The Best Towns in Tuscany: Visit the Most Beautiful Towns on Your Tuscany Itinerary
There are some remarkably beautiful towns in Tuscany, and today we’re walking you through which Tuscan towns absolutely need to be on your central Italy itinerary. From medieval towns to red wine vineyards, let this travel guide take the guesswork out as you plan your next trip!
The Italian region of Tuscany is one of those places on earth that is just "as advertised." That is to say, it's a place that is a perennial tourist beacon, yet it still doesn't come close to disappointing visitors.
I don't mean to suggest that tourist beacons typically disappoint, but I would argue that they're not always as advertised. Something like the Leaning Tower of Pisa comes to mind as, when you arrive, you end up spending more time looking at people taking "leaning pictures" for Instagram than you do looking at the tower itself.
While Pisa and Florence are top places to go in Tuscany, there is so much more to this romantic region of Italy. From sightseeing to cooking in Tuscany, you can experience the best of Italy here. This is partly due to the size of the region, and the fact that many of the larger sized cities are really quite quaint, at least when comparing them to cities like Milan, Naples, or Rome.
Whether you are planning to visit the many charming towns Tuscany has to offer over a few days or a few weeks, then you’re going to want to plan in advance and decide what exactly will make your heart tick under the Tuscan sun. We’ve done our best to outline all of the best ways to approach your trip to the region, so make sure you read through to the end to discover what’s best for you.
If you’re planning a longer visit to Italy, don’t forget to check out our travel tips and guides to help plan an epic 10 day Italy itinerary, and one week in the Amalfi Coast.
Now that you are intrigued let’s take a look at some of the best towns in Tuscany to visit and what to do in each of these Tuscan villages and towns.
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Planning on Where to Base Yourself in Tuscany
On a visit to Tuscany, if you’re looking to see parts of the region over a few short days, your best bet is to likely base yourself in a larger Tuscan town. The most common place that tourists base themselves is Florence, followed closely by Siena. Both towns vary greatly in terms of their size and what they offer to tourists, so there isn’t necessarily one that is “better”.
I have to admit that despite Florence’s fame and popularity, I tend to gravitate more toward Siena. In my opinion it has more of a local, intimate feel than Florence. But each town truly offers different experiences, so read ahead through the full article so that you can learn more.
If you’re looking for more of a quaint “storybook” sort of setting along the lines of waking up in a small cluster of villas looking over olive groves or opening your accommodation’s shutters to reveal the 12th century streets of a walled town below, then you’ll likely want to look into staying in a smaller Tuscan town. Accommodations in and around San Gimignano, Chianti or Montepulciano would fit the bill nicely for this type of trip.
This type of travel may require a few more days to dedicate to exploring the region, arranging for a car rental and more careful planning, but if this is the quintessential Tuscan experience you seek, then the reward will be amazing.
If you’re looking to find the perfect place to stay in Tuscany, then there’s no shortage of options. Feel free to use the map below to help you plan for the best places to stay on your trip.
The Most Beautiful Towns in Tuscany to Visit
Picking the best small towns in Tuscany to visit on your trip is no easy feat, and that’s because Tuscany is remarkably beautiful.
It also depends on what you’re looking for—is the medieval history of Tuscany something you’re after? Are you merely looking to visit vineyards and try delicious wines? Are you keen to learn about Tuscany’s culinary delights through cooking classes or visiting olive groves and local markets? Or are you simply looking for the best towns in Tuscany to stay in for a few days?
In short, each Tuscan town and Tuscan village brings something different, so it’s largely a matter of which aspects of Tuscany you’re looking to experience.
Here are a few of my favourite spots in the region.
Siena
One of the best cities in Tuscany that is on the larger size, yet is still very quaint is Siena. To me, Siena is one of the most impressive cities in all of Italy, even if you’re just fresh from doing some Florence sightseeing, or other perhaps more popular Italian destinations.
As functional as it is picturesque, Siena has a charming, subtle confidence. We only were able to spend a handful of nights here, but I would have loved to spend more, just based on the vibe.
At lunch, we were dining on incredible lunches overlooking the main square, Piazza del Campo, then night would come and we'd be in the middle of a street party as rowdy as any in Europe. It seems like there's a street party just about every other night in Italy in the summer.
Alas, before I digress into a post about street parties, let me just say that Siena is a jewel, and I'd recommend it higher than almost any other Italian city. Namely, because the wine is good and reasonably priced, the food is delicious (particularly the salami and wild boar), and it's just downright pleasant.
It really seems like not much has changed in the last few hundred years. I can only hope that trend continues. It just may have ended up being my favourite city in all of Italy.
What to Do in Siena
Within the Piazza del Duomo, you will find the magnificent Cathedral of Santa Maria Assunta. It is one of Italy’s most beautiful Gothic cathedrals, and worth a visit inside or at the very least admire it from the outside.
You can’t go to Siena without soaking up the architecture and atmosphere in the Piazza del Campo, the main square in Siena. If you time your visit right, you may get to see the famous Palio di Siena (horse race) here. They take place in July and August each year.
For beautiful views of the city, climb to the top of the Torre del Mangia. The long climb will be worth it when you reach the top!
I think it’s fair to say that Siena is a city that needs to be prioritized on your Italy itinerary.
Monteriggioni
Monteriggioni is small, compact, and worth a visit on the way to other towns on the Tuscan route. It was one of the Sienese fortifications, which was built to keep Florence away from the heart of Siena. It is well worth the coffee break and the time spent walking along its fortification walls, making it a nice, quick stop on your trip.
On a humorous note, I distinctly remember the information sign outside initially referring to Monteriggioni as the "unconquerable castle," then going later to talk about all the many times it was conquered. I should also add that, as a literature major, I was pleased with the notion that this town is actually mentioned in the 12th century poem “The Divine Comedy” by Dante Alighieri.
It’s easily one of the most compact and endearing towns in Tuscany.
What to Do in Monteriggioni
Walking the castle walls of Monteriggioni.
You will of course want to visit the Castello Monteriggioni and walk on the walls overlooking the walled city. Walking through this medieval town will make you feel as if you have stepped back in time.
If you are visiting in July, you will be able to be part of the medieval feast, Monteriggioni di Torri si Corona. The streets are filled with people wearing medieval costumes, knights, musicians and more.
San Gimignano
A town has stood in place here since at least the 3rd century BC, and it's a absolute must-see.
San Gimignano is a UNESCO World Heritage Site with towers, churches, and piazzas galore, making it one of the best small towns in Tuscany. The problem is that many other tourists realize this, too. The town has three parking lots outside the walls to accommodate the masses, and masses there are.
What to Do in San Gimignano
Sam Gimignano is especially worth the visit if you traverse your way up Torre Grossa for some unstoppable views.
To avoid the crowds wander around on the side streets. It’s surprising how many tourists stick to the historic centre.
Taking a look at the San Gimignano 1300 exhibit is a good way to learn about the town’s history. There’s a large model of what the town looked like hundreds of years ago.
I'd recommend getting food elsewhere, as the prices reflect the tourist boom. Except for gelato, that is! San Gimignano has some of the best gelato in the country. Gelateria di Piazza is world-famous, and offers very unique flavors.
If you choose to stay in San Gimignano during your time in Tuscany, you’ll have the luxury of enjoying it in the morning and the evening, after many of the day-trippers have left its medieval city walls.
Castellina in Chianti
Well there's no shortage of wine in Chianti, and I would have indulged in many more glasses had I not had to drive a Vespa home.
It is a beautiful town, and though it is the most off the beaten path, the area surrounding it is simply stunning. We putted along on our Vespa with the Tuscan sun pouring down over us, and rightfully said that there was no place we'd rather be.
What to Do in Castellina in Chianti
One of the highlights of visiting Tuscany is sampling as much red wine as is humanly possible. You won’t regret going to Poggio Amorelli for a wine tasting.
Sant'Agnese Farm is another good spot for wine tours and tastings. You can also taste their speciality balsamic vinegars, olive oils, honey and truffles.
Lucca
What makes Lucca one of the best towns to visit in Tuscany is its traditional renaissance town walls and architecture. The town walls are tree-lined, and make for the perfect place to stroll along. Really the whole town is very walkable.
Within the city’s walls you will find a city rich in history. It’s worth spending a night in Lucca to explore more, but if you are short on time, you can easily take a day trip from Florence.
What to Do in Lucca
The beautiful city walls of Lucca.
Many cobblestone streets within Lucca will lead you to Piazza dell’Anfiteatro where you will find restaurants, bars and shops. It is al-fresco dining at its finest!
Lucca is known for being the birthplace of the composer Puccini. An annual festival takes place in his honor. Concerts are also performed other times of the year.
Lucca’s city walls should of course not be missed. The 4km long walls are wide enough for walking or biking, offering beautiful raised views of the town and surrounding area below.
The city is often referred to as the city of 100 churches. There’s certainly no way to visit them all, but the church of San Michele is one of the most popular to visit.
Montepulciano
If you are searching for medieval towns in Tuscany, look no further than Montepulciano. The area feels like you have stepped into a fairytale. It’s hard to go wrong with wine in Italy, but Montepulciano’s wine, Vino Nobile di Montepulciano, is a cut above the rest. It is world-renowned!
This Tuscan village makes the perfect place to relax and enjoy the beauty of the village and the surrounding countryside while sipping wine.
What to Do in Montepulciano
Have a wine tasting at one of the local cantinas that store their wine.
There has not been any large scale building work done in Montepulciano since 1580! The red-brick and terracotta architecture is so impressive to admire as you wander around the town.
Some of the village’s most interesting and important buildings can be found around the main square, Piazza Vittorio Emanuele.
If you have any interest in the more gruesome side of medieval life, take a visit to the Museo della Tortura.
Livorno
Livorno, located along the western coast of Tuscany on the Mediterranean Sea, is quite different from the other Tuscan cities and towns on this list. As a port city, Livorno has a mix of new and old. While the seaport is modern, there are also medieval fortifications and cobblestone streets lining the city itself. It’s interesting to watch the happenings at the busy port, and then venture further into the city to check out the historical sights.
What to Do in Livorno
Walk through the grounds of Fortezza Nuova, which provided defense to the city starting in the 1500s. In addition to exploring the fort passages you can also enjoy views of the city’s canals from inside the walls.
Within the historic center take a boat trip on the canals. Many locals still use boats as transportation. It’s a charming area seeing all the boats outside of homes.
Shop at the over 200 shops and stalls of the central market, Mercato Centrale. Even if you aren’t hungry or looking to make a purchase, the market is a good way to experience local Italian life.
Florence
Arguably the most famous of Tuscan towns to visit on a trip to Tuscany, Florence is absolutely jam-packed with notable sites, historical artifacts and famous works of art.
Because of its fame, you’ll find that the city will be crowded no matter the time of year (but especially in the summer), and it’s recommended to book your entrance to famous museums and galleries, like the Uffizi Gallery, weeks in advance of your trip. If you arrive in Florence without a plan and would like to see Michaelagelo’s David, chances are you’ll be out of luck.
It’s a city well worth visiting though, despite its challenges of overcrowding at many points throughout the year.
What To Do in Florence
The most famous and popular attractions in Florence are likely the Uffizi Gallery and the Duomo, but there are countless other incredible attractions to visit, too.
The Ponte Vecchio Bridge is another famous site in Florence, set up with several historical shops along it. It’s recommended to walk along the Ponte alle Grazie bridge for a look at Ponte Vecchio from a distance.
Make your way across the Arno River to Piazzale Michelangelo for beautiful views of Florence and the surrounding hills from above.
Visit the Florence Leather Market, or a leather goods store. Florence is famous for its leather, and is an excellent place to buy a souvenir or functional gift here.
Consider visiting the Galileo Museum. Bri and I happened upon this museum by accident, and were so happy we did. It walks you through Galileo’s early scientific discoveries and tools, with exceptional displays showcasing them. If you’re interested in the history of map-making, or Galileo’s challenges that Earth was in fact, round, then this is definitely the museum for you.
You’ll Remember Your Visit to Beautiful Tuscany Forever
Once you’re able to visit the region, I’m sure you will agree that these are some of the most beautiful towns in Tuscany. While they vary vastly in size, history, culture and character, they each individually make up one of the most famous regions in all of Europe.
On your way through the beautiful towns of Tuscany, make sure you save some time to stop and admire the picturesque Tuscan countryside. One of the highlights of our time in Tuscany was using our Vespa to shoot around the countryside between each of these Tuscan villages.
Many of the local roads have turnoffs for viewpoints. But drive carefully and use your indicators—we witnessed an accident when a tourist slowed down without signalling to admire the view.
Whether you’re visiting from Greece or Ireland Italy is a special place indeed, and Tuscany is one of its absolute gems. Whether you’re planning on spending time taking cooking classes in Tuscany, or doing some typical Florence sightseeing while building out your Italy itinerary, you really can’t go wrong.
Until next time, ciao!
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