Tuscany is one of the most beautiful, most charming regions in Italy. Your trip can be about food, countryside, wine, culture, or nature. Everything is covered in Tuscany in the most amazing way possible. Discover the top 10 towns in Tuscany, from the beautiful Florence to the most hidden ones as Cortona. On our list, you’re going to find the most beautiful towns in Tuscany that you must visit!
Top 10 towns in Tuscany
So which are some of the most beautiful towns in Tuscany? If you’re visiting Florence, and you’re looking for the best towns in Tuscany countryside, where you could plan a day trip from Florence, we’ve got a separate post for that too! For now, you can see the prettiest towns, and some of the small towns in Tuscany to visit if you’ve got some spare time. Also, you can travel to these places by public transport, such as train or bus, but if you’ve got a car, that’s always the best and easiest way to travel around!
Our first on the list of 10 towns in Tuscany, is actually one of the best cities you could visit in Italy! Florence is the birthplace of the Renaissance, and the center of Italian culture and arts! Traveling to Florence and towns in Tuscany near Florence is really easy! Florence has an international Airport, the Amerigo Vespucci Airport, but you can also reach it by train or bus from Rome, Bologna, Milan, or Venice too.
One of the highlights of the city, and a reason why Florence is one of the best towns in Tuscany is the Cathedral of Santa Maria del Fiore. You can also climb up to the top of the duomo and enjoy a beautiful panoramic view, or visit Piazzale Michelangelo, and get an even better view over Florence and the cathedral.
Besides the many museums and art galleries, Florence is known also as one of the best shopping towns in Tuscany, since you can find anything from luxury to local artisan products. The Ponte Vecchio bridge, besides its beauty, is also known as the artisan bridge, where you can find many pieces of jewelry and leather shops with products made in the area. We also cover the best restaurants in Florence!
Siena is definitely one of the most beautiful towns in Tuscany! It’s just about 1.5 hours away from Florence, and it is definitely our second pick for the most charming towns in Tuscany! The town is located south of Florence and you can visit by car, bus, or train too!. It’s also close to making it a day trip from Rome!
Siena is also one of the best shopping towns in Tuscany, with many local products, such as truffles, wine, cheese, meats, but also ceramics. This Tuscan town is also the home of one of the most stunning gothic and renaissance pieces of architecture. The most important square of Siena is Piazza del Campo, that’s one of the largest and most significant medieval squares in Europe.
Besides the shell-shaped square, you can visit here the Palazzo Pubblico and the Tower of Mangia. Moreover, in Siena you can visit one of the most fascinating Renaissance cathedrals, the Duomo di Santa Maria Assunta, then try some truffles, wine, and other great local dishes! Make sure you check out the best hotels in Siena too!
3. San Gimignano
San Gimignano is definitely one of the 10 best towns in Tuscany that you should see! One of the prettiest towns in Tuscany, which stands still with its many towers on top of the Tuscan hills. If you’re looking for pretty hill towns, we’ve found San Gimignano to be one of the most breathtaking small towns in Tuscany Italy.
If you’re looking for day trips from Florence for example, and you want some towns in Tuscany near Florence, so you could reach them fast, San Gimignano is a top choice! mushrooms, cheese, great wine, and sweets. Moreover, you can find dozens of local shops to buy famous Tuscan olive oil, more wine, and ceramics. The ceramics are stunning!
Can’t be missed in San Gimignano:
While you’re roaming the cute town of San Gimignano, make sure not to miss this pastry and chocolate bar called Armando e Marcella. The story of this place is so beautiful on its own, that it just can’t be missed. This bar is a family-owned business, Armando e Marcella are those who opened it, and you can still find Marcella (who I’d say is around 80 years old) making amazing cappuccinos and serving their clients so fast, that a bartender in their 20s’ wouldn’t do it like her!
A local man recommended this place to us, and I must say that I have never had such a great brioche with cream, and brioche with chocolate as what they make! They also sell sandwiches, all types of sweets, but homemade chocolate balls (THEY ARE INCREDIBLE!) as well as homemade chocolate cream, hazelnut cream (better than Nutella!), and homemade pistachio cream! I spent more money shopping in this one bar than during my whole Tuscany trip! The charming town, the towers, the food, and this bar all together make San Gimignano definitely one of the best day trips in Tuscany!
Volterra is one of the most beautiful towns in Tuscany. A hilltop town that will make everyone fall for! If you’re looking for some of the most charming towns in Tuscany near Florence, Volterra is another of the greatest choices! Volterra is close to San Gimignano as well as to Florence. However, a car is really much helpful to have a comfortable trip.
Volterra isn’t as famous as Siena or San Gimignano, but it is definitely a stunning destination with an incredible panorama over the Tuscan hills. The best in this town is that it actually has these medieval vibes with dragon symbols around the town. Volterra’s historic center and these medieval vibes are absolutely fascinating, and sometimes you might find yourself looking if a knight covered fully in armor will show up on the next corner.
The town is steeped in mystic folklore, and those who loved the Twilight saga, I’d remind you, that the Volturi vampires had their residence in Volterra, while the town is also visible in the New Moon movie. Possibly the town was picked for the Twilight saga due to the many vampire stories originating from Volterra.
While you’re exploring this stunning town, make sure to stop by at the Alabaster Museum, and plan a lunch or dinner in the town, to try some delicious local dishes! If you like porcini mushrooms, the Risotto con Funghi Porcini is definitely something you want to try in Volterra!
5. Greve in Chianti
One of the top 10 towns in Tuscany is definitely Greve in Chianti! The land of the perfect grapes, vineyards, and the land of the most famous Italian wine, the Chianti wines. Definitely, Greve in Chianti is one of the prettiest towns in Tuscany that you should see! Actually, the whole wine region is great to be visited as a road trip, to explore multiple towns like Greve. You can add to your list Radda, Castellina, and Montefioralle.
The squat wine bottled held in straw baskets that are called a fiasco, you can recognize a Chianti wine easily, and no sommelier will pass the opportunity to explore the wine region for sure! To visit this area, the best is always by car, since the vineyards are spread in the area. Otherwise a bicycle or a motorbike.
Greve of also one of the best shopping towns in Tuscany when it comes to local wine, truffle, cheese, and meat products. Also, since the wine region is worldwide famous, you can expect to find some of the highest quality restaurants from Italy, that are usually serving traditional Tuscan dishes, many times with a modern twist. Anyhow, any foodie will definitely leave Greve with a happy stomach!
Montepulciano is another of the most beautiful towns in Tuscany that you must see! A prime example of Tuscan beauty! The medieval hill town is home to Renaissance buildings, a labyrinth of cobbled streets, beautiful churches, great food, history, and wine. Definitely one of the best small towns in Tuscany to visit!
If you want to think about day trips out of Florence, and you’re looking for elegant, yet rustic, beautiful locations, day trips to Tuscany countryside from Florence, we say Montepulciano. To be honest, the best is always to get a car, and travel around 5-10 towns in Tuscany during a trip instead of doing 1-1 random day trips, however, in each case, Montepulciano is one to consider.
For wine lovers a day trip from Florence to Montepulciano can be a perfect option, so you can visit vineyards, and try some of the most famous Italian wines that you’ve ever tasted. Since Montepulciano isn’t big either, if you’re in the area, you can combine a visit also to Cortona from here.
Cortona is definitely one of the most charming towns in Tuscany that you must see! It’s draped over the hillsides of the pre-Apennines on the eastern fringes of Tuscany, close to Siena. A stone-clad town topped with a beautiful medieval tower. Winding alleyways, cute streets, stunning main piazza, that’s all Cortona.
Cortona offers beautiful views over the beautiful Tuscan hills of Chiana Valley and Lake Trasimeno. Also, don’t miss the cute market between Piazza Garibaldi and the Cortona Cathedral over the weekend for red wine and lampredotto sandwiches!
Cortona is one of those small towns in Tuscany to visit, that became famous thanks to a book or a movie. You may have seen already, or read the book Under the Tuscan Sun? It was written by Frances Mayes, where she falls in love with the villa in Cortona and buys it. Well, if the book doesn’t help you imagine it, the movie will give you a glimpse of how Cortona is.
Here’s another of the most beautiful towns in Tuscany, and one of the best towns in Tuscany near Florence, Lucca! Lucca is a perfect choice for some of the best day trips in Tuscany. The medieval town center that’s really unique since it has a perfect round form, thanks to the buildings surrounding it.
While you’re in Lucca, you must explore some of the most stunning architecture, such as the Guinigi Tower. You can see on the top the holm oak trees that stand proud on top of the tower, that’s absolutely incredible to see! Also, the above-mentioned round square, Piazza dell’Anfiteatro is packed with lovely cafes and restaurants serving local dishes and wine.
You’d expect that Pisa should be higher on the list of the 10 towns in Tuscany, right? Well, even though the Piazza dei Miracoli is one of the most famous places in Italy, Pisa didn’t convince me enough to put it before the charming towns that I’ve listed above.
The Leaning Tower of Pisa is probably one of the most iconic landmarks not just in Italy, but the whole of Europe. If you’re looking for the best day trips from Florence by train, Pisa is always a winner, since you’ve got a direct line there.
The first thing to visit in Pisa is always the Piazza dei Miracoli, where you can find the Cattedrale Metropolitana Primaziale di Santa Maria Assunta (Cathedral of Pisa, or in Italian it’s also called Duomo di Pisa), with the stunning baptistery on the side, and the Leaning Tower of Pisa behind it. Though, if you want to visit Pisa, it’s always best to think about 2 destinations. A day trip to Pisa and Lucca from Florence could be a great pick for good day trips from Florence.
And the last one on the list of the best towns in Tuscany countryside is Arezzo! The hilltop town is easily reachable from Florence. It is definitely a must-see since, beyond the medieval architecture and stunning panorama, there’s also a Roman amphitheater to visit. Moreover, there are plenty of churches and a fortress as well to explore in Arezzo!
The stunning historic center, the Piazza Grande, is just stunning. Moreover, the Medici Fortress on the top of the hill is unmissable, also for the spectacular panorama that it offers. Definitely, a lot of good food, wine, and local delicacies are to be found in Arezzo, so everyone can satisfy their curiosity and stomach too!
Wrapping up the top 10 towns in Tuscany
We’ve covered the 10 most beautiful towns in Tuscany that you must visit. From the largest city, Florence, to the smallest yet most charming towns in Tuscany, everything has been listed for you! These are definitely some of the prettiest towns in Tuscany! If you ask me to pick, I’d say that my 3 favorites were Siena, San Gimignano, and Volterra! Florence is stunning on its own, but when you want to relax and enjoy some beautiful views over Tuscan vineyards, you want to go to places outside Florence!