a glass of Montelpuciano while eating delicious bread and cheese.

Montalcino Town

Next stop, wine tasting of Brunello!

Azienda Agricola Patrizia Cencioni – Brunello di Montalcino Winery

I must say I really lucked out when discovering this winery located just outside of Montalcino.

I ended up buying a few bottles because Brunello di Montalcino bottles outside of Tuscany can be very expensive.

San Quirico D’Orcia

Had a quick aperitivo here before heading back to Montepulciano for dinner.

Day 3: Chianti Region

The next day was focusing on exploring the Chianti wine region of Tuscany. Chianti is the largest and most well known of the areas in Tuscany. It produces about half of the total wine output of Tuscany.

There are also countless wineries in Chianti to choose from so of course one day is not nearly enough to experience everything.

Castello Brolio

The grounds of this castle are beautiful, albeit not as pretty as the castles I’ve become accustomed to living in Germany . Nevertheless, the views from the winery are absolutely gorgeous. You can see the whole valley of Chianti here.

I will say that I found the landscape near Montepulciano and Montalcino more picturesque than in Chianti. You will not go wrong in either place however!

La Lastra Winery

Next stop was a wine tasting at La Lastra Winery just outside of the town of Siena. This winery was one of the first BIO wineries in Italy. The owner came and gave us a fantastic wine tasting giving us hearty pours and very descriptive explanations.

The property was also fantastic and screamed of Tuscan charm.

For lunch, I decided visiting Siena was a must. Siena is the second largest city in Tuscany after Florence and makes for a very easy day trip.

Montecchiello Viewpoint Point

If you have time and energy, make sure to go to the ultimate viewpoint in Tuscany that shows off its natural beauty. This is the “famous” Cyprus tree lined road that winds and curves around to a beautiful farmhouse estate.

This is actually a hotel you can stay at but most people stop here to take beautiful photos of the landscape.

Day 4: Pitigliano

The following day started with a drive south to the beautiful hold town of Pitigliano. Located on top of a hill (which city in Tuscany isn’t at this point?) this town had old school charm that kind of reminded me of my visit to Matera in Puglia. 

The town itself is not that big and there are only two main streets to walk through. However, the streets are very pretty as well as the views of the nearby valley.

I think looking back on it, I probably would not come to Pitigliano as a day trip from Montepulciano. It is quite far and not worth going all that way for. The weather was particularly bad on this day so I ended up calling the day early.

If I could go back, I would probably just spend another day driving around the Val D’Orcia and visiting the wine regions I wanted to see. I particularly liked the Brunello wines from Montalcino and I would have spent more time there.

My original plan was to actually go to Pitigliano and then to a winery in the Montalcino area like Banfi winery specializing in Brunello.

Terme Di Saturnia

If the weather was nicer, I would have surely visited the Terme Di Saturnia which are the famous and ultra picturesque thermal pools of Tuscany. However, with these places, I suspect the pictures are almost always better than reality. The pools look absolutely amazing given the right filters and the absence of crowds. Just look at this drone photo!

If this doesn’t make you want to visit, I don’t know what will. Sadly, this place gets super busy in the summer months. I think I would only come and visit this place during the off season months, and I would only come here right as the sun rose to avoid the crowds.

Day 5: Antinori Winery, San Gimignano

It’s a modern architectural wonder and also home to its wine shop where you can taste the many wines Antinori has to offer, as well as a Michelin style restaurant with beautiful views of its vineyard.

Antinori has multiple labels and multiple brands of wine in many locations around the world which was a big change from the smaller wineries I had visited previously. This place is famous for wine tasting tours with their cheapest tour option starting from €35 a person. However, if you do not want to book a scheduled tour, anyone can show up and walk around the estate and enjoy wine tastings at their leisure. This place is expensive however so keep that in mind.

San Gimignano Town

San Gimignano is an old fortified medieval town whose walls date back to the year one thousand. It is famous for its historic and artistic heritage and its architecture, especially its towers. In 1990 it was declared a World Heritage Site by Unesco. Also very popular its local products including saffron and white wine, Vernaccia di San Gimignano.

This is probably one of the, if not the most picturesque town I saw in Tuscany. Highly recommended for a quick stop before going to Florence.

Day 5-8: Florence

Last but not least, the trip ends in Florence, the capital of Tuscany. Florence, as many might know from history classes, is one of the most important cities in Europe and the birthplace of the Renaissance. The Medici family, whose name I heard so much of in high school history, more or less ruled Florence for centuries and helped cast the Renaissance movement that took over the rest of Europe.

Eat Paninis in Florence

Florence is famous for their paninis, an in particular the Schiacciata bread. When in Florence, no trip is complete without gorging on many of these oversized sandwiches.

The most famous place of all is without a doubt All’Antico Vinaio. This place is an institution in Florence and attracts thousands of people every day to eat their sandwiches. The sandwiches are stuffed with meat, cheese, and veggies depending on your preference. All of it is then pressed and warmed between two pieces of Schiacciata bread, which I can compare to Focaccia bread.

All’Antico Vinaio attracts lines that can wrap around the street. On my first visit, I came around 1pm which is rush hour. The line was wrapping around the corner so I decided to come back the following day around their opening time of 10am. There are multiple locations of All’Antico Vinaio literally on the same street (that’s how much demand there is) but all of them fill up with hungry tourists and locals alike.

After waiting about 15 minutes, I was able to finally purchase one of these delicious sandwiches. I went with the original Favalosa and the thing is massive. Bring it with you to the river nearby and enjoy your sandwich with a view. It’s likely there will be many others near you also doing the same thing.

Alternatively, if you don’t want to wait in line, I had paninis in other institutions nearby. I can recommend Panini Toscani and Il Bufalo Trippone. Both sandwiches are delicious and on the cheaper side (€5 or so).

Eat Florentine style steak

La Bistecca Florentina is an  absolute must eat when visiting Florence. Turns out the city is also famous for its exceptional cows and steak. There are numerous restaurants in the city that serve the famous steaks which are essentially extra thick porterhouses.

The steak is incredibly tender and juicy. More tender than most other steaks I’ve had with the exception of Japanese Wagyu of course .

What to do in Florence

This deserves a post in its own right and I might just make one eventually. There are so many things to do and see in Florence. Here are my main highlights of the city

• Go to the Duomo: You can’t miss this. You literally cannot. It is in the center of the city and its huge dome is visible throughout the city. The pictures are also very stunning of the narrow Florence streets with the Duomo at the end
• Piazza Michelangelo: For the best views of the city, go to the Piazza Michelangelo and enjoy the sunset with some drinks
• David of Michaelangelo:  The ultra famous Statue of David sculpted by Michaelangelo is in this museum. Try to visit right before closing time to avoid the crowds
• Ponte Vecchio:  Famous arched bridge with Roman origins. Definitely a must see.

Here are some more pictures to help inspire your Florence trip.

Day 8 or 9: Pisa

I actually had a flight booked out of Pisa Airport which is 1 hour west of Florence since that is the Ryanair hub. There were many cheap flights to Frankfurt and other European cities that it made sense for me to take this flight home. Along the way, it only makes sense to stop in one of the most visited and well known tourist attractions in the world, the leaning tower of Pisa!

If you are not flying out of Pisa, simply make a day trip from Florence. The trains leave from the Florence central station frequently and takes 1 hour to get to Pisa. From Pisa train station, it is a 20 minute walk to the famous leaning tower of Pisa.

If you are flying out of Pisa airport and want to visit on your way out but worried about your luggage, there is a luggage storage option just outside of the main station called Stowaway Lockers.

There’s not much to say about the Leaning Tower of Pisa that you don’t already know. It was originally designed to be a bell tower in the 12th century. The plan was to never build an actual leaning tower, but it only progressed in this manner while it was being built. Floor after floor would go up and people noticed the lean to horror and dismay. Eventually, they just left it leaning and it still stands today as the penultimate symbol of Pisa.

Make sure to take your standard perspective photos here of you pretending to hold it upright, kissing it, etc.

Of course, there will be hundreds of other people doing it too which always makes for a good photo in and of itself.

Tuscany Itinerary Day by Day

This is my Tuscany itinerary on a day by day basis to summarize everything that I wrote. I will also give you some ideas for other itineraries depending on your allotted times!

Remember that I stayed in Montepulciano for the duration of my stay in the wine region. If I had more time, I would have split my stay between Montepulciano and a town in the Chianti region so I could explore the areas easier without driving so much. I will give numerous options below to inspire!

Rome to Florence – One week

Day 1: Arrive in Rome, drive to Orvieto for lunch and then arrive in Montepulciano Day 2: Wine tasting in Montepulciano area, lunch in Pecorino Farm, afternoon in Montalcino and wineries around the area Day 3: Drive to Chianti and visit wineries in the region, lunch in Siena Day 4: Full day of wine tasting in Tuscany Day 5: Montepulciano to Florence, stop at San Gimignano and Antinori Winery along the way Day 6: Full day Florence Day 7: Full day Florence Day 8: Pisa day trip, fly out of Florence/Pisa

Florence to Florence – One week

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Montepulciano Day 5: Explore Montepulciano and wineries surrounding Day 6:  Explore Montalcino and the Brunello making wineries of the region Day 7: Free day to explore the Tuscan wine region Day 8: Drive back to Florence to fly home

Florence to Florence – Ten days

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Siena Day 5: Explore Chianti Region wineries Day 6:  Drive to Montepulciano while wine tasting along the way, overnight in Montepulciano Day 7: Explore more of Montepulciano Day 8: Explore Montalcino and wine region around Day 9:  Day trip to Pitigliano and the villages nearby Day 10:  Drive back to Florence

Florence to Florence – Two Weeks

With two weeks, I think you can really do the region justice. I would also include Cinque Terre as this is an incredibly beautiful and well known spot that is nearby to Florence.

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Full day in Florence Day 4: Drive to Pisa and Lucca, overnight in Cinque Terre Day 5: Full day Cinque Terre Day 6:  Full day Cinque Terre Day 7: Drive back towards Tuscany and overnight in the Chianti area (San Gimignano, Siena, etc.) Day 8: Wine tasting in Chianti region Day 9:  Drive to Montepulciano, wine tasting along the way Day 10:  Full day wine tasting in Montepulciano Day 11: Full day wine tasting in Montalcino area Day 12: Full day wine tasting in your preferred area Day 13: Day trip to Pitigliano and Terme Saturna baths Day 14:  Drive back to Florence to fly home

Tuscany and Amalfi Coast Itinerary

Tuscany and the Amalfi Coast of Italy are perhaps some of the most desirable locations to visit in Italy. I am a huge fan of the Amalfi Coast and absolutely love the city of Naples.

Once you’re done with wine tasting Brunellos in Tuscany, then traveling to the birthplace of pizza in Naples is the logical next step right? Round it off with a visit to the wonderful island of Capri and the incredible views on the Amalfi coast and you have the ultimate Italian itinerary.

I spent a week traveling around Tuscany and about ten days in Naples and the Amalfi Coast. If you have two to three weeks for your trip you can easily do this trip by combining the itinerary in this post, and the itinerary from my Amalfi Coast itinerary .

Something like this:

Day 1: Arrive in Florence, explore city Day 2: Full day in Florence Day 3: Day trip to Pisa and Lucca Day 4: Drive to Antinori Winery and San Gimignano, overnight in Montepulciano Day 5: Explore Montepulciano and wineries surrounding Day 6:  Explore Montalcino and the Brunello making wineries of the region Day 7: Free day to explore the Tuscan wine region Day 8: Drive to Florence and fly to Naples Day 9:  Full day Naples Day 10:  Full day Naples Day 11: Naples to Capri Island Day 12: Full day Capri (Anacapri and Capri) Day 13: Full day Capri (Anacapri and Capri) Day 14:  Capri island to Positano Day 15 : Positano & Praiano Area Day 16 : Positano & Praiano Area Day 17: Ravello Day 18: Ravello Day 19 : Ravello Salerno to Naples

Of course you can shorten or lengthen this itinerary depending on your time frame but it is totally doable!

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tuscany TRAVEL GUIDE

Do picturesque Medieval towns, rolling green hills covered in vines, cypress lined roads, and some of the most delicious food in Italy sound like your idea of paradise? Then you need to visit Tuscany.

Home to the Renaissance capital, Florence, the region is renowned for its art history, Chianti wine, beautiful cities, and charming small towns that have inspired films like Under The Tuscan Sun and a whole suite of dreamy literature. Considered by many to be ‘quintessential Italy’, Tuscany is one of Italy’s biggest regions and it offers visitors many diverse experiences from city, to countryside as well as the seaside along the Mediterranean coast. 

Whether you’re dreaming about a trip to visit the Leaning Tower, sipping a glass or two at a Chianti winery, or eating the famous Florentine steak , travel in Tuscany is truly a dream come true for many. Keep reading to find out how to make the most of your time there with our Tuscany travel guide. 

Article contents

Where is Tuscany

Tuscany is nestled in the middle of Italy and on its western border are the Ligurian and Tyrrhenian seas. including an archipelago of 7 islands off the coast. The region borders Liguria, Emilia Romagna, Le Marche, Umbria and Lazio.

Florence is the capital of Tuscany and is easily reached from Rome in an hour and a half on the fast train; from Milan in two hours; and Venice in just over two hours. When visiting Tuscany by car, it is remarkably quick to enter into the countryside from Florence – the Chianti region is just 35km away. 

Map of Tuscany

Main cities and towns in tuscany.

Tuscany is the fifth largest region in Italy and is divided into different areas that each offer something new to discover from art and local traditions to wine, olive oil and the seaside. Some of our favorite Tuscan towns to visit include: 

• Florence: A trip to Tuscany is not complete without passing through Florence considered to be the birthplace of the Renaissance. Art and history lovers will delight as they stroll the streets once home to Leonardo da Vinci, Michelangelo, and Botticelli, and visit the Uffizi and Accademia Galleries as well as the Pitti Palace and Boboli Gardens. 
• Lucca : Encircled by Renaissance-era walls, Lucca is one of the most charming towns to visit in Tuscany (and beyond!) A trip to this gorgeous small city could include a bike ride along the walls, visiting the Piazza dell’Anfiteatro (built over an ancient Roman amphitheater), stunning villas like Villa Garzoni and Palazzo Pfanner, as well as Casa di Puccini – home to the great opera composer. 

Chianti / Siena Area

• Siena : Long time rival of Florence, this medieval city is stunning in her own rite. Siena is a place where traditions run deep, best embodied by the continuation of the Palio horse race that has been running since 1232! Explore the UNESCO Heritage listed old town, 12th century Cathedral, and of course the Piazza del Campo where the Palio is held every year. 
• Greve in Chianti : In t he heart of the Chianti wine region, Greve is a gorgeous town famed for wine, extra virgin olive oil, and the truffles that grow in the surrounding countryside. Wine shopping is on the cards here, as well as a delicious lunch in one of the town’s many excellent restaurants. 
• San Gimignano : Considered the ‘Medieval Manhattan’ thanks to its dozen towers still standing, San Gimignano is one of the most picturesque and atmospheric towns in Tuscany. Don’t miss climbing up one for a fabulous view! While you’re there, feast on their famous saffron, ham, with a glass of local wine – Vernaccia di San Gimignano.

Val D’Orcia

• Pienza : Cheese lovers will want to visit Pienza to try their incredible Pecorino sheep’s milk cheese! Redesigned by Pope Pius II to be a ‘utopia’, the town is full of charming cobblestoned lanes, romantic street names, and the scent of fresh cheese wafting through the air at every turn. Enjoy breathtaking views of the Val D’Orcia countryside from the Piccolomini Palace gardens.
• Montepulciano : In the heart of Tuscany’s southern wine country, Montepulciano is said to be o ne of the most beautiful Tuscan Medieval hilltop towns. Indulge in wine tasting of the Vino Nobile di Montepulciano and feasting of cheese, pork, thick hand-rolled pasta, honey, and lentils here. 
• Montalcino : To enjoy some of the most stunning views over the Arbia, Asso, and Ombrone valleys, you can’t miss a stop in Montalcino. Covered with olive orchards and vineyards, Montalcino is known for its Brunello di Montalcino wine so plenty of tasting is recommended here.

READ: Our full guide to visiting the glorious Val d’Orcia .

Arezzo Province

• Arezzo : The setting for Academy Award winning film La Vita e’ Bella (Life is Beautiful), Arezzo is a total gem. Settled by Etruscans, it is full of fascinating history and architecture that also spans across Roman, Medieval, Renaissance, and Romanesque periods. Visit to enjoy quiet piazzas, long lazy lunches and the monthly antiques fair.
• Cortona : Made forever famous thanks to Frances Mayes’ Under the Tuscan Sun , Cortona is a sweet Medieval town with Etruscan roots and incredible hillside views across the Valdichiana valley and Lake Trasimeno. Wander its narrow streets, admire the Medieval architecture, and pay a visit to the Museo dell’Accademia Etrusca to learn more about its past.

Province of Pisa

• Pisa : Made forever famous thanks to the Leaning Tower , you can’t miss the main attraction of this city. However, you should linger a little longer in Pisa. A trip to this university city will uncover beautiful historic churches, Medieval castles, and ancient bridges across the River Arno. Strolling through the beautiful old town pre or post ‘tower-selfie’ is something many visitors miss out on in their rush to see the main attraction.
• Volterra : We think it’s impossible to visit too many pretty hilltop towns, and Volterra is a highlight. A walled town perched atop a mountain, Volterra has a long and fascinating history that dates back to before 8BC. Explore along the ancient walls and fortresses and go shopping at one of the many artisan shops in town.  

Tuscan Coast

• Grosseto : The capital of Tuscany’s ‘ Maremma ’ coast, Grosetto is an interesting town rebuilt by the Medici family in the 16th century. Visit the Archeological Museum, Dante Alighieri square, and Cathedral of San Lorenzo. 
• Porto Ercole : Don’t miss this  pretty seaside town in the Maremma along the Monte Argentario peninsula. Enjoy swimming and boat trips, exploring Spanish forts and indulging in the delicious seafood focused cuisine. 
• Capalbio : A charming town on the border of Tuscany and Lazio, Capalbio is also known as the city of artists. Don’t miss the Tarot Garden full of gigantic, grotesque statues created by Franco-American artist Niki de Saint Phalle.  It’s also particularly famous for its wild boar sagra (food festival) in September.
• Elba Island : Enjoy sparkling blue waters, and nature on this little piece of Tuscan paradise. Devoid of the crowds that flock to the more well known coastal areas of Italy, you can enjoy some tranquility and gorgeous beaches here. 

Top things to do in Tuscany

Whether you are a foodie, wine connoisseur, history buff, art lover, beach goer, or nature enthusiast, there is truly something for everyone in Tuscany. Here are some of the best things to do when traveling in Tuscany: 

Taste the celebrated local wines

Home to some of the best known wine in Italy, wine tasting is one of the best things to do in Tuscany. Visit the Chianti region to try the famous Chianti Classico wines made with Sangiovese grapes or head to the Val d’Orcia to try Brunello di Montalcino or Vino Nobile di Montepulciano.

Enjoy a stroll along the vines, and pay a visit to the cantina (cellar) to see how wine is made, before sampling the wine. Be sure to make an appointment to visit a winery in advance as you can generally not just turn up unannounced in Italy. An exception to this is Marchesi Antinori where you can drop in for a tasting at their futuristic wine room. Or, better yet, relax while everything is taken care of and consider joining this popular small group wine tour from Florence .

Explore Tuscany’s many Medieval towns

There are endless beautiful Medieval towns to visit in Tuscany so be sure to add some to your itinerary. Sweeping views over vineyards and olive groves are guaranteed, as is delightful meandering along cobblestoned paths, fantastic local food and popping into artisan workshops. If you’re not planning to drive, consider joining a day tour like this day trip from Florence to explore some of the top towns in Tuscany plus have lunch at a winery.

Relax at a thermal spa

Did you know Tuscany is famous for its healing thermal spas? The most famous to visit is Saturnia where thermal warm water cascades down the slope of a hill into gorgeous pools of 37°C water for you to bathe in. Besides the free baths, you can also visit many luxury thermal spa hotels in and close to the Val d’Orcia area like the Terme di Saturnia Resort .

Explore the best art galleries in Florence

If you’re a lover of art, then you really cannot miss a trip to Florence. Start with the world renowned Uffizi Gallery, home to Botticelli’s “Birth of Venus”, statues by Michelangelo and more. Next, you’ll want to visit the Galleria dell’Accademia where you’ll find Michelangelo’s original and magnificent statue of David. Get the most out of your trip with a guided tour with Liv Tours .

Go truffle hunting

Try your luck finding the elusive white or black truffle when in Tuscany! The best area in Tuscany for truffle hunting is near the town of San Miniato. Try this tour that includes a delicious truffle laden lunch after your hunt in the area.  In fact, the town hosts a spectacular truffle sagra (festival) every weekend in November which is well worth the trip. 

Bike around Lucca’s Renaissance city walls

Lucca is a jewel of the region and easily reached from Florence by car or train. Do as the locals do whilst there and hire a bike for the day to ride around the city walls and take in the gorgeous views with the wind in your hair. Try this bike tour that includes some stops to sample typical cuisine too!

What to eat and drink in Tuscany

Tuscany is home to many delicious specialties, but some favorites you can’t miss include: 

• Bistecca alla Fiorentina: Perhaps the most famous food in Tuscany is Florentine steak. This cut of beef comes only from the white Chianina cows found in Val di Chiana, is served on the bone and is dry aged for between 15 to 20 days. Florentine steak must be served rare for the ultimate mouth watering experience.
• Lampredotto : Florence’s favorite street food is a panino filled with the fourth stomach of a cow and a zesty salsa verde
• Cinghiale pasta : wild boar pasta served with long pappardelle noodles.
• Ribollita : a hearty Tuscan bread and vegetable soup, including locally grown cavolo nero (black kale)
• Finocchiona Salami: Tuscany is known for its spectacular cured meats, but perhaps the best is the finocchiona – a pork salami flavored with fennel.  
• Schiacciata di Uva: Look out for this treat during the harvest season (Sept-October). It’s a fluffy bread made with focaccia dough and small, sweet, black grapes called uva fragola . 
• Castagnaccio : A Fall/Autumn favorite, this chestnut flour cake is made with new olive oil, raisins, and pine nuts and is both gluten-free and vegan friendly.
• Extra Virgin Olive Oil: Peppery Tuscan EVOO is revered throughout Italy. If you are lucky enough to travel to Tuscany in Fall/Autumn, look out for ‘olio nuovo’ or new oil that has just been pressed for the best olive oil tasting of your life.
• Chianti Classico: Tuscany is known for many wines, however Chianti Classico is the most quintessential. Don’t miss tasting some on your trip. 

Where to stay in Tuscany

There are many different accommodation options available in the region including hotels, apartments, B&Bs, and agriturismi (farmhouses). Tuscany is no stranger to tourism, which means that there are well-established facilities built up in the region to suit a range of group sizes, budgets, and accommodation needs. 

Florence makes for a great base to explore Renaissance art as well as day trips into the Chianti countryside. Whether you’re driving, going with a tour group, or taking public transport, you can also easily visit Siena, the Val d’Orcia, Pisa, Lucca, and Arezzo for the day from here.

We like the St Regis Hote l for 5 star luxury or try a more budget friendly option that’s extremely well located like Hotel Perseo . Take a read of our article on where to stay in Florence for more ideas.

If you’d like to immerse yourself in the countryside for a few days, then consider staying in the Chianti or Val d’Orcia areas. Castellina in Chianti, Pienza, and Montepulciano all make wonderful bases for exploring wineries, and hilltop towns. Consider staying at a winery like Querceto di Castellina or an agriturismo like Merigge Montepulciano for a more immersive experience. 

Lucca is another excellent base to escape the crowds with easy access on the train to Florence. From here, you can explore the Garfagnana area too with a car. Find our recommendations in our guide on Where to stay in Lucca .

Siena is perfectly placed for visiting the southern part of Tuscany, the Val d’Orcia, if you prefer to have city accommodation and are prepared to drive as this area is not well serviced by efficient public transportation.

For those looking to soak in what life in a real Tuscan town is like, consider basing yourself in beautiful Arezzo instead. It’s well connected by train and lacks the crowds of Florence and Siena. 

When to go to Tuscany

Spring is a wonderful time to visit Tuscany as the countryside turns green and temperatures are pleasant for exploring (46-66°F or 8-19°C). Enjoy new season artichokes, fresh fava beans, fresh cheese and plenty of food festivals like the cherry sagra or the frog festival.

Summer in Tuscany can get very hot with temperatures easily reaching 86F(30C) and beyond. Florence gets particularly hot and humid during this time, so staying outside the city and having access to a swimming pool or the beach is a good idea. 

Fall/Autumn is a wonderful time to visit as the region comes to life with the harvest season . If you’re a foodie, you’ll enjoy truffles, porcini mushrooms, saffron, new wine and extra virgin olive oil as well as a suite of sagre or food festivals. Look out for the sagre (food festivals) in Panzano and Greve where the towns are decorated with flags and colorful decorations, as well as the Pecorino di Pienza festival dedicated to the delicious sheep cheese. 

The wintertime in the region can get very cold and even snow with temperatures around 38-42°F (3.5°C – 5.5°C). During the festive season, there are wonderful Christmas markets held all over the region particularly in Florence, Sien a, and Arezzo. Prices are a little cheaper and crowds a little thinner too after the new year. 

How to get to Tuscany

It might surprise you to learn that the main airport in Tuscany is Pisa and not Florence. Florence is a very small airport that doesn’t have great connections so consider flying into Pisa instead from abroad or other major Italian cities. 

Traveling by train to Tuscany is easy from the major Italian cities. Take the high speed rail services and you can be in Florence in 90 minutes from Rome, 2.5 hours from Venice, under 2 hours from Milan and around 40 minutes from Bologna.

If you’re driving, you can reach Florence from Rome along the A1/E35. The average travel time ranges between 2 hours and 30 minutes and 3 hours and 15 minutes depending on traffic. From Milan, you’ll travel south along the A1 with travel time around 4 hours. From Venice, the trip is a little shorter around 3 hours along the A13.

How to get around Tuscany

Florence is best explored by foot and a car will only frustrate so it’s best to leave this parked during your stay in the Renaissance city.

There are reliable and fast regional train routes to Lucca, Arezzo, and Pisa. Florence to Lucca takes around 1 hour and 40 minutes, whilst Pisa and Arezzo are quicker and take less than an hour by train. Getting to Siena however takes about two hours so is much slower via train. Book your train tickets in advance online with Omio . 

It’s best to hire a car to explore the countryside including the Chianti, Val d’Orcia, and Maremma regions. We recommend renting your car with Autoeurope or Car Rental by booking.com from the airport (Pisa or Florence) to avoid navigating through sometimes stressful driving in the city centers. Read our driving tips for Italy for more information.

For those not wanting to drive, consider hiring a private driver or joining a tour to experience the best of the countryside. 

Let’s go to Tuscany!

Are you inspired to visit after reading our travel guide to Tuscany? If you would like to learn more about this gorgeous region of Italy, have a listen to our podcast episode about the Chianti region , or exploring Florence .

We have a wealth of further information available on our site to read including articles on best agriturismi in Tuscany , hidden gems in Florence , best museums in Florence , and Florence highlights . 

Want to discover Tuscany with us? For a deeper local connection, why not join one of our Tuscany small group tours . 

Italy Travel Guide: The Ultimate 2-week Road Trip

Italy, the country of pasta & pizza, architecture & history, jaw-dropping sceneries, world-famous cities & medieval little towns, and mouth-watering gelato. That’s right – Italy has it all, and that’s why it is one of the most-traveled destinations in Europe . Multiple visits are needed to see all the country’s highlights. Discover the best of Italy within 2 weeks in this Italy Travel Guide.

Italy Travel Itinerary

All popular cities, like Venice and Rome , are well connected by train, car, or airplane. The best and fastest option is traveling by train, and the best way to see the country is by car, so this Italy travel itinerary is a mix of those.

Also have a look at our 7-day Italy itinerary !

Day 1-3: Rome

Start your trip in the capital of Italy: Rome . Rome has some of the world’s most popular tourist attractions; the Colosseum and Vatican City. Flights to Rome are usually the most affordable, which makes it a great start location.

Where to Stay in Rome

Rome offers accommodation for every kind of budget, including plenty of great hostels ( search all hostels in Rome here ).

Hotels in Rome 😴

Piazza Navona and San Lorenzo are central areas within walking distance of many of the top attractions. However, San Lorenzo is slightly cheaper if you’re traveling on a budget.

Day 4: Tuscany – Best of the Italy Travel Itinerary

Tuscany, with its rolling hills and vineyards, is one of the most picturesque regions in Italy. Escape the city, rent a car in Rome, Italy , and drive 3 hours along Lago Di Bolsena to Saturnia , the thermal area. Spend the afternoon and have dinner in this tiny medieval village called Montemarano.

We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here .

Day 5: Tuscany ( Siena )

No better way to start your day than by dipping into the natural hot springs in Saturnia. Between 7-8 AM is the best time to visit, and if you stay at this hotel , it is just a 5-minute walk.

Here are all your hotel options in Saturnia.

Hop back into the car and continue your Italy travel itinerary for 3 hours along the most scenic roads toward Siena. Do note that your navigation has to be set to ‘Avoid Highways’. Siena is a beautiful old city with a UNESCO status.

Close off the day by having a delicious Italian dinner at Osteria Permalico . After that, spend the night in charming Siena ( this was our hotel ).

Where to Stay in Siena

If you’re only staying for one night in Siena, stick to the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants.

Hotels in Siena 😴

Alternatively, if you want to get back on the road early the next day, opt for rural accommodation within easy driving distance of the city.

Day 6: Tuscany (Siena to Florence)

On your last day in Tuscany, roam around Siena for a couple of hours, and visit Piazza Del Campo and the cathedral Duomo di Siena.

Siena’s old city center has a great ambiance. Cars are not allowed inside the old city center. Therefore, the city is a favorite on every Italy travel route. Read more information about where to park your car in our Tuscany Guide .

Read: The best things to do in Siena, Italy

Around noon, continue to your last stop: Florence . Optionally, visit San Gimignano or Volterra and drop off the car in Florence.

Day 7: Florence

Welcome to Florence. Spend the next 24 hours wandering around this ancient city and discover sites like the Duomo of Florence and the ancient bridge Ponte Vecchio.

While you’re in Florence, don’t miss out on a foodie adventure. Hop between cafes and restaurants, trying delicious fresh pasta and finding the best gelato!

Where to Stay in Florence

Florence has plenty of great accommodation options, from cute guesthouses and budget-friendly hostels ( search for your hostel here ) to luxury hotels.

Hotels in Florence 😴

Santa Croce is the best area to stay with loads of small bars and walking distance from all the things to do in Florence.

Day 8-10: Cinque Terre

In the morning, take the train from Florence to Cinque Terre , a 2.5h journey. Cinque Terre is a national park with five incredibly picturesque villages with hiking routes where you want to spend as much time as possible.

Spend two nights in Riomaggiore , Monterosso , or La Spezia, which is right outside the national park. ( Find the best train tickets here )

Read: Everything about Cinque Terre

Where to Stay in Cinque Terre

Accommodations inside Cinque Terre National Park are booked far in advance. Hotels are mostly available in Riomaggiore and Monterosso but expect to pay way over your typical budget per night.

Hotels in Cinque Terre 😴

A more affordable choice is to stay in La Spezia , where hotels start at 35 EUR a night. Alternatively, for the most budget-friendly option, search for a hostel in the area .

Day 11: Cinque Terre to Venice

It’s time to head to Venice , your final stop on your Italy travel itinerary. Take the train from La Spezia to Venice, a 5-hour ride with one transfer in between. The train is super convenient in Italy as some of the best you will see in Europe.

Find the best train tickets here

Day 12-14: Venice

Welcome to the city where everything goes by boats and bridges. Venice is one of the world’s most unique cities and an absolute must-see when you travel to Italy. Spend your last days in Italy strolling along the canals or crossing bridges sipping Italian coffee.

The mornings or late afternoon are the best times to stroll down the narrow streets of Venice as the city center gets busy during midday as the day trippers arrive in the city.

See the best things to do in Venice

Where to Stay in Venice

Stay in the middle of the city but tucked away in a quiet street 5 minutes walking from San Marco Square at Novecento Boutique Hotel .

Hotels in Venice 😴

If you’re on a tight budget, your best option is to stay outside of Venice on the mainland.

Costs of Traveling in Italy

The costs of traveling in Italy depend on where you eat, sleep, and how you get from A to B. These are the average expenses when you follow this Italy travel itinerary, eat at medium-priced restaurants, and travel by train + car.

Travel on a budget in Italy, from $570 − $630 USD weekly per person, mid-range $1220 − $2800 USD, and high-end from $2660 − $4090 USD. However, costs depend on factors like accommodation, transportation, and activities. We did not include flights. Check flight prices here

• Hotels: $65 − $300 USD Check available hotels
• Hostels: $20 − $40 USD Check available hostels
• Transport: $20 − $30 USD Book public transport
• Car Rental: $50 − $150 USD Book a rental car
• Food: $20 − $80 USD
• Activities: $20 − $45 USD See tickets & tours
• Sim: $1 − $3 USD Get an eSIM or SIM here
• Travel Insurance: $2 − $6 USD Get Travel Insurance

How to Get Around Italy?

Transportation plays an essential part in your Italian experience. Your Italy travel itinerary can be done by train, car, or plane. The fastest and most affordable way to travel in Italy is by train. However, a car gets you to those scenic country roads.

Renting a Car in Italy

For full flexibility and to go off the beaten path, driving a car is a perfect option. All major cities in Italy are well connected by train, but to visit Tuscany or the Dolomites, you need to rent a car. Avoid popular cities by car, as parking costs are sometimes the price of a train ticket.

Italy by Train

Traveling around Italy by train is excellent. They are incredibly fast (up to 350 km/h!), affordable, and much cleaner for the environment compared to an airplane. Book the train tickets a few days in advance to secure your spot on the train.

See tickets and availability for your train trip in Italy

Italy by Airplane

Just like the train, all major cities have international airports with domestic flights that connect cities internally as well as international flights.

However, the train might be a faster option for your trip around Italy, as the extra airport time adds up quickly.

Best Time to Visit Italy

Tourism in Italy is huge because it is one of the most-visited countries worldwide, so it is recommended to avoid the high season.

The best time to go to Italy is in spring, from April to June, and fall, from September and October. Prices are lower, fewer tourists, and comfortable temperatures.

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Hi, just wondering what you guys did with your rental car after Saturnia springs? Wondering if going back to Rome & returning it would be the best option to take the train to Florence. Definitely want to do Rome the first couple of days, Saturnia springs, as well as Elsa trail & Diborrato waterfall in Tuscany, then either Florence or Venice (would love if you could suggest one over the other) and definitely would like to stop in Cinque De Terre for a day or two. Just wondering if returning the car and going by train is best in that case. Any advice would be appreciated. Thank you!!

Hi Victoria, time-wise it’s better to rent a car for the part from Rome to Florence and carry on by train from Florence :-) However, it depends on how much the rental company charges you for returning the car at another city. If that’s way too much, you can drive back to Rome and take the train.

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Bagno vignoni: timeless village in valdorcia, aia mattonata relais, romantic hotel de charme in siena, unknown tuscany: discover the wonderful val di merse, the tuscan way, for all who love tuscany.

This Travel Blog about Tuscany will help you discover this extraordinary region of central Italy, providing practical info and useful travel tips as to the best sights and destinations in Tuscany, the must see visits, the best areas to explore, the recipes of the tradition, and the best hotels, farmhouses, and apartments to stay in Tuscany. Whether you’re looking for a touch of culture, a sandy beach, an unforgettable landscape, or an adventure break, Tuscany may well be the holiday destination you’ve been looking for. Happy traveling!

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Tuscany ! One of the most beautiful, surprising and extraordinary regions of Italy , il Bel Paese! Centuries of history, sensational landscape, and incredible works of art, from the Etruscans and the Romans to the amazing Renaissance and the rise to power of the now famous dynasty of the Medici family .

Unique frescoes, paintings, buildings, sculptures and masterpieces of any kind, everywhere! Just think of the Gallery of Uffizi , the Leaning Tower of Pisa , the David by Michelangelo , Piazza del Campo in Siena and its Palio , the unique towers of San Gimignano .

Why Visit Tuscany in Italy?

The reasons to come and visit Tuscany are countless, here you can find everything you may desire: unique art, unique nature, unique food and fine wines, unique landscape, unique people. The main art cities in Tuscany , Florence , Siena, Pisa, Lucca, and Arezzo , are works of art in themselves and full of immense treasures to discover. The fantastic journey continues with an endless number of smaller medieval hilltop towns and villages that will leave your breath away! First of all the ancient town with many medieval towers: San Gimignano! Then Volterra, Pitigliano, Monteriggioni, Montepulciano, Pienza, Montalcino, Cortona … the most beautiful villages in Tuscany .

The natural territory of Tuscany is also extraordinary: scenic and breathless countryside with rolling hills, castles, hill villages, endless vineyards, beautiful mountains and paths, wonderful sea coast and islands. Chianti , Valdorcia , Monte Argentario , Crete Senesi , Val di Chiana, Costa degli Etruschi, Casentino are all areas of exceptional beauty and home of world-famous wines like the Chianti Classico , the Brunello of Montalcino , Bolgheri Sassicaia .

TuscanyChic Food & Travel Blog; your free Travel Guide to discover Tuscany

I’m Elena , Tuscany born, mum and blogger living in the beautiful countryside near Florence , and I love this incredible region! My Tuscany Travel blog is for all who love Tuscany and want to know more about it: tasty Tuscan recipes , unique places to stay , art and traditions , beautiful hill towns , top destinations, and lesser known and hidden corners! 

I love to give free travel tips about Tuscany and Italy , and, as a local, I can help you planning your holiday in Tuscany (you can ask me here for a customized travel itinerary ) or simply help you realize traditional Tuscan recipes and suggest cooking courses of Italian and Tuscan Cuisine .

My recipe of the famous saltless homemade Tuscan Bread is very popular! 🙂

Enjoy Tuscany!

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