best road trip tuscany

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

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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!

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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3 Scenic Drives in Tuscany, Italy

Here we whisk you away on three scenic drives in Tuscany . Take it slowly, pack the camera, and meander your way through stunning panoramas and picture perfect views. And believe us, you’ll take a lot of pictures.

For best results start early in the morning to enjoy the magical light. Late afternoon is good too, so be prepared catch a view of the sun slipping behind the cypress trees. And if you’re travelling in the Summer months, these times make sense as you’ll avoid the hottest hours of the day.

The Chiantigiana. Endless vineyards and ancient castles

The SR222 ‘Chiantigiana road’ winds south from Florence to Siena. It’s probably the most famous of all scenic drives in Tuscany. And definitely one of the best ways to sample the beauty of Tuscany’s countryside. At the end of a day’s driving, you can taste some of the wonderful wines produced in the region. But for now let’s keep our eyes on the road.

Peaceful scenery is your companion on the drive from Greve in Chianti , the gateway to the Chianti area, to Panzano . The show carries on along the way to Castellina in Chianti , where the winding road embraces perfectly combed vineyards and silvery olive groves. Here we are at the heart of the Chianti Classico area, where wine and olive oil have been devoutly produced for hundreds of years. Ancient castles and beautifully restored farmhouses dot the countryside, often converted into agriturismi that offer accommodation and wine tasting.

BOOK YOUR CHIANTI CLASSICO E-BIKE TOUR => Explore the Chianti hills, visit a Medieval castle, taste some delicious wine!

=> 8 Inspiring Places in Tuscany that’ll Spark your Imagination !

From Castellina take the SR429 to Radda in Chianti , the most scenic of all Chianti towns. Then go back to Panzano via the SP2bis , a lovely road that spirals through more vineyard and ancient woods.

Detour: visit the small Medieval hamlet of Montefioralle (4 km. above Greve in Chianti) for pure picturesque.

1 day :  Florence-Radda in Chianti (roundtrip: 100 km.)

Planning: For a more detailed version of this itinerary, check out our Chianti road trip .

=> Planning a trip to Tuscany’s wine region? Check out the best places to go in the Chianti .

Val d’Orcia. One of the top scenic drives in Tuscany

The Val d’Orcia is an area south of Siena , famous for its classic landscapes that have graced many a postcard. It’s an iconic side of  Tuscany that has been seen all around the world. As countryside goes, it’s probably the most idyllic scenery you can imagine, and one of the highlights of the region .

Soft rolling hills, wheat fields that turn bright green in Spring and an intense yellow in Summer, and the occasional cypress tree, make the view just perfect. So perfect it is a UNESCO protected panorama . If you can tear yourself away from the view, carry on to the next stage.

JOIN A WINE TASTING TOUR OF AN ANCIENT CELLAR IN MONTEPULCIANO

From Siena take the SR2 to Buonconvento and the sleepy town of  San Quirico d’Orcia with its splendid early Romanesque church . From there turn left onto the SP146 to Pienza and Montepulciano , arguably the most attractive towns of the Val d’Orcia. This is where the real spectacle begins.

A relaxed drive along the SP146 rewards you with some of the most spectacular views over the Val d’Orcia countryside . Take it easy, and stop when you can for a photo call. Things get quite special around sunset, as the trees cast shadows over the landscape and the setting sun turns the valleys deep shades of ochre and pink.

⇒ Useful tips to Plan your road trip to Tuscany .

Not to miss:  On the SS146, halfway between San Quirico and Pienza, you’ll spot the  Vitaleta Chapel on your right, a small church flanked by cypresses crowing the hill. This must be the most photographed spots in all of Tuscany.

Detour: visit tiny Monticchiello (a few kilometres south of Pienza on the SP88) for more awe-inspiring views and a pretty stone square.

1 day –  Siena-Montepulciano (roundtrip 140 km.)

=> For the perfect day in the Val d’Orcia, check out our driving itineray in Val d’Orcia .

Central Tuscany. A taste of classic Tuscany in a day

This itinerary is perhaps not as spectacular as the ones above, but it gives a perfect introduction to central Tuscany and includes some of the most scenic towns in the region . You’ll get a taste of the Chianti , see San Gimignano and the area of the ‘balze’ cliffs near Volterra .

The drive starts in the heart of the Chianti region . From Radda take the SR429 to Castellina in Chianti and savour the landscape of vineyards and verdant woods that characterise this area. Then bear on past the less attractive area of Poggibonsi, and carry on along the SP1 to San Gimignano . This is the epitome of the Tuscan hilltop town , with its Medieval towers still intact. One of the region’s top destinations of all time .

From San Gimignano follow the SP1-SP62 and then head south onto the SP15 to Volterra . This town has a fascinating Etruscan past and amazing views over the surrounding countryside. It’s one of the most charming small towns in Tuscany . The area around Volterra is characterised by the ‘ balze ‘, steep clay hills that create a unique and otherworldly panorama.

1 day –  Radda in Chianti-San Gimignano-Volterra (90 kilometres)

It’s not hard to find scenic drives in Tuscany , as the region is blessed with gorgeous natural landscape . They have been kept unspoiled thanks to strict regulations that prevent building so that the area maintains the charm Tuscany is famous for. Driving around the countryside, the woodland, and the southern coastal areas is a very rewarding way to explore this enchanting part of the world.

If you’re planning a trip to Tuscany, here are some suggestions for itineraries that you might find useful. Don’t forget to check our 20 favourite things to do in this wonderful region.

And remember, no trip to Tuscany would be complete without visiting some charming small towns  and picturesque villages that are off-the-beaten-track.

More ideas for your driving trips?

Check out our driving itinerary to discover the highlights of the Maremma , in southern Tuscany , including the scenic ‘tufa towns’, the Medieval walled village of Capalbio and the Mount Argentario.

Explore a less travelled part of Tuscany with our 2 Day Road trip to the magical land of the Casentino .

Discover the Less Travelled Part of Chianti, central Tuscany, with out itinerary .

Buon viaggio! 🙂

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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: The Ultimate 5-Day Itinerary

Tuscany: birthplace of the Italian Renaissance and home to beautiful rolling hills, hidden vineyards, ancient hilltop villages, and mouthwatering food. Spend days of an Italy itinerary winding your way through the Tuscan countryside, strolling the cobbled streets with a gelato in hand, and stocking up on local wine and pecorino cheese. Discover all the hidden gems this stunning corner of Italy offers with our ultimate 5-day Tuscany road trip itinerary.

A Tuscany Road Trip Itinerary

The easiest way to see this incredible region is by renting a car . This gives you total freedom to change your trip as you go. Nothing beats a road trip through Tuscany with the windows down and the sun on your face, discovering new and unexpected delights around every corner. Here’s how to spend five days on a Tuscany road trip.

Tip: If you have more time, discover the underrated neighboring region of Umbria (just as impressive but with fewer crowds!).

We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here .

Day 1 – Florence or Pisa

It’s the first day of your 5-day Tuscany itinerary; welcome to Italy ! You’ve likely begun your trip in the beautiful cities of Florence or Pisa , so spend at least a day exploring before heading off to Siena . 

You can pack a lot into one day in this relatively small but beautiful city, famed for its incredible architecture, delicious food and wine, and fascinating art culture. 

You can’t visit Florence on your Tuscany road trip without seeing the iconic Cattedrale di Santa Maria del Fiore, one of the world’s biggest cathedrals, with a stunning white, pink, and green marble exterior.

From here, head to the Arno River to cross Florence’s oldest bridge, the Ponte Vecchio. This bridge is famous for being lined with jewelry shops, so it’s a shopper’s heaven! If you have time, allocate a few hours to also explore the quieter neighborhoods on the other side.

Read: Best Things to do in Florence

Now it’s time for food! You can spend days discovering all the city’s foodie spots but start with the famous panini from All’Antico Vinaio. Afterward, grab a creamy gelato from Gelateria La Carraia and end your day with a delicious plate of fresh pasta at Trattoria San Pierino.

Here are all your hotel options in Florence

Where to Stay in Florence

Florence in Tuscany has plenty of accommodation options depending on your budget and style. We’d recommend the Santa Croce neighborhood, as it’s close to the center and has a lively cafe and bar culture. 

Hotels in Florence 😴

Pisa is another small but mighty city that makes for a relaxed day of wandering. Don’t miss the famous Leaning Tower of Pisa for your iconic photo as a memory of your road trip through Tuscany. However, don’t miss out on exploring the other beautiful buildings in the same square.

For example, the Camposanto, the Baptisterium, and the intricately designed Romanesque Cathedral. The pedestrianized space is a lovely spot to rest your feet for a while. Plus, it’s the perfect spot to sunbathe on the grass while you take in the stunning architecture. 

Here are all your hotel options in Pisa

Next, head to the ancient street Borgo Stretto for the best shopping in Pisa! This beautiful street is lined with beautiful colored townhouses, making for a picture-perfect shopping experience. From here, get lost amongst tiny alleyways and pretty squares as you search for a delicious spot for lunch or dinner.

Read: Best things to do in Pisa!

Where to Stay in Pisa

If you don’t have much time, we recommend staying in the Santa Maria area, which is very central. However, Pisa is small enough that most places are within a reasonable walking distance. Choose accommodation in the San Giusto neighborhood if you’re on a budget.

Hotels in Pisa 😴

Day 2 – Siena , Tuscany

This charming and atmospheric city, with its steep, winding, cobbled streets and dusty-colored houses, is a must-see on your Tuscany road trip!

Read: Top things to do in Siena, Italy!

Start your day in the Piazza del Campo, a lovely shell-shaped square, before a short walk to the Duomo di Siena. This stunning cathedral was uniquely built using black and white striped marble and has beautiful frescoes inside.

From here, get lost in the winding streets, explore the grand Palazzo Pubblico, and discover beautiful hidden corners. We recommend finishing off the day with a delicious dinner at Osteria Permalicoa.

Here are all your hotel options in Siena

The Elsa Trail : Highlight of your Tuscany road trip

If you have more time on your Tuscany itinerary, escape the bustle of Siena by taking a hike along the peaceful Elsa Trail. Conveniently, it’s located just a 30-minute drive from the city. The trail leads to the Diborrato Waterfall, where you can cool off in the bright blue water surrounded by greenery.

Read: Exploring the Elsa Trail and Diborrato Waterfall in Tuscany

San Gimignano , Tuscany

You could also combine the Elsa Trail with a trip to nearby San Gimignano , a small medieval village known as the ‘Manhattan of the Middle Ages’ for its unusually tall towers. Spend an afternoon exploring the historic town with its pretty streets and squares. Additionally, don’t miss out on trying ‘The World’s Best Gelato’ at Gelateria Dondoli — a must-do on your Tuscany road trip!

Read: San Gimignano – the Manhattan of the Middle Ages

How to get from Florence / Pisa to Siena

It is two hours from Pisa and one hour from Florence to reach Siena by car. However, we recommend selecting the option ‘avoid highways’ on Google Maps, which will direct you along the longer, windier routes. Taking these smaller roads allows you to see all the incredible natural beauty of Tuscany. 

There are fairly frequent trains and buses from both cities if you don’t have a car on your Tuscany itinerary.

Book your train tickets in advance

Where to Stay in Siena

If you’re only staying for one night in Siena, stick to the hotels in the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants. Alternatively, opt for accommodation within easy driving distance of the city.

Hotels in Siena 😴

Day 3 – Pienza or Montepulciano

Both these beautiful hilltop towns are good options to add to your Tuscany itinerary, particularly as they’re only 20 minutes apart. Montepulciano is slightly bigger and offers more options in terms of places to eat and wine tours. Alternatively, for a more relaxed destination, choose the more peaceful Renaissance town of Pienza.

Pienza : Must-see on a Tuscany road trip

Unusually, this small village perched on a hill is famed for its pecorino cheese! However, it’s more importantly known for its stunning Renaissance architecture , which has led to its UNESCO World Heritage Site status. Located in the Val d’Orcia, the hilltop village has spectacular views of the rolling Tuscan hills surrounding it. It is also a lovely place to shop for souvenirs like cured meats, pecorino cheese, and local artwork.

Pienza, Italy: The beautiful hilltop town of Tuscany

Spend an afternoon wandering Pienza’s tiny streets and alleyways, exploring piazzas and palazzos, and admiring the views from the ancient city walls. 

Tip: If you’re doing your Tuscany road trip in September, don’t miss out on the Fiera del Cacio. This annual festival is dedicated solely to pecorino, complete with a cheese rolling competition and lots of tasting opportunities!

Here are all your hotel options in Pienza

Montepulciano

Known for its delicious wine, this medieval hilltop village just 20 minutes from Pienza is full of charm and history; it’s a great place to slow down on your road trip and enjoy all the delights that Tuscany has to offer. 

Here are all your hotel options in Montepulciano

Start in the Piazza Grande and climb to the top of the clock tower to get panoramic views of the village and surrounding Val d’Orcia. From here, wander through the pretty streets and browse the shops and gelaterias before heading to Veduta Panoramica or Palazzo Comunale for another spectacular viewpoint.

If you’ve got time on your 5-day Tuscany itinerary, spend the afternoon sipping wine on an underground cellar tour or visit a nearby vineyard. Alternatively, take a cooking class to learn something new and fill your belly with delicious Tuscan cuisine. There are plenty of options in Montepulciano!

Read: Best things to do in Montepulciano, Italy

How to get from Siena to Pienza / Montepulciano

From Siena to Pienza/Montepulciano is roughly an hour of driving, depending on your route. However, we recommend staying off the highway as much as possible to see some beautiful scenery. There are some fantastic wineries in this area, so if you’re lucky enough not to be the designated driver, take the opportunity to taste some local wines in a stunning vineyard setting. 

Tip: If you are looking to buy wine to take home with you, it is much cheaper to buy directly from a winery. They will also be able to give you great recommendations.

See availability for a wine tour in Montepulciano

Where to Stay in Pienza / Montepulciano

Stay in the historic centers of Pienza or Montepulciano to be close to shops, bars, and restaurants. Alternatively, opt for a more rural setting in any of the incredible ‘agriturismo’ properties. These farmhouses normally have pools and beautiful gardens, so enjoy relaxing after your road trip with a glass of wine while you take in beautiful views of the hills of Tuscany.

Hotels in Pienza 😴

Hotels in Montepulciano 😴

Day 4 – Saturnia and Montemerano

Spend day 4 at the wonderful hot springs of Saturnia before spending the night in one of the most beautiful villages in all of Italy: Montemerano.

Saturnia in Tuscany

Saturnia is an ancient spa town famous all over the world for its beautiful blue hot springs. The springs cascade over several levels into a series of pools, all looking out over the stunning Tuscan countryside. Our B&B was just a 5-minute walk from the baths!

Known by the Italians as Cascate del Mulino, the thermal springs are a great place to soak for a couple of hours in healing volcanic water, which is 37°C (98.6°F) all year round. It is especially lovely at sunrise or sunset when the light is beautiful and there are fewer people. 

Tip: Bring shoes you can wear in the water, as the bottom of the pools can be a bit rough.

Opening Times: The hot springs are open 24 hours a day, seven days a week. If you can get here before 7 AM, you will skip most of the crowds. The best thing about Saturnia Hot Springs is that it is completely free! Find out all you need to know about visiting Saturnia here .

Montemerano

After some time enjoying the hot springs, head to the small and charming town of Montemerano for the evening (just 15 minutes from Saturnia). Spend an hour or two exploring one of the most beautiful villages in Italy; stroll along quiet streets lined with ancient stone buildings and balconies filled with pots of flowers before tucking into traditional Tuscan dishes at a local trattoria.

Here are all your hotel options in Montemerano

How to get from Pienza / Montepulciano to Saturnia

Pienza and Montepulciano are located close to each other, so both have a similar driving time to Saturnia. Pienza to Saturnia is just over an hour and a half. Alternatively, if you’re leaving from Montepulciano, it is just under two hours. 

It is difficult to do these routes by bus, as it requires so many connections. Because of this, if you don’t have your own transport, your quickest option will be taking a taxi.

Where to Stay in Montemerano on this Tuscany road trip

There are a few cozy inns and apartments in the villages of Saturnia and Montemerano. However, you’ll find a wider variety of accommodation options further out, with big rustic farmhouses, vineyard hotels, and beautiful villas dotting the countryside. 

Hotels in Montemerano 😴

Day 5 of the Tuscany Road Trip – Finish in Rome via Orvieto

It’s time to head to your final stop on your Tuscany road trip: Rome ! Take your time getting there; we recommend stopping at the beautiful and historic town of Orvieto in the Umbrian hills.

Orvieto : Must see on your Tuscany road trip

The ancient hill town Orvieto is packed with beautiful churches and fascinating museums and temples. Plus, you’ll find a variety of cute ceramic shops and a fascinating network of underground tunnels and caves.

Book an e-bike tour of Orvieto, including entrance to the underground city

Alternatively, if you want a more relaxing activity, just wander the pretty streets and have a few glasses of Orvieto Classico Wine over a long lunch. In many places in the city, you’ll be able to take in the beautiful hilltop views of the surrounding countryside.

Read: Things to do in Orvieto, Italy

When in Rome (!), spend the last part of your Tuscany itinerary visiting a few of the city’s most iconic sights, like the Colosseum or the Pantheon. Don’t forget to make a wish at the famous Trevi fountain!

Squeeze in a final plate of fresh Roman pasta in the picturesque Trastevere neighborhood before heading to the airport. If you have more time on your Tuscany road trip, we recommend spending 2-3 days here, enjoying all the top things to do in Rome .

Here are all your hotel options in Rome

How to get from Saturnia to Rome

It is a 3-hour drive from Saturnia to Rome if you go via Orvieto. This route means you can experience a taste of Umbria , the region to the east of Tuscany, which is just as beautiful but with fewer crowds. If you can, spend a few nights here, too! 

If you are traveling by public transport on your Tuscany itinerary, there is a train to Rome from the nearby coastal town of Albinia. The journey takes approximately two hours.

Book your train tickets from Albinia to Rome in advance

Where to Stay in Rome

We recommend staying a few nights in Rome to fully explore this incredible city. 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. Trastevere is another great neighborhood by the river, which has a more authentic ‘Roman’ feel and loads of cute shops, restaurants, and bars to explore.

Hotels in Rome 😴

How to Visit Tuscany in 5 Days

Both Pisa and Florence have international airports with frequent daily flights available to many destinations worldwide. 

If you are traveling overland, the train is a great option, as the Italian railway connects with many other cities in Europe. The good news is that night train routes are becoming increasingly available, too. 

Check availability for train routes through Italy

An even cheaper alternative is the bus, although this will take a lot longer and take time away from your Tuscany road trip!

Getting Around Tuscany

The best way to see the region is by renting a car, so you have complete flexibility. A Tuscany road trip means you can stop whenever the mood strikes and visit the smaller villages that are less accessible by public transport.

Travel distances vary, with the longest stretch on our Tuscany itinerary being around three hours. However, we recommend stopping off for pasta and cappuccino breaks as often as possible! You can rent a car in Pisa or Florence and drop it back in Rome to see more of the region.

By Public Transport

Another option is taking buses and trains on your Tuscany itinerary, which can work out cheaper. It’s also incredibly convenient when traveling between cities as you don’t need to worry about navigating busy roads and parking. However, you may have to take taxis from bigger towns to the more remote places, which can be expensive.

Book your public transport in advance

If you are basing yourself in one city and want to explore the surrounding countryside, the best option is to take day tours. Many tours leave from the bigger cities like Florence, Siena, and Pisa and take you out into the Tuscan countryside to explore the wineries and hilltop towns.

Our Favorite Accommodations in Tuscany

The Tuscany region offers some fantastic accommodation options, whether it’s rustic farmhouses, luxurious country villas, cozy city apartments, or budget hostels. Here are some of our favorites from each destination on the Tuscany itinerary:

• Florence: Velona’s Jungle Luxury Suites , Santa Croce 14 , Casa Botticelli
• Pisa: Rinascimento Bed & Breakfast , La Torre Garbata , The Rif Boutique Hotel
• Siena: Ca’ Bianca Tuscany Relais , Residenza d’Epoca Le Aquile , B&B Alle Due Porte
• Pienza: Castello di Spedaletto da Laura , La Chiocarella , Il Mastio di Spedaletto
• Montepulciano: Il Tosco , Lupaia , Agriturismo San Gallo
• Montemerano: The Nest in Maremma , Acquaviva Wine Resort , La Casa di Nonna Libia
• Rome: Colosseum Palace Star , Casa Modelli , Sentho Roma

How Much does a 5-Day Tuscany Itinerary Cost?

Tuscany is one of the more expensive regions in Italy to visit as it is a popular tourist destination. Remember that prices will increase even more during the summer, and Florence , in particular, can be costly.

Costs of Traveling in Tuscany

Travel on a budget in Tuscany, from $480 − $360 USD weekly per person, mid-range $1210 − $2670 USD, and high-end from $2600 − $3770 USD. However, costs depend on factors like accommodation, transportation, and activities. We did not include flights. Check flight prices here

• Hotels: $100 − $300 USD Check available hotels
• Hostels: $20 − $30 USD Check available hostels
• Transport: $5 − $15 USD Book public transport
• Car Rental: $50 − $150 USD Book a rental car
• Food: $30 − $60 USD
• Activities: $10 − $20 USD See tickets & tours
• Sim: $1 − $3 USD Get an eSIM or SIM here
• Travel Insurance: $2 − $6 USD Get Travel Insurance

If you are on a tighter budget, stay in hostels instead of hotels where available, eat in small local trattorias or make picnic lunches, and avoid pricier tourist attractions. 

Best Time to do a Tuscany Road Trip

The best time to complete your Tuscany itinerary is from April to October, when it is sunny and warm, and all the tourist attractions are open.

Try to avoid peak tourist season in July and August when it can get crowded, and the heat is intense, which can make sightseeing more uncomfortable. For this reason, the shoulder seasons of April/May and September/October are ideal.

October is also a great time to visit for foodies as it is harvest time, with fresh truffles, newly-pressed olive oil, young wines to try, and lots of local food festivals.

By purchasing through our links, you support us at no additional cost. Thank you for your support. ♥️

• Find Hotels via Booking.com
• Find a Rental Car via Sunny Cars
• Find Flights to Tuscany via Skyscanner
• Get a Travel Insurance via Heymondo
• Book Tours & Attractions via GetYourGuide
• Book a Bus/Train/Transfer via 12Go

Best Things to do in Montepulciano, Italy

15 best things to do in palermo, sicily, best things to do in siena, italy.

Looking for more travel information? Plan a chat with us for personalised travel advice or get an answer from the Salt in our Hair Travel Community on Facebook.

Thanks very much for these very helpful itinerary suggestions. One recommendation—please change out the photos of Cascate del Mulino! They are not crystal blue and untouched, as in the photos. They are greenish and full of people.

Hi MP, we visited the place a long time ago and this truly was what it looked like. We are aware it’s now extremely crowded, and the green color must be because of that reason.

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The Best Tuscany Road Trip Itinerary (Map & Tips 2024)

By: Author Milijana

Posted on Published: October 28, 2022  - Last updated: April 21, 2024

Categories ITALY , ROAD TRIPS , TRAVEL ITINERARIES

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Road trip to Tuscany is in your mind? I am not surprised. The best way to visit Tuscany is to make a road trip to Tuscany. Trust me, I made a Tuscany road trip! Arere you looking for some Tuscany road trip ideas? You are at the right place. My Tuscany road trip is one of the most beautiful road trips I have ever taken! Here is my road to Tuscany.

THIS POST MAY CONTAIN COMPENSATED LINKS. PLEASE READ MY  DISCLAIMER  FOR MORE INFO. 

Want to see the best of Tuscany and the most amazing Tuscany points of interest? Want to make the ‘ best of Tuscany tour by ca r’? Are you interested in the most scenic Tuscany drives? Are you researching: →Where to go in Tuscany? →What are the best towns to visit in Tuscany? →What’s the best part of Tuscany? →How long to stay in Tuscany? →Where to stay in Tuscany? →What would be the best location to stay in Tuscany?  → Looking for the best places to stay in Tuscany in Italy ? ‼ If so, check out my Tuscany road trip.

The perfect Tuscany road trip, a must-take in 202 4

Let me start with a short introduction to this awe-inspiring Italian region (in case you have stumbled upon this article, and you are not familiar with Tuscany yet).

1. What is Tuscany?

Tuscany is a world-celebrated region in Italy famous for its masterpiece towns of Florence, Siena, and Pisa, charming hilltop towns, striking landscapes, rich history, artistic and architectural heritage, and world-class wine. Stunning Tuscany is one of the top vacation destinations in the World.

2. Where is Tuscany?

This famous Italian region is located in central Italy. The capital of Tuscany is Florence (or, Firenze in Italian). Neighboring Italian regions of Tuscany are Liguria in the northwest, Emilia Romagna in the northeast, Marche in the east, Umbria in the southeast, and Lazio in the south of Tuscany.

3. What is the best time to visit Tuscany?

The best time to visit Tuscany is from May to October.  The peak of the tourist season is July and August with daily temperatures going above 30°C degrees. May or September are the best months for visiting Tuscan y if you wish to escape tourist crowds and enjoy the Tuscan nature and countryside with pleasant temperatures. April is a good month for visiting Tuscany. In April days get warmer, nature awakes, and the countryside gets colorful, while hotels, B&Bs, and farm stays reopen. April marks the start of tourist season in Tuscany.

4. How to plan the best Tuscany road trip

I was interested in visiting the best places in Tuscany by car. I wanted to see the ‘ crème de la crème’  of Tuscany. So, when I was tailoring my perfect road trip to Tuscany I was researching the best places to visit in Tuscany by car. Soon several must-see towns in Tuscany showed up on my Tuscany bucket list. Those towns in Tuscany have regularly appeared on numerous lists of the most beautiful towns in Italy and the most romantic towns in Italy. Needless to say, the cities of Florence, Pisa, and Siena were at the top of my Tuscany road trip itinerary.

But, most of all, I was looking forward to the best scenic drives in Tuscany, visiting charming medieval hilltop walled towns in Tuscany, picturesque Tuscan villages, hills, fields, vineyards, farmhouses, old fortresses, castles, villas … and of course, tasting flavorsome authentic food in Tuscany and sipping some popular Italian drinks .

I wanted to stay in the serene Tuscan countryside. I wanted to be away from the hustle and bustle of the main tourist spots, but still, easily reachable. I was looking for a base in the heart of ethereally beautiful Tuscany.

So, I opted for a Tuscany road trip from one base. I didn’t want to see Tuscany in a rush and to take one of those ‘ drive until you die road trips’ as I call them. I wanted to visit Tuscany slowly. I wanted to enjoy Tuscany!

I looked at the Tuscany map, and I found Montaione . Montaione is a small Tuscan town, located in the middle of the Florence-Pisa-Siena triangle, in the Chianti region in central Tuscany.  Montaione is about 22 mi (35 km) southwest of Florence, 47 mi (75 km) northeast of Siena, and 40 mi (64 km) south of Pisa. Roughly Montaione is only one hour’s drive from Florence, an hour’s drive from Pisa, and an hour’s drive from Siena. The small town of Montaione happened to be my perfect base in Tuscany for touring Tuscany by car. Montaione was my Tuscany road trip base. If you are looking for the best places to stay in Tuscany by car, I can highly recommend Montaione in the Chianti region. Montaione distances: Florence: 22 mi (35 km); 1 hour Siena: 47 mi (75 km); 1 hour Pisa: 40 mi (64 km: 1 hour San Gimignano: 13 mi (20 km); 30 min Colle di Val d’Elsa : 25 mi (40 km); 40 min Monteriggioni: 28 mi (45 km); 45 min Volterra: 19 mi (30 km); 40 min Lucca : 38 mi (62 km); 1 hour Viareggio: 56 mi (90 km); 1 hour 15 min Livorno: 43 mi (70 km); 1 hour In addition, if you are looking for where to stay in the Tuscany countryside, or the best region to stay in Tuscany, undeniably the best area to stay in Tuscany is the world-famous Chanti region. In that sense, I would recommend Montaione again. Montaione is one of the best places to stay in Tuscany.

The 4-star Boccioleto Resort in Montaione in the middle of Tuscany is absolutely beautiful and peaceful with stunning views of the Tuscan hills. It offers spacious apartments, a seasonal outdoor swimming pool, excellent breakfast on the terrace, and free parking. This outstanding resort offers good value for money.

Roadtrip Tuscany

5. Best places to visit on a Tuscany road trip

My research about the best places to visit in Tuscany before my Tuscany road trip resulted in including the following places in Tuscany in my Tuscany road trip itinerary.

FLORENCE – Florence is the capital of Tuscany and the cradle of the Renaissance. The historic center of Florence is a UNESCO World Heritage site. The city of Florence is one of the most beautiful cities in the world. Like anyone else, I wanted to see one of the most beautiful Italian cities! After all, no trip to Tuscany is complete without visiting Florence! SIENA – Siena is one of the most beautiful medieval towns in Italy. It is famous for the Piazza del Campo and Il Palio horse race, museums, art, Siennese cuisine, and Siena Cathedral. The historic center of Siena is a UNESCO World Heritage Site. It is not a secret, that Siena is one of the most beautiful Italian towns! PISA – Pisa is best known for the Leaning Tower. The Square of the Miracles with the Leaning Tower in Pisa is a UNESCO World Heritage Site. Since I am a World Heritage sites lover, the Reclining Tower of Pisa was a must-see site in Tuscany! SAN GIMIGNANO – San Gimignano is one of the most picturesque hilltop towns in Tuscany. It is nicknamed ‘ Manhattan of the Middle Ages ‘. It is famous for its 14 medieval towers, great wines, and the best gelateria in Italy (the World’s champion in gelato making is in San Gimignano). LUCCA – Lucca is one of the most charming towns in Tuscany and Italy overall. It’s a walled medieval town. The historic center of Lucca is on the tentative list of UNESCO World Heritage Sites. Regardless of the UNESCO listing, Lucca is a must-see medieval town in Tuscany. VIAREGGIO – Viareggio is a famous seaside resort town in Tuscany with beautiful Art Nouveau architecture. Viareggio is one of the main cities of the Tuscan Riviera. Of course, I wanted to see Tuscan beaches on my road trip to Tuscany! LIVORNO – Livorno is a seaport town with great seafood-based local cuisine and great beaches. Some more beach time in Tuscany, always! VOLTERRA – Volterra is a scenic medieval hilltop town known for its Etruscan origins and fictional Volturi vampires from the Twilight series. Volterra is a must-see hilltop town in Tuscany and a must-stop on a Tuscany road trip! MONTERIGGIONI – Monteriggioni is an impressive medival hilltop village. It’s one of the oldest villages in all of Italy. Of course, I wanted to see one of the oldest villages in Italy on my road trip to Tuscany! COLE VAL D’ELSA – Cole Val d’Elsa is a cliff-standing medieval town between San Gimignano and Monteriggioni. Do you find a cliff-standing town awe-inspiring? I do! Cole Val D’Elsa was added to my Tuscany road trip itinerary! MONTAIONE – Montaione is a viillage in Chianti near Florence, Pisa and Siena. It is i n the middle of the Florence-Pisa-Siena triangle in Tuscany. Montaione is an excellent base for exploring Tuscany by car. Naturally, I chose Montaine for the base of my Tuscany road trip!

6. Where to start a road trip to Tuscany

I started my road trip to Tuscany by car from Zagreb (Croatia) and drove to Italy.

I passed by Venice which I have already visited several times and continued to the city of Bologna. I made an overnight stop and a quick visit to Bologna (Read: Things to Do in Bologna Italy ) before rushing to Florence the next day.

My ultimate goal was to reach Tuscany as soon as possible. After all, Tuscany was my ultimate goal. The distance between Bologna and Florence is about 75 mi (120 km), or roughly a 2-hour drive.

Even though I started my Tuscany road trip driving from Croatia, you can start your road trip through Tuscany in Florence, Pisa, or even Rome. If you fly to Florence, Pisa, or Rome, you can rent your car at the airports in Florence, Pisa, and Rome and start your Tuscany roadtrip from there. DiscoverCarRentals  is my favorite site for renting cars. It is an aggregator website that provides rental cars from multiple companies.  The offer of rental cars and their prices are easily checked online from the chair of the home in a few minutes. Once you have chosen a car, it will wait for you at the airport. It will be ready to be picked up upon your arrival.  The process of renting a car via DiscoverCarRentals and picking it up at the airport is quick and smooth.

Start your road trip to Tuscany in Florence: Check out car rentals ad Florence Airport Start your road trip through Tuscany in Pisa: Check out car rental s at Pisa Airport  Start your Tuscany road trip in Rome: Check out car rentals at Rome Airport  

7. Tuscany driving itinerary

Driving Itinerary Tuscany – 11 perfect stops on the ultimate road trip to Tuscany:

7. 1. The 1st stop on a Tuscany road trip: FLORENCE

Florence was my first destination in Tuscany. How to find proper words to describe the center of the Italian Renaissance and one of the most beautiful cities in the World?! How many pages should be written to decently describe the charm and beauty of this UNESCO World Heritage Site?! In short, have ever the art, architecture, and history of Florence left any visitor indifferent?! It is hard to believe so. I fell in love with Florence at first sight. My absolute favorite things to do in Florence were admiring Botticelli’s The Birth of Venus in the Uffizi Gallery and Michelangelo’s David in the Accademia Gallery, climbing the Cupola del Brunelleschi and enjoying breathtaking panoramic views of Florence, visiting the glorious Palazzo Medici with stunning Boboli Gardens, and strolling Arno riversides. Unquestionably, the best sites to see in Florence are the famous Uffizi Gallery, the unique Florence Cathedral with its marvelous cupola, the grand Pitti Palace and Palatine Gallery, the celebrated Palazzo Vecchio, and the famed Medici Palace.

RECOMMENDED THINGS TO DO IN FLORENCE TUSCANY Must-visit places in Florence :

• Uffizi Gallery
• Galleria dell Accademia with Michelangelo’s David
• Florence Duomo
• Cupola del Brunelleschi
• Palazzo Vecchio
• Pitti Palace and Palatine Gallery
• Giotto’s Bell Tower
• Santa Maria Novella
• Palazzo Medici
• Book: Uffizi Galery Priority Entrance Tour – The queues in front of the Uffizi Gallery, the Academia Gallery, and the Cathedral are often extremely long. Book in advance your tickets to skip the lines and save your precious time in Florence.

Plan your Tuscany road trip Rent a car at Florence Airport:  Rent a Car at Florence Airport   Buy tickets: Uffizi Gallery Skip-The Line Ticket Galleria dell Accademia with Michelangelo’s David Entry Ticket Pitti Palace and Palatine Gallery Book tour: Cupola del Brunelleschi

7. 2 The 2nd stop: MONTAIONE

I headed to Montaione after visiting Florence. People often ask how far is Tuscany from Florence. Well, first of all, Florence is in Tuscany, and Florence is the capital of Tuscany. But, when someone mentions Tuscany, gorgeous Tuscany countryside is most likely on everyone’s mind. In my case, an hour’s drive took me from Florence to Montaione. In other words, I drove an hour from Florence to central Tuscany.

I booked my stay in the 4-star Boccioleto Resort in Montaione before starting my trip to Tuscany. This exceptional resort was a perfect choice! Its superb location paired with beautiful decoration and outstanding hospitality made all my dreams of a relaxing Tuscan countryside stay come true. For the next several days, the peaceful countryside setting of Boccioleto Resort in Montaione was my home base for exploring Tuscany. However, if you prefer a more upscale stay for your Tuscany road trip, check out a 5-star boutique hotel Il Castelfalfi in the nearby medieval village of Castelfalfi. Il Castelfafi Hotel is a dream-like luxury retreat featuring a nature preserve, olive grove, vineyards, 27-hole golf course, swimming pools, and villas spread out over 2,500 acres of countryside.

7.3 The 3rd stop: LUCCA

After a relaxing time spiced with delicious Italian food and Tuscan wine in the Tuscan countryside in the Castellare di Tonda area, I headed to explore Lucca. The distance between Montaione and Lucca is 38 mi (62 km), or about one hour drive. Lucca is a small walled town that can easily be walked on foot. It is the hometown of the composer Giacomo Puccini . Every year Lucca hosts a few music events such as the Lucca Summer Festival , Lucca Blues Festival , and Lucca Jazz Donna .

RECOMMENDED THINGS TO DO IN LUCCA TUSCANY

Must Visit Places in Lucca in Tuscany, Italy

• Climb Guinigi Tower to enjoy the most beautiful view of Lucca
• Admire Lucca Cathedral
• Have a cup of genuine Italian cappuccino at Piazza dell’Anfiteatro
• Observe the intricate architecture of San Michele in Foro church
• Visit Puccini’s Birth Home
• Stroll Walls of Lucca
• Visit Clock Tower in Lucca (Torre Delle Ore)

Insider and off-the-beaten-track Lucca :

• Enjoy in Hot Air Balloon Ride over Tuscany from Lucca 
• Join Aperitivo and Food Tasting Tour in Lucca
• Attend a Cooking Class in a Private Home
• Explore Lucca’s countryside by E-Bike and sample some wines

Plan your visit to Lucca Book Lucca: 2-Hour City Center Walking Tour Buy Lucca: Puccini Festival Opera Recitals and Concerts Ticket

7. 4 The 4th stop: VIAREGGIO

After visiting Lucca, the city of Viareggio was the next stop on my road trip in Tuscany.

The distance between Lucca and Viareggio is about 19 mi (26 km), or a 30 min drive.

Viareggio is a popular and glamorous seaside resort in northern Tuscany on the Ligurian Sea facing the Tyrrhenian Sea. I strongly believe that strolling the Passegiata Margarita, the seafront promenade with beautiful Art Nouveau architecture, and tasting some Italian seafood at the restaurants or just drinking a cappuccino in one of the cafes on the promenade should be on any Tuscany itinerary.

7. 5 The 5th stop: PISA

The city of Pisa was the next stop of my Tuscany road trip. Pisa is easily reachable from Viareggio. The distance between Viareggio and Pisa is 14 mi (23 km), or only a 30 min drive. The driving distance between Pisa and Florence is an hour and 40 min drive. The Pisa Cathedral with the iconic Leaning Tower of Pisa and the Baptistery of St. John on the Piazza Dei Miracoli ( the Square of the Miracles ) are world-famous exquisite examples of Pisan-Romanesque architecture. If you doubting about visiting Pisa on the same day as Lucca and Viareggio or not, you need to know that the distance between Montaione and Pisa is about 37 mi (60 km), or one one-hour drive.

RECOMMENDED THINGS TO DO IN PISA TUSCANY

Must Visit Places in Pisa : Visit Pisa Cathedral, Pisa Baptistery and climb the Leaning Tower of Pisa for marvelous views of the Miracle Square (Piazza Dei Miracoli)

Insider and off-the-beaten-track Pisa : Take a Food Tour in  Pisa

Plan your visit to Pisa Buy an Entry Ticket to the Leaning Tower of Pisa & Cathedral Rent a car at Pisa Airport:   Rent a Car Pisa Airport 

7 .6 The 6thstop: LIVORNO

Don’t miss out on visiting the city of Livorno on your Tuscany road trip! A 40-minute drive from Pisa will take you to Livorno, called Leghorn by Brits.

This port town on the Ligurian Sea with a medieval fort is also well-known as the birthplace of the famous painter Amadeo Modigliani. In the 15th century, Livorno became a part of Florence when the Medici family bought Livorno and Pisa from the Genova.

Walking along the town’s waterfront promenade or taking a boat tour in the New Venice district deserves to be on a Tuscany bucket list.

RECOMMENDED THINGS TO DO IN LIVORNO TUSCANY

Must Visit Places in Livorno :

• Visit the central market in Livorno with more than 200 stalls selling local vegetables, fruits, cheese, and salami
• Go to the Porto Mediceo to watch the ships going to the islands of Elba, Sardinia, and Corsica
• Head to New Venice (Nuova Venezia), Livorno’s district with channels and bridges from the 17th century
• Visit Santuario di Montenero
• Stroll Terrazza Mascagni, the waterfront promenade of Livorno

Experience Livorno in a different way : Explore Livorno by Hop-On Hop-Off Bus

7. 7 The 7th stop: VOLTERRA

After visiting Pisa, Lucca, and Viareggio in western Tuscany in a day, I suggest going back to Montaione. Plan to visit charming places like Volterra, San Gimignano, Colle di Val d’Elsa, and Monteriggioni in central Tuscany in the next few days. Volterra is one of the most beautiful hilltop towns in Tuscany and one of the oldest towns in Italy. It dates back to the 7th century BC and the Etruscan era. Recently the town of Volterra has become known as the fictional hometown of the Volturi ancient vampires from the TV series Twilight. Talking about distances, Volterra is a 40-minute drive from Montaione (19 mi, 30 km). THINGS TO DO IN VOLTERRA TUSCANY Must Visit Places in Volterra :

• The Fortress of Volterra
• Palazzo di Priori, the city hall in Volterra
• Teatro Romano, the Roman amphitheater in Volterra
• Palazzo Viti, one of the most beautiful historic private residences and art museums in Italy
• Volterra Museum of Torture
• Pinacoteca, the art gallery with works of Tuscan artists from the 14th – 17th century
• Etruscan Museum

7. 8 The 8th stop: SAN GIMIGNANO

San Gimignano, or the Town of Fine Towers, is one of the most visited medieval hilltop towns in Tuscany. The historic center of San Gimignano is protected by UNESCO as a World Heritage Site. 14 remaining towers, out of 72 towers, built by noble and wealthy families in the 12th century dot the town’s landscape. The towers were symbols of power and wealth. The higher the tower, the more power, and money the family had. Sampling the best gelato in the World is a must-do in San Gimignano. Gelateria Dondoli   in San Gimignano was awarded as the World’s champion in gelato-making for many years. San Gimignano is also home to one of the finest Italian wines, the fabulous Vernaccia di San Gimignano . San Gimignano is a 40 min drive from Volterra. The distance between Volterra and San Gimignano is 20 mi (33 km). RECOMMENDED THINGS TO DO IN SAN GIMIGNANO TUSCANY

Must Visit Places in San Gimignano

• Palazzo del Popolo
• Piazza del Duomo
• Torre Grossa
• Collegiate Church of San Gimignano
• Santo Agostino Church

Experience San Gimignano in a different way : San Gimig nano by Horseback Riding

Insider and off-the-beaten-track San Gimignano :

• Vineyard Walk & Lunch with Wine Tasting
• Truffle Hunting with Wine & Lunch

Best trips from San Gimignano : Explore Chianti by Vespa from San Gimignano  

Plan your visit to San Gimignano Book San Gimig nano by Horseback Riding Vineyard Walk & Lunch with Wine Tasting Truffle Hunting with Wine & Lunch

7. 9 The 9th stop: COLLE DI VAL D’ELSA

Colle di Val d’Elsa is a 20 min drive (9 mi, 15 km) from San Gimignano. It is a true hidden gem in Tuscany, located just a 10-minute drive from the Chianti Classico area. The Chianti region with towns such as Castellina di Chianti or Panzano in Chianti, Greve di Chianti is just around the corner. In short, the best Tuscan wines are just in front of your nose. The ‘ Hill of Elsa Valley’  on the river Elsa is another medieval hilltop town in Tuscany. Colle di Val d’Elsa is a well-preserved and genuine Tuscan small town with narrow paved lanes, beautiful old palaces, and homes of noble families from the 16th and 17th centuries.

To give you a better perspective of where Colle di Val d’Elsa is, let me add that Colle di Val d’Elsa is a 45-minute drive from Florence and a 35-minute drive from Siena.

Luckily, Colle di Val d’Elsa is not a touristy place. So, if you want to escape the crowds, noise, and prices of Florence and Siena, head to this hidden gem of Tuscany. An interesting fact is that this small town holds 15% of the world’s crystal glassware and art. If you want to shop for some world-class glass and crystals, put Colle di Val d’Elsa on your Tuscany road trip itinerary.

7. 10 The 10th stop: MONTERIGGIONI

The town of Monteriggioni is another walled historic town on the way from Cole Colle di Val d’Elsa to Siena. Monteriggioni castle was built in the 13th century as one of the most important strategic castles in the province of Siena. Today you can take a short walk along the town’s walls overlooking roads to Siena and contemplate the battles once fought between warriors of medieval Florence and Siena.

A 15-minute drive from Colle di Val d’Elsa will take you to Monteriggioni, as the distance between Colle di Val d’Elsa and Monteriggioni is only 7 mi (12 km).

7. 11 The 11th stop: SIENA

A 20-ish min drive (12 mi, 20 km) from Monteriggioni took me to the last destination on my Tuscan road trip – Siena! Does the UNESCO World Heritage Site of Siena need some special introduction?! Who hasn’t heard of this Gothic masterpiece city yet?! Who hasn’t dreamed of drinking a glass of Aperol spritz, or a glass of famous wine from the nearby Chianti region and people-watching on one of the most beautiful squares in the World?! Stunning Siena is one of the most beautiful towns in Tuscany, Italy and its Piazza del Campo is one of the most beautiful squares in Italy. The legend says that Siena was founded by Senius, the son of Romulus. Hence, you will find the statues of the mythical Capitoline Wolf all over the city. Globally known for its beauty, Siena sits on the three hills connected by three main streets forming a Y shape that ends with the Piazza del Campo, the heart of the city. From its rich history, let me just point out that in the 14th century, Siena was a rival to Florence, Genoa, and Venice. But not only for its power but also for its beauty!

RECOMMENDED THINGS TO DO IN SIENA TUSCANY Must Visit Places in Siena :

• Piazza del Campo, the public square and historic center of Siena that hosts the famous Palio, the horse race twice a year (in July and August)
• Siena Cathedral (Siena Duomo)
• Palazzo Publico, the 13th-century palace in Siena
• Basilica of San Domenico, a gothic cathedral in Siena
• Torre del Mangia, the 14-century tower is the most famous landmark of Siena
• Piccolomini Library, the library with Pinturrichio frescoes within the Cathedral of Siena
• Palazzo Chigi-Saracini
• Baptistery of San Giovanni with a bronze relief by Donatello and 15th-century frescoes

Best trips from Siena : Vespa and Chinati Tour in the Tuscan Hills Horseback Riding from Siena Tour Chianti countryside  by Vintage Fiat 500  Please keep in mind that queues for the main attractions in Pisa are often long.

Plan your visit to Siena Book Siena 2-Hour Walking Tour & Skip-the-Line Duomo Tickets

After visiting Siena I suggest going back to Montaione and just relaxing in the tranquil Tuscany countryside.

8. Tuscany road trip map

Tuscany Italy Map: Tuscany road trip map with driving directions through Tuscany

Please press button ‘+’ on the map to enlarge the map

Tuscany driving route

9. Road trip to Tuscany route

Tuscany road trip route : stops + driving distances + driving times

10. How many days to spend on a Tuscany road trip?

My trip through Tuscany lasted 10 days, but you can squeeze your Tuscany road trip into one week. If you would like to see all these places in Tuscany, please don’t make your tour Della Toscana less than 7 days. Otherwise, you will be jumping from one Tuscan town to another without enjoying it. This ultimate road trip to Tuscany deserves 7 days in Tuscany at least! You want to experience Italian la dolce vita and eat Italian gelato, drink Aperol spritz, or visit a fabulous Tuscan winery  on your Tuscany vacation, right? Then, follow the road to Tuscany I took and take 10 days it.

RELATED READ: Italy Travel Italian Drinks You Want To Try Traditional Italian Desserts Tuscan Cuisine: Must-Try Food in Tuscany Amazing Italian Cuisine: Traditional Italian Dishes 20 Incredible Villas in Tuscany To Rent

11. Options for your Tuscany driving itinerary

You can start your Tuscany trip by flying to Pisa or Florence. There, you can rent a car at Pisa Airport   or Florence Amerigo Vespucci Airport .

Unfortunately, there’s no airport in Siena. But, if you want to start your Tuscany road trip with Siena , you could fly to Rome airport. Siena is about a 3-hour drive from Rome. In Rome at the Leonardo da Vinci – Fiumicino Airport , you can rent a car and head to Tuscany.

Car Rental Florence: Check out car rentals in Florence Car Rental Pisa Airport: Check out car rentals at Pisa Airport  Car Rental Rome Fiumicino Airport: Check out car rentals at Rome Airport 

Recommended travel accessories for traveling to Tuscany

Water-resistant anti-theft day bag that charges your gadgets Canon G7 X Vlog Camera Travel scarf with secret hidden pockets Anti-Theft Rfid blocking travel wallet 3 in 1 carry-on wheeled backpack with a detachable day bag OR, Samsonite travel suitcase with spinner wheels –  one of the best suitcases for traveling to Europe currently on the market

Like this Tuscany by car itinerary?! Bookmark this post and look for your flight to Italy!

Is Rome in Tuscany? 

Rome is not in Tuscany. Rome is in the Lazio region, a neighboring region to the Tuscany region.

How far is Tuscany from Rome?

The distance between Rome and Tuscany is about 125 mi (200 km). It takes about 2 hours and 20 min from Rome to Tuscany by car.

How far is Florence from Rome?

The distance between Rome and Florence is about 168 mi (270 km). It takes about 3 hours from Rome to Florence by car.

How far is Siena from Rome?

The distance between Rome and Siena is about 137 mi (220 km). It takes about 2 hours and a half from Rome to Siena by car.

How far is Pisa from Rome?

The distance between Rome and Pisa is about 217 mi (350 km). It takes about 4 hours from Rome to Pisa by car.

How far is Pisa from Florence?

The distance between Florence and Pisa is about 53 mi (85 km). It takes about an hour and 20 min from Florence to Pisa by car.

How far is Siena from Florence?

The distance between Florence and Siena is about 55 mi (89 km). It takes an hour and 10 min from Florence to Siena by car.

How far is Lucca from Florence?

The distance between Florence and Lucca is about 52 mi (83 km). It takes an hour and 15 min drive from Florence to Lucca by car.

How far is Chianti from Florence?

The distance between Florence and Greve in Chianti is about 52 mi (28 km). It takes about 40 min from Florence to Chianti by car.

How far is Venice from Florence?

The distance between Florence and Venice is about 160 mi (258 km). It takes 3 hours from Florence to Venice by car.

How far is Cinque Terre from Florence, Tuscany?

The distance between Florence and Cinque Terre is about 118 mi (190 km). A drive from Florence to Cinque Terre takes 2 hours and a half on average.

Do you want to see more beautiful places in Italy? Take a look at my photo gallery of Burano in the Veneto region  here  or my photo gallery of Urbino in the Marche region here YOU MIGHT ALSO ENJOY : Ultimate San Francisco to Los Angeles Road Trip 

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Saturday 18th of February 2023

After Rome, Venice, and Riomaggiore we only will have 6 days left. We have seen enough of Pisa. From your list, are there towns we should skip this time so we are not so rushed. We like to see the sights without stress of hurrying to the next place.

Thank you for reading about my Tuscany road trip.

Florence, Siena, and San Gimignano are must-visits. Lucca is a beautiful city and worth a visit.

Places like Volterrea, Col Val d'Elsa, and Montereggioni are smaller towns/villages. They could be quick stops in the Siena - San Gimignano area.

Consider taking a Wine Tour with Wine Tasting in Siena ( don't drive that day, stay overnight in Siena :-) ), and don't forget to sample gelato at Gelateria Dondoli in San Gimignano.

Six days are enough, and you shouldn't be in a hurry. The distances are not huge.

Have a great trip!

Tuesday 15th of December 2020

Absolutely stunning! Thank you on a detailed impressive guide!

Doreen Schmidt

Monday 14th of October 2019

Me and my husband are planning a road trip through Tuscany during December 2019. It is the only time of year that we can have a holiday. Do you think we will have the same experience?

Hey Doreen,

every season in Tuscany is different.

For example, in winter you won't see lush green vineyards in Tuscany, but you will see evergreen cypress trees, olive trees ..and you can always enjoy the castles, villas, forts... In winter can be cold in Tuscany and you might be spending less time outdoors, but you can go for wine tasting in some charming wine cellars, enjoy sampling food in lovely restaurants ... or spend more time in the cities than in the countryside. It depends on your personal preferences.

And in offseason, you can expect fewer crowds and cheaper accommodation. For instance, Uffizi Gallery in Florence is always the same no matter the season, but with fewer crowds. The same goes for Piccolomini Gallery in Siena, the Leaning Tower in Pisa ...

It really depends on what you are looking for and what you enjoy the most.

I hope this helps you, and please let me know if you have any other questions.

My Travelogue by Bhushavali

Friday 10th of August 2018

If only I could live in Italy! Its such a beautiful country which really cannot be enjoyed thoroughly even in multiple trips. Tuscany is an absolute beauty. Montaione looks just gorgeous. Perfect way to relax but still be so close to Florence.

Saturday 28th of July 2018

Tuscany is at the top of my road trip bucket list and reading your itinerary guide is seriously making me wanna just hop on a plane over! Definitely gonna check out San Gimignano's best gelato in the world along with all the other beautiful recommendations you've suggested. Bookmarked!

Monday 30th of July 2018

Eating the best gelato in the World is a must in San Gimignano!

A gelato devotee speaking here ;-)

xoxo Milijana

10 Day Tuscany Road Trip Itinerary

Tuscany, quite rightly, is one of Italy’s most popular destinations. A collection of historic towns and cities, beautiful countryside, thermal springs and of course incredible food. To see a bit of everything, you really need a car, as many of the best spots aren’t easily accessible by public transport. Having visited the region almost every year since I was born, I know (and love) it well, and have shared what I think is the best Tuscany road trip itinerary. 

Disclosure: This article contains affiliate links. This means that if you click a link and purchase something I’ve recommended I may earn a small commission. This does not affect the price you pay but helps me to run this site. You can read my full affiliate disclosure here.

Where to start your Tuscany road trip?

This Tuscany trip follows a loop, you can start and finish at any point of the itinerary, but I recommend starting in Florence as it has an international airport and good rental car options. An alternative would be to start in Pisa.  

This 10 day Italy itinerary is relatively relaxed, allowing 2-3 days in most destinations. If you want to spend a week in Tuscany, then follow the itinerary reducing Florence, Montepulciano and Lucca by a day. I have included options for a 14 day Tuscany road trip at the end of the article. 

If you want to travel to other regions, check out our Northern Italy itinerary and Southern Italy road trip . 

Tuscany Road Trip Itinerary Summary

Day 1-3 florence.

• Day 3-6 Montepulciano

Day 6-7 Siena 

Day 7-8 san gimignano, day 8-10 lucca via san miniato.

• Day 10 Florence 

Discover the best things to do in Tuscany

Tips for driving in Italy

I recommend hiring a small car for this trip. Many Italian towns have narrow streets and low bridges in the centre, which can be tricky to navigate with a big car or motorhome. (I know this first-hand after almost getting stuck under a bridge in Montepulciano!). However, if you do plan to travel in a camper or motorhome, there are lots of great camping spots – just stay outside of the town/village centres. Expect to be beeped at often – it’s just to let you know someone else is there – and watch your speed in towns and villages, it’s usually 50km/h, even if there aren’t signs and there are often speed cameras.

Hire a car in Italy.

Hire a motorhome or camper in Italy.

Fly into Florence, grab a rental car/camper , and head into the city. You won’t need the car while in Florence, so another option is to leave the car until you depart in a few days’ time, this way you don’t need to worry about finding accommodation with parking. Florence is the capital of Tuscany, and one of Italy’s most loved and visited cities. Home to incredible artwork, stunning architecture, and delicious food it is a cultural and gastronomic paradise. 

Things to Do in Florence

• Eat Bistecca alla Fiorentina (Florentine Steak)
• Stroll across Ponte Vecchio 
• Visit Piazza della Signoria and admire Palazzo Vecchio, the Fountain of Neptune and Perseus with the head of Medusa
• See Michelangelo’s David in the Accademia Galleries
• Admire the Cattedrale di Santa Maria del Fiore (The Florence Cathedral/Duomo)
• Walk up to Piazzale di Michelangelo for the best view across the city
• Visit the Uffizi to see Botticelli’s The Birth of Venus and da Vinci’s Annunciation

Where to stay in Florence 

Budget –  Residenza Conte di Cavour & Rooftop  is situated 200 m from Accademia Galleries and has a rooftop terrace. (Note parking is €40 per day – so worth picking up the rental car after Florence if you’re on a budget).

Mid-Range –  Relais Piazza Signoria  is located on the corner of Piazza Signoria and offers studios and apartments, some with terraces. (Parking as above). 

Luxury – The 4-star  Hotel Berchielli  is located on the River Arno, with views of Ponte Vecchio. Rooms are decorated in a classic style with antique furniture and details. (Parking €37 per day).

Campsites –  Florence Park Scandicci  is a 15 minute drive from the city centre with regular buses.

Find accommodation in Florence  

Day 3-6 Montepulciano 

From Florence drive 1.5 hours to Montepulciano. This beautiful walled medieval town sits on top of a hill, with panoramic views of the Val d’Orcia and Val di Chiana valleys surrounding it. Spend a few days here to enjoy the excellent wine of the same name and explore some of the surrounding areas. 

Things to Do in Montepulciano

• Try Vino Nobile di Montepulciano (not to be confused with varietal wine merely made from the Montepulciano grape). 
• Go wine tasting – I recommend Cantina De’Ricci, located in the Renaissance-era Palazzo Ricci. Part of the cellar here dates back to the Etruscan period. 
• Wander along Il Corso – the main street
• Explore the Piazza Grande
• Climb the tower in Palazzo Comunale (the town hall) for beautiful views 
• Eat pecorino cheese from nearby Pienza, pici alle briciole (pasta with breadcrumbs), and Chianina steak
• Visit the Tempio di San Biagio – Renaissance church

Day trips from Montepulciano

Bagni san filippo (san filippo thermal springs).

Tuscany is home to a number of natural thermal springs. Some have been converted into hotels and spas, but there are still a few that have been left in their natural state and are free to visit. One of these is San Filippo. Located in a small town of the same name, natural pools have formed from calcium carbonate deposits, and are filled with hot sulphuric spring water. It’s a bit smelly but very relaxing and a lovely spot to spend the afternoon. 

Chianciano Terme

Only 15 minutes drive from Montepulciano is Terme di Chianciano . The town of Chianciano is another spot known for its thermal waters and the spa here is excellent. Unlike Bagni San Filippo, this is a man-made, pay spa – using waters from the town’s thermal springs, and it is excellent. Explore the 20 wonders of the Sensory Baths including whirlpools, a mud bath, ice crash, saunas, Turkish baths and emotional showers, there is even a pool which plays music underwater. Treatments are available and you can also book babysitters for your visit if you’re travelling with kids. 

Val d’Orcia

A UNESCO World Heritage Site and an area of outstanding beauty that includes several towns and villages, surrounded by rolling hills and stunning countryside. Visit the hilltop town of Montalcino for a taste of one of Italy’s most celebrated (and most expensive) wines – Brunello di Montalcino. Explore the gorgeous countryside, some of which was featured in the movie Gladiator (as Maximus’ house and land). Take a tour of Castello Banfi I borgo – Europe’s biggest wine producer and enjoy lunch at their lovely restaurant. 

Where to Stay in Montepulciano

Budget –  Pacifico is a farm stay a short walk from Montepulciano. Rooms have private bathrooms and share BBQ facilities and a garden. Breakfast and parking is included.

Mid-Range – We had a great stay at Locanda San Francesco , which has an excellent bar and restaurant and views of the valleys. Free parking on site. 

Luxury – The 4-star Palazzo Carletti is located in Montepulciano’s historic centre, set in a Mediaeval building that features original frescoes, high ceilings and views over the Chiana Valley and Lake Trasimeno. Rooms are individually designed with separate sleeping and living areas. Free parking is available 300m from the hotel.

Campsites – Area Comunale P5 is centrally located with waste and water disposal. (Not suitable for tents). 

Find accommodation in Montepulciano

It’s just under an hour’s drive to Siena from Montepulciano, depending on the route you take. If you haven’t visited already, you can drive via Val D’Orcia, or take the faster route past Sinalunga. Siena city centre is a UNESCO World Heritage Site, with an impressive fan-shaped main piazza – Piazza del Campo. Every summer this is the setting for the famous horse race – Il Palio. 

Things to Do in Siena

• Spend some time exploring Piazza del Campo, including Palazzo Pubblico (the town hall – now the Civic Museum) and Fonte Gaia (fountain of joy), 
• Visit the Cathedral of Santa Maria Assunta (Duomo)
• Go to Santa Maria della Scala – which was one of the oldest hospitals in Italy, and is now an impressive museum complex
• Admire Basilica of San Domenico 
• Climb Torre del Mangia, which overlooks the Piazza del Campo. There are 400 steps up the tower which was built in the mid-14th century and stands at 289 feet tall – exactly the height of the Duomo.  
• Eat pici (this time with pork/wild boar ragu) and the famous panforte – a Sienese dessert containing candied orange and citrus peel, honey, cinnamon and vanilla. 

Where to Stay in Siena

Budget –  Domus Il Palio is located 1km from Piazza del Campo. Rooms are spacious with private bathrooms, many with terraces or patios. Parking is free (on street). 

Mid-Range – Piazza Paradiso is set in a historic building 300 m from Siena’s Cathedral. 

Each floor has a shared living room and guests can enjoy the use of the shared garden. Parking is €25 per day.

Luxury – For luxury, stay at the 5-star Grand Hotel Continental Siena . Set in a 17th-century building, it offers elegant rooms with frescoed ceilings and period furnishings. Parking is a pricy €55 per day.

Campsites –  Camping Siena is a holiday village located a 10 minute drive from Siena. There is a bus service into town and the resort has a pool, pizzeria and cafe. 

Find accommodation in Siena 

Drive 50 minutes to San Gimignano. This small town is famous for having many towers, which were a symbol of wealth for the local families. At one point there were 72 towers, though today 14 remain, which is still plenty when you consider the size of the town.

Things to Do in San Gimignano

• Have a gelato at prize-winning  Gelateria Dondoli  in Piazza Della Cisterna
• Climb the Torre Grossa – the town’s tallest tower – for spectacular views
• Visit the wine museum, so you can enjoy a glass of the region’s speciality Vernaccia
• Eat saffron and visit a Saffron farm – Casanova di Pescille (You can also stay here). 
• Head up to the Florentine fortress – Rocca di Montestaffoli 
• Visit the Duomo di San Gimignano 
• Check out the San Gimignano 1300  exhibition – a model of what the town looked like 700 years ago.

Where to Stay in San Gimignano

Budget –  Casa dei Potenti is located in the centre of San Gimignano overlooking Piazza delle Erbe. Each room is unique and furnished with antique furniture. Parking nearby is free. 

Mid-Range – We stayed at  Hotel La Cisterna  in Piazza Della Cisterna – a few steps from the gelateria – in a 14th-century building. Rooms have views over the piazza or over the Tuscan countryside. Parking (€15 per day) is outside the city walls a short walk away or via a shuttle service. 

Luxury – Tenuta Sovestro is a farm stay located in the countryside with a free shuttle service into the town. There is a restaurant, pool, garden and free parking. Breakfast is included. 

Campsites – Area di Sosta camper S. Lucia is about 3km from the centre. There is an 8 minute bus into San Gimignano every 30 minutes. Camping Boschetto di Piemma is 100m away and has tent pitches and a restaurant. 

Find accommodation in San Gimignano

From San Gimignano, it’s a 50 minute drive to San Miniato. Book in advance with Massimo from  Truffle in Tuscany  for a morning of Truffle Hunting. You will be taken to the forest with one of the expert truffle dogs to search for black truffles. Afterwards, Massimo cooks up a feast at his home and you can taste some of your findings. 

Continue another hour onto Lucca. This is my favourite Tuscan city and one I’ve spent a lot of time in. The walled city has fewer tourists than some of its neighbours and offers a wonderful Tuscan experience, with cobbled streets and laneways full of restaurants and bars. 

Things to Do in Lucca

• Hire bikes and cycle around the 4km path on top of the city’s walls 
• Climb Torre Guinigi to enjoy the views and the trees at the top
• Wander the narrow streets and stop for coffee, focaccia and gelato, and to shop in the city’s centre
• Visit Piazza dell’Anfiteatro, a huge circular piazza that was once a Roman amphitheatre – there are often concerts here in the summer with big international artists

Where to Stay in Lucca

Budget – We had a lovely stay at Al Tuscany inside the city walls. It’s a great location to get everywhere and many of the rooms have views over the city. You will need to park outside the city walls and walk in.

Mid Range/Luxury – Palazzo Rocchi is a gorgeous guesthouse inside the walls, with opulent decor. We loved our stay here – it feels like a luxurious little secret and the owners are so welcoming. Parking nearby for €2 per hour.

Luxury – Located outside the city walls, Villa La Preziosa is a 4-star property with beautiful gardens. There is a pool and breakfast is included. The property offers a shuttle service for an additional charge. Parking is free. 

Campsites – Parking del Borgo is located a 5 minute walk outside the city walls and has camper spots for €15 per night.

Find accommodation in Lucca

Day 10 Florence

Drive 1 hour 15 back to Florence for your flight home. 

Two Weeks in Tuscany 

If you have a longer trip, then I suggest heading west from Lucca to the coast. Here you have a few options: 

Take a ferry to the idyllic island of Elba. This is the third largest island in Italy after Sicily and Sardinia and is part of the National Park of the Tuscan Archipelago, the largest marine park in Europe. It is known for unspoilt beaches and clear blue water and is a good spot for diving and snorkelling as well as hiking and mountain biking. 

Find accommodation in Elba

Tuscany Beaches

Stay at one of the Tuscan beaches, such as Viareggio , Forte dei Marmi or Camaiore . 

Around 30 minutes drive from Lucca.

Liguria Beaches 

Head to Liguria, to one of my favourite Italian beach spots – Lerici and Fiascherino – an hour’s drive from Lucca. I personally think the beaches here are more lovely than the Tuscan beaches further south and while you are here, you can easily take a day trip to the famed Cinque Terre and the beautiful villages of Porto Venere and Tellaro. You can read all about it in our Liguria guide. 

Find accommodation in Lerici

How many days do you need for a road trip to Tuscany?

A 10 day Tuscany road trip allows you time to see the main cities, smaller towns and villages, as well as the beautiful countryside in between. If you’re short on time it can be done in 7 days, and for a really relaxed Tuscany itinerary, 2 weeks is excellent.

What is the famous road in Tuscany?

The SR222 ‘Chiantigiana road’ is Tuscany’s most famous drive, connecting Florence to Siena through the Chianti region.

Do you need a car to explore Tuscany?

To really explore the region it’s really worth having a car. The main cities are connected by train, but it’s more difficult to get to the smaller towns and see the countryside without a car in Tuscany.

Where should I stop on a Tuscany road trip?

Include a mixture of iconic cities such as Florence and Siena, along with smaller towns and villages like San Gimignano, Lucca and Montepulciano and visit the beautiful area of Val d’Orcia.

Have you taken a road trip in Tuscany? We would love to hear your thoughts in the comments below.

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Your Ultimate Tuscany Road Trip, Planned: Best Itinerary Ideas & Practical Tips

Last Updated on March 12, 2024 by Michela

Sun in your face, wind in your hair and the iconic Tuscan countryside all around you: what could be better than a Tuscany road trip ? A trip through Italy’s most famous region is a bucket list item for many and for good reason.

I have been to Tuscany several times (I even lived there for awhile) and I keep going back. Even though it may seem overrated, it really is one of the most beautiful places in Italy and, arguably, the world.

So, if you are getting ready to head off on your own Tuscany road trip, look no further than this practical and inspirational guide with helpful travel tips and, most importantly, the top spots that belong on your itinerary.

Some of these links are affiliate links. This means if you make a purchase through that link, I receive a small commission at no extra cost to you. Read my full disclosure !

First things first – how long should a Tuscany road trip be?

Can we just make it forever? Of course, one of the first questions to have a clear answer on is how long you have available to road trip Tuscany.

Maybe it is just one stop on a larger Italy itinerary or it’s the prime focus of your adventure. Honestly, you could make a road trip in Tuscany your whole vacation, there is that much to see.

Ideally, I suggest a Tuscany road trip of 7 to 10 days . This way, you are able to spend at least one night in each of the most beautiful places in Tuscany.

However, you can definitely adapt the itinerary suggestion I have laid out from my experience to fit your needs.

The length of your trip may also depend on what areas you are more interested in seeing

If you are figuring out this road trip on your own and want some personalized help, I got you! If you would like me to create a custom itinerary for you, check out my trip planning services. Or if you just have a question or two, ask me in the comments.

Tuscany Road Trip Itinerary

This itinerary outline highlights the top destinations I recommend you visit and in what order for the most efficient drive.

If your timing allows it, I highly recommend staying even more than 1 night in several of these destinations where I believe there is more to discover! I will highlight what I think these destinations are based on how much there is to do and see in the area. This way you can get a better grasp on what destinations can be done in one day and which ones you may want to extend your trip on.

Day 1 & 2: Florence

A trip to Tuscany is incomplete if you don’t visit Florence. The cultural and artistic capital of Italy, Florence is a place where you could spend weeks and still not see all it has to offer.

Florence is the perfect place to kick off your Tuscany road trip as it is also the most convenient place from which to pick up a rental car/arrive in Tuscany.

Check out my guide to 2 days in Florence for specific ideas and tips on how to enjoy the city.

If you plan on staying in Florence longer and want a few day trip ideas up your sleeve, check out my favorite day trips from Florence .

Day 3: Panzano in Chianti, San Gimignano & Volterra

After picking up your car in Florence, it is time to hit the road!

The first stops are just outside Florence at a maximum of an hour distance.

Pass first through the world-famous wine region of Chianti. If you are a wine connoisseur, you may already want to extend your trip a little to make time for a winery visit.

My favorite small town in the Chianti area is Panzano in Chianti . Here, you will find two amazing restaurants: the Antica Macelleria Cecchini (by famed butcher Dario Cecchini) and a place with an epic view, Ristorante Oltre il Giardino.

The other thing that makes Panzano so special is that it has a middle-of-nowhere feel, just completely surrounded by the rolling hills of vineyards.

Next, head over to the Medieval mecca of San Gimignano . San Gimignano is well-known for the “first skyscrapers”, as it is a town with many towers (insert how many towers in the past) One of my favorite areas is the castle ruins of Rocca di Montestaffoli.

Last but not least, pass through Volterra , another stunning Medieval village at the top of a panoramic hill.

Day 4: Pisa & Lucca

Continue heading west towards one of the world’s most iconic monuments. Arrive in Pisa and make your way through the lively town center to the Piazza del Duomo.

Here you can snap your iconic photo with the Leaning Tower of Pisa !

I personally didn’t find much else to do in Pisa, so I suggest you continue on the road to visit the quieter and charming Lucca .

Lucca is small but holds many treasures! The walled historic center feels like a storybook. Don’t miss walking on the walls, the unique oval-shaped Piazza Anfiteatro and the quirky Torre Guinigi , which has trees growing at the top of it!

Day 5 & 6: Orbetello & Porto Santo Stefano

The next day is a longer drive along an area that is often underrated by tourists: the Tuscan coast !

Because Tuscany is so famous for its iconic countryside landscape, I think many forget that Tuscany also has a huge coastline full of beautiful beaches.

So, if you are interested in seeing this hidden gem side of Tuscany, make your way to the peninsula of Orbetello . This is the area of the Monte Argentario, a place with some of Tuscany’s best beaches, like Feniglia Beach and Cala del Gesso .

Pro tip: If you have the time, I recommend staying at least 2 or 3 days in the area, as the main activity is going to the various beaches. So typically, you would go to a different beach each day.

Day 7: Saturnia & Pitigliano

Continue heading south to the very border of the Tuscany region.

Your first stop is going to be at the once hidden gem, now Instagram famous Saturnia hot springs . These springs are free to visit, in an extremely beautiful setting and they provide a relaxing, skin-nourishing benefit from the natural minerals.

After a bit of relax, head to what is one of my favorite towns in Tuscany. Pitigliano is right at the border of Tuscany and Lazio, so it has a really interesting Roman and Etruscan mixed history.

Moreover, it’s just simply beautiful. The town is known as the “Città del Tufo”, or city of rock, because it is literally coming out of the ground from this red clay rock above a steep valley. Read my full Pitigliano travel guide to find out the best things to do and see.

Day 8: Montepulciano & Pienza

Next, hit two of Tuscany’s classic wine country towns. These are villages you’ve likely heard of, whether you are an avid traveler or wine taster.

Montepulciano is a hilltop town that not only produces some of the world’s most famous reds but is beautiful to explore.

Make your way up to the cathedral at the top of the hill. If you get tired climbing the narrow streets, stop at the café for an iconic view at Caffè Poliziano.

And if you are going to do a wine tasting, Montepulciano is one of the best places.

Pienza, instead, is the gem of the Val d’Orcia, which is that iconic valley that you picture when someone says Tuscan countryside. It is also the home of Pope Pius II, so much of the town’s architecture and planning was influenced by him. In fact, it’s one of the first towns in which Renaissance architecture was implemented.

You can’t miss a stroll along the Via dell’Amore in Pienza, taking in the surrounding valley. Check out my full guide to Pienza .

Good to know : We had a great stay at Poggio Olivo , a stunning farmhouse in the Tuscan countryside. Not too expensive, amazing view and amenities and a very gracious host!

Day 9: Siena

Before you arrive in Siena, head to some of the best places to see cypress trees in Tuscany , like the Crete Senesi and the Cipressi di San Quirico.

Then head to Siena , one of the most beautiful small cities in Italy. From the terra cotta buildings to the unique Piazza del Campo to the breathtaking facade of the Duomo, Siena is just a seriously amazing place to discover with so much to see.

If you can, I would recommend staying 2 days in Siena. It is so beautiful and, while you can see most of the city in half a day, it would be best to give it at least a full day or two.

Day 10: Monteriggioni & Return to Florence

All good things must come to an end!

As you make your way back to Florence, stop by Monteriggioni , a 25-minute drive from Siena and a very unique, very small destination to close out your Tuscany road trip itinerary.

It is a Medieval walled town, one of the best preserved in the world. Entering the town is literally like entering a fortress of a different era.

The center is so small but still bustling. I had lunch here, a great Florentine steak at Ristorante da Remo.

Tuscany Road Trip Planning Tools & Tips

Renting a car & driving in italy.

One of the essential road trip tips I can help you with is on renting a car and driving in Italy.

Renting a car in Italy is straightforward and similar to other countries. The minimum age for rental is 26 years old. I prefer to use aggregator sites like AutoEurope that pull together all the different prices and options from various rental companies to find the best deal.

One thing you will definitely need is an International Driver’s Permit.

Pro tip: Keep in mind that the majority of vehicles in Italy are manual. If you cannot drive manual and prefer to drive a car with an automatic gearshift, you must specify this in your rental car reservation. Renting an automatic car typically comes at a higher cost.

Before you hit the open road, check out my guide to driving in Italy . There are quite a few differences and particular tips you should be aware of in order to avoid fines or any trouble!  

Calculating road trip cost

The resources I am about to share are some of my overall favorite road trip planning tips.

Budget is a huge part of planning a road trip and it can get out of hand if you don’t set up a plan beforehand.

One first step is to calculate the estimated cost of gas of your whole trip. Luckily, ViaMichelin makes this easy. It is one of my favorite tools to calculate the cost of different routes.

Input your destinations and the order in which you are visiting them to get an estimate gas price.

You should also use the site Autostrade , which is the website of Italy’s national highway system, as a resource for fuel prices, calculating your route and updated road information.

Also, use my free downloadable road trip budget planner to have an overview of all the main expenses that could come your way, beyond just gas and tolls! Just sign up below to my newsletter to get access to this free resource and many more in The Travel Library.

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Locating gas stations

Autostrade.it is also a great resource for locating your nearest gas station or, if you are looking beforehand, the gas stations that are along your route.

You can just input where you are starting and where you are ending up, as well as add other specific parameters (like if you need regular gas, methane, diesel, etc) to get a list of the gas stations along the way.

Organizing your itinerary

Keeping your itinerary organized and handy isn’t as easy as it seems. That’s why I love Google Maps Trip Planner .

This tool allows you to create your own personal maps and separate the pinned locations by layer. You could separate them by category or, how I prefer, by day of trip, to see what’s the plan for each day of your itinerary.

It is also a great way to save extra ideas and stops in case you find yourself with extra time.

Learn how to make the most of using Google Maps Trip Planner for any of your travel itineraries!

The SGTD Take

I think it is obvious how I feel about a Tuscany road trip – it is one of the best road trips in Italy, a total dream and something I wish every traveler has the opportunity to do!

I was a “travel snob” who had been to Tuscany once and said, well what more could there possibly be? And now I have been several times after, always discovering something new and, of course, beautiful and charming.

There’s a reason it is one of the most popular destinations in the world and I must say, it deserves all the credit.

Italy Trip Planning Resources

• Accommodation : For Italy, I mainly use Booking.com to search and book places to stay.
• Booking flights : I like to search for flights through Skyscanner , but I also book direct depending on the airline.
• Activities & experiences : For things to do that require a ticket, and for more unique trip activities, I use Musement .
• Road trip : For renting a car, I get the best prices by comparing companies with AutoEurope . I then use ViaMichelin to estimate road trip costs and Autostrade.it to find gas stations/have live updates on traffic.
• Transportation : Traveling by public transportation is a great way to see Italy. I use Trenitalia or Trainline to book tickets for trains and Flixbus for long-haul bus trips.
• Accessories : I always travel with this portable charger to stay connected and with a universal adapter to accommodate Italy’s plug types.
• Need help planning an itinerary? Fill out my form for a custom itinerary request !

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Plan your Tuscany road trip with me in the comments!

Michela is a travel writer and photographer living in northern Italy. She is passionate about helping people make the most of their travels by sharing advice gained from her personal experiences, off-the-beaten-path destinations and time-saving quick itineraries. Browse her top articles or have her help you plan your itinerary to your dream destination!

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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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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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Best of Bari: Our Travel Guide, Tips & Favourite Spots

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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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The perfect tuscany road trip itinerary.

Rolling hills covered in vineyards, and dotted with charming villages is a dream for a road trip. You’re in Tuscany, one of the most glorified regions in Italy. And it undoubtedly lives up to its reputation!

I’ve traveled around large parts of Tuscany and loved every bit of it. It’s surely a region you’ll go back to again and again!

A Tuscany road trip is the best way to explore the region and I’m here to help you with the route so that you get the most out of your trip.

This 10-day itinerary takes you through some of the best places to visit in Tuscany by car, but feel free to mix things up, shorten it, or prolong it with more destinations if you have the time. You can also check out my post with some of the best Tuscan towns here .

Disclosure: This post may contain affiliate links. That means that if you make a purchase through one of those links, I will get a small commission at no extra cost to you.

Table of Contents

Prepare for a Tuscan road trip

Before heading out on a road trip in Tuscany you need to make sure you have all the essentials. You can read my complete road trip packing list here .

Then you’ll need a car and travel insurance.

Since Tuscany is such a popular road trip destination, I do recommend that you book a rental car a good time in advance of your trip so that you don’t risk paying extra for the most expensive cars or even worse, that there are no cars left at all.

Some tips for renting a car in Italy is to consider how much space you’ll need in the car for luggage and how many people you are. It’s always recommendable to have enough space for all your belongings in the boot so that you can leave the car without anything to be seen when you park.

If there is anything in the car that indicates that the boot could be full, there are more chances for anyone breaking into your rental car. And you don’t want that.

Book your rental car here

When is the best time to go on a road trip to Tuscany

You can enjoy road trips to Tuscany all year round, but the spring and autumn are particularly beautiful and the temperatures are pleasant. That said, they’re also the busiest tourist months.

The winter can get cold with temperatures as low as 3-4 degrees Celsius in the hills and usually 3-4 degrees warmer by the coast. In the mountains, you’re likely to get snow. However, daytime temperatures can be much higher in the sun, so I do recommend dressing in layers if you travel to Tuscany in winter.

The hottest summer months are July and August and temperatures can easily hit 30+ degrees Celsius and are best enjoyed where you can cool down in the sea or a pool. But if this is the only time you’re able to go on a Tuscan road trip, don’t let it stop you!

The region is absolutely mesmerizing in summer too and the hills tend to be a little bit cooler. Keep the air-con on in the car and walk in the shade of medieval buildings in quaint Tuscan towns while eating gelato, and you’ll love it nonetheless.

Driving in Tuscany

Driving in Tuscany is absolutely lovely, especially through the mesmerizing countryside. There are only a couple of large roads on this road trip and it’s the motorways connecting Florence and Siena and Florence and Pisa. These are toll roads .

However, if you’re not used to driving on small, narrow roads it might feel a bit overwhelming at first, especially when meeting other cars. Then a smaller car can be a good idea for you so that you feel more comfortable.

One thing that I notice every time I’ve been road tripping in Tuscany is that a few months later, I get a fine sent to me for some traffic infringement that I haven’t been aware of. I’ve got them sent both to Norway when I lived there, and to Spain where I live now. So there is no hiding if you live in Europe.

So take note of the speed limits . In rural areas and small roads, it’s usually 50 km/hr unless other is marked. When it says end of 50 km/hr, usually it goes up to 70 km/hr. There are both fixed and mobile speed cameras, so the best advice I can give you is to drive within the speed limit at all times and if you’re unsure, drive slower rather than faster.

But there are also parking tickets. I do recommend that you always ask a local if you’re allowed to park for free or if you need to pay as well as where and how to pay if you are unsure.

Those things aside, I’ve never had any bad experiences with driving in Italy, let alone Tuscany, and it’s really all about following the rules (even though it might seem that the Italians don’t.)

Tuscany road trip itinerary

This Tuscany road trip itinerary starts and ends at Florence airport, but you can easily start or end it in Pisa airport too, as it’s only an hour away. For each town you’ll stay at, I’ve included a few hotel alternatives with parking for different budgets so that you can choose what fits you best.

The places we’ll cover in this Tuscany road trip itinerary are the following:

• San Gimignano
• Monteriggioni

Day one – Florence

Make sure you read my guide to where to stay in Florence before you go.

The first of your 2 days in Florence , start off with heading up to Piazzale Michelangelo for the iconic city views. There is paid parking there if you come by car, otherwise, take bus 12 or 11 if you’re not walking.

After having a coffee and enjoying the staggering views, leave your car at the hotel if you brought it and head to the Cathedral of Saint Mary of the Flower, known as Duomo di Firenze in Italian. The most prominent landmark in Florence is not to be missed.

Appreciate masterpieces of Michelangelo, Donatello, and other amazing artists in the Opera Duomo Museum and climb the dome for the day’s second winner view.

For lunch, check out the food market, Mercato Centrale, or find a cute restaurant in the old town.

Spend the rest of the day exploring the Uffizi Museum. Among the Renaissance masterpieces, you can expect to see is the Birth of Venus by Botticelli. But you can also admire art from a large number of Italy’s most famous artists as you wander through corridors lined with sculptures and paintings.

The Giardino di Boboli garden is also a must-visit while at the Uffizi. The museum and gardens deserve at least 2-3 hours but if you find that you have spare time, it’s perfect to wander around the streets soaking in Tuscany’s capital city before dinner.

Round off the day with a nice pizza or pasta in a nice restaurant.

If you want to swap out anything on the itinerary for something more adventurous, why not embark on one of the epic cycling tours of Tuscany’s breathtaking countryside with some wine tasting or a Tuscany Vespa tour ?

For affordable luxury, stay at Alfieri Signature Suites – Alfieri Collezione , a short stroll from Ponte Vecchio and Florence’s old town. However, if your budget isn’t quite there, check out Guest House L’Aranceto only a couple of kilometers from the center. This cute guest house has a free bike rental and a bus stop right outside that takes you into the main sights.

Day two – Florence – San Gimignano

After breakfast, start your second day of this Tuscany road trip itinerary by heading to the Basilica di San Lorenzo and the Medici Chapels. The church once used to be Florence’s main basilica and dates back to the year 393.

The highlight is the Medici Chapel where the Medici family is buried. Michelangelo himself built the sculptures of Giuliano and Lorenzo Medici’s tombs in the New Sacristy, which is one of three parts, the others being the Chapel of Princes and the crypt.

You should also explore the Cannon’s Cloister and the Museum of St. Laurence Treasure and Cellar, Donatello’s burial place.

After this cultural visit, have some lunch before it’s time to get the car and head to San Gimignano. But don’t worry, you’ll be back in Florence for the last day of this Tuscany road trip to explore more.

READ MORE ABOUT FLORENCE

• One day in Florence
• Winter in Florence
• Is Florence worth visiting

It takes one hour to drive from Florence to San Gimignano , but if you’re in the city center, you might take a little longer to get out of the city chaos. Drive south towards Siena and follow the signs right towards San Gimignano just before you get to Poggibonsi.

You can either walk around San Gimignano and soak in the medieval town before dinner or stay at a vineyard and drink nice wine and wander in the Tuscan countryside to relax a bit after a couple of culturally rich days in Florence.

If you’re going to spend extra money on one hotel and one experience during your Tuscany road trip, I highly recommend you spend your evening in the countryside surrounded by vineyards tasting the local produce.

Nothing can really compete with that and this is the place to do it! I’ve recommended a place to stay that I loved for just this below and you can take a leisurely walk through the vineyards in the morning to reach San Gimignano in under an hour.

For a true Tuscan experience, stay at Fattoria San Donato in the middle of the vineyards 3,5 km from San Gimignano. You can stay for dinner and as they produce their own organic wine and olive oil, there is no reason to go anywhere else for the night. There’s even an outdoor swimming pool. However, if you prefer staying in the heart of town, try Hotel Bel Soggiorno . For smaller budgets, stay centrally in the historic 1300’s building Locazione Turistica Totti .

Day three – San Gimiginano – Siena

Spend the day exploring the highlights of the medieval hilltop town. For being such a small place, there are a lot of things to do in San Gimignano .

Head into the heart of the historic center to Piazza della Cisterna where you can see an ancient stone wall in the middle of the square, surrounded by medieval houses and towers.

San Gimignano is famous for its towers. Now there are only 14 remaining, a reminder of the once-wealthy community that featured 72 towers built by the patriarch families to show off their wealth.

The highest of the remaining towers is the 54 meters tall Torre Grossa that’s worth a climb to get a bird’s eye view of the village and surrounding vineyards.

Then head to Piazza del Duomo where you find the Duomo di San Gimignano and Palazzo del Popolo where you can admire frescos painted by some of Tuscany’s leading artists.

Finally, make sure you check out the ancient fortress ruins of Montestaffoli which once protected the town from Siena. Also, make time to stroll around the cobblestoned streets and have a nice lunch at one of the restaurants during the day.

When you’ve explored San Gimignano, it’s time to continue your Tuscany road trip to Siena. The drive takes about 45 minutes past Colle di Val d’Elsa and Monteriggioni.

After you’ve settled in at your hotel, go for a stroll in the old town while looking for a nice place for dinner. The cobblestoned streets are super charming at night and bustle with life.

For a serious luxury experience next to Piazza del Campo, stay at the Grand Hotel Continental Siena – Starhotels Collezione . The 5-star hotel is almost like staying in a museum with beautifully decorated walls and ceilings covered in frescos. For a mid-range budget, stay at Hotel Athena and for a budget stay, try B&B La Verbena 3 km outside town or Villa Socini at walking distance from the historic sites.

Day four – Siena

It’s fully possible to see Siena in one day and still leave a bit of time for enjoying a nice lunch at one of Italy’s most famous squares, Piazza del Campo.

The shell-shaped square is home to a few of Siena’s main attractions, like Torre del Mangia, where you can climb the top for a bird’s eye view of the square, The Civic Museum, Palazzo Publico, and the Fonte Gaia fountain.

You can easily explore all of that before lunch and after lunch, you can head to the Duomo of Santa Maria Assunta, Siena’s mesmerizing cathedral where you also can visit the Baptistery of San Giovanni, the Crypt, Museo dell’Opera, and the astounding library, Libreria Piccolomini.

If you have any remaining time before dinner, spend it getting lost in the streets and soak in the medieval feel this amazing town still breathes.

RELATED: Siena from Florence day trip

Day five – Siena – Monteriggioni – Volterra

On day five of this Tuscany road trip, you need to get up early as you’ll be starting the day, after a good breakfast and aromatic Italian coffee, with driving to the walled town of Monteriggioni. The drive only takes 20 minutes and there is a big paid parking lot outside the walls with a short walk up a set of stairs to enter the gates.

Monteriggioni might just be the smallest town in the whole of Tuscany, but that doesn’t mean it’s a grand place to visit and with its proximity to the main road it’s become a popular stopover.

The dramatic history of the fortified town started in 1213 when it was built as a Siena defense strategy to protect the region against the Florentine. From the early 14th century, the Monteriggioni served as the Italian Brotherhood of Assasins’ headquarters. Further, the world-famous video game Assasins Creed is among other Tuscan destinations, set in Monteriggioni.

With this history, it’s hard to pass on this tiny corner of Tuscany. Walk through the town to the main square Piazza Roma, where you’ll find the Romanesque-style church of Santa Maria Assunta. There are also a few restaurants where you can have lunch before continuing on your road trip through Tuscany – or you can wait until you arrive at your next destination.

But before you leave, this unique place, make sure you climb the city walls. There is a small entry fee of 1,50 Euros (at the time of writing) but it’s absolutely worth it.

When you’re ready to leave, you have a 45-minute drive westwards, to the bigger walled town of Volterra .

When you’ve settled in your hotel and had lunch if you didn’t eat in Monteriggioni, head to the Pinacoteca and Civil Museum. Take in the astounding paintings and sculptures from different artists featured in the 15th century Renaissance structure. You’ll also find ancient ceramics and even the Medici coin collection.

The rest of the evening you can wander the streets and find a nice restaurant for dinner and wine.

Stay in the historic center of Volterra at Hotel La Locanda or for lower budgets, check out Chiostro Delle Monache Hostel Volterra set in a 15th-century monastery and only a short walk from the city walls.

Day six – Volterra – Pisa

Start the morning early with a good breakfast and head outside the city walls to see the Teatro Romano, a large archaeological site where you can maze at the remains of a Roman theater dating back to the first century. You should also visit the Parco Archeologico Enrico Fiume to see the remains of a second-century Etruscan Acropolis.

Nearby, you can see the Medici Fortress, though not open to visitors (it’s actually a prison now,) it’s still a unique structure with a dramatic history.

For lunch, head to Piazza dei Fiori where you also find the 13th-century Palazzo Pretorio and the oldest Town Hall in Tuscany, Palazzo dei Priori, built between 1208 and 1257.

After lunch, head to Palazzo del Popolo and visit Duomo Santa Maria Assunta which is a beautiful blend of different architectural styles from different centuries.

The 13th-century baptistery is the most prominent structure in Volterra and stands individually from the cathedral. You can also visit the Diocesan Museum of Sacred Art that’s found in the monastery next to the baptistery.

Before continuing your Tuscany road trip to Pisa, make time to wander the cobblestoned streets of Volterra to soak in the dramatic history that lived in the medieval walls. Make sure you don’t miss out on the Arco Etrusco, and the ancient gate in the walls that was later rebuilt by the Romans.

The drive from Volterra to Pisa only takes about an hour , but if you plan on having dinner in Pisa, you shouldn’t leave it for too late so you get time to get settled at your hotel too.

In Pisa, stay centrally at B&B Di Camilla , a wonderful and homely feel. For lower budgets, check out My Way . It’s a super friendly hotel within walking distance from the Leaning Tower of Pisa – great value for money!

Day Seven – Pisa-Lucca

You’re on the seventh day of your Tuscany road trip and in the city of one of the world’s most famous landmarks, the leaning tower of Pisa. So get up early, have a breakfast of champs, and head to Piazza dei Miracoli and this iconic tower.

On top of taking fun pictures of the tower, make sure you climb to the top. It’s a steep price of 18 Euros, but I’d say it’s a bucket list experience. You can see all updated information about tickets and opening hours on the official website here .

Next to the Leaning Tower of Pisa, you can visit the Cathedral of Maria Assunta, an astounding Romanesque basilica.

Make sure you head to Museo dell’Opera del Duomo to admire impeccable pieces of ancient art such as paintings, sculptures, tombs, and embroideries.

The Sacred Field, Campo Santo, is another great site on Piazza dei Miracoli worth seeing.

The cloister was built towards the end of the year 1200 and has an astounding courtyard lined with beautifully decorated arches.

According to legend, it was built on imported soil from Golotha so that the citizens could be buried in sacred ground. Today, the floor is a mosaic of tombs belonging to Pisan patricians.

After exploring all the sites at Piazza dei Miracoli it’s time for lunch and there are numerous restaurants to choose from. I do recommend removing yourself a little from the square as prices tend to be higher than necessary.

After lunch, it’s time to explore some of the lesser-known yet wonderful attractions in Pisa. The cutest church in Pisa deserves a visit, the Santa Maria della Spina, is a lovely, small Gothic church.

It was actually taken down and rebuilt at the current location in 1871 due to water damage from the river where it used to be.

Head to Piazza dei Cavalieri to maze at the beautifully decorated Palazzo della Carovana and visit the Church of Santo Stefano.

Finally, if you get the time, you should not miss the 10th-century Basilica Romantica di San Pero a Grado. It’s said that St. Peter landed in Italy on the exact spot the basilica is built in the year 44 AD when the Mediterranean reached that far up.

Driving from Pisa to Lucca only takes half an hour , so you can have dinner in Pisa or Lucca as you please.

For a Tuscan feel, stay at the medieval B&B Villa Corte Degli Dei just a short walk outside of Lucca’s city walls. For a charming stay inside the city walls, you can stay at B&B Relais Inn Lucca .

Day eight – Lucca

There are a lot of things to do in Lucca so get ready for yet another jam-packed day of medieval history and intriguing legends. Though you can see Lucca in one day , I’ve left two days to soak in this town as we’re getting close to the end of the Tuscany road trip and you do want to take the time to walk the streets and feel Tuscany when you’re there.

So why not start the day by walking on top of the city walls? This is a popular place for locals to jog or cycle so pay respect when you stop for pictures so you don’t block the road for others.

After your stroll, head to Lucca Cathedral, one of the most unique in Tuscany where all the columns are unique. It’s said that the city held a competition to choose the artist that was going to design the columns, but the citizens couldn’t choose among the finalists, thus they used all the different columns.

Next, get a bird’s eye view of the old town from the top of Torre delle Ore before lunch at one of the restaurants at Piazza dell’ Anfiteatro. The unique square is built on top of an amphitheater that now is buried under the ground. Only some arches are above ground and are incorporated in the pastel-colored, round-shaped buildings shaping the outlines of the structure below.

After lunch, explore the impressive basilicas of San Michele in Foro and Basilica of San Fernando. Then spend some time walking around the cobblestoned streets eating gelato. Maybe you see a nice hidden restaurant where you want to come back for dinner later too.

Day nine – Lucca – Florence

Start the day with an abundant breakfast with an aromatic Italian coffee before heading out to soak in more of wonderful Lucca.

Begin with another startling view of the old town by climbing the 14th-century Guinigi Tower. This is one of the few remaining towers in Lucca from the era when affluent Tuscan families competed to build the highest towers to show their wealth.

You should also explore the Museum of Villa Mansi where you can admire Flemish tapestry collections and other pieces of art. Especially beautiful are the Hall of Mirrors and the Music Hall.

Next, head to Piazza Napoleone where you find Palazzo Ducale di Lucca, a political and administrative center over the last 8 centuries where you can appreciate frescoes and statues.

After lunch, you can either spend a few hours wandering the streets of Lucca or head straight to Florence and wander the streets there.

It’s about an hour’s drive from Lucca to Florence and you might want to return to the same hotel you stayed at last time, or you can check out the options I outlined on day one of this itinerary.

Day ten – Florence

This is the last day of your Tuscany road trip itinerary and you’ll spend it in the incredible capital of Tuscany. After breakfast, I recommend that you go straight to the Ponte Vecchio, one of the most unique bridges you’ll ever see.

Crossing the Arno river, Ponte Vecchio was the only bridge in Florence that survived World War II. Back in the day, it used to be a defense bridge. Now, it’s one of the most photographed sites in Florence. The charming pastel houses with little Mediterranean-style windows look like little dollhouses from afar.

Crossing the bridge, you’ll find lines of jewelry and antique shops competing with art vendors to get tourists’ attention. Once across, you’ll step into Florence old town full of gelato bars (because you HAVE to have more gelato before you leave Tuscany!)

The rest of the day, let yourself get lost in the charming streets of Florence Old Town , eat as much pasta and pizza as you can before you leave, and take lots and lots of photos!

If you would prefer to visit one of the beautiful towns near Florence instead on this last day, you can easily take a day trip from Florence .

Reflections on this road trip in Tuscany

This is by far the best Tuscany road trip with only ten days in my opinion. You get to see the highlights of both larger and smaller towns as well as a couple of days to discover Florence.

If you don’t have a whole week, you can still explore quite a bit of Tuscany on a long weekend break in Italy .

There is no end to the beauty of Tuscany and I really hope you enjoy this road trip through Tuscany as much as I did!

Still haven’t booked your rental car? Make sure you do it straight away so you don’t risk they’re all sold out! Book here .

Heading to Rome next? Make sure you read my complete 4 day Rome itinerary before you go!

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4 thoughts on “ The perfect Tuscany road trip itinerary ”

Love this! I have done 3 road trips in Tuscany and I cannot wait to go again…it is so fantastic! I love your itinerary, I did something very similar the first time and had an amazing trip.

Thank you! I just can’t get enough of Tuscany:)

wow this looks amazing! giving me the travel blues already!

Hopefully you can go soon:)

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Take a road trip through Tuscany's breathtaking countryside

This scenic route links fairy-tale castles, artistic treasures, picture-perfect vistas, and vineyards galore.

Sure, it’s possible to zip between Siena and Florence , two of central Italy ’s most beloved towns, in about an hour. But why rush the trip? The Tuscan countryside is like the wine produced there—meant to be savored rather than gulped. There are countless places to explore, each with something gorgeous or delicious to discover.

This roundabout route is just a sampling of what’s available. It links up fairy-tale castles, artistic treasures, picture-perfect vistas, outdoor adventures, and vineyards galore. What’s not on the itinerary: mobs of tourists. Be prepared for curvy roads and some unexpected twists.

1. Buonconvento

From Siena, drive about 18 miles south to Buonconvento, a pristinely preserved medieval village that lives up to its name, derived from the Latin for “happy gathering place.” Hikers on the Via Francigena , a pilgrimage route now popular with today’s trekkers, routinely gather here. President Obama was spotted last summer checking out the 14th-century Chiesa dei Santi Pietro e Paolo. (He stayed for nearly a week at the village turned luxe lodging Borgo Finocchieto .) For folk history, visit Museo della Mezzadria Senese , which is housed in a centuries-old barn and tells the story of the area’s sharecroppers.

2. Montalcino

Just 15 minutes away, in a landscape dominated by grapevines and olive groves, find a Montalcino farmhouse built in 1840. The rustic spot is Azienda Agricola le Chiuse , a winery and agriturismo that offers four apartments. Guests can splash in the pool and enjoy tastings led by owner Lorenzo Magnelli, whose great-great-grandfather created Brunello, the local wine celebrated internationally for its notes of licorice, tobacco, cherry, and chocolate.

3. San Giovanni d’Asso

In the Crete Senesi hills, San Giovanni d’Asso has a thing for white truffles. The town’s castle houses the Museo del Tartufo , complete with a giant walk-in replica of a fungus. Up the street is Osteria delle Crete , which sells its own truffle-infused grappa. The restaurant arranges truffle hunts, accompanied by a specially trained dog. All truffled out? Wander around Bosco della Ragnaia , an artist-designed park with tranquil paths and quirky sculptures.

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4. Rapolano Terme

Thermal hot springs bubble up all over Tuscany, and several famously steamy spots, such as Saturnia and Bagno Vignoni , are worth a detour. But the town of Rapolano Terme, where ancient Romans once relaxed, is conveniently on route. Follow the whiff of sulfur to Terme San Giovanni , a reasonably priced, family-friendly spa that’s open year-round for soaks in a series of pools with varying temperatures and enriched by calcium bicarbonate. (You’ll feel the sediment squish between your toes.) A signature treatment? Naturally, the “mud ritual.” Bring a bathing suit, towel, and flip-flops—plus a bathrobe to blend in with the locals. On weekends the spa stays open for dips after dark, which can be combined with Campari cocktails in the adjoining lounge.

5. Castello di Ama

In a quiet corner of the Chianti Classico region sits Castello di Ama , which attracts attention for more than just quality reds. For almost 20 years, the winery’s owners have invited artists, Anish Kapoor and Louise Bourgeois among them, to create installations for the cellar and grounds, now an open-air museum. Some pieces stand out immediately, such as the telescope set up to spy on the countryside, but finding them all requires signing up for a guided tour and tasting. The kitchen at Il Ristoro di Ama uses veggies grown on the property; tuck into pappa al pomodoro (tomato-bread soup) and other Tuscan specialties before retiring to one of five lavish villa suites.

6. Il Borro

One criticism of some Italian towns is that they’ve been taken over by tourists. But that’s the appeal of Il Borro , a 700-hectare estate owned by the Ferragamo family, which includes a painstakingly restored medieval village. The stone streets now all lead to five-star accommodations—with amenities like fireplaces and private gardens—and a handful of artisan stores, many of which teach craft workshops. Parents can send the kids to painting class while they design and create all kinds of jewelry. Other on-site activities include a tour showcasing Il Borro’s wines (five of which are organic), golf, and horseback riding. For a more affordable rate, book a farmhouse apartment outside the village.

7. Anghiari

A breathtaking hilltop hamlet in the Valtiberina Valley, Anghiari was the site of a big-deal 1440 battle. Florence won, Milan lost, and Leonardo da Vinci started to make a painting about it. He never finished, but sketches survive—and are featured in a cool touch screen exhibit at the Museo della Battaglia e di Anghiari . Start a visit at the bottom of town with Busatti , a luxury textile manufacturer established here in 1842. (Free factory tours show off century-old looms still in use.) Then walk up winding streets for ever shifting views.

8. Sansepolcro

Neighboring Sansepolcro delivers a crash course on native son Piero della Francesca, the noted Renaissance painter. The Museo Civico ’s star attraction is the “Resurrection” fresco, featuring a strikingly buff Jesus standing above sleeping soldiers (one of them a self-portrait). A combo ticket also gives access to the artist’s recently opened house museum, near a public garden dedicated to (who else?) della Francesca.

The 13th-century Poppi Castle is the stuff of fantasies, starting with the deep moat that surrounds it. At the bottom is a prison, which originally had no windows. (Inmates were dropped through a trap door.) At the top is a working bell tower, with 360-degree views of the lush Casentino Valley . Find more Instagram-worthy subjects inside the charming walled town lined with sidewalk porticoes.

Dense pine trees crowd the hills of Pelago, site of new gin distillery Peter in Florence . Book a tasting at the gleaming lab for a spirited lesson on the 14 Tuscan-grown botanicals in the gin’s recipe. The key ingredient? Petals from Florentine iris. For an additional fee, tack on a meal with cocktail pairings. The whole operation is run out of Podere Castellare Eco Resort , a rustic-mod hideaway for an overnight before turning the wheel to Florence.

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The Ultimate Tuscany Road Trip: Five Days in Tuscany

I know that choosing an Italian road trip route can be difficult. Who wants to restrict themselves to one region in a country with so much to see? Even so, this road trip through Tuscany takes some beating.

Words by Torie Ross

From landmarks known the world over to hidden medieval towns nestled deep within the hillsides of Tuscany, this awesome road trip will ensure you see the best that the region has to offer.

Of all the fantastic road trips from around the world , there’s nothing more iconic than driving through Italy’s winding hillside region with the top of your convertible down, scarf elegantly blowing in the wind.

It doesn’t matter if your trip embraces the effortless elegance of Grace Kelly or the hilarious hijinks of the Griswolds, a road trip through Tuscany offers something for everyone to enjoy.

Read on to discover how you should spend ​​5 days in Tuscany.

Handy Tips for Planning Your Tuscany Road Trip Itinerary 

Group Tour or Independent Travel? 

In general, Italy is a place where I favour independent travel. And Tuscany is no different (especially if you’re seeing the best of Tuscany in 5 days). 

While you can (and should) book entrance tickets in advance, there’s nothing quite like planning your own itinerary and allowing yourself to wander the streets without a time constraint.

If you do prefer taking group tours, I recommend checking Get Your Guide for individual day tours (like this Florence guided tour ). It gives your day some structure while still allowing you the freedom to plan your own itinerary.

What to Pack for Your Tuscany Itinerary

Luckily, a road trip to Tuscany doesn’t require any specialist equipment/clothing. But here’s some ideas for what you need to bring.

• Whatever you take, you need to make sure it fits in your suitcase. Check your airline’s requirements in advance to avoid extra fees at the airport (I’ve witnessed people snapping wheels off their suitcases to avoid this – don’t be that person).
• Comfortable sneakers for walking around the cities/countryside.
• A small bag for carrying the basics around with you – I like to use bumbags as it’s easier to keep valuables close to the body
• Sun cream/hats/ refillable water bottle – stay sun safe and hydrated, thank me later.
• Light layers, especially if you’re visiting in the shoulder seasons. It can seem super hot in Tuscany, but the evenings cool down a LOT and I promise you’ll be grateful for that extra jacket.

Useful Resources 

Here are some valuable tools that can help make your Seychelles itinerary trip planning a little easier: 

• Skyscanner : This site allows you to search and compare flights around the world.
• Booking.com: I rarely book hotels through any other site. This is a fantastic tool for comparing a wide range of hotels (at different price ranges, too).
• Tripadvisor: It’s no secret that Tripadvisor is the best place to book tours and read genuine reviews on tour experiences and restaurants. 
• Get Your Guide: My top choice for tours. GYG offers a wide selection of planned tours around the world at reasonable prices.
• Viator: Another tool that allows you to compare and book different tours and trips. 

Getting Around 

If you’re travelling through Tuscany, you’ll likely want o rent a car (though public transportation is also pretty good) – I like to use Rentalcars.com as I find they often have the best rates.

Book a Rental Car Here

Tuscany Road Trip Day 1: Take off from Florence

Florence’s conveniently located airport, wide range of amenities and iconic architecture make it the perfect introduction to the region and an ideal place to begin an Italian road trip through Tuscany.

Things to do in Florence

Florence is stuffed with famous landmarks around every corner. It’s no wonder that it often features on many a Tuscan honeymoon itinerary. 

The expansive Piazza del Duomo, which dominates this city both in popularity and in history, is a sight to behold.

The highlight of the piazza, The Santa Maria del Fiore Cathedral, usually just referred to as the Duomo, is one of the most recognizable landmarks in the city and the main draw for visitors to this famous piazza.

The adjacent Giotto’s Bell Tower and St. John’s Baptistry are also remarkable. It’s well worth the time and the patience it takes to explore them all, especially for a first time visitor.

The Ponte Vecchio, another iconic Florence landmark, is perfect for window shopping at the historic jewelry stores that line the bridge or enjoying the buskers that perform to captivated audiences as the sun sets over the River Arno.

Beyond the crowds of flag waving walking tours and selfie sticks, the alleyways and secret corners of Florence offer a breadth of museums, restaurants and bars just waiting to be discovered.

On the slightly macabre side, visitors can gaze upon several of Galileo’s bony fingers and teeth at the Florence History of Science Museum.

After a long day of walking and exploring, prepare yourself for the journey ahead with an expertly tossed pizza at the popular Gusta Pizza or a fine glass of Chianti paired with local cheeses at the intimate cafe Mangiafoco.

It’s almost impossible not to fall in love with the food in Florence – what better reason to try and learn some Florentine cooking skills while you’re there.  It’s no wonder that food tours in Florence are all the rage . 

Getting to Florence 

Getting to Florence is fairly easy – you’ll likely arrive at either Florence’s (small) airport or Pisa Airport. From Florence airport, the easiest way to get into the city is by taking the R04 bus.

From Pisa, you can rent a car and make the hour drive. Alternatively, you can hop on a direct train.

Suggested Stay for Florence on your Tuscany Itinerary 

Despite the name, Hotel Roma is a deliciously sophisticated place to bed down in Florence. Each room is spacious and filled with quirky features that make it so distinctly Italian – think random arches and pillars embedded into the walls.

Alternatively, check all accommodation in Florence Read More: The Best Things to do in Italy

Tuscany Road Trip Day 2: Escape to Lucca

Heading northwest, roadtrippers can make a quick stop in Pisa for a photo op before escaping the crowds and heading into the lovely town of Lucca.

All of Tuscany’s cities and towns are within easy reach of one another, ensuring you won’t be so tired from the drive that you can’t enjoy the destination.

Things to do in Lucca 

Lucca, located about 70 kilometres of Florence, is best known for the Renaissance era walls that surround the town’s historic centre.

The walls are one of the last remaining examples of the type of fortification that used to surround so many of Tuscany’s towns and cities.

Pleasant promenades and tree lined walks now exist where military lookouts used to keep watch. Today, visitors can take a leisurely stroll around the perimeter or see even more of the city by renting bikes to explore the walls and surrounding areas.

Within the city itself, also known as the City of 100 Churches , Lucca’s cobbled streets and spacious piazzas make it one of the easiest places in Tuscany to explore on foot.

For history buffs, the Piazza dell’Anfiteatro maintains the shape of the Roman amphitheatre which would have once stood in the area, while the climb to the top of the nearby Guinigi Tower offers a remarkable view over the narrow streets and historic buildings of Lucca’s centre.

For a bit of modernity, Via Fillungo is Lucca’s main shopping street and offers a range of internationally recognized shops alongside more local brands.

Nature lovers and hiking enthusiasts will love the city’s locale at the foot of the Apuan Alps. The area’s stunning drives and hikes throughout the region allow visitors to enjoy a bit more of Tuscany’s natural settings in any season. Read more about Tuscany in Autumn .

Getting to Lucca

It takes around an hour to travel between Florence and Lucca (although add plenty of time for a Pisa stop!) by car, or you can hop on a train, which takes around an hour – an hour and a half.

Suggested Stay for Lucca on your Tuscany Itinerary 

You’re not exactly spoilt for choice when it comes to accommodation in Lucca, but La Gemma is a charming hotel. Decor is bright, bold, and unashamedly Italian – I love it.

Alternatively, check all accommodation in Lucca

Tuscany Road Trip Day 3: Climb the Towers of San Gimignano

Next up: San Gimignano. This destination is a little bit of a gem within Tuscany, but one I highly recommend you make time for on your Tuscan road trip.

Things to do in San Gimignano 

As you head even further south and drive into San Gimignano, the prominent 14 towers of the city provide just a hint of the medieval offerings the town has to show visitors.

The towers, which were built as a 13th century version of keeping up with the Jones’ by San Gimignano’s most prominent families, provide an interesting challenge to tourists committed to climbing as many of them as possible.

Torre Grossa, San Gimignano’s tallest tower, and Torre della Rognosa, one of the city’s oldest towers, are two of the most popular with those looking for stunning views and a good workout.  

For visitors who prefer to save their leg strength or want to avoid a strong case of vertigo, San Gimignano has far more to show than just the towers which attract busloads of day trippers each day.

Museums including the Torture Museum, the Archaeology Museum and the Civic Museum, which is located inside the Palazzo del Popolo, offer an intimate look into San Gimignano’s rich history.

For gelato lovers, no trip to San Gimignano would be complete without a stop at Gelateria Dondoli , centrally located in Piazza della Cisterna. The gelateria boasts back to back Gelato World Championship wins and is well loved for their extensive menu of unique flavours.

For far reaching views over the whole of the city and the surrounding countryside, head straight to La Rocca, San Gimignano’s 14th century fortress.

Although it may be a bit of a climb, the effort it takes to get up the hill is well worth it once you reach the top.

Getting to San Gimignano 

Driving is the easiest way to get between Lucca and San Gimignano – that is, unless you fancy a multi-stop train ride that takes you the most part of your morning. 

Nope, drive the 90 minute journey – trust me on this.

Suggested Stay for San Gimignano on your Tuscany Itinerary 

Looking like it belongs in a cheesy romance novel, Il Coltro is a Tuscan farmhouse of dreams. The fully-contained apartments are fitted with everything you could possibly need for a cosy stay – not to mention the incredible views.

Alternatively, check all accommodation in San Gimignano

Tuscany Road Trip Day 4: Race to Siena

Located about 70 kilometres south of Florence, Siena is often referred to as Tuscany’s “second city”, but this bustling town should not be overlooked on your Italian road trip.

As Florence’s rival for centuries, much of Siena’s architecture, culture and rich history may have been bred from competition, but today it stands as a gem of its own within the region of Tuscany.

Things to do in Siena

Any trip to gorgeous Siena would be amiss without a visit to the expansive Piazza del Campo .

While the city’s central square is always a buzz of activity, no matter the time of year, in summer the Campo comes alive with the historic spectacle that is Il Palio, Siena’s famous horse race.

Here, the city’s notoriously competitive districts, or contrade , compete for bragging rights and for the elusive Palio , a painted silk banner.

Trial races, parades and a lot of conniving between jockeys and their contrada occurs in the days leading up to the main event.

The rest of the year Siena’s famous striped cathedral, the Cathedral of Santa Maria Assunta , steals the show.

If you want to see the impressive interior of the cathedral, or Duomo, buy an Opa Si Pass from the nearby tourist office. This will allow you access into the Duomo, the Baptistry, the crypt and the Museo dell’Opera which houses many of the cathedral’s rarest artefacts.

While the city of Siena is the buzzing centre of the region, a quick trip in the car will take you through winding hillsides and into tiny medieval towns, just minutes from the heart of the city.

San Gusme, Lucignano d’Asso and Montefollonico are just some of the hidden gems waiting to be discovered.

Getting to Siena

Whether you choose to drive or take public transport (bus 130 from Piazzale Montemaggio), travelling between San Gimignano and Siena takes around an hour and is incredibly easy. 

Suggested Stay for Siena on your Tuscany Itinerary 

A former monastery, now transformed into a plush pad – can you see why I love Hotel Certosa so much? Rooms are elegant yet modern, while the lantern-filled trees make for a romantic evening under the stars.

Alternatively, check all accommodation in Siena

Tuscany Road Trip Day 5: Reminisce Over a Bottle of Wine in Montalcino

After exploring Florence’s bustling city streets, the quiet respite of Lucca, the imposing towers of San Gimignano and the competitive heart of Siena, head to the most southerly, and the final, point on the route, Montalcino .

Set within the stunning Val d’Orcia region, Montalcino is renowned for its natural beauty, medieval architecture, rich artistic history and, of course, its production of the famous Brunello wine.

Things to do in Montalcino

No Italian road trip would be complete without some wine tasting and Montalcino is the place to do it.

Wine bars and shops line Montalcino’s stone streets, interspersed with cafes, antique shops and award-winning restaurants.

In the city centre, the views from the town’s 14th century fortress offer the perfect place to reflect on all the places your journey has taken you, as the scenery stretches back to Siena and across the surrounding hillsides.

While the nearby region of Umbria has become increasingly popular with wine aficionados over the years, Tuscany, and Montalcino in particular, still remains one of Italy’s most loved wine regions.

Montalcino’s surrounding hillsides are dotted with vineyards and olive groves making it a paradise for culinary enthusiasts and the ideal place to relax, rejuvenate and reminisce over the fantastic sights and sounds experienced during your road trip through Tuscany.

Getting to Montalcino

You’ve got two options when it comes to getting to Montalcino: Either you drive the 50 minute highway-based route (this is what I would choose), or you hop on a 90 minute train journey with a change in Buonconvento. Either way, both are pretty simple.

Suggested Stay for Montalcino on your Tuscany Itinerary 

Sipping wine by the pool with epic views? It’s no wonder this hotel is called Si Montalcino . Rooms are daily simple (yet still gorgeous), but it’s the surrounding area that really makes this one of the best Tuscan hotels.

A lternatively, check all accommodation in Montalcino  

Road Trip Tuscany: Final Thoughts

The beauty of the Tuscan road trip is that travellers can spend anywhere from a few days to a few weeks exploring this region and always find something new to discover and enjoy.

From relaxing drives down country roads to hectic jumps from city to city, an Italian road trip through Tuscany truly is what you make it.

Tuscany Road Trip Itinerary – Map 

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I’m Julianna Barnaby - a professional travel writer and geek extraordinaire. I started The Discoveries Of to help you to discover the best of new destinations from around the world.

Discovering new places is a thrill - whether it’s close to home, a new country or continent, I write to help you explore more and explore differently.

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Tuscany Road Trip: Scenic Drives Through Tuscany

One amazing tuscany road trip to discover an unforgettable scenery.

A car is all you need! 🙂 for an unforgettable Tuscany road trip….Tuscany offers a rich territory not just in terms of traditions and culture, but also in terms of its varied geographical composition; hills, plains, mountain ranges, islands and seacoast. The beautiful lush landscape of Tuscany with its extensive green fields, hill towns and cypresses is probably the thing for which the region is best known.

Tuscany is in fact the ideal setting for scenic drives! Driving through Tuscany is a sight in itself, and is the perfect solution to really experience the atmosphere of this unique land.

The best thing is to avoid motorways, and enjoy the Tuscan scenery on winding roads in the countryside and panoramic routes far from the traffic; then driving becomes a truly rewarding experience.

Driving Tours of Tuscany: Tuscany Road Trip Itinerary

There are two main driving routes crossing Tuscany that we highly suggest you go through; both are famous for their sensational scenery and their beautiful sights, the Via Chiantigiana , and the Via Cassia .

Tuscany road trip 1: Via Chiantigiana, the scenic drive through Chianti: Scenic Drives from Florence

The Via Chiantigiana, SR222 (see Map at the end of the page), that connects Florence to Siena through the stupendous countryside of the Chianti region, is one of the most beautiful routes of Italy.

Well known for its vineyards, cellars and extensive views over a pristine landscape, Chianti is the place where to get lost among centuries of history, hidden treasures and excellent food and wines.

Leaving Florence and heading south, you are soon surround by the typical Tuscan countryside and by small villages up the hills, like Strada in Chianti and Chiocchio.

Here are also intriguing medieval castles like the ones of Meleto and Verrazzano , also producing a fine Chianti Classico wine that you can taste, not too much though if you’re the driver 🙂

The castle of Montefioralle was home to the enigmatic Monna Lisa, portrayed by Leonardo da Vinci. This small charming hamlet is actually worth a visit for its atmosphere lost in time.

Continuing south we get to Greve in Chianti , heart of the Chianti Classico wine production, where to find lots of tempting food shops sheltered by lovely arcades, and a whole Museum devoted to wine.

Past Greve you find yourself in the nice hill town of Panzano in Chianti , the perfect place to enjoy some great local food, like the superb Florentine steak by the whimsical butcher Mario Cecchini.

After Panzano you go through woods inhabited by wild boars, hares and squirrels, until you get to the old military outpost of Castellina in Chianti , one of the nicest towns in the area.

Here was built the Consorzio del Chianti Classico, that in 1984, gets the DOCG brand for local wines.

Taking a little detour you might want to visit the villages of Radda and Gaiole where to find excellent restaurants, wineries for tastings, and workshops. Now make your way to the beautiful Castle of Brolio, where the recipe of the Chianti Classico wine was born, and where the ghost of the Baron Bettino Ricasoli is believed to wander at night, according to the legend.

Curvy roads then follow one after the other, until you get to the splendid Siena.

The Via Chiantigiana is an extraordinary road riding through times.

Tuscany Road Trip 2: Via Cassia, ancient driving route running across centuries

The Via Cassia, SS2, (see Map below) is a very ancient Roman road connecting Florence and Siena to Rome through the Val d’Orcia.  For most of its route the Via Cassia coincides with the historic Via Francigena, that the pilgrims were used to cross on their spiritual journey from Canterbury to Rome.

This secular route passes through the most spectacular countryside of Tuscany and probably of all of Italy; the type of landscape found in the most common postcards about Tuscany.

The Val d’Orcia is a unique combination of history, art, and scenic beauty, declared a Unesco World Heritage Site.

Start your itinerary driving south of Siena along the SR2 Via Cassia, so entering the Val d’Arbia and the fascinating Crete Senesi territory ; wheat fields, undulating hills, isolated cypress trees and a mostly deserted landscape. We pass through the nice villages of Monteroni d’Arbia and Buonconvento . Buonconvento is a very nice medieval town encircled by walls, worth a visit.

Val d’Orcia Tour: Scenic Drives from Siena

Past Buonconvento, shortly after Torrenieri, the Via Cassia faces the inimitable landscape of the Val d’Orcia near San Quirico d’Orcia. Here begins the most spectacular stretch of this historic road.

East and west the Cassia, lie sensational villages and hamlets atop scenic hills.

San Quirico d’Orcia is one of the oldest villages in the area, and is perfect to take a pleasant walk, especially at the Horti Leonini, a wonderful example of Italian garden.

10 Km east of San Quirico is Pienza , the jewel of the Val d’Orcia, enchanting hill town with incredible 15th century architecture and a fabulous location. The views from the walls surrounding the village will leave you breathless.

Pienza is the perfect place to stop for lunch; wine and cheese specialties are not to be missed, while the many craft shops are all to discover.

15 kilometers west of San Quirico is the magnificent Montalcino , splendid medieval hill town with thick walls and an imposing fortress, famous for its Brunello red wine. Here are many wine bars and wine shops. The walkable walls of the castle will give you a breathtaking panorama on the countless vineyards surrounding Montalcino.

Returning on the Via Cassia, south of San Quirico, you find the lovely small town of Bagno Vignoni , with its magnificent square of water and its thermal baths. From the thermal waters of Bagno Vignoni we continue the road trip to the foot of the ancient volcano Monte Amiata up to Bagni di San Filippo, another thermal village where the water flows out from the earth at about 50 degrees.

During the ride is impossible not to notice a perfectly preserved fortress that dominates the entire Val d’Orcia, just 20 kilometers from Montalcino; the village of Rocca d’Orcia is a sight not to be missed. The Rocca a Tentennano dominates the entire valley with an unforgettable and never ending panorama.

We can then leave the Cassia for a while to get to the spectacular Fortress of Radicofani from which to enjoy another stunning vista all over the valley and all its beauty.

The drive then continue towards Rome…with many more sights to enjoy along the way. For additional scenic drives through Tuscany, check here .

Map of the Via Chiantigiana route through Chianti

Map of the via cassia, scenic route from siena to rome.

elena nacci

• Accommodation in and near Siena
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Top 10 sights to visit in val d’orcia: the paradise of tuscany, 103 comments.

Hi Elena, We were planning this vacation in Umbria and Tuscany. (July 4 drive from Rome to Orvieto (halt 2 hours) – via Todi (halt 1 hr) – Deruta (halt 1 hr) – Passignano sul trasimeno (arrive around 1845 hrs). July 5 – drive Passignano – Gubbio ( halt 1.5 hrs) – Assissi (halt 2 hrs) – Spoleto ( halt 1 hr) – Spello (halt 1 hr) return to Passignano around 2030 hrs. July 6 – Passignano – Cortona (halt 2 hrs) – Perugia (halt 4 hrs) return to passignano by 1830 hrs. July 7 – drive from Passignano – Montepulciano (halt 2 hrs) – Montalcino (halt 2 hrs) – Sienna (stay overnight) reaching by 1715 hrs. July 8 – sight seeing in Siena. July 9 – Sienna – your via Chiantigani route to Florence in reverse. Night Florence. July 10 – Florence. July 11 – Florence – Pisa – Lucca – Florence (by train). July 12 – Florence. July 13 – Florence to Venice by train. Does this sound doable and nice according to you. Thanks in advance. Hope to get a reply soon.

Hi Nitin, Thanks for your message. Your itinerary through Umbria and Tuscany is fantastic! My compliments 🙂 It’s doable and covers some of the best sights of both regions. Maybe the first day is a bit full of things to see, but doable anyway. This blog post about a road trip from Rome to Tuscany can be of further inspiration. On July 7 before heading toward Montalcino you might stop for a brief walk in Pienza’s beautiful historic center . On July 9 departing from Siena, you may consider a brief detour to reach the famous San Gimignano , ancient villages by medieval towers, and then head east to ride on the Chiantigiana road in Castellina in Chianti. If you consider San Gimignano is too far (45 minutes) you can stop in the wonderful Monteriggioni walled town. For any further advice just get back! Enjoy your summer trip to Italy!

Hi, how much time do I need if I wanted to follow your itinerary to Tuscany? Thanks

Hi Monika! Thanks for your message. Glad you like my itinerary. If you have in mind both routes, both the Chiantigiana and the Via Cassia up to Radicofani, then you might need from 4 days to one week according to how many places you stop along the way. The most logical way would be to stay 1 night in Florence, then head south through Chianti where to pass about 2 nights, then continue on to Siena where to stay one night or 2, and finally drive south of Siena on the Cassia and stay in Val d’Orcia for about 2 days. Much depends on what are your must see places in Tuscany and the time you have.

Let me know if I can be of further help, Ciao from Florence. elena

Hello Elena, Needed your advice. Travelling with oldish parents and two young kids (3yrs) and not sure where to base in Tuscany for 2 nights( 15th & 16th June). I’ve been to San G earlier and enjoyed it but did not get to see the rolling hills that so many have been talking about to the south Tuscany.

Considering we are a mixed group want to make sure its comfortable driving and looking around the place as well. Further if I did think of Pienze to the south will June still have the green soft hill views etc ? I would not want something too steep of a climb. Any advise will be very much appreciated Many Thanks

Ciao Patrik, The Val d’Orcia hills are very gentle and the landscape is spectacular; you might note however, that there can be curvy roads mainly when you can to go uphill to reach the fantastic hill towns of the area. But nothing to worry about! Driving in this unique territory is a pleasure! The area near Pienza and particularly Bagno Vignoni can both make a perfect base! and June still has the green soft hill views 🙂

Find some info on the best sights to visit in Val d’Orcia here .

I remain at your disposal for any further help, Enjoy your trip, elena

Buon giorno Elena, I will be traveling to Rome July 10th through the 18th. My first time to Rome. I would like to spend a few days in Tuscany and probably make a stop in Montalcino and sleep for a night. Can you recommend an inexpensive place to stay or somewhere nearby maybe even two nights.

Grazia e rividerci,

Ciao Ricardo, Montalcino and the surrounding area is enchanting! In its hitorical center, I recommend the B&B Palazzina Cesira and Affittacamere la Torre .

Take a look and let me know if you wish any additional suggestion, Enjoy your trip!

My husband and I have left 2 full days to explore Tuscany in our itinerary. We will be leaving from Florence the morning of the first day and will need to be in Rome at the end of the last day. Our goal is to enjoy beautiful countryside, some vineyards and small towns along the way. We are unsure about our timeline and where we should aim to “just drive on through” vs slow down and enjoy the sights. I realize ideally we would do this drive in up to 4-6 days to enjoy the entire route. Do you have any recommendations for us as we plan?

2 Days is not quite a lot of time, but you could still drive on the same routes I suggest on the post and have fun!

Day 1: Leave Florence early in the morning and take the Via Chiantigiana admiring the landscape, you might stop in 2 villages in Chianti like Greve and Castellina in Chianti and taste wine at some winery; then proceed towards the beautiful Siena for lunch time. Siena is a must see, spend some time there. Leave Siena and just drive on through the Crete Senesi before reaching the amazing Val d’Orcia, where I would actually spend the evening and the following morning to enjoy the sights. I would spend the night in the unique thermal village of Bagno Vignoni , that is on your way to Rome, there are great restaurants all around the famous ancient Renaissance pool.

Day 2: Start to explore the area, the Val d’Orcia , leaving Bagno Vignoni: Montalcino , Pienza , and Montepulciano . In order to spare time, once in Montepulciano you might consider running on the fast A1 Motorway to Rome, maybe with a stop to visit the stunning Orvieto. Taking the fast motorway will allow you to spend more time visiting the sights of the Val d’Orcia.

Feel free to contact me again for any further help, elena

Hi Elena, My husband and I will be arriving in Florence on June 3 and driving to a B&B outside of Empoli to spend 4 nights. We hope to spend the days exploring the towns around that area. We then will travel to Siena for 3 nights and do the same around that area. We are thinking about visiting 1 maybe 2 towns a day, having lunch there and then returning to our B&B. We will then drive back to Florence drop off the car and stay 3 nights in Florence before flying home on the 13th June. Can you suggest the best towns and villages to explore and some very good restaurants? Thank You, Marian

Hello Marian, I’m happy to give some tips for your upcoming Tuscan holiday 🙂 Among the day trips to make from Empoli, I recommend: – Vinci , lovely small village atop a hill where is the very interesting Museum of Leonardo da Vinci. – Pisa, where is the spectacular Square of the Miracles and the Leaning Tower – Lucca, beautiful town encircled by thick medieval walls and offering a pleasing walkway right on its walls. Lucca is also the perfect place to enjoy excellent local food, try the restaurant Gli Orti di via Elisa . – Certaldo and San Gimignano , this last one not to be missed

You might visit Chianti , one of the most scenic areas of Tuscany, when leaving Empoli to head towards Siena or even better the day you’re driving back to Florence. In Chianti some of my favorite places to eat fantastic food are the Osteria di Passignano and Badia a Coltibuono .

And here is my list of the best restaurants in Florence.

Siena is a fantastic medieval art town, among its best restaurants are Ristorante La Taverna di San Giuseppe and Ristorante Bagoga .

Siena is a great starting point to explore Tuscany, from there do not miss Monteriggioni, the Crete Senesi and particularly the wonderful villages of the Val d’Orcia area , so scenic a place! Pienza, Montalcino, and Montepulciano are full of great places to eat. I love Otsteria Baccus in Pienza, famous for its delicious pecorino cheese.

Find a full list of all the day trips to enjoy from Siena . I remain at your disposal, Enjoy your Tuscan stay! elena

My girlfriend and I will be travelling to Italy in September and would like to drive from Florence to Rome to enjoy Tuscany. Our trip lasts only 13 days so we are trying to make a plan that allow us to see and experience the cities and enjoy the Tuscany and at least spend a few days in the Amalfi coast. Our idea is to explore the Italian fields, food, architecture and wine, of course.

1Sun: Venice p.m. 2 Monday: Venice 3 Tuesday: Venice / Florence pm 4 Wednesday: Florence 5 Thursday: Pisa/Lucca Daytrip – Florence p.m. 6 Friday: Day 1 Road Trip to Rome (Stops????) 7 Saturday: Day 2 Road Trip (Stops????) 8 Sunday: Day 3 Road Trip (Stops) / Rome p.m. 9 Monday: Rome 10 Tuesday: Rome 11 Wednesday: Capri 12 Thursday: Capri/Amalfi 13 Friday: Amalfi / Naples p.m. 14 Naples flight out 7:00 a.m.

Do you think is possible to make a memorable 3 day Tuscany road trip? What are your recommendations? Due to our tight itinerary in the Amalfi, we would consider cutting the road trip to 2 days if you think it is necessary to enjoy the Amalfi. Thank you for your suggestions.

Hi George, Thanks a lot for getting in touch and sorry for the delay! The drive from Florence to Rome is full of many incredible sights to visit! I see your tour is starting in Venice, a must see! My suggested tour of Italy actually include the sights you mention from Venice to the splendid Amalfi Coast.

Now let’s study your plan: 2 nights in Venice are ok, I imagine you are taking a fast train that will then take you to the city center of Florence, from where you will visit both Lucca and Pisa on a day trip by train. When you’re ready to leave Florence with a rented car, the stops I suggest on your way to Rome are: Chianti, San Gimignano, Siena, the Val d’Orcia, Orvieto, Civita di Bagnoregio and finally Rome. I would spend 1 night either in Chianti or in Siena after you’ve visited both Chianti and San Gimignano, and the other night in the heart of the beautiful Val d’Orcia. Take a look at this road trip from Rome to Florence , just follow it conversely. The time to spend in Rome is ok, then I suppose you will first reach the Amalfi Coast, and then also visit Capri. I’m in love with this area of Italy! I think it’s possible to make a memorable 3 day Tuscany road trip, 2 days would be not enough. Follow my road itineraries:-) Of course Tuscany and Amalfi Coast are very different from each other, so much depends on your personal preferences as to pass one day more here or there, Have a great Italian trip! elena

Hello Elena,

I have read your recommendations. I wanted to know how long the first route would take? I have two days in the area. Any recommendations? Thanks in advance!:)

Hi Karen, Here I am 🙂 The first route, with no stops along the way, takes about 2 hours’ time. As you will have 2 days in the area, I suggest you take our time, and stop all the times you like to visit a hill town or a winery. A good idea would be to spend one night in the heart of Chianti, and then visit also Siena or other sights in the area on the following day, Have a great time 🙂 elena

Hi Elena. We need to drive from Siienna to Soreento in one day! Will we be able to go via the Via Cassia route you have described? Thanks for the help Ivann

The fast A1 Highway from Siena to Rome takes around 2 hours and half while the Via Cassia around 4 hours and half. Honestly I wouldn’t recommend you take the Cassia. You need to add other 3 hours or more to reach Sorrento from Rome. Driving on the A1 you can still enjoy some stops that are on your way, like the beautiful Montepulciano and Orvieto.

Enjoy your holiday! elena

I love your blog and it seems that you are very knowledgeable. My husband and I have 7 nights to stay in Italy. Being that we do not drink at all do you think that Tuscany is a good choice or should we do the Almalfi coast? I know that they are two different trips entirely but we are doers and need to keep ourselves busy. Looking forward to your expert answer.

Bonjorno Laura

Dear Laura, I’m very happy you love my blog 🙂

You’re right when you say that Tuscany and the Amalfi Coast are very different! Both are beautiful however, so you may well decide to pass some days in each location. I love the Amalfi Coast; its beautiful scenery and lemon trees right facing the sea, the breathtaking views, the delicious food and all the local specialities. The same can be said of Tuscany, that is not just wine! Every region of Italy has its own famous wine labels; there are many also in the Amalfi Coast.

Tuscany offers a lot in terms of hill towns, fascinating villages, unique treasures of art, varied scenic landscape, even seacoast, and of course great food. Here is a list of the top attractions in Tuscany for instance, while here is a list for things to do in Tuscany, so be sure you’ll never get bored:-)

Please contact me again for any other question, Enjoy planning your holiday, elena

Hi Marion We are planning a holiday to Italy in May we want to spend 5 days touring the tuscanny hill side villages and wineries. We are think about making are base at San donanto. Will be having a couple of days in Florence and also Sienna so will do day tous from there but would like help planning day trips on back roads around Tuscanny We are in our early 70. Need your help.

Hi Jenny! Thanks for contacting me! I think you mean the nice hill village of San Donato in Poggio, in the Chianti wine area . Enjoying a central location in Tuscany it’s ideal for making day tours. Chianti itself is full of back roads, simply follow secondary roads to hill towns, wineries, and castles. An example is the visit to the beautiful Badia a Passignano . Both moving west towards San Gimignano and Volterra or south down to Siena and the Val d’Orcia all roads are curvy and very scenic.

In the blog there’s a post with a list of the best day trips I recommend having Chianti your home base. Take a look and for any other suggestions, just get back to me,

Have a nice day, elena

Hi Elena – We have travelled to the typical hilltowns of Lucca , Sienna , San Gimigano etc. We will be renting an apt. in Montelpulciano for 5 nights and would like to visit some unusual hilltowns as photography is our favorite thing to focus on, not restaurants etc. Can you give a more detailed idea of a drive through Val Dorcia, Pienza etc, using scenic roads ( I know they all are) and also what can we see if we drive to La Foce (can we visit gardens etc.) Thanks so much for all the info on this site. Mary A

HI Mary, thanks for coming here 🙂

I love Montepulciano and I think it is an ideal home base to go exploring great Tuscan sights. Among the unusual hilltowns to visit from there, I recommend the sugestive village of Bagno Vignoni , Monticchiello , Rocca d’Orcia, and further south the amazing villages of Pitigliano , Sorano and Sovana. Also find my suggestions for the day trips to make from Montepulciano to be found at the end of the article.

All drives in Val d’Orcia are actually scenic, as the road from Pienza to reach the near Monticchiello or the one from Montalcino to reach the Abey of Sant’Antimo. The road leading to La Foce gardens, that can be visited, is particularly scenic and lined by cypress trees, take a look at the pics here .

Let me know if I can be of further help, Enjoy your trip! elena

Glad to have stumbled upon your blog as we have really enjoyed your insights to get the most of the region. My wife and I are making castellina our home base to explore the countryside for 3 nights before heading up to Florence for 2 nights. Are there a couple good day loops you could recommend? We want what most people look for when visiting… Small hilltop towns, great scenery and excellent food/wine! Thanks in advance for any tips. Going next week for what it’s worth.

Cheers! Jon

Hi Jon, Hope it’s not too late to answer you!

Castellina is one of the most charming hill towns in Chianti 🙂 Among some of the best day trips in the area I’d recommend a visit to the tiny and characteristic hill village of Montefioralle , where a fine Chianti wine is produced, a visit with lunch at the scenic Badia di Passignano osteria and ancient winery, the Castle of Brolio , and possibly some other hill town like Gaiole or Radda in Chianti. Here I speak about Chianti, take a look,

Enjoy your stay in Tuscany! elena

Great suggestions and we will certainly work these towns into our daily plans. We leave for Tuscany tomorrow so your response was timely! Thanks again, Jon

Jon I’m very happy my message came in time 🙂

Have a great stay! elena

Hi Elena, We are planning to travel in October to Italy, spending 3 days in Rome and 4 days in Tuscany. Would you recommend for us to rent the car in rome and move up towards Florence and then return by train to Rome, or go by train to Florence and rent there and move south to go back to Rome.. Any way, we need to go back to Rome.

Hi Martha, It’s really quite the same. I would probably rent the car in Rome and then move up north towards Florence. Where are you staying in Tuscany? This road trip from Rome to Tuscany can be helpful and give you some ideas.

Let me know if you need any more tips, elena

Hi Elena, We will be traveling from Rome to The Mall in Leccio via A1 for time saving purposes. Do you recommend any restaurants or traditional Tuscan places where we may stop to have a quick lunch on this route? We will be staying in San Gimignano a few days and will be taking day trips from here. Upon our return to Rome we will be taking the scenic road Via Cassia back. Thank you so much for your blog, it has been very helpful for planning our vacation.

Dear Sunen, Glad to hear my blog was helpful in planning your vacation 🙂

On your way from Rome to the Mall in Leccio I would stop in Montepulciano for your lunch. This hill top town is incredibly beautiful and has lots of great places to eat, also for a quick lunch. You can in fact opt for a wine bar serving excellent local dishes and excellent wine like Osteria del Borgo di Montepulciano or a good osteria like Osteria del Conte . I imagine you’ve already seen my suggested day trips from San Gimignano 🙂 and the ones on the scenic road Via Cassia back to Rome.

Let me know if I can be of further help.

Have a great time in Italy, elena

Ciao Elena,

Your blog has wonderful information, and I enjoy it very much.

I will be in Tuscany next month and will be driving from Siena to Florence and need to arrive by 15:00. I am interested in your scenic drive through Chianti, Via Chiantigiana, and I was hoping to see many of the highlights you recommend. Since I need to be in Florence by 15:00, what time do you recommend I leave Siena? Also, what places do you recommend I absolutely must see or I may skip since my time is limited? I am an avid photographer, but I am not a big wine drinker. I enjoy visiting small villages and the peacefulness of the countryside. Consequently, I could skip drinking wine in villages while driving through the Chianti, unless the location is very picturesque 😉

Grazie, -JJ

Ciao JJ, Happy to give some advice 🙂 You could leave quite early in the morning like at 8 am, so you will have time to drive on the Via Chiantigiana and also take your time.

Your first stop maybe in Monteriggioni , northwest of Siena; though not on the Chiantigiana road, this beautiful walled hamlet is unique for its intact medieval architecture, it’s very picturesque and offers fantastic views from its ancient bastions. Then retuning on the Chiantigiana road Radda and Gaiole in Chianti may be worth visiting, as is the lovely Castellina in Chianti. You might skip Panzano and Greve in Chianti and proceed to visit the small but picturesque village of Montefioralle before continuing on to reach Florence. On your way, if you see you’re running out of time, you may skip another village between Radda and Gaiole.

Feel free to contact me again, elena

Ciao Elena, grazie for the wonderful suggestions. I will follow your itinerary and try to see as many places as possible but make sure I arrive on time in Florence.

I will rent a car in Pisa and drive through Tuscany. I plan to purchase a map, Touring Club Italiano Toscana, when I rent my car in Pisa. Is it easy to purchase these maps or recommend a better Tuscany map in Pisa? Where may I buy one of these?

If you like, I can share some pictures with you of my trip through Tuscany. The pictures you post on your blog are very beautiful and inspiring 🙂

Ciao JJ, Here I am 🙂

A map of the Touring Club will work great, you can easily find maps everywhere, especially at kiosks. You can buy it right in Pisa.

I would be really happy if you share some of your pictures 🙂 you’re also welcome to tell about your trip and see your story published in this section of the blog!

I’m here for any other info needed, Have a nice day! elena

Ciao Elena, thanks for sharing your tips and I had a great time in Tuscany. That was probably the highlight of my entire trip 🙂

If you would like me to share a few pictures, then where would you like me to post them or do you prefer I email them directly to you? The picture file sizes are a bit big, which are about 30MB each. However, I could shrink the file size, if that’s too big for you. Email me directly with instructions, if that’s easier.

Let me know if you would like me to share a few pictures and thanks again for everything. Keep up the great work!

Ciao JJ, I’m so happy to hear from you and that you had a great time in Tuscany 🙂

I’d be more than happy to receive your pictures by email at [email protected] ; you can send them through wetransfer.com.

If you like the idea you’rr also welcome to tell something about your Italian holiday and see it published here on the blog together with some of your pics. a presto, elena

We’re in Sienna for two nights and then have two free nights. Best to go to SG or Bagno Vignoni, or both? Or Montepulciano? Thanks! Love your blog: it’s inspiring and helpful

Hi John, so happy you love my blog 🙂 As you have 2 more free nights, I would visit both. The day you’re leaving Siena you can go visit San Gimignano and stay there the morning and maybe have lunch there, and then head south to reach Bagno Vignoni as well as Montepulciano. The villages of the Val d’Orcia area small so you can see more of them. Also Pienza is stunning! Feel free to contact me again, Enjoy your stay! elena

Ciao Elena, First of all congratulations for such a nice blog, full of interesting tips! I’m planning to spend one week in Tuscany with my husband. We will travel to Pisa early in the morning in September 5th and return back to Madrid on Sept. 12th. We are planning to rent a car either in Pisa or in Florence and travel around. Our idea is to explore the Italian medieval cities, the countryside…, and we love food, architecture and wine, of course! Do you have any recommendations for a memorable one week trip? Do you think that we have enough time to visit Tuscany and also make it to Cinque Terre? What are your tips? Thank you for your suggestions. Have a nice day! Sandra

Ciao Sandra, I’m happy you like my blog 🙂

I think you will also have time to visit the Cinque Terre. as you’re arriving to Pisa, you can soon reach the near Cinque Terre and spend there the first night. The following day, maybe in the afternoon, I would start the itinerary to discover the beautiful Tuscany.

How to plan one week on Tuscany? In this blog post I give tips on how to make the best of Tuscany in 7 days; the must see visits should particularly include Florence, Chianti, San Gimignano, Siena, and the stunning Val d’Orcia, so full of beautiful medieval cities and a unique countryside. Where to stay? you might choose 1 or 2 different locations to base yourself. The first in Chianti or San Gimignano, and the second in Val d’Orcia.

Let me know if you need any more suggestion, I’l be happy to help 🙂 elena

You have a great blog, congratulations!!! I love it.

I was wondering if you could help me out organising a 2 nights 3 day trip from/to Rome around Tuscany. I’m planing going on July 15th to 17th. I’m considering to do your first route from Rome to Siena and stay the first night there. What I’m not sure about is which route take from Siena to Rome considering that I still have 2 days and 1 night ahead. I’m sure that with your wise advices I could have an even greater time around Tuscany. I will really appreciate any suggestion.

Hi Pao, Very happy you like my blog 🙂 thank you!

So you start by driving on the Via Cassia from Rome to Siena that passes through the stunning Val d’Orcia and the Crete Senesi. The following day I would pass some of your time visiting the beauty of Siena, and then go visit the beautiful villages of San Gimignano and Monteriggioni. Never been to Florence? In alternative you may soon head to Florence from Siena, and pass a the night there. Then from Florence stat your way back to Rome passing from the amazing sights of Cortona, the Trasimeno Lake, Orvieto and Civita.

I’m sure my post dedicated to a road trip from Rome to Tuscany and back will be of great help 🙂

Have a great holiday, elena

Thank you soon much for your kind reply, I really appreciate it!! 😀

Yes, I’ve been in Florence many times and that’s exactly why I would like to stay just around Tuscany, not really Florence.

I think the best would be to opt for the tour you suggested until Monteriggioni, and may be sleep over there? Is there any other adventurous and exciting route from there to Rome?

Here I am Pao 🙂 You might certainly sleep near Monteriggioni or Siena, and then from there decide to continue to Rome passing thorough the Crete Senesi, the Val d’Orcia and then south with a deviation toward west to visit the amazing villages of Pitigliano , Sorano, and Sovana.

Have a nice weekend, elena

Hi Elena, My husband and I will be arriving in Pisa on Monday August 24th. We are staying at Piombino until 16th September. Could you please suggest places that we should visit, a cooking class plus any other tours or attractions. We intend hiring a car but haven’t organised that yet. Love reading your holiday blog and looking forward to spending time in Tuscany. Cheers Nancy

Dear Nancy, Thanks for your message 🙂 Renting a car is the best thing you can do for visiting and exploring Tuscany. As you are in Piombino, I suggest you don’t miss visiting the beautiful Elba Island and the fascinating seacoast running south passing from Castiglione della Pescaia to reach the splendid Monte Argentario .If you move inland, I suggest you visit Massa Marittima , the suggestive villages of the Val d’Orcia Park, Siena, Florence, San Gimignano and all of Tuscany main attractions . Some destinations like Florence are farther than others but worth to visit.

As for the cooking class, where would you like to have it? Have a great holiday, elena

Hello Elena

My wife and I are in the initial stages of planning a trip to Tuscany/Emilia-Romagna in October 2016 and need some advice. We hope to miss most of the crowds with that timing, but my first question is can we get good pictures then? I understand we may not see the lush, green hills of summer but still hope to see good color and interesting landscapes. We’re planning on three weeks, which is adjustable by a few days pending your advice. We will take daily driving tours and would like advice on the number of days we should spend in each area and where to stay as a single base of operations in each area. We expect to fly into Rome and rent a car and then spend several days and nights in: Cinque Terre; Parma/Modena/Bologna; Florence/Chianti; and Siena/San Gimignano, visiting as many towns as we can. We started with four days at each but that was arbitrary, and we don’t want to stay too long in one if there is more to see in another. Can you offer specific recommendations?

We have two additional concerns. Your Val d’Orcia tour got us thinking. Are we making a mistake by not spending fewer days in Tuscany and more in Umbria? The second concern is what are the “don’t miss” locations in each of the areas? One of our fears is driving past a spectacular location due to ignorance. Admittedly, the above is very general, but thanks for any thoughts you can give us.

Hi John, Happy to receive your message! In October you can still be able to see interesting landscapes, but with autumnal colors, so a different landscape from the one you see on postcards. 3 weeks is really enough time to see the destinations you mention. Have you planned spending at least 2 days in Rome? I think 4 days at each destination are ok; 3 or 4 to see Parma/Modena/Bologna, 4 to see Florence/Chianti, and 4 or more to see Siena/San Gimignano/ Val d’Orcia . This 2 weeks itinerary of Tuscany can be helpful you focus on the most fascinating sights to see across Tuscany. Also visiting Umbria in addition to Tuscany/Emilia-Romagna? Umbria is actually beautiful and boasts really so many amazing hill towns, Orvieto, Assisi, Perugia, Spello, Gubbio. You may spend some days in the beautiful Cortona, on the border betwen Tuscany and Umbria and explore the attractions of both regions, take a look here for that. Read though the links and get back to me at anytime for any other question, Have a nice weekend, elena

Thanks very much for your recommendations. We can start building an itinerary now adding the villages you mentioned. I’m looking forward to getting some “nontraditional” pictures so October may be perfect.

Hi Elena, Great suggestions and write up! Wife and I are visiting Rome for a short trip of four days in first week of September. One day we are renting a motorcycle from Rome to ride a scenic route.

Do you think Rome to Siena to Rome can be done in one full day with stops to see historic and scenic places?

Thanks, Kumar

Hi Kumar, Rome to Siena and back to Rome can be done in one full day, but I would suggest passing an overnight in Tuscany so to have more time visiting the sights and get not too tired at the end of the day.

I also suggest you take a look at this road trip from Rome to Tuscany . I remain at your disposal, elena

Thanks Elena. This is really helpful…

Ciao Elena My wife and I are driving from Pisa to Follonica. We see there is a motorway S1 and also the main road SR439. Do you have any thoughts, suggestions for a nice relaxing drive. We will be staying at Castiglione Della Pescaia for one week in an agriturismo in September. Or would be good to get the train from Pisa to Follonica and then hire a car in Follonica itself..

Will & Claudia

Dear Will & Claudia, thanks a lot for getting in touch, If you take the fast motorway you can reach Follonica from Pisa in about 1 hour and 20 minutes. If you like driving and would like to try a scenic route you may take the SR439 passing through Volterra and then Massa Marittima , both real gems of Tuscany.

In any case I would reach Follonica by car,

I remain at your disposal, elena

We want to take a motorcycle through tuscany. We are going in the beginning of november and i know the roads are curvy think it would be OK? Have three days there i though the first day stay in florence cause it might be a half day. Then rent motorcycle for two days. I want to get the most of two days Wine food and scenery are very important. Any suggestions?

Hi Michelle, thanks for contacting me. In Tuscany roads are curvy, but that’s actually the pleasure of driving a motorcycle:-) However, the beginning of november can be cold and rainy, so I honestly would rent drive a car.

I would do Florence the first day, then direct towards Chianti and San Gimignano on the second day, and on your 3rd day I would go to visit Siena and possibly some small village south of Siena, like Pienza or Montepulciano in Val d’Orcia . Be sure to find wine, food, and scenery, especially in Chianti and in Val d’Orcia.

We will be arriving on the 16th of September into Rome and driving up to an Agriturismo outside of San Gimignano. We will be there for 5 days before heading back to Rome. We would like to drive to Cortona and back through Montalcino stopping in Montepulciano, Pienza, and see the Abbey di S. Antimo. Should we break this up or can this be done in a day? What other sites should we see while on that excursion as well as others from San Gimignano for day trips? We have been to Florence and Siena wouldn’t mind a stop in Siena again. Any Suggestions, reccommendations or itineraries would be welcomed.

Thank you, Randy

Hi Randy, Thanks a lot for contacting me. The area of San Gimignano is very scenic and very strategic to visit Tuscany. First of all, take a look at my suggested day trips to make from San Gimignano. As for an itinerary, I would suggest you start your day early visiting Monteriggioni , passing from Siena, and then reaching Montalcino and the Abbey of Sant’Antimo . At this stage you’ve reached the scenic Val d’Orcia area , where I would pass the overnight so to have time to visit Pienza, Montepulciano and Cortona before heading back to San Gimignano again.

I remain at your disposal for any further suggestion, have a nice day, elena

We are considering flying from the UK next June (2016) to Pisa for 2-3 weeks, we wanted to have a number of days staying and exploring Tuscany and also drive down visiting the Amalfi coast, arriving in Naples to fly home to the UK.

Do you have any suggestions for routes or places to stay and typically how low is required in the different areas.

We visited Venice earlier this year and spent 5 days there, anything less and I would have felt cheated that we hadn’t seen it all.

Kind Regards

Hello Corinne, Thanks a lot for your message.

You’re so right about Venice! What a unique place 🙂

In 2-3 weeks you’ll be able to see a lot of Italy and Tuscany. You may stay in Tuscany for 1 week and explore its main and most beautiful sights. This one week itinerary of Tuscany can be of help. You may stay in one possibly 2 different places in the region, one maybe in San Gimignano or Chianti , and the second maybe in the splendid countryside of the Val d’Orcia Park south of Siena. Moving south towards the Amalfi Coast you can have the opportunity to visit incredible sights, like Pitigliano , Sorano, Sovana, Orvieto, and Civita di Bagnoregio .

Moving further down towards Naples, I suggest you visit the wonderful Reggia di Caserta. The Amalfi Coast is stunning and incredibly full of fantastic places to stay, for suggestions on where to sleep just let know,

For places to stay in Tuscany you may start by having a look at the accommodations I recommend on the blog, and for any further tip, just ask. Have a nice weekend, elena

My husband and I will be visiting Italy in May 2016 for 15 days. We plan to stay 5 days in Rome, 6 days in Tuscany and Florence, 3 days in Venice and 1 day in Milan. I am thinking of following your itinerary on the drive from Rome to Florence. I have allocated 3 days to do this drive so that we could stop by the interesting and beautiful places. Thereafter, we will drive to Florence and stay there for 3 nights. we will be renting a car for 3 days from Rome and return in Florence at the evening of day 3. after visiting Florence for 2 days, we would like to visit Lucca and Pisa by train on our last day in Florence. Could you please advise us whether this is a good arrangement for our Tuscany & Florence trip. Should we drive from Siena to Pisa and Lucca instead of going to Florence then catch a train there. Please advise us a good place to choose as a base for our driving trip in Tuscany. Where will be a good place to rent a car in Rome, should we rent it from the city centre as I am concerned about driving into ZTL zone. This is our first trip to Italy, appreciate your help and suggestions.

Best regards, GH

Hi Lee, thanks for your message. I’m happy you have decided to follow my itinerary on the drive from Rome to Florence, great choice:-) You mean the road map on this article or this road trip from Rome to Florence , that is more detailed and also includes amazing sights like Orvieto and Civita di Bagnoregio. Take a look and let me know. In case, a great place to stay during your driving trip is the scenic natural countryside of the Val d’Orcia with its many beautiful hill towns. Here are some accommodations ideas in the area.

Your plan is really very good! 3 days for the drive, then Florence, and from there Lucca and Pisa by train on a day trip. It’s better to reach Pisa and Lucca by train from Florence, both cities has centrally located train stations.

A good place to rent a car in Rome would be directly at the airport, like Fiumicino, as it is right close the motorway.

Please do not hesitate to ask any other question, Have a nice day, elena

What a fab blog. I love it!

My sister and I are planning a mini road trip through Tuscany. We’re arriving on 3rd October in the evening in Pisa and flying out from Pisa on 7th October in the evening. I’m not sure if we have the time to do everything on our list and was hoping that you could help.

Our route is currently mapped out as follows: – Leaning Tower of Pisa – Volterra – Cortona – Rome – Naples – Positano

We then drive back up to Pisa for our flight back on the 7th. My sister wishes to see Florence if there’s time. But I’m not too sure. Do you think this route is doable in the time that we have? And where do you think we should stop and spend the night along this route (I have yet to book our accommodations)? We’ve always wanted to see Positano, hence the reason that it’s our final destination before looping back towards Pisa. Your insights are very much appreciated. Thanks in advance, Elena.

Hi Sue, I’m so happy you like my blog 🙂 So you have 4 full days or a bit less for your plan. I honestly think your route is too full of things to see. Consider that the jorney from Pisa to Positano takes about 6 hours and half with no stops on the way. This way you’ll spend of your time traveling. You have 2 possibilities; taking a plane from Pisa to Naples to visit Positano and the Amalfi Coast, or skip something for this trip to Italy. You may visit Tuscany and Florence more calmly and reach Rome by car but skipping Positano. Or visit Positano by plane, skip Rome, and spend the rest by visiting the fantastic attractions of Tuscany .

Get back to me for any further suggestion, elena from Florence

Hello Elena, We are visiting Italy for 15 days (14nights) arrining in Milano and departing from Rome. We will rent a car and want to do both routes you mention on the article. We are planning to spend a couple of days in Milan and then head to Florence, visiting 5 terre on our way. Any ideas for the way between Milan and Florence, is it nicer to go from Genova area or Parma? After 5 terre we will head to Pisa and then Florence, is Pisa worth spending a night? Also we have visited on the past Roma so we are not planning to stay att all, just head to Ciampino airport.

Hello Nondas, I’m glad to hear you’re going to follow my suggested road trips through Tuscany, as they cover much of the best Tuscan sights . This further road trip from Rome to Tuscany and back can also be of your interest.

As for the way between Milan and Florence, of course it is nicer to go from Genova area and the Cinque Terre. I would spend half a day in Pisa, mainly visiting the wonderful Piazza dei Miracoli and the Tower. Let me know if you need any more help, elena

Hello again! Can you take a look at my girlfriend’s itinerary?

You think that we should spend more nights in one place and have it as a base for day trips than spending every night in another town? If so which ones would be the more convenient ?

Thanks again, the itinerary is as follows.

Tuscany Itinerary suggestion Day 1. 5/11 Arrival Milan Sightseeing and Overnight

Day 2. 6/11 Milan Bergamo. Pick up car. Bergamo Cinque Terre Manarola. Approx. 4hours Overnight

Day 3. 7/11 Cinque Terre. Overnight

Day 4. 8/11 Manarola Castelnuovo di Carfagnana (95km 2h30min) Castelnuovo di Carfagnana Lucca (48km 1h) Overnight Lucca

Day 5. 9/11 Lucca Pisa (30min). Sightseeing. Pisa San Miniato (48km/1hour) Overnight http://www.san-miniato.com/

Day 6. 10/11 San Miniato – San Gimigiano (40km/1hour), via Voltera 81km/2hours http://www.sangimignano.com/en/ http://www.volterra-toscana.net/eng/welcome.html

Day 7 11/11 San Gimigiano Florence (61km 1h36min) Overnight Florence

Day 8. 12/11 Florence. Sightseeing. Overnight Florence

Day 9 13/11 Florence drive through Chianti region. Greve in Chianti, Radda in Chianti, Gaiole in Chianti, Castellina in Chianti, 76km/2h15min Overnight

Day 10. 14/11 Chianti region – Sienna Overnight Sienna

Day 11. 15/11 Sienna Sightseeing and overnight

Day 12. 16/11 Sienna – San Quirico d’Orcia, Pienze, Montepulciano (69km/ 1h 30min) Overnight Montepulciano http://www.turismo.intoscana.it/allthingstuscany/aroundtuscany/two-days-in-tuscany-a-car-ride-in-val-dorcia/

Day 13. 17/11 Montepulciano Castiglini D Orcia Pitigliano (91km/2h30) Overnight Pitigliano http://www.borghiditoscana.net/pitigliano/

Day 14. 18/11 Pitigliano Bagnoregio (43km/1hour) Overnight Bagnoregio http://www.tuscanychic.com/traveling-in-tuscany/most-beautiful-villages-in-italy

Day 15, 19/11 Bagnoregio Rome (2h30mi)

Hi Nondas, Sorry for the delay! Your itinerary id good and absolutely doable. Being quite full of beautiful sights to see, I would not add any more destinations/stops. Of course you’re sleeping almost every night in a different place, so you may consider spending more nights in San Gimignano and make these day trips including Chianti. I remain at your disposal, Have a nice day, elena

Hi I need your kind suggestions about the trip to Tuscany territory. We will be in Italy betwren dates 22.09.2015 to 28.09.2015. We will be back to Turkey from Rome. We have seen Rome, Florence & Venice before. Now we would like to see different places in Tuscany and our tour would be for historic places, to joşn to the local residents, eat traditional foods and drink wines. Now I urgently need your reccommendarions for; 1) Do you agree if we start this trip from Genova and finish in Rome? 2) Do we have to rent a car or we can manage this trip with public transports? 3) Where we should stop for the accommodation, as a cheapest way? 4) Can we follow your comments which had mentioned on your articles or any alternatives that you can suggest?

Please I urgently need your kind reply

In advance thanks dor your kind assitance

Look forward to hearing from you soon

Kindest Regards

Hi Tolga, Thanks for your message! Hope my answer is not coming too late.

>1) Do you agree if we start this trip from Genova and finish in Rome? Yes, do you intend to visit the Cinque Terre also?

>2) Do we have to rent a car or we can manage this trip with public transports? For Tuscany a car is always recommended, from Genova to Pisa you can take a train and then rent your car once in Pisa and start explore the region.

>3) Where we should stop for the accommodation, as a cheapest way? You can find a lot of good and cheap accommodations also on your way, look for B&Bs. Any idea where in Tuscany? So I can send some suggestions.

>4) Can we follow your comments which had mentioned on your articles or any alternatives that you can suggest? Of course you can follow my comments. For any other specific question, just ask.

Hi Elena, I am traveling to Italy October 10-25. Itinerary includes 4 days in Rome. 3 days in Naples. Taking the train from Naples to Florence. Picking up rental car then driving from Florence to a cottage right outside Siena, where I will be in Siena for 4 days, others in my group are lucky to have another week in Tuscany. We are a little nervous about driving. Should we have any concerns about driving around Tuscany ? Any suggestions on top winery around Siena ? I don’t want to miss anything I “shouldn’t ” miss while in Tuscany so any insight would be helpful I am ending my trip with 3 days in Venice. Thank you !

Hi Barbara, thanks for your message. Your itinerary is good! While in Naples, do not miss a tour of the wonderful Amalfi Coast! You should not have any concerns about driving in Tuscany. Once you’ve left Florence, the drive into the countryside or any other hill town, will be a pleasure. Here are some for driving in Tuscany. As for top wineries around Siena, I can recommend Poggio Grande and Ciacci Piccolomini . Others tips here . Siena is perfect to explore Tuscany and its many sights . This is a list of the best day trips to make from Siena. Let me know if you have other questions, Have a nice stay, elena

Thank you so much for all the info ! What is the weather typically like in mid October ?

Ciao Barbara, The weather in mid October is generally very mild with most sunny days 🙂

Not sure if you will get this message in time. We are in Cortona, and will be driving to Montisi (Siena) on Sunday…. we would like to go on a scenic route vs. highway…. we are making use of a GPS, don’t have an old fashioned map at this point. Just wondering if you could share with us some tips or names of towns or roads that we can enter into the GPS to follow, which would take us to scenic places, photo opps, etc.

Also, while we are in Montisi (near Sinalunga, Buenconvento, etc) we will have about 6 days to drive around (I’ve been there before, but without a car… and now we have a car, so I want to go find the gems!!)

Grazie mille,

Dear Tawna, I’m so sorry for my late reply. Please tell me if you might still need some suggestions, Have a nice day, elena

Hello!! I love your blogg. Congratulations. Incan really see your passion for writting and the love you have for Italy. It is really nice funding that! I felt in love with Italy right after I saw “Under the Tuscan Sun” movie!!!

I am planning a trip to Italy with my husband for our 1 year annyversary next summer. We are a young couple (25-28 years old). We are going to rent a car and make a road trip! And we have 15 days!!

We have only been in Rome/Florence in a Cruise ship basis.

We want to see everything (Rome, Florence, Milan, Venice, Amalfi Coast, Tuscany) but unfortunately there is not enough time!

What do you recommend we do? What would you visit each day and in which cities/towns would you sleep each Day?

Thank you again for your time and enthusiasm! I really appreciate it

Hi Cristina, Many thanks for your nice message! I’m very happy you like my blog 🙂

“Under the Tuscan Sun” is a lovely movie, I saw it again the other day! So you have 15 days to see the best of Italy, let’s see how to plan your time at its best. You can start your trip either from Rome or Venice depending on where you’re arriving. In case you’re arriving in Rome, you can spend there 2 days, then I would move south to reach the enchanting Amalfi Coast. You might rent a car in Rome and reach Amalfi where I would stay 3 days. Then come back towards Rome but continue for Tuscany, maybe following this interesting itinerary that takes you though some fantastic Italian destinations, including Orvieto and Civita di Bagnoregio. Your next base can be south of Siena, amid the dreaming countryside of the Val d’Orcia ; Pienza and Montepulciano are great to stay; you could stay there 3 days. Here are some ideas on how to spend 2 weeks across Tuscany best sights.

Go north and dedicate a full day visiting the marvelous Siena , then make San Gimignano or Chianti your next base for other 2 or 3 days. After reach Florence, where, if you wish, you may spend 1 night or 2. Leave your car in Florence and reach Venice by a fast train; I would spend in Venice the remaining of your holiday.

You can find some more ideas for your Italian tour reading through this article about the best tour of Italy. Do not hesitate to contact me again, elena

Elena, thank you posting this valuable info. Next Saturday my wife and a few friends need to travel from Rome to Lucca. They plan to leave a hotel near FCO around 7:00 a.m and need to be in Lucca at 4 pm. I was trying to find the most scenic route for them to travel, and the Via Cassia seems to be a must as part of that journey. They may have time to stop in just two places along the route. What two stops would you recommend the most along that route?

Dear Jeff, I’m very sorry for my late reply. Which route did you take? How about your holiday?

For any other info do not hesitate to contact me again, Have a nice day, elena

My husband and I are planning a 3 week trip to Italy in May 2017. Looking at Rome, Venice, Tuscany, Siena, San Gimignano, Lucca, and Florence. Would like time to see beautiful countryside, meet locals, eat eat and eat wonderful Italian food. Probably take train for some sections, drive, and hopefully moderate easy walking as we are Seniors. We can rent a car at 76yrs old correct?

Any help would be greatly appreciated. Looking at a trip for a long time and this is our first trip. Places to stay, cooking lessons, any input appreciated greatly.

Thanks very much Suzi

Hi Suzi, Many thanks for contacting me. I’m happy to give some suggestions for your first trips to Italy. You may start by having a look at this itinerary of Italy that I usually suggest. In 3 weeks you will have time to admire the best Italian sights and relax at the same time. Tuscany is actually the right place for relaxation thanks to its unique countryside, vast views, wonderful food and wine… and an endless number of other things. Of course you can rent a car 🙂 Train is useful when moving to reach Venice and Rome to and from Florence. When staying in Florence’s center you’ll not need the car as you can use public transportation to move around. For Tuscany you may start by reading this post about planning the ideal trip. For places to stay in Tuscany I particularly love Villa Bordoni in Chianti that also offers great cooking lessons, and Farmhouse il Rigo near Pienza in Val d’Orcia, also offering cooking lessons. For other accommodations take a look through the blog:-)

Start having a look and get back to me for any further help, Have a nice day, elena

Hi Elena..im in italy with 2 of my friends and instead of taking the conducted tour of pisa and Chianti on one day and the train the next day to Rome, i would like to do a road trip to these places. What would be the cheaper and better plan? Road trip or the conducted tours $135 per person for pisa and Chianti and then train the next day to Rome?Our 2 night stay in florance and two nights in Rome are already booked. Would you know how much it costs to hire a car for 2 days? Thank you so much Shantala

Hi Shantala, Thanks for your message.

You can also do your day trips on your own. Are you staying first in Florence? while in Florence you can take a fast train to Pisa while rent a car to explore Chianti and the Tuscan countryside. If you like driving you may also reach Rome from Florence by car on this scenic itinerary on the road.

On this website you can check the price to hire a car for 2 days, that is approximately 40 US $.

Do not hesitate to contact me again, elena from Florence

Dear Elena, Your website is awesome! Can’t thank u enough for information you share. But I have questions. I plan to visit Tuscany around 19 – 22 Feb, my plan is driving from Rome to maybe Siena. I plan to drive because I want to witnessing my self the famous beauty of Tuscany landscape. My questions are: Which city I should visit? Is it snowy around the city that I might visit? Is the view still beautiful? or it all will look flat and just white?

Grazie 🙂 Citra

I read your recommendation here and here So the my questions now are 1.Is it snowy around the city that I might visit? 2. Are those city still have beautiful view like you mention even on February? My priority is to enjoy the view, taking pictures.. so if the wine area are close, it’s okay for me. 3. This is my first time visit Italy, first time driving in euro zone, is it safe to driving on February?

Thank you again, Elena 🙂 Citra

Hi Citra, Thanks for your messages! The Tuscan landscape is beautiful also in February 🙂 Driving from Rome to Siena is a good idea, also take a look at this other road trip I recommend. Siena is incredibly beautiful, take the time to visit it carefully. If you’re staying in or near Siena you can make a lot of fantastic day trips , including Monteriggioni and San Gimignano, splendid medieval hill towns. Usually February is not snowy, and driving during this time of the year is absolutely safe. For any further question just get back, Have a nice day, elena from Florence

Hi Elena Thank you so much for the info. It has been very useful in planning our trips in Tuscany. My friends and I will be driving from Florence to Siena and intend to do the Via Chiantigiana route as you suggested. One question I have is the vineyards that you would recommend that we could possibly visit for wine tasting and lunch.

We will spend overnight in Siena and will then proceed to Pisa through San Gimignano the next morning. Do you have a suggested route that we could take, the vine yards that we could visit?

Thanks very much in advance.

Cheers, Jimmy

Sorry for answering you only now! In case you still need my help, get back, on the contrary, you’re welcome to tell about your Italian trip!

Elena: LOVE your website, thank you so much! My husband & I plan to fly into Florence and out of Milan. The amount of time we will allow is flexible 1-2 weeks. This is why your advice is needed. We have already visited the city of Florence and do not want to spend additional time there. We would like to position ourselves at one location and do day trips. We are not interested in museums, big cities or churches but would rather enjoy small town villages, scenic country roads, wineries, and medieval towns. We are good with popular destinations as well as ‘off the beaten path’. We are most interested in seeing how the locals live, culinary tradition & products, wine & cheese & some shopping. We have been to San Gimignano and loved it! We would like to go back to San Gimignano and also visit Sorano, Pienza, Montalcino, Chianti, Montepluciano, Val d’Orcia and Valdichiana. Where can we position ourselves for our day trips? How much and what in each day is doable? After visiting the Tuscany region we plan to go to Cinque Terre. Do you have a route suggestion with stops? Any recommendation on time needed for our plan? Also, do you suggest wineries for tasting? Do we need to make reservations for tastings? A wine & cheese pairing and a pizza making class would be of interest to us as well. Thank you so much for your assistance! Our visit will be late October 2017, prior to a cruise from Barcelona to the USA. Nora

Dear Nora, I’m so sorry for my late reply, I’m back after a long pause! How was your trip to Italy? You’re welcome to tell about it 🙂

Dear Lauren, though with a great delay, I thank you a lot for mentioning my blog as useful 🙂

Hello Elena! Thank you for sharing your amazing roadtrips with all of us! I was wondering if you find it possible to do both of them (starting in rome and finishing in Firenze) in just 3 days, visisting all the places you mentioned. Or should I skip some? Thank you 🙂

Ciao Joana! thanks a lot for coming here! I’m happy you like my road tips for Tuscany 🙂 It’s actually doable, though I would skip some stops/villages on your way; this also to make you appreciate these fantastic destinations better. And you may also consider an overnight in between Rome and Florence, in Val d’Orcia or in Siena itself. On your way from Rome to Siena via the Cassia road I wouldn’t miss Bagno Vignoni, Montalcino, and Pienza, while on your way from Siena to Florence don’t miss Castellina, Greve and Gaiole in Chianti, and maybe have some wine tasting at some scenic castela like the Castle of Verrazzano or the Castle of Brolio. Some other tips you may find interesting are in this post about a road map from Rome to Tuscany and back 🙂

For any other suggestion, I’m here 🙂

We are two over 60’s friends coming to Italy for two weeks in late June 2019. I have booked 4 nights in Rome at the beginning and 4 nights in Venice at the end. With those two cities in mind, I think we will need more of a relaxing pace for 6 days in the middle. I have been to Lucca once and loved it. Until I read your blog above I had thought we could stay in Florence and do day trips out to a winery and then spend 3 nights in Cinque Terre. But you inspire us to hire a car and stay in the countryside, old farmhouse with a pool or similar and see Val d’Orcia and Siena. What would you suggest? I look forward to hearing from you Kind regards Robyn

Dear Elana,

We are planning a second time trip to Tuscany this May. This time we will also making a day trip to Montepulciano, Val D’orcia , Montacino area driving from Arezzo area. Could you recommend me the best route involving lunch and/or early dinner?

Thank you very much, Demet

Ciao Bella!

My fiancé and I are planning 3 days and 2 nights at Monticchiello. After our wedding on the 1st of june 2020 to the 3rd of June. Then proceed to Venice afterwards. Can you suggest an itinerary for us? Florence and rome not included.

Grazie Mille!

Ciao! Angela❤️

Ciao Angela 🙂 ❤️ Wedding in Tuscany? Wonderful! Monticchiello is lovely, so, a tour of the best sights of the Val d’Orcia is recommended, mybe also including Montepulciano and Cortona. Then, you may continue with a visit to the Chianti area south of Florence, and a visit to the wonderful and fascinating hill towns of San Gimignano and Volterra would be great! I’m here if you need any more suggestions 🙂

We will be traveling to Tuscany/Florence from with 2 kids ages 6 & 10 Rome April10th-14th and taking the train to Venice We want to rent a car. Trying to decide where to stay in Tuscany and we wanted to spend the last day in Florence. It’s Holy Week and just saw that the Museums are closed on Mondays. Would it be better to take a train and start there on the 10th? We want to visit Orvieto, Civita di Bagnoregio, Pitigliano, Thermes de Saturnia, Montepulciano, Siena, Pienza, San Gimignano. Any recommendation on where to stay and best to travel to these towns.

My wife and I wanted to do a driving trip by ourselves through Tuscany. We would to get a route designed that would allow us to explore all the small country side towns. We would like to eat at smaller home style restaurants in the different towns while exploring the countryside. We would have 2-3 weeks.

Can you advise if you or anyone could provide a route and map with suggestions.

Terry Yates [email protected]

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Tuscan Road Trip: Itinerary, Map & Tips

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A road trip through Tuscany is a spectacular drive through rolling hills, picturesque towns, and some of the most incredible landscapes across all of Italy. Tuscany is known for its charming medieval villages, historic cities, world-renowned viticulture, and culinary traditions. 

A Tuscan road trip offers a wealth of experiences! From exploring charming medieval towns and the beautiful Tuscan countryside to admiring the region’s famous art and architecture, you can also take time to stop and visit local wineries, and sample delicious Tuscan cuisine on this most photogenic of Italian road trips.

We spent months exploring the region and in this Tuscany road trip planner we share insider tips, the best routes between towns and cities, and recommendations for things to do and see along the way, to help you plan your perfect Tuscany itinerary.

Where is Tuscany Italy?

Tuscany, or in Italian Toscana , is a region in west-central Italy. Tuscany lies along the Tyrrhenian Sea to the south and the Ligurian Sea to the north, and comprises the provinces of Massa-Carrara, Lucca, Pistoia, Prato, Firenze, Livorno, Pisa, Arezzo, Siena, and Grosseto.

The landscape of Tuscany is made up of fertile rolling hills, Apennine mountains, and plateaus which border the region to the south, north, and northeast, and lowland interior valleys and coastal plains like the Maremma.

Is this your first time visiting Italy? Get all the information you need in our Italy Travel Guide , including what to pack, the best time of year to go, getting there, and practical tips to help you have the best trip!

Getting to Tuscany

Whether you’re taking a road trip to Tuscany in a car , motorcycle, or campervan, self-driving is absolutely the best way to explore this spectacular region of Italy.

You can stop whenever you want, try new activities, visit places you see along the route and have the freedom to change plans at the last minute.

Fly into Florence International Airport , called Aeroporto di Firenze-Peretola in Italian. With direct flights from America, Europe, and the UK, we recommend booking through Skyscanner for live deals and the best prices.

Are you planning to rent a car in Italy? As one of the largest car hire aggregator companies in the world, we recommend Rentalcars.com because they have massive purchasing power which enables them to secure the best rental car prices, which benefits you when you’re planning a road trip.

For a real adventure, hire a motorhome or campervan in Italy . We recommend Motorhome Republic , an aggregate booking site who pull together all the best deals from a number of rental agencies, to offer you a wide choice of options alongside an excellent English speaking expert motorhome Concierge Team.

Driving in Italy

Lots of people will tell you that renting a car in Italy is madness, that driving through Italy is dangerous and the roads are dreadful.  

Don’t let your fears about driving in this beautiful country put you off taking a road trip in Tuscany. Take your time as you drive Tuscany and be prepared for the differences in driving styles from back home. Follow our driving in Italy tips to stay safe and stress-free!

Make sure you have travel insurance you can trust when visiting Italy . We recommend True Traveller for their 5-star TrustPilot reviews, variety of cover options, best activities cover as standard, great prices, and excellent service.

Best Time to Take a Road Trip in Tuscany

March to may.

Spring is a wonderful time to visit Tuscany, with temperatures warming up across the country. Blooming wildflowers in Tuscany’s fields, vibrant greenery in the mountains, and the outdoor cafés opening up mean spring is a fantastic time to experience Tuscany by car. You’ll find the roads and cities less crowded, and most attractions will be open.

June to August

In summer, Tuscany enjoys beautiful weather, stunning coastlines, and the prospect of swimming and dining al fresco. However, the roads, cities and attractions will be at their busiest and it can get really hot, especially in the lowlands. But, we still think a summer holiday in Italy is hard to beat!

September to November

Autumn is a fantastic time for Tuscan road trips . The grapes and crops are being harvested, food festivals celebrate the bounty and you might enjoy an Indian summer, with the fall colors of the vine aflame.

December to February

The winter months in Tuscany can be very cold and wet. But, the big attraction of a Tuscany trip in winter is that there is no one else around, although some attractions may well be closed. If you travel from late January through February, you’ll get a taste of Italy’s loud and colorful carnivals, the most famous being the Carnival of Viareggio in Versilia, west of Lucca.

Tuscany Road Trip Map & Route

This bucket list one week Tuscany driving itinerary hits all the highlights and key sights, including iconic cypress tree-lined roads, Renaissance culture, historic hill villages and chic Mediterranean ports. We think it has to be one of the best road trips in Europe !

Plan your Tuscany road trip itinerary as a circular route, beginning and ending in Tuscany’s capital, Florence. Not only is Florence a stunning city, rich in culture and history, but it also has a large airport to fly in and out of following your Italian road trip. 

After exploring Florence, we recommend renting a car and heading south to the hilltop towns of Arezzo, Siena, Montepulciano and San Gimignano, known for their culture, food, medieval towers, and charming streets.

No road trip through Tuscany would be complete without a visit to the region’s most famous town, Pisa, home to the iconic Leaning Tower of Pisa, as well as the impressive Pisa Cathedral and the Pisa Baptistry. From Pisa, you may also find time to explore Lucca.

Finish the ultimate Tuscan road trip in Cinque Terre. These stunning Mediterranean towns are found worldwide on people’s bucket lists!

This road trip around Tuscany can fit into one week or one month, depending on the time you have available. Combining towns like Pisa and Lucca into a single day will allow you to see more, in a shorter amount of time. However, to get the true feel of Tuscany, we recommend slow traveling and taking your time at each stop. 

• Get the Travel Guides
• Lonely Planet Florence & Tuscany
• The Rough Guide to Tuscany & Umbria
• DK Eyewitness Florence and Tuscany
• Tuscany Road Trip Itinerary

Florence – Arezzo – Montepulciano – Siena – San Gimignano – Pisa – Lucca – Cinque Terre – Florence

• Distance 675km
• Duration 7-14 days
• Drive Time 11 hours

How to use this map – Use your fingers (or computer mouse) to zoom in and out. Click or touch the icons to get more info about a place, and click the arrow in the box top left to open the index. To add to your own Google Maps account, click the star next to the title of the map.

Tuscan Road Trip Highlights

Florence, known as Firenze in Italian, is the capital of Tuscany and widely considered the birthplace of the Renaissance.

The must-see sights in Florence include the Cathedral of Santa Maria del Fiore; more commonly referred to as the Duomo, topped magnificently by Brunelleschi’s famous dome; the Ponte Vecchio, a medieval bridge lined with shops; and the Uffizi Gallery, one of the most famous art museums in the world. 

Other notable sights include the Palazzo Della Signoria, the Biblioteca Nazionale Centrale, the Pitti Palace, the ancient church of Santa Croce and the lesser-known hidden gems of Brancacci Chapel, the Bardini Museum, and the Palazzo Davanzati.

As you meander between these must-see historic attractions, you’ll enjoy a taste of Florence’s lively street life, with cafés, performers, markets, and statues all playing their roles on the incredible stage that is Florence.

For a unique experience, consider booking this highly-rated vintage Vespa day trip . Explore the rolling hills of the Tuscan countryside riding Italy’s iconic scooter, the Vespa. These Vespa day trips are so much fun and a bucket list worthy experience. Leave Florence in a swarm of roaring Vespas, heading to a local viewpoint for Tuscan wine and prosciutto. 

Tuscany is known for its food and wine and, as its capital, Florence has an abundance of restaurants to choose from. Did you know Trattoria is a term given to an establishment less formal than a ristorante? Look out for this term if you’re hunting for a traditional and relaxed meal!

Founded in 1953, Trattoria Mario serves traditional Tuscan cuisine in a cozy atmosphere and is proud of its selection of regional wines and Tuscan soups. Known for its lively atmosphere, Il Latini serves hearty meat dishes in a homely tavern. Trattoria da Enzo al 29 provides authentic outdoor dining while Cibreo Trattoria provides a more modern take on traditional Tuscan cuisine.

Top Tip: If you are planning a trip to Florence, especially during the summer months, we would highly recommend pre-booking tickets to some of the more popular tourist attractions or booking a guided tour where you’ll enjoy skip-the-line tickets and have the benefit of a knowledgeable and experienced guide.

• Where to Stay in Florence

Upmarket: Hotel Spadai – Booking.com | Agoda

Mid-Range: Soprarno Suites – Booking.com | Agoda

Budget: Hotel Perseo – Booking.com | Agoda

RELATED POST: One Day in Florence – Itinerary, Map, Tips & Guide

Next up, head south to Arezzo from Florence. Arezzo is known for its rich history and culture including the spectacular hilltop Cathedral, the Piazza Grande, the Basilica of San Francesco, Casa Vasari, and the Medicean Fortress. 

The Piazza Grande is a large, rectangular piazza in the heart of the city and home to many important historical and cultural events, such as the Giostra del Saracino, a medieval jousting tournament.

Make your visit to Arezzo unforgettable with this recommended cooking class with a local and learn the techniques needed to make delicious Tuscan food at home. Alternatively, why not book a guided tour in a vintage vehicle ? This unique experience allows you to whizz around charming Tuscan towns while an audio guide gives you an overview of the region’s history. 

• Where to Stay in Arezzo

Upmarket: La Corte Del Re – Booking.com | Agoda

Mid-Range: Graziella Patio Hotel – Booking.com | Agoda

Budget: Hotel Arezzo ASC- Booking.com | Agoda

Montepulciano

Famous for the classic, rustic wine of the same name, the gorgeous medieval town of Montepulciano is nestled into the chalky hills at the meeting point of the Val d’Orcia and the Vall di Chiana.

Surrounded by the undulating Tuscan landscape of rolling green hills and golden fields dotted with cypress trees, this is a picture-perfect Tuscany road trip destination.

The small town itself is a masterpiece of ancient city walls, cobbled streets, charming piazzas, restaurants, and craft shops that can easily draw you in for a deliciously pleasant afternoon and evening.

Enjoy an evening stroll around the lively old center and stop in one of the many restaurants for a traditional meal of wild boar ragu followed by local cheese and honey, all washed down with the famous local Vino Nobile di Montepulciano.

The town is also one of the best spots in this itinerary for a  wine-tasting tour of a local vineyard , to understand the history and process of making wine in Italy.

Top Tip: You cannot park within the town walls and need a permit to park in one of the numbered car parks on the outskirts, which your hotel will provide for you. The car parks are around a ten to fifteen minute walk from the center of the town, so maybe pack a small and easily carried bag for your overnight stay.

• Where to Stay in Montepulciano

Upmarket: Palazzo Carletti – Booking.com | Agoda

Mid-Range: Il Rondò Boutique Hotel – Booking.com | Agoda

Budget: Albergo Duomo – Booking.com | Agoda

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Heading west from Montepulciano, the drive to Siena takes approximately 1.5 hours. However, if you decide not to visit Arezzo and Montepulciano, the trip south from Florence to Siena will take a couple of hours on the winding SR222, the ‘Chiantigiana Road’, which snakes through the heart of Chianti wine country, internationally renowned for its vino .

From Montepulciano, take the scenic SP146 to San Quirico d’Orcia, through the iconic Val d’Orcia, one of Europe’s best driving routes .

This journey will take you through vineyards and olive groves, and you’ll pass row upon row of majestic cypress trees lining the roads and on the skyline, and you might even spot the famous house from the film ‘Gladiator’, some of which was filmed in Tuscany.

Siena, a medieval hilltop town famous for its historic center, is a destination that deserves a place on your ultimate Tuscany road trip. 

The city’s main attraction is its central square, the Piazza del Campo, which is considered one of the most beautiful medieval squares in Europe and is recognized as a UNESCO World Heritage Site.

The square is home to the Palazzo Pubblico, the town hall of Siena, the Torre del Mangia, a tall tower with stunning views of the city, and the often-overlooked Fonte Gaia on the northern edge of the piazza, whose water is still supplied by a 500-year-old viaduct.

Alongside its UNESCO World Heritage Site, Siena is also famous for its art and cultural events. The city is home to the Museo Civico, the Pinacoteca Nazionale, and events including Palio di Siena, a horse race that takes place twice a year in the Piazza del Campo.

A highlight of any visit to Siena’s UNESCO World Heritage Site is the Duomo which is an incredible representation of medieval architecture. Its popularity with tourists is well known, therefore we’d recommend pre-booking these tickets online and skipping the queue!

Alternatively, why not consider booking a city-guided tour? Our recommended Siena city tour comes with skip-the-line tickets for the cathedral and going with a professional guide will ensure you truly get to soak up the city’s history. 

Top Tip: Make sure to stop for lunch at one of the many lively restaurants lining the streets around the main square and sample delicious Ribollita, a traditional Tuscan soup made with vegetables and bread.

• Where to Stay in Siena

Upmarket: Palazzetto Rosso – Art Hotel – Booking.com | Agoda

Mid-Range: Hotel Athena – Booking.com | Agoda

Budget: Hotel Palazzo di Valli – Booking.com | Agoda

Looking for the best SIM card deals in Europe for your trip? Check out our guide to the best data SIMs in Europe and get the best deal for your trip to Italy.

San Gimignano 

The drive from Siena to San Gimignano is just 33km taking roughly 45 minutes depending on the traffic. This spectacular drive will provide unforgettable views of rolling Tuscan hillsides, olive groves, and vineyards. Along the way, why not stop at a local winery and enjoy a tasting?

Along this route, you will pass through the medieval town of Monteriggioni, a walled town recognized by its watchtowers. You can enter Monteriggioni’s old town through the Porta Franca gate. Once inside and from the vantage point of the town’s castle walls, you can take in breathtaking views of the Chianti region, internationally renowned for its wine.

San Gimignano is a medieval hilltop town that boasts a bucket list UNESCO World Heritage Site in its incredibly well-preserved historic center. San Gimignano is famous within the Tuscany region for its fourteen medieval towers built by wealthy families during the 13th and 14th centuries.

A vineyard wine tasting and lunch in the heart of Tuscany is on everyone’s bucket list. San Gimignano, with its excellent wineries, is the perfect spot for this experience. In fact, San Gimignano has its own famous white wine, Vernaccia di San Gimignano, which has been produced in the area since the 14th century.

A trip to San Gimignano wouldn’t be complete without a visit to its historic and lively main square, Piazza Della Cisterna. It’s surrounded by medieval buildings and is home to the Palazzo Comunale, which houses the town hall, and the Museo Civico, which has a collection of art and artifacts from the medieval period.

Volterra, along with Monteriggioni and San Gimignano, makes up the trio of hilltop villages along the Val di Cecina. Famous for being a film set for the Twilight films, Volterra is as medieval as they come!

Top Tip: As well as its wine-tasting opportunities, San Gimignano is home to incredible olive oil producers. This historic hilltop town is a great place to sample Tuscany’s delicious local products.

• Where to Stay in San Gimignano  

Upmarket: Agriturismo Mormoraia – Booking.com | Agoda

Mid-Range: Hotel Bel Soggiorno – Booking.com | Agoda

Budget: Relais Cappuccina – Booking.com | Agoda

Pisa is an iconic destination on the ultimate Tuscany road trip. The city is most famous for the Leaning Tower of Pisa, a freestanding bell tower that began to tilt during its construction in the 12th century. The tower has stood for over 800 years, despite its tilt, and is now one of the major tourist attractions within Tuscany.

Elevate your Pisa experience with a reserved entrance trip up the Leaning Tower and climb the 294 steps up the tower and witness unrivaled views over Miracles Square.

Pisa is also home to several other historical sites, including the Piazza dei Miracoli, also known as the Square of Miracles, which contains the Leaning Tower, the Cathedral of Santa Maria Assunta, and the Baptistery. The Piazza dei Cavalieri, or Knights’ Square, is another point of interest. It was once the political center of the Republic of Pisa.

Make the most of your time in Pisa and book a local tour guide. Within Pisa, residents are offering unique activities including truffle hunting in San Miniato, pasta-making classes , Pisa food tours and e-bike trips through the rural Tuscan countryside .

A visit to Pisa would not be complete without a visit to the Ristorante Trattoria da Mario . Just a five minute walk from the Leaning Tower of Pisa, this highly regarded hidden gem serves an array of traditional Tuscan food and wine. 

• Where to Stay in Pisa

Upmarket: Palazzo Cini – Booking.com | Agoda

Mid-Range: Hotel Di Stefano – Booking.com | Agoda

Budget: Hotel La Pace – Booking.com | Agoda

Don’t forget your road trip essentials! Our free road trip checklists help you remember everything, including road trip snacks , podcasts , and road trip songs for the journey!

Following a visit to Pisa, we recommend heading north to the charming Tuscan town of Lucca. Lucca is found on the Serchio river and boasts the Cathedral of San Martino, a Romanesque-style building with an impressive facade, and the Basilica of San Frediano, dedicated to the patron saint of Lucca. 

One of the most distinctive features of this area is the city walls. The walls were built in the 16th century to protect the city and are now a popular spot for walking and cycling, with panoramic views of the city and surrounding Tuscan countryside.

While visiting Lucca, we recommended taking this highly rated walking food and wine tour with a local , this excellent pasta and tiramisu-making course (which you get to eat afterward!), or a half-day Tuscany Chianti Wine tasting tour . All three of these foodie adventures will make your trip to Lucca an unforgettable cultural experience.  

• Where to Stay in Lucca

Upmarket: Palazzo Dipinto – Booking.com | Agoda

Mid-Range: Hotel Alla Corte degli Angeli – Booking.com | Agoda

Budget: Hotel Melecchi – Booking.com | Agoda

Cinque Terre

The drive from Lucca to Cinque Terre will take roughly an hour and a half. This route passes through the seaside towns of Lido di Camaiore, Forte dei Marmi, Marina di Massa, and Marina di Carrara. If you are lucky enough to be taking a slower drive on this Italian road trip, we recommend spending an afternoon in Forte dei Marmi and admiring the views of the Apuan Alps. 

Cinque Terre is not actually in Tuscany, but in Liguria, a picturesque region located on the Italian Riviera. Known for its five coastal towns of Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore, Cinque Terre is worth leaving Tuscany for!

The stunning natural beauty of Cinque Terre, meaning five lands in Italian, charming villages stacked with colorful houses, and delicious local cuisine combined with the views of the Mediterranean sea make it a must-visit destination when creating your ultimate Tuscany road trip.

Monterosso Beach, boasting clear waters and a bustling atmosphere, is the perfect place to take a boat trip and explore the coastline or a slightly more energetic kayak tour along the coast , to discover hidden caves, rugged cliffs, and the brightly painted towns from a unique perspective.

Cinque Terre is also the perfect destination to stretch your legs after a long road trip due to its many picturesque hiking trails including the Sentiero Azzurro which runs through the Cinque Terre National Park, a Unesco World Heritage Site.

Sentiero Azzurro, also known as the Blue Trail, connects the villages of Monterosso al Mare, Vernazza, Corniglia, Manarola, Riomaggiore, and the Sentiero degli Dei. This hiking trail offers panoramic views of the coast and the villages.

Top Tip: If you do decide to stay in Cinque Terre, head for delightful Monterosso al Mare, the largest of the Cinque Terre towns, and start your amble along the hiking route from there. Parking in the five villages is very restricted – we suggest parking your car at Park Centro Stazione secure   underground parking garage at the La Spezia Centrale train station and getting the Cinque Terre express train or passenger ferry to Monterosso.

• Where to Stay in Cinque Terre

Upmarket: Sesta Terra – Booking.com | Agoda

Mid-Range: Ca’ D’Andrean – Booking.com | Agoda

Budget: La Taverna del Metallo Rooms – Booking.com | Agoda

Want to plan your own road tri p? Get our step-by-step road trip planning guide to help you organize the perfect trip.

Tuscany Road Trip Resources

Here are the websites and services we personally use and recommend for traveling in Italy.

• Search for affordable flights to Italy with Skyscanner
• Search for availability and book hotels and accommodation in Italy with Booking.com
• Find and book the best campsites in Italy with Eurocampings
• Book the cheapest and most reliable hire cars in Italy with Rentalcars.com
• Find and hire your perfect motorhome or campervan with Motorhome Republic
• Get highly rated, reliable, and trustworthy travel insurance with True Traveller
• Check if you need a visa and arrange your documents with Visagov

Are you looking for more road trip inspiration? Check out these top posts…

Spain Road Trip: 8 Amazing Routes for an Epic Trip

Croatia Road Trips: Five Incredible Routes

Route des Grandes Alpes: An Epic French Road Trip

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How to plan an epic Tuscany road trip | Guide + Itinerary + Map

Occupying an area of more than 23,000 square kilometers, Tuscany is the absolute gem of Italy. Apart from its stunning landscape, Tuscany has a long artistic and historical tradition. That’s the area where the Italian Renaissance was born, and as you’ll see in this article, its impact is still visible throughout Europe. Therefore, if you’re about to plan a Tuscany road trip , there are plenty of places to add to your itinerary: a combination of world-famous works of art, stunning nature, and Chianti wine tastings should be part of your Italian journey.

After traveling extensively around Tuscany, I decided to share everything I know about the most prominent Italian region. In this guide, you will find the must-see Tuscany locations and the best places to base yourself while traveling around the area. Moreover, I’ll share hidden gems to enrich your road trip to Tuscany and add a suggested itinerary for a fuller experience. Last but not least, at the bottom of this post, you’ll find a separate section with Tuscany travel tips and answers to the most commonly asked questions.

So, let’s start with the Tuscany road trip itinerary. Simply navigate through the sections of this article and find everything you need to know before visiting the region.

Table of Contents

*Some links are affiliate links. It means that if you buy something, I might earn a small commission at no additional cost to you.

Tuscany road trip: how to reach the region

Tuscany has two international airports: the Americo Vespucci in Florence and the Galileo Galilei in Pisa . While both airports receive a fair amount of traffic, when planning your Tuscany road trip, it’s also a good idea to check for flights to Bologna’s airport. Despite not being technically in Tuscany, the Guglielmo Marconi airport in Bologna is the biggest in the area. Bologna is just an hour’s drive from Florence, and most air carriers fly directly there.

That said, before booking your flight to Tuscany, check all three airports for flights from your hometown. Moreover, in Bologna, you can usually find more competitive prices for car rentals. Apart from its proximity to Tuscany, Bologna is a stunning city that is assumed to be one of Italy’s culinary capitals ( see my guide to the best food tours in town ). So, Bologna will be a great option if you arrive after a long flight to Italy and need to stretch before starting your road trip to Tuscany.

Regarding the cheapest flights to Tuscany , the best option is to head to Kiwi and compare prices. Whenever I’m about to fly anywhere, I always check Kiwi to find the cheapest fares available. Make a comparison and decide which of the three airports you’ll fly to.

Car rentals in Tuscany: where to find the best fares for your road trip

Ideally, your road trip to Tuscany should start the moment you land in Italy. Therefore, after booking your plane tickets, you should try to pick up a car at the airport on arrival. Apart from not having to deal with public transport the moment you land in a foreign country, you’ll also be able to start your Italian road trip straight. Therefore, it’s better to pre-book a car that awaits you at the airport instead of searching for one upon arrival.

Now, here’s another Tuscany travel tip : if, for example, you find cheap flights from your hometown to Florence, but it’s cheaper to fly back home from Pisa, most car rentals in Italy offer you the option to return the car to another airport . Of course, this comes at an extra cost; however, it’s usually much cheaper than the airfare difference.

I always use Rental Cars for booking a car abroad. The company belongs to Booking.com , and it’s the best aggregator for car rentals. Their powerful search engine will compare the prices of local and international car rentals. In addition, you can select your pick-up and drop-off locations, the timeframe, and several other things like insurance, the number of drivers, etc.

Find the best prices for renting a car in Italy here .

Tuscany road trip: the must-sees

After booking your flight tickets and your car, it’s time to start planning your road trip to Tuscany. While the number of days will define the amount of sightseeing you can do, there are some places you simply can’t miss. For example, it’ll be a different journey if you have one week in Tuscany instead of two weeks. However, I recommend at least 5 days in Tuscany to see the most important locations.

Before starting with the Tuscany must-see places, I’d like to add a note. I’m a fan of slow traveling , which means I always prefer a less action-packed itinerary. In general, I always think that it’s nice to have breathing space when traveling, and immersing in the local culture is a must. Therefore, I’d rather sacrifice a place and enjoy the moment. The selection you’ll see below is based on that travel attitude of mine. Straight after this section, you’ll also find a bunch of other places to include in your itinerary.

Let’s start.

No journey to Tuscany (or Italy) is complete without a visit to Florence . The cradle of the Renaissance is one of the most legendary cities in the world, and you simply can’t miss it if you’re on a road trip around Tuscany. The stunning Italian city is an open-air museum, and you’ll see incredible architecture and art with every step you take. World-famous art institutions like the Uffizi Gallery or the Galleria dell’ Accademia can occupy you for hours. On the other hand, the Duomo of Florence and the Ponte Vecchio are iconic spots full of history and odd tales.

I can’t imagine a road trip to Tuscany without spending a couple of days in Florence. It’s up to you to decide if you’ll spend some days in Florence at the beginning or the end of your Italian journey. However, walking the streets of Florence and coming across art masterpieces is something unmissable.

My Florence guides & resources

I wrote several separate posts about Florence. In the first one, you can read various facts about Florence  and find the best boutique hotels in the city. In the second post, I wrote down the best art tours in Florence with their prices . Finally, you can also find a very thorough guide about the best Tuscany wine tours from Florence to enjoy top-class Chianti wines.

Since Florence attracts millions of visitors annually, booking your museum tickets in advance is always recommended. Moreover, a guided tour will save you time because you’ll skip the line and learn more about what you see from a registered tour guide. Check both articles and plan your Florence itinerary.

Florence tip : If you can only visit one museum in Florence, this should be the Uffizi Gallery. However, the queues are long, and you shouldn’t miss travel time. Pre-book your Uffizi ticket here and skip the line .

If you have a thing for medieval cities, Siena won’t let you down. Apart from its undeniable architectural beauty, Siena is also an excellent base for further exploring Tuscany . Located in the region’s heart, the walled city of Siena has a fantastic atmosphere, and walking through its cobblestone streets feels like a journey through time. The iconic Piazza del Campo is Siena’s main square and the broadest spot you’ll find in town. That’s where the locals gather, and if you want to blend in with the locals, the so-called il Campo is the place to be.

Besides its beauty, Siena is one of the best spots to discover the famous Chianti wine region. Dozens of wineries are located nearby, and joining a wine tour will be an unforgettable experience. The beautiful Tuscan landscape hosts bigger and smaller wineries, and drinking Chianti wine in the region it’s produced is one of the must-do things in Tuscany.

My Siena resources

As mentioned in the previous lines, Siena is a perfect base for further exploring the Chianti wine region and joining wine tours and tastings. I wrote a comprehensive guide about the best wine tours from Siena . If you feel like leaving your car for some hours and having somebody drive you to the best wineries in the region, this guide will help you discover the best wine experiences in Chianti.

Moreover, since the city’s historical center is a ZTL Zone , you should think twice before parking your car. To avoid fines and unwanted vacation stress, I wrote a separate article about the things you need to keep in mind when visiting Siena with a car. You can find my article about how to visit Siena with a car here . You’ll also see a list of hotels with private parking.

Siena tip : If you use Siena as your base, you might miss some of its highlights. There’s a fantastic Siena walking tour that will take you to the city’s highlight. Moreover, you’ll get to the city’s stunning Cathedral without queueing. Book this fantastic Siena walking tour here .

San Gimignano

One of the best places to see in Tuscany is definitely San Gimignano . This Tuscan gem is located halfway between Siena and Florence, and it’s one of the most picturesque towns you’ll come across on your Tuscany road trip. Known as The Town of Fine Towers or even Medieval Manhattan, San Gimignano is famous for its stunning architecture. Fourteen medieval towers occupy its skyline, and a couple of them are converted into hotels.

The number of San Gimignano towers might sound insignificant; however, once upon a time, it had 72. For a town that compact, the number is really impressive. While you won’t need more than a couple of hours in San Gimignano, I highly recommend spending at least one night there. Most people visit San Gimignano on a day trip and depart late in the afternoon. However, after the daytrippers are gone, the small Tuscan town becomes quiet, and wandering through the narrow streets at night is an unforgettable experience.

My San Gimignano guide

San Gimignano significantly impacted me, and it was definitely one of the highlights of my road trip to Tuscany. I wrote a thorough travel guide about the town, including the best things to do, some great places to eat and drink, and the best hotels. You can read here my San Gimignano travel guide .

San Gimignano travel tip : How about spending a night in one of San Gimignano’s towers? The Torre Salvucci offers accommodation in a 12th-century tower in the town’s heart. Book your room at Torre Salvucci here .

Being one of the most famous Etruscan cities, a civilization that flourished centuries ago in this part of Italy, Arezzo is nowadays one of the must-see Italian cities. The city has a population of almost 100,000 people, but it feels more compact. Exactly like Siena, Arezzo is a beautiful walled city, and its most famous spot is the stunning Piazza Grande . The biggest square in the city was featured in the famous Roberto Benini movie La Vita è Bella , and it hosts an art bazaar on the first Sunday of every month.

Located just 80 km (50 mi) from Florence, Arezzo is home to various notable churches. Even if you are non-religious, visiting a couple of Arezzo churches is a must due to the Renaissance masterpieces they host. The most famous of all is the Basilica of San Francesco, which is built in Tuscan Gothic style, and you can see up close an iconic Pierro della Francesca “History of the True Cross” fresco.

My Arezzo guide

Arezzo feels quieter than Florence and Siena; however, it’s an excellent base for discovering this part of Tuscany, and there are plenty of things to see. I wrote a travel guide to Arezzo, where you’ll find the must-see attractions and the best hotels in the city. You can read here my guide to Arezzo, Italy .

Arezzo tip : Italian cuisine is famous worldwide. Don’t miss the chance to dine with a local when visiting Arezzo. Meet your host, buy groceries together, and enjoy a delicious homemade meal at your host’s place. Book a dinner with a local in Arezzo here .

Last but not least, here’s one of the hidden gems of Tuscany. Pienza appears to be a sleepy little town with less than 2,000 inhabitants. Its picturesque yet humble style might make you think it doesn’t deserve to spend time here. However, Pienza is one of the ideal cities of the Renaissance and among the most important locations in Tuscany.

While the Palazzo Piccolomini and the Duomo will magnetize your eyes, Pienza’s urban planning actually made the little town famous worldwide. The concept of the ideal city was first introduced in Pienza, and it’s a cornerstone element of most modern cities. Taking a humanistic approach to architecture is a Renaissance concept. In brief, that’s an attempt to encompass moral and spiritual aspects in urban structures. Geometric patterns are at the heart of ideal cities, and making cities a place where people can thrive is the concept’s soul.

My Pienza travel guide

Despite its small size, Pienza is one of the must-sees when driving around Tuscany. Apart from encompassing various Renaissance ideas, the town is beautiful beyond words. While you can see Pienza in an hour, spending a night here will add a special touch to your Tuscan journey. You can read my Pienza travel guide to discover more about Tuscany’s hidden gem.

Pienza tip : The Palazzo Piccolomini is a must-see for your visit to Pienza, and it hosts (probably) the first roof garden of the Renaissance. Pre-book your entry ticket at Palazzo Piccolomini here  and skip the line.

Tuscany road trip: other places to add to your itinerary

While the above places can be your bases while visiting Tuscany, there are plenty of other locations to add to your road trip itinerary. Driving between any two cities mentioned above and towns will bring you to picturesque villages that deserve a stop. The Tuscan landscape is stunning, and part of your road trip to Tuscany will be about enjoying nature.

Therefore, in this section of this Tuscany travel guide , you’ll find a bunch of places to add to your itinerary. Depending on which side of Tuscany you want to explore, some of these places can be great bases for further exploring the area.

Montepulciano

Just 13 km (8 miles) out of Pienza, you will come across the small town of Montepulciano . Renowned for its famous Vino Nobile di Montepulciano red wine , the small city is a great addition to your Tuscany road trip itinerary. Its car-free city center makes it a great option for strolling around, and its beautiful buildings will definitely make it to your camera roll. Despite its size, Montepulciano attracts thousands of visitors, and if you happen to stop here, make sure to taste (at least) one glass of its famous red wine.

Settled since Etruscan times and a few kilometers west of Pienza, Montalcino is one of the most beautiful towns in Val d’Orcia. Montalcino’s poetic name most likely derives from an oak tree that once occupied the area. Today, Montalcino is one of the most beloved Tuscany stop-overs due to the tremendous views of the Asso Valley. A stop at Montalcino will expose you to views that resemble impressionistic paintings, and it’s better to stop by late in the afternoon and enjoy a fantastic sunset.

There’s a great possibility to begin or end your Tuscany road trip itinerary in Pisa . The city is famous for the Leaning Tower , and it’s one of the biggest cities in Tuscany. I didn’t add Pisa in the Tuscany must-sees in the previous section because the city didn’t meet my expectations apart from the Leaning Tower. I probably had high hopes, which is why I think it’s better to stop over in Pisa and not spend days there. However, save a day for the city if you have a flight to or from Pisa. Pisa has its moments, and the Leaning Tower is definitely something to see and photograph.

Volterra is one more walled city in Tuscany, enjoying great views and featuring a history that dates back to the 8th century BC. The famous Piazza dei Priori is one of the finest examples of Tuscan squares, and the Roman Theater of Volterra is one of the best-preserved Italian theaters. Volterra is an excellent addition to your Tuscany itinerary if you are in San Gimignano and planning to travel west toward the coast.

On the other hand, if you are close to Arezzo and want to see more of this side of Tuscany, a stop at Cortona is recommended. Occupied and extended by the Etruscans, Cortona is famous for its stunning medieval architecture and steep, narrow streets. The city walls the Etruscan built are still intact in some places, and the small city has some incredible viewpoints of Valdichiana.

Tuscany road trip map

In this section of the travel guide, you can see a map for your road trip to Tuscany . As you can see above, the itinerary starts and finishes in Florence. Apparently, if you land in Bologna, you can drive to Florence (it takes an hour) and start your trip. On the other hand, if you land in Pisa, you can start from there and drive around the region.

Travel Tip : Click on the star on the map’s black banner and save it to your Google Maps account. You can retrieve it anytime and check the locations. The map will appear in Google Maps under “Saved” –> “Maps.”

Suggested itinerary for your road trip to Tuscany

As I already wrote, the number of available days will define what you’ll see and do in Tuscany . In general, if you have less than 5 days in Tuscany, you won’t easily see everything unless you drive all day. If you only have two or three days in the region, choose a few places depending on your interests and try to combine a bigger city (like Florence) and a couple of small towns (like San Gimignano and Montepulciano).

The Tuscany route on the above map is roughly 500 km (310 miles) , and driving time should be anything between 8 and 10 hours in total. Therefore, on a 5-day road trip , you’ll need to drive approximately two hours per day; obviously, if you have two days, you’ll practically have to drive the best part of the day.

That said, the Tuscany itinerary you saw above works best if you have 7 days in Tuscany . A week in Italy’s most famous region will give you a relaxing time, and you won’t have to be on the road continuously. There will be enough time for relaxing, enjoying, or even changing plans and visiting the X place that a local said is worth seeing. Of course, if you have more time -like ten days or even two weeks in Tuscany- you can further stretch the itinerary and drive to places on the region’s coast, like Livorno.

So, let’s now see the route.

Road trip to Tuscany: Detailed Itinerary

A one-week Tuscany road trip:

Day 1 . Start from Florence and dedicate the day to the city’s various museums and sightseeing. Spend the night in Florence.

Day 2 . If there’s any Florence sightseeing left, do it early in the morning. Then, take your car and drive to Arezzo . Explore the beautiful Etruscan city and decide if you’d like to stay there or if you’re up for a small town. If you decide on the latter, drive to nearby Cortona and spend the night there.

Day 3 . After breakfast, drive towards Montepulciano . Explore the picturesque town and taste some wine. After lunch, start driving towards Pienza , the ideal city of the Renaissance. I suggest spending the night here and exploring both the town and the stunning Val d’Orcia.

Day 4 . Leave Pienza behind and drive to Montalcino . This small town is a great option for sightseeing and lunch breaks. Then, go to Siena and explore one of Europe’s most iconic medieval cities. Spend the night here and have dinner around Piazza del Campo.

Day 5 . Today is all about wine tasting and exploring the Chianti region . Siena is an excellent base for going on wine tastings, and if you feel like skipping the car, you can join a guided tour (see the top wine tastings from Siena here ). After the tour’s conclusion, take your car and drive to San Gimignano . Explore the town of medieval towers and spend the night here.

Day 6 . After breakfast, get in your car and drive to Pisa . The Leaning Tower awaits you, and after strolling around the city, consider visiting nearby Lucca . If you don’t have an early flight the next day from Florence or Bologna, spend the night in Pisa. Otherwise, drive to the city of departure.

Day 7 . Assuming you’re still in Pisa (or Lucca), stroll around town and head to the city of departure. If that’s Florence, well, there’s always something to see in Florence before heading to the airport.

Travel tips for your road trip to Tuscany

Before heading to the final section of this travel guide to Tuscany, I thought of adding a couple of tips for your journey. Feel free to keep these things in mind for a fuller Tuscany experience.

Skip the highways . Although it’s inevitable to drive sometimes on the motorway, Tuscany’s beauty is on the smaller roads. Highways are a great shortcut when you’re in a rush, but you’ll miss the region’s stunning nature. Therefore, whenever possible, don’t take the fastest way: instead, try to avoid it and immerse yourself in Tuscany’s landscape.

Save some coins for the toll roads . In case you find yourself driving on the motorway, make sure to have some coins with you. You’ll have to pay for using Italian highways, and although they accept cards, sometimes it’s good to have some cash. My card wasn’t accepted once, resulting in a long queue.

Don’t park in city centers . Most cities and towns in Tuscany have dedicated parking lots outside the walls. Park your car there, and don’t risk getting a fine for illegal parking. You’ll pay per hour of use, and usually, a daily money limit can’t be exceeded. In San Gimignano, for example, you can’t pay more than 15 euros per day, although the parking costs 2 euros per hour. Don’t risk a fine.

Rent a small car . Unless you’re more than 4 people traveling, don’t rent a big car. Tuscany’s streets are small, and the roads are in fairly good condition. You won’t need a big car to drive around Tuscany; it’ll be more of a hassle to drive through the narrow streets -let alone park it.

If worried, buy full car insurance . Full car insurance comes at an extra cost, but it’ll give you peace of mind. It is available in every rental, covering everything that might happen to your car -even scratches. On Rental Cars , you can see the added cost in the final step. It’s usually a small amount, like 5 or 10 euros per day, depending on the car.

Embrace spontaneity . Apart from this Tuscany travel guide, you will probably read several other guides. While it’s important to be well-prepared for your road trip, I always suggest being spontaneous. If a village’s name sounds tempting, visit it. Or, if you feel like skipping driving for the day and prefer enjoying nature, do it. The best moments of your road trip will be the carefree ones.

Book your museum tickets in advance . That’s the only thing you can’t be spontaneous in Tuscany. Everyone wants to see stunning art or go on day trips in the region. Therefore, everything sells out fast. If you don’t want to queue for half a day in Uffizi (I did), it’s better to be on the safe side. Websites like GetYourGuide can smoothen the process. Visit the website, add the attraction’s name, and check the skip-the-line options.

Google Maps (or GPS) is your Tuscan friend . Before starting your road trip to Tuscany, make sure to download the map of Tuscany from Google. The region has plenty of tiny streets, and you might often be confused. Moreover, even if you enable roaming, it doesn’t mean you’ll have an internet connection everywhere. If your car doesn’t have a GPS installed, make sure to have the map on your smartphone.

Tuscany road trip FAQ

In the final section of this long travel guide to Tuscany , you’ll find some of the most frequently asked questions about the region. Consider the answers as extra travel tips for your road trip. If you have more questions, please add them in the comments section below, and I’ll do my best to reply.

So, here’s the Tuscany FAQ.

How many days do you need for Tuscany?

You will need at least 5 days to see Tuscany . You can only see parts of the region if you have fewer days. On the other hand, if you have one or two weeks in Tuscany, you can see smaller villages.

What is the best month to visit Tuscany?

September and October are the best months to visit Tuscany. The weather is still warm, and it’s pure joy to drive around. May to mid-June is also a good timeframe to visit the region.

On the other hand, July and August tend to be hot, and the area is crowded. If you have the option, it’s better to avoid these months.

How long does it take to drive through Tuscany?

This largely depends on your Tuscany itinerary. You’ll have to drive approximately 500 kilometers (310 miles) to see most places in Tuscany. Apparently, if you want to add tiny villages to your itinerary, you might need to drive ~800-1000 kilometers (~495-620 miles).

Is it difficult to drive around Tuscany?

Definitely not. The road network is in good condition. However, the regional roads tend to be small, and you can’t speed up: apart from being dangerous, you’ll also risk a fine. Plus, you’ll visit Tuscany to enjoy the landscape; there’s no reason to rush.

Use common sense when driving, and you’ll have a great time.

Is a car necessary in Tuscany?

Renting a car in Tuscany will give you flexibility. However, it’s possible to see most places (especially the famous ones) with public transport or guided tours. You can even hire a driver to take you around . That’s obviously a costly option, but if you can afford it, it’s a great option to make the most of your Italian trip without a car.

How many UNESCO World Heritage Sites does Tuscany have?

Tuscany is home to 8 UNESCO World Heritage Sites . These are:

• The historic center of Florence.
• Val d’Orcia.
• Pisa’s Square of Miracles.
• The San Gimignano historic center.
• Medici villas.
• Montecatini Terme.
• Siena’s historic center.

What is the ZTL?

The ZTL is a controlled zone in Italy , usually in and around the city center. It practically means that non-residents are not allowed to drive or park. However, don’t think that they won’t see you: police cameras will photograph your license plates. Therefore, if you see a ZTL zone, avoid driving or parking.

Is Tuscany expensive?

Tuscany is relatively expensive . This isn’t a surprise since it’s Italy’s most famous region -and among the most famous worldwide. You should expect elevated costs on everything: from food to accommodation and from museum fees to car rentals. However, the quality of services somehow balances the costs. It won’t be easy to visit Tuscany on a budget, especially if you want to see everything. Therefore, budget accordingly and be prepared to spend some extra cash.

What is the best town in Tuscany?

Florence . The so-called cradle of the Renaissance is undoubtedly Tuscany’s most important city. If you have more than 6-7 days in Tuscany, I recommend spending as much time as possible in Florence. The city is an architectural gem and a place to see Renaissance art.

What’s the best place to base yourself in Tuscany?

If you prefer to stay in the same city every night and go on day trips, your best options are Florence and Siena . Siena is more conveniently located in the center of Tuscany. On the other hand, Florence is in Tuscany’s northern part, making it a good base if you plan to explore this side of Italy.

Where is the circle of cypresses in Tuscany?

One of the most Instagrammable places in Tuscany is the so-called circle of cypresses. You’ll find it at San Quirico d’Orcia, one of the most beloved spots for drone photography. See the San Quirico d’Orcia cypresses on Google Maps .

Is Chianti wine sweet or dry?

Chianti wine is dry . Specifically, the world-famous Chianti Classico is a dry red wine produced in Tuscany.

Plan a road trip to Tuscany: conclusion

Most international travelers daydream about a road trip to Tuscany, and that’s understandable. The region is known for its iconic art and stunning landscapes, and together with the divine Chianti wine, it ranks among the top places to see in Europe. Embarking on a road trip to Tuscany means immersing yourself in one of the most beautiful places on earth.

My final advice is to travel slowly around Tuscany and set yourself in a relaxing mood. As a rule of thumb, it’s better to miss one or two places and enjoy the time. To travel to Tuscany means to enjoy everything it offers: wine, food, landscape, and art. Don’t do it fast; make it count.

More about Tuscany : My Florence Travelogue

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Last Updated on January 27, 2024 by George Pavlopoulos

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Tuscany Road Trip: The Perfect Itinerary Through Italy’s Stunning Countryside

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It’s imperative to feel comfortable and safe while traveling. Medjet provides premier air medical transport and travel protection, providing peace of mind for an affordable price.

There are many good road trips out there, but driving through Tuscany is on a whole other level. Tuscany is a very manageable region, size-wise, roughly the size of New Jersey, and has a good and easy to maneuver road system. The countryside is picture-book perfect, with green hills dotted with slender cypress trees standing in line, vineyards, and sunflower fields at every corner, and pretty much every single town and village worth stopping off at.

It is gorgeous in summer, but it gets extremely hot in the narrow medieval town centers — too hot to sightsee, really. In spring you can get a fair bit of rain, explaining the lush green countryside, but early fall is quite perfect. If you can aim for early or mid-September, then you get the best of everything.

Read our top picks for hotels in Tuscany before booking your next trip.

And, while you should obviously choose a car in accordance with your budget and level of driving comfort, can I suggest that this is the time to get a small-ish convertible? Small enough to maneuver through the narrow village lanes and the cities, but with a nice retractable roof to allow you to not only see Tuscany but to feel the Tuscan sun on your face and the Tuscan breeze in your hair. Cliche? Too right, but so worth it.

As for the itinerary detailed here — I have driven around Tuscany a few times, and these are the places I keep revisiting every time. They do not encompass every beautiful village and hilltop Tuscany has to offer, but this itinerary gives you a good overview, especially if this is your first time in the region.

Buon viaggio!

Robert Bertold / Shutterstock

We start in Florence, as it is the capital of Tuscany and most likely the airport you will fly into. Florence is a gorgeous city with much to see, so I suggest that you spend a night or two at either end of the road trip here. Get over the jetlag, find your feet, rent a car , study the map, and then, when you’re ready to leave Florence (will you ever be?), set off.

Pro Tip: When I first came to Florence, I glimpsed a lovely hotel in a side street in the city center, but at the time could not afford it. I vowed that one day I would stay there, and I did. And it was worth the wait. The Hotel Monna Lisa is not just stunning in itself, but it has the loveliest hidden garden and one room covered in paintings of the Mona Lisa, all very different and quite funny.

stefano marinari / Shutterstock

Head out of Florence on the main autoroute toward Pisa, turning off after Empoli toward the little town of Vinci, some 27 miles, or roughly a 45-minute drive, away. This is your first stop on your road trip, and it is a stunner. This is the gorgeous town of Vinci, named after Leonardo da Vinci, who was born here. Head straight to the hilltop and the Leonardo da Vinci Museum and be prepared to spend at least two or three hours there, as it is packed full with models of his inventions, sketches, details and so much information that your head will burst after taking it all in. What an amazing man.

Afterward, walk around the castle, enjoying the views across the countryside; meander along the steep lanes, and stop for lunch before heading on.

Pro Tip: Have a bruschetta at Antica Cantina bi Bacco , just down from the museum. It’s a simple place, cheap and cheerful, and great for a lunch in the sunshine.

Fernando Tatay / Shutterstock

Back on the main road to Pisa, turn off to Lucca after roughly 30 miles. Here you will stop for the night, allowing you to spend the afternoon and morning exploring Lucca. Walking around Lucca is a little like stepping back in time, a sentiment which is quite true for a lot of the towns around Tuscany, but Lucca’s towers and cobbled streets, especially if you catch them early in the morning without people, have changed little over the centuries. Look out for my favorite of all the towers, Torre Guinigi, with trees growing on the top of it, and marvel at the church of Chiesa di San Michele in Foro, which is eerily like the Cathedral of Pisa, which you will see tomorrow.

In the afternoon, or morning, walk along the city’s walls, designed by none other than Leonardo da Vinci from Vinci.

Pro Tip: Stay the night in a 16th-century city-palace-turned-hotel and have a wood-fired pizza in Pizzeria da Felice , where they have been preparing pizzas for more than 100 years.

Rosty McFly / Shutterstock

Pisa is one of those stops along a Tuscan road trip, which is usually just that: a brief stop for coffee, a glimpse at the tower, and off you go again. This itinerary allows you to stay the night. So this is a relaxing day, as Pisa is only a 20-minute drive from Lucca. Arrive around lunchtime and start looking around. Take your time, explore along the river, linger until the last minute before the Place of Miracles closes for the day, to get it to yourself once the coaches have left. And after spending last night in a city palace, consider spending tonight in the Grand Duke of Tuscany’s former summer palace , a lovely building with a spa that takes advantage of the local hot springs. Make sure you book yourself in for a treatment before having dinner in the candle-lit courtyard.

Pro Tip: In the morning, for a taste of home, why not breakfast on Italian coffee and American-style bagels at the Filter Coffee Lab ? This will set you up for the day’s driving ahead.

gary yim / Shutterstock

Montepulciano

This is the longest driving day of the trip, basically taking all day, as you will drive down the E80 along the coast down toward Follonico, stopping off to explore the coast whenever you want to. Then you will turn inland, where the roads get smaller and you will meander through the typical Tuscan countryside, through small villages, past vineyards and sunflower fields. Do not follow the advice of the GPS, as that will send you round via Florence — faster, yes, but you will miss all the fun. Stay on or near the E80 instead. Check in at Fattoria San Martino , a converted rustic farmhouse, eco-friendly and cute, set in beautiful grounds for the night. Then walk into Montepulciano for some sightseeing, and simply enjoy another gorgeous Tuscan town.

Sit in the fabulous Piazza Grande and sip a refreshing spritz, or try a glass of the local Vino Nobile, which many say is the best of the region’s, and even the country’s, many wines.

Pro Tip: And talking about wine, if you happen to be in Montepulciano in August, on the last Sunday the festival of Bravio delle Botti takes place. People dress in medieval costumes and participants roll wooden wine barrels through the steep lanes trying to win a cloth banner, a trophy that has been fought over since the 14th century.

JeniFoto / Shutterstock

Thirty-eight miles up the SS715 will take you to Siena . Siena is simply amazing. The tall, medieval brick buildings make for shady lanes, opening into the large fan-shaped Piazza del Campo, which dazzles you with light and is the site of the famous horse race, the Palio de Siena . The duomo is spectacular, the various towers and ancient city walls are just as they were when they were built centuries ago, and the various streets (which fill up very quickly in summer) offer many cafes and good shopping down Via di Citta. Stop for some superb pasta at Il Bargello off the main square.

I always get lost in Siena, but it does not matter, as you will eventually find yourself back in the main square. Take your time getting lost, and look out for the small details on the architecture, such as the 17 animals and symbols representing the different districts of Siena in the Palio. Can you spot the dragon or the tortoise?

Pro Tip: Go to your hotel, such as the Hotel Palazzo Ravizza , where you can spend the afternoon on their terrace overlooking the hills. A cool drink and a book will entertain you while the crowds of day-trippers are slowly thinning out, and you can venture out for a stroll and dinner in the evening. For even more recommendations, consider my take on How To Spend A Beautiful Long Weekend In Siena .

StevanZZ / Shutterstock

San Gimignano

After a slow start, maybe taking breakfast and an espresso on the piazza, head to San Gimignano , some 30 miles away. This is one of my favorite places in Tuscany — is it quite simply enchanting. This small community is famous for its tall towers, which you will see on the horizon as you approach. Built between the 11th and 13th centuries, they were a symbol of wealth and power, with the rich families competing over who would build the taller tower. Today only 13 remain, but they still make for quite a skyline.

Pro Tip: The town is great to explore at night, and the countryside around San Gimignano is just lovely, so you might want to stay another night before heading back. Try the simple Casa de Potenti , right in the center of San Gimignano, surrounded by towers.

muratart / Shutterstock

Back To Florence

An hour’s drive, and you are back in Florence for hopefully some more sightseeing and art and culture.

Pro Tip: Please note that this itinerary only lists the main stops on your road trip, but on this road trip, it is not so much the destination, even though each and every stop is superb, but it is about the journey in between. The small villages, the fields full of sunflowers, the stops by the side of the road to take pictures of the hills studded with cypress trees and beautiful villas. Take your time, breathe deep, and enjoy.

A travel writer and guidebook author for the last 20 years, Ulrike's work has been seen in National Geographic , BBC , The Independent , Australian Women's Weekly , The Telegraph , The Australian , Fodor's , France Today , CNN Travel , Lonely Planet , Travel + Leisure , CNTraveler , numerous inflight magazines, and many others.

She has written three books for Moon Travel Guides: 'Living Abroad in Australia' (3rd edition), 'Sydney & the Great Barrier Reef', and the shorter version 'Spotlight Sydney' and are all available in print and as e-books.

Having lived in seven countries (Germany, UK, Qatar, Oman, UAE, Australia, and France) to date and traveled to more than 100, she specializes in writing about travel, art and architecture, expat living, and life and style.

Tuscany Road Trip Itinerary: The Best of Tuscany

Tuscany is one of the most popular tourist destinations in Italy because this central region of the country is renowned for its diversity. A Tuscany road trip can truly cater to any taste, being a food and wine haven for travelers, as well as being a cultural, artistic and historic marvel.

There are rolling hills, UNESCO World Heritage city centers, medieval villages, world-class wineries, and spectacular coastline. With so much to offer, the best way to experience the region is on a road trip.

This gives you the freedom to get out into the countryside to explore the lesser-known wonders in your own time.

Start your journey in Florence, the Renaissance heart of Europe, before exploring the Chianti wine region, the medieval center of Siena and of course, the classic leaning tower of Pisa.

There is a lot more to our Tuscany road trip than that though, so to guide you through the hills and along the beaches, here is our ultimate guide to planning your own adventure.

Don’t leave home without: Lonely Planet Florence & Tuscany (Travel Guide)

Planning Your Tuscany Road Trip

Table of Contents

The ultimate Tuscany road trip will take you through some of the most pristine Italian countrysides, as you travel from classic city destinations to charming rural villages. It’s the best way to experience this part of the world, as you’ll be able to travel as fast as you want or as slow as you want.

Getting Started

Starting your trip in Florence will give you the chance to either pick up your rental car at the airport or spend a few days in the city before picking one up in the center, to begin the road trip itself.

Florence has excellent flight connections across Europe and is the perfect base for starting and ending the trip. There are also great domestic connections across Italy, including the high-speed rail, if you are only looking at a Tuscany Road Trip, rather than a countrywide road trip.

Rental Cars & Driving

You can book rental cars in advance online, for pick up when you arrive, and with a lot of competition, you can get some excellent deals ahead of time.

Be sure to check what insurance is provided with your rental, as you won’t want to get caught out. You’ll also want to check your license is valid in Italy – most driving licenses are for short periods at the very least – and you’ll want to check if roadside assistance is included.

Driving in the cities can be rather hectic, as most have narrow, medieval streets – which is part of the charm! – so it can get some getting used to.

In the countryside, there are lots of winding, rural roads, so always be aware. There are also plenty of wineries to stop off at, but just ensure the driver doesn’t indulge over the limit!

Need to book a car for your road trip adventure? We use Discover Car Hire for comparing car prices to find the best deal. They search both local & international rental companies.

Drive Times

For the itinerary below, you’ll never need to drive for longer than 2 hours at a stretch between each destination, giving you plenty of opportunities to actually explore the places you are traveling to.

We’d recommend at least one night in each of the destinations below, with perhaps two or more in Florence overall. Of course, this is your Tuscany road trip though and the joy of driving is that you can tailor the trip to your own preference.

Read reviews and check prices with our Hotel Search Engine , that gives you the best hotel deals found on the web. Our search engine pulls results from all of the major booking places, including Expedia, Hotels, Booking and more. All the options, all the deals, all in one place and just for you.

Top Places to Visit in Tuscany

Your trip begins and ends in Florence , the capital of Tuscany and the heart of the region. This is where you pick up your rental car after flying in or catching the train but don’t leave straight away, because the city is a must-visit destination in its own right.

Florence is one of the major cultural centers in Italy and is often cited as the ‘birthplace of the Renaissance’. The medieval city center is awash with beautiful architecture, incredible basilicas and cathedrals, and endless museums and art galleries.

Call in at the Uffizi Gallery to see some of the most iconic works of art from European painters and sculptors on display, and don’t miss the Galleria dell’Accademia for a glimpse of Michaelangelo’s David.

Indulge in a true taste of Florence on this food and walking tour . Led by a foodie guide, travel through the streets of the Renaissance city and stop at the top local haunts.

Check out the fresh produce at the San Lorenzo Market, try the bold flavors of an Italian coffee, and peruse a Florentine delicatessen. You’ll sample plenty of specialties along the way, including cheeses, bread, olive oils, gelato, and Italian wine.

Accommodation in Florence: Hotel Pendini – great breakfast and location

Greve in Chianti

After enjoying the historic, Renaissance-era sights of Florence, it’s time to drive out into the countryside, to begin your Tuscany road trip. A short, but pleasant 30-kilometer drive will take you along winding, rural roads to the small town of Greve in Chianti.

The Chianti region is one of the most famous wine-producing regions in Italy, and here you can find wineries in beautiful settings around every corner.

Call in at the local wineries, enjoy some fresh local cheese, olives and cured meats, and of course a few tastings. You will want to spend the night in Greve to truly appreciate the fine wines.

Accommodation for Greve: Albergo del Chianti – beautiful pool and great location

In the morning, set off south-east to the edge of Tuscany to visit the city of Arezzo. Just over an hour of straight driving will bring you from Greve in Chianti to Arezzo, where you can find an off the beaten track city that’s full of intriguing history.

Arezzo has a history dating back to at least the 9th century BC. Almost 3000 years of human history can be discovered here, but unfortunately, much of the ancient center was destroyed during the second world war.

For that reason, many travelers choose to visit other, more preserved locations in Tuscany, but the big benefit to that is the fact that Arezzo is much quieter, and in many ways more authentic culturally than other Tuscan destinations.

You can visit old churches, the beautiful main plaza and enjoy glorious views of the Tuscan countryside from the city’s hilltop position.

Indulging in local wine is a must when you visit Tuscany. On this private tour , you’ll go behind-the-scenes at one of the region’s most scenic and esteemed wineries, located just on the outskirts of Arezzo.

Learn about organic winemaking processes when you tour the vineyards, delve into the cellar to discover how wine is aged, and finally taste three organic wines, along with locally made pecorino cheese and cured meats.

Accommodation in Arezzo:  Hotel L’Aretino – great breakfast and good location

Montepulciano

An hour’s drive south of Arezzo takes you to Montepulciano, a wonderfully well preserved medieval town. Like many Tuscan settlements, Montepulciano was founded on a high hilltop, offering the inhabitants protection, and today offering tourists excellent views.

In Montepulciano, you’ll want to park up and stroll through the charming streets, admiring the Rennaisance era architecture that the city is famous for.

Although you can easily see all the major sights in a few hours, it’s worth spending the night here, because Montepulciano is well regarded as a foodie destination.

Enjoy a late evening indulging in excellent local dishes and wine, including the high-quality Vino Nobile which is produced locally.

Explore a wine cellar in Montepulciano with this tasting and tour . See rows of large oak barrels full of aging wine and learn about how it is made. Taste three local wines alongside pecorino cheese, Tuscan salami, and bruschetta.

Accommodation in Montepulciano:  Etruria Resort & Spa – splurge a little on this lavish oasis in Tuscany

Val D’Orcia

Montepulciano makes for a great base from which to drive out into some of the most spectacular Tuscan countrysides in the region. Val D’Orcia is a long valley that leads towards the city of Siena, and the best part of driving through this part of Tuscany is the landscapes.

You’ll be stopping on the side of the country roads to photograph the incredible scenery, calling in at small villages and rural farmsteads and enjoying the great, open air.

This is your Tuscany road trip at its best, so just enjoy the drive and enjoy the outdoors.

The next destination on the Tuscan road trip itinerary is Siena. This is one of the larger cities in Tuscany, and also one of the most historic. Siena is one of the highlights of any Tuscan road trip, but you won’t be driving through the narrow, maze of cobblestoned streets, you’ll be walking.

Siena is famous for its twice-yearly Palio, a horse race through the city itself, and if you can time your trip with a visit to this cultural festival, then you’ll see one of the most fascinating spectacles in Tuscany.

Any time of the year though, the Renaissance architecture is, with numerous Palazzos and Duomos waiting to be explored.

Indulge in one of Italy’s most beautiful cities, Siena, during this sightseeing tour . An expert guide gives you an insider’s view of this UNESCO World Heritage-listed town. Linger for a while in Piazza del Campo, the superlative square that is home to the Palio, a wild horse race that takes place every July and August. Stroll the streets with your guide learning about the history of the place.

Accommodation in Siena:  Hotel Athena Siena – great parking and location

San Gimignano

San Gimignano is a small town with a huge reputation because the extensive medieval walls are some of the best-preserved in Italy. The town is found atop a high hill, making this a dramatic sight to see as you drive towards the gates.

Inside San Gimignano, you’ll find even more medieval architecture, as towering above the walls are 14 stone towers, raised high to protect the town against attack.

There are few towns in Italy with such a high number of surviving towers, and this really is a must-visit stop on your Tuscany road trip. Most tourists just pass through, but hang around, spend the night and see the city without the crowds early in the morning.

Accommodation in San Gimignano: Leon Bianco – great breakfast and location right in downtown

From San Gimignano, it’s a one and a half-hour drive to the coast, where you can explore a different side of Tuscany in Livorno. This is an important port city, and you can enjoy some of the best seafood in Tuscany along the waterfront.

Using Livorno as your base, you can drive out along the coast in search of hidden beaches and secret spots, alongside superb views out over the sea.

There are many ways to discover coastal Livorno’s charms and a private walking tour of the city’s central market is certainly an engaging way to explore. Meet your guide at your local accommodation or near your port, and set off for the Mercato Centrale one of Europe’s largest markets.

Accommodation in Livorno:  Hotel Villa Margherita Livorno – great views and a nice pool

The final stop on your Tuscany road trip will undoubtedly need to be Pisa. Despite its huge popularity amongst tourists and despite the crowds, it’s still a must-visit destination, if only to take a picture of yourself posing in front of the iconic leaning tower at the end of your trip.

Aside from the tower, Pisa also has a wealth of largely ignored Renaissance history, museums, and galleries too, alongside a great culinary scene. From Pisa, it’s a one and a half-hour drive to Florence, where you started the road trip.

Explore Pisa without the hassle of planning on a walking tour of the city’s highlights , from the Square of Miracles to Pisa Cathedral. In addition to navigating, your guide offers little-known facts and anecdotes about Pisa’s ancient history.

Accommodation in Pisa:  Grand Hotel Bonnano – beautiful rooms and good location

Recommended Multi-Day Tuscany Tours

If renting a car in a foreign country is not your thing, no worries! It is possible to join one of several amazing tours that will take you to all of the above places we mentioned and more. 

• G Adventures Local Living Italy Tuscany- If you’ve ever wanted to forge a deeper bond with a destination, this is your chance. Centered in San Gimignano, this Local Living adventure places you in the heart of central Tuscany. You’re free to explore the town, visit vineyards, discover medieval highlights, or embrace your inner artist wandering the Tuscan countryside. If you’re looking for a deeper dive into Italian cities, there’ll be day trips to visit Siena and Florence. You’ll share the main accommodation with like-minded travelers and a CEO there to point you in the right direction. Prepare to fall in love with Italy.
• G Adventures Wellness Italy – If serenity has a palpable form, surely it can be found under the Tuscan sun. This seven-day tour of Italy will have you second-guessing your departure date from the moment you land in Rome. After a morning yoga session and a leisurely day on the grounds of Palatine Hill and the Colosseum, your path will take you to lush landscapes of Tuscany. There, you’ll have ample time to saunter through welcoming villages, taste exceptional local food and wine, and cycle your way through the Tuscan hills. A dip in healing thermal waters will leave a rejuvenating warmth radiating through both body and mind long past your final stop in Florence.
• Best of Italy Summer (Start and end in Rome! With the in-depth cultural tour Best of Italy Summer, you have a 13 day tour package taking you through Rome, Italy and 12 other destinations in Italy. Best of Italy Summer includes meals and more.)
• Taste Of Italy (Start and end in Rome! With the discovery tour Taste Of Italy – 8 Days, you have a 8 day tour package taking you through Rome, Italy and 9 other destinations in Italy. Taste Of Italy – 8 Days includes accommodation as well as an expert guide, meals, transport and more.)
• The Italian Dream (Start and end in Rome! With the coach/bus tour The Italian Dream, you have a 8 day tour package taking you through Rome, Italy and 7 other destinations in Italy. The Italian Dream includes accommodation in a hotel as well as an expert guide, meals, transport and more.)

More on Italy:

• Ultimate Italy Travel Guide
• Ultimate 10 Day Italy Itinerary
• 15 Easy & Amazing Day Trips From Venice
• 3 Days in Rome: Things To Do in Rome
• 10 Best Day Trips from Rome Worth Taking
• Rome to Pompeii: The Best Way to Make it Happen
• 3 Days in Florence: What to do in Florence
• Best Day Trips from Florence: Our Top Recommendations
• 5 of the Best Places to Visit in Italy

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Travel planning resources, about lina stock.

Lina is an award-winning photographer and writer that has been exploring the world since 2001. She has traveled to 100 countries on all 7 continents. Member: SATW, NATJA, ATTA, ITWA

3 thoughts on “Tuscany Road Trip Itinerary: The Best of Tuscany”

Epic pictures and well written!!! Thank you for sharing 🙂 Now I need to go back to the places I missed … Thank you for sharing!

You’re welcome! Glad you found it useful. Tuscany is an incredible place to visit.

Arezzo is my favourite among the listed; though I have not visited all. I would really recommend visiting Poppi for tasting the delicious Tuscany wine there!!!!!!!! Really had an awesome time there. Lina, you could have included Poppy too to this awesome article. Otherwise awesome! You have succeeded in drawing the splendid beauty of the places in the article. Thanks Lina.

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The ultimate road trip around Tuscany, Italy

By Toby Skinner

Somewhere beyond the medieval citadel of San Gimignano , I shift the Aventador’s paddle gears down to second and wait for the apex-predator roar as the RPM needle spikes furiously. I am not a Car Person, and never knew quite how glorious this would be, driving a real-life Top Trump.

Part of my prior suspicion of Lamborghinis stemmed from seeing them in West London , where they appear like Siberian tigers trapped among the marbled terraces. In the big city, the gull-wing doors seem absurd; the window to the ludicrously powerful engine like some faintly indecent peephole.

Pictured: room keys at Castello di Casole

But here on a warm September day, this immodest future-machine feels right somehow, even on narrow streets watched over by coy Renaissance torsos. Not far from Florence , an old lady waves her handkerchief as if greeting the pink jersey of the Giro d’Italia, and at a roundabout near hilltop Ulignano, a group of children cycle alongside, giving thumbs-ups and approving devil signs.

In Monticiano, a silent little town of thermal waters, rusting Fiat Pandas and war statues, some old boys leave their espressos on Formica tables and come to mutter and point. It’s as if these people are appreciating one of the Big Five, except that in Italy it’s really the Big Three of Lamborghini, Maserati and Ferrari. Rather than envy, there seems to be a collective pride in these marques; their almost sculptural creations, and the very human stories behind them.

Ferruccio Lamborghini was the son of grape farmers who struck it rich making the tractors that fuelled Italy’s post-war agricultural boom. He turned to cars in 1963, and initially produced sleekly curved touring models until a group of engineers went off-piste in 1966 with the muscular Lamborghini Miura, widely considered the world’s first supercar. It was the engineering of speed that always fascinated Ferruccio.

Pictured: the gardens at Villa San Michele

And for all that his cars became increasingly ostentatious, at heart he remained a country boy, eventually retiring to hunt on his vineyard near the village of Panicale. This is perhaps why the Aventador makes so much sense on a tour of Tuscany . My route is a figure of eight around two Belmond hotels: Villa San Michele , once a Franciscan monastery, in the Fiesole hills overlooking Florence; and Castello di Casole , a 10th-century Etruscan castle with its own medieval hamlet.

Pictured: a view at Villa San Michele

At the end of one day, I stop at the Tenuta Torciano winery to hunt truffles with Adolfo Moreno, who looks a bit like Stanley Tucci but with tattoos suggestive of a backstory. Later, we eat Nonna Giachi’s pancotto soup and lasagna with a roll call of Chiantis served by almost as many members of the Giachi clan, who all seem to wear Rolexes and have a list of metaphors linking wine and love-making.

Pictured: Roccia d’Orcia

It’s almost too much; a bit Peak Tuscany, like later watching the pinkish sky over the village of Casole d’Elsa from Castello di Casole’s pool. But, then, when you’re behind the wheel of a Lamborghini Aventador, nothing is too much.

Pictured: a bedroom at Castello di Casole

CNT Editors

CNT Editors , CN Traveller

The next morning, it growls down the hotel driveway, lined by tall, narrow cypress trees. I have to press a button so the nose of the low-slung machine can clear the speed bumps. It seems to strain at some invisible leash.

Pictured: the Lamborghini at Castello di Casole

At the end of the lane, we turn towards Florence and I put my foot down, ready for a roar I’ve become oddly addicted to. In this place, in this big beast of a car, it seems like the only proper thing to do.

Ultimate Driving Tours offers a five-day Tuscany Self-Drive from £3,490 per person, including a choice of car, visit to Torciano Vineyard and stays at Belmond Hotels. ultimatedrivingtours.com

Keep scrolling for more images from this Tuscany road trip

Like this? Now read:

Things to do in Florence, Italy

The 11 prettiest small towns in Italy

The most beautiful places to visit in Tuscany

Balcony at Villa San Michele

A room at Castello di Casole

The Lamborghini at Castello di Casole

A fireplace at Castello di Casole

Bar Visconti at Castello di Casole

A bust at Villa San Michele

Castello di Casole's exterior

Statue at Castello di Casole

Best Places to Visit in Tuscany

J oin EuropeUpClose as we take a journey to some of the best places to visit in Tuscany. We will begin in Florence, then drive to San Gimignano with a stop at the fabulous Antinori nel Chianti Classico Winery. From San Gimignano we venture to the compelling town of Siena with its fantastic cathedral and famous horse races in the Palio. Another hour south and we’ll stop at Caparzo Winery near Montalcino before heading east to the beautiful hilltop walled city of Montepulciano.

Also read these articles on Tuscany:

• Best Tuscany Wine Tours
• Where to Stay in Tuscany
• Tuscany Holiday Planning
• Tuscany Itinerary

Visit Florence

Florence is a natural starting point to begin your journey to the best places to visit in Tuscany. Known for the imposing red-roofed Duomo and Michelangelo’s David in the Accademia, Florence is a mecca for art, food, architecture, and history. You don’t want to miss the Uffizi Museum, the Central Market, and Ponte Vecchio, the bridge across the Arno River filled with shops displaying jewelry, crafts, and other fun products.

Also, read these articles on Florence:

• Where to stay in Florence
• Best Florence Walking Tours
• Best things to do in Florence
• Best Day Trips from Florence

Florentine Bisteca

And, of course, if you are in Florence, you must try the famous Florentine Bisteca. It is often referred to as some of the best steak in the world. We were lucky to have reservations at Trattoria dall’Oste Chianineria on  Via dei Cerchi. Just a few minutes south of the Duomo, this iconic restaurant is well known for their Bisteca and other fine cuts of meat.

Florentines do like their steak rare, so be aware. You can order yours medium or medium rare, and it will most likely still come out very pink. One thing I liked about Trattoria dall’Oste Chianineria is that they brought out a hot plate along with the steak. That way, anyone who wanted their steak more done could cook it a bit more right at the table. Most of us ate it like it came, but there were a few in our party who preferred their steak more done. Sides included roasted potatoes, pasta with thinly sliced truffles, and some tasty bruschetta. For dessert, we completed our meal with a glass of Vin Santo served with tasty biscotti.

Wine Tasting and Lunch at Antinori Winery

With options of several great Antinori locations, we chose to tour the Antinori nel Chianti Classico vineyards just 20 minutes south of Florence. In a country where wine is a way of life, for twenty-six generations, the name Antinori has stood out.

We booked the special CRU Tour. This included a tour of the winery, a wine tasting of seven great wines, followed by a delicious lunch. This fully immersive experience featuring the wine-making philosophy of Marchesi Antinori following years of family tradition. Led by our outstanding sommelier, our tasting was held inside the fabulous wine cellar. Then we enjoyed lunch on the outdoor patio at the Rinuccio 1180 restaurant. This modernistic rooftop restaurant overlooks the gently rolling hills of the scenic Tuscan countryside.

Some of our favorite wines included a crisp Cervaro Della Sala Blend of Chardonnay and Grechetto and a Tignanello red blend of Sangiovese, Cabernet Sauvignon, and Cabernet Franc. The crowd favorite was the outstanding Brunello di Montalcino Pian Dellevigne Sangiovese. The following lunch on the beautiful outside terrance at Rinuccio made for a most pleasant day. This special vineyard among special vineyards in Tuscany is certainly worth a visit.

Explore the Hilltop Walled-Town of San Gimignano

After being totally wowed by Antinori nel Chianti Classico, we headed south to nearby San Gimignano. This was our third visit to this iconic Tuscan town – and we will be back again. No article about best places to visit in Tuscany would be complete without this idyllic town.

We stayed at the cozy Orto di Emma at Piazza delle erbe 4 . The location is conveniently in the middle of this walled city. Restaurants, spectacular views, and attractions are just a few steps away. Without any train station in town, most visitors come via personal car or with a tour group. There is a bus that comes from the closest train station (~ five miles away), but check the schedules.

Eat at Fuoriluogo Ristorante

Fuoriluogo Ristorante is a wonderful family restaurant just a two-minute walk outside the walls. In addition to having wonderful food, the service, the artwork, and the friendliness of Mauro, Davide, Enrica, Christian, and the rest of the staff are all top-notch. It’s no wonder Fuoriluogo is one of the highest-rated restaurants in San Gimignano.

Mauro was gone for important meetings with Barolo. He continues to work on the fine wines the restaurant offers to diners. In his absence, the rest of the staff did a superb job of welcoming us and making us feel so special. Our outstanding waiter, Rafael, kindly suggested a recommended menu along with wine pairings, and we were so glad we agreed to take his advice. Julie and I enjoyed a fantastic meal with just the right wines paired with each dish.

Favorites included the Wild Boar Ravioli with citrus fruits in a saffron cream sauce, and a delectable Soft Organic Egg with sausage, red peppers, and gorgovino mousse. We also both loved the pizza, some of the best I’ve ever tasted. The light, tender crust had just the right flavors to complement the fresh tomatoes, cheeses, and fresh herbs. For dessert, we could not resist the tempting tiramisu.  

In addition to the fantastic food and service, the artwork and ambiance of Fuoriluogo is superb. Davide is a wonderful artist and painted much of the beautiful artwork in the restaurant. The friendly staff, elegant but comfortable ambiance and outstanding food and drink make Fuoriluogo one of the top restaurants in San Gimignano.

Check Out Intriguing Siena

It was hard to leave San Gimignano, but we had Siena waiting for us. The charming walled city of Siena is famous for its beautiful cathedral and for the exciting Palio di Siena Horse Races held twice a year in the large central Piazza del Campo. We unfortunately just missed this exciting event. It normally takes place twice a year on July 2 and August 16 every year. Preliminary events take place the three days before the official race. Since this is a very popular event, plan early if you want to attend during the races.

Following lunch on the lovely outdoor terrace at ViVace Ristorante and Wine Bar , we walked the short 10 minutes to the beautiful gothic Siena Cathedral. This impressive structure was built between 1215 and 1267 and features artwork from artists like Michelangelo, Donatello, and Pisano. With its iconic greenish-black and white stripes, this historic icon is striking inside and out. Other great attractions in and around the cathedral include the Piccolomini Library, the Museo dell ‘Opera, Baptistery, Crypt, Oratory of San Bernardino, and Diocesan Museum of Sacred Art.

Drink Brunello Wines at Caparzo Winery in Montalcino 

With so many outstanding wineries around Montalcino, we picked Caparzo Winery to have a tasting and to explore. My new daughter-in-law became acquainted with Caparzo while watching the fun Letters to Juliet movie from 2010. There are some scenes in the movie from one of the many Caparzo winery locations in Tuscany. We thoroughly enjoyed our tour and tasting at Caparzo Winery, especially their world-famous Brunello di Montalcino. An added bonus was the spectacular scenery on our road trip from Montepulciano to Caparzo. Located in the picturesque hills of Montalcino, with fields of red poppies next to golden fields of wheat blowing in the breeze. 

Eat and Drink your Way through Montepulciano

So, after visiting the walled cities of San Gimignano and Siena, we had another walled hilltop city on our itinerary: Montepulciano. Our return to this fantastic village was equally full of great food, wines, views, history, and special people of the town. This very walkable small town is anchored by the Grand Piazza, and is famous for its Vino Nobile red wines . Another notable landmark includes the Torre di Pulcinella. This clock tower is topped by the whimsical figure of the Pulcinella, a classical comedic character. 

We also found the “underground city” of this hill town fascinating. Miles of tunnels, rooms, and cellars have been carved into the rock underneath Montepulciano, making for a fun and educational tour. We went to the popular Cantina Ercolani for a tour and wine tasting. Other popular wineries in Montepulciano include Cantucci Winery and Cantina de‘Ricci. 

Eat at L’Altro Cantuccio Ristorante

L’Altro Cantuccio Ristorante is a fabulous family-run restaurant just a few minutes’ walk from where we stayed at the lovely Montepulciano Bed & Breakfast at Via Di Gracciano. Chef Mattia Putzulu and his lovely wife, Monica, a Sommelier, have created one of the best dining experiences in Montepulciano. L’Altro Cantuccio exudes old-world charm. Modern appointments along with the historic stone, wood, and brick is the perfect blend of old and new. 

Mattia and Monica graciously hosted us for an extremely memorable evening. For starters, we enjoyed an outstanding Tuscan and Cinta Senese salami, Pecorino cheese of Pienza, and a selection of homemade fruit mostarda. Our server also brought a stuffed golden tomato held by a sculpted hand along with an excellent 100% Sangiovese wine. 

For my main course, I had the Cheek of Chianani Beef cooked for 50 hours, with spicy vegetables, citrus fruits, and dill. The beef cheek was extremely tender and flavorful. It was one of my favorite dishes during our three-week visit to Europe. My wife had the equally excellent grilled Chianani flank steak. Other enticing mains on the menu included the Lamb with ember, coconut, mint, and radish, and a crispy salt cod with artichokes and burrata cheese.

Dessert was the amazing Underworld, an artistic and decadent concoction of chocolate mushrooms, acorns, and undergrowth – a true masterpiece! Each bite brought out the intense flavors of chocolate, cream, and nuts. I would loved to have brought one back to the states to share with family and friends, but I don’t think it would travel well (plus, I would probably eat it all before our return!).

L’Altro Cantuccio has deservedly earned its reputation as one of the top restaurants in Montepulciano. Do yourself a favor, and let Mattia and Monica treat you to a fantastic dining experience in their lovely hilltop restaurant.

Discover Top Places in Tuscany For Yourself

Obviously, there are so many great places to visit in Tuscany that no one article can capture them all. Many are relatively unknown and just waiting for you to discover them. We hope by introducing you to just a few of the many options you will be inspired to come visit for yourself. Tuscany is indeed one of Italy’s treasures and should not be missed on any Italy itinerary .

Best Places to visit in Tuscany was written and photographed by Scott Kendall for EuropeUpClose. Thanks to our gracious hosts, including Fuoriluogo Ristorante and L’Altro Cantuccio. All opinions are those of the author.

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