19 Best Tuscan Towns to Visit in Italy in 2024

Tuscany is a vision. The green rolling hills, towering cypress trees, curvy roadways and those beautiful Tuscan towns.

The best way to explore Tuscany is by car. Driving through the countryside going from one Tuscan town to the next.

With so many places to visit in Tuscany, how do you choose which ones? That’s where I come in, your travel expert who’s been travelling to Europe for over 35 years. I’ve been to my fair share of small towns and cities and know exactly how to spot one that’s worth visiting.

Here are the best towns of Tuscany to visit. Some you’ll recognize from other ‘Tuscany Best Towns’ lists, others you won’t. As a holidaymaker who likes to find hidden gems, I will always seek out those places that are under the radar and off the beaten path. If you do too, you’ve come to the right place.

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19 Best Tuscan Towns to Visit

1. Arezzo is a treasure hunter’s delight

Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Arezzo is an ancient Etruscan city that is older than Alexandria in Egypt making it one of the top towns to visit in Tuscany.

Mostly developed in the 9th century, wander the historic centre and admire the medieval details. The balconies, lanterns, courtyards and all of its lovely alleyways.

Arezzo is so charming it served as the backdrop to one of my favourite movies Life is Beautiful. When I found that out, I knew I needed to visit here!

My recommended tips for visiting Arezzo:

  • Shop! Visit the chic boutique shops and the well-known monthly antique market held on the first weekend of every month (it’s a bucket list experience!)
  • Explore the old historic centre, with notable landmarks of San Francesco Basilica (seen in the movie The English Patient), and the stained glass windows of the Cathedral of San Donato
  • Try my favourites, restaurants Caffe Vasari or Chiave D’Oro
  • Market day is on Saturday

2. Cortona is made for strolling

Perched on top of a hill, Cortona is an ancient walled town with lively piazzas, endless winding alleyways and many churches. Cortona lies in the Chiana valley of southern Tuscany in Italy

Cortona looks and feels a bit different than the other towns in Tuscany.

This hilltop is an elegant stone-clad town from the 13th century with a larger and busier piazza and an endless amount of winding streets chock-full of dreamy places to stay.

If you are a fan of Under the Tuscan Sun, first, the book then the movie you’ll know the town of Cortona was where it all started. That was my reason for going here and so glad I did, without a doubt, this is one of the best towns to visit in Tuscany.

My recommended tips for visiting Cortona:

  • Admire the Etruscan wall, the noteworthy Church of San Francesco and the Museo dell’Accademia Etrusca
  • Shop for local artisanal products like ceramics, leather goods, and wine
  • I ate at La Buccaccia, Osteria del Teatro and Enoteca Molesini
  • Market day is Saturday

3. Lucignano is known as the Pearl of the Val di Chiana

tiny alleyway with red brick houses in tiny town in tuscany

Lucignano is an under-the-radar hilltop town overlooking the beautiful Val di Chiana.

As one of the best-kept secrets of towns to visit in Tuscany, Lucignano receives very few tourists.

It’s one of those must see Tuscany towns to visit if you love nothing more than an authentic experience. That’s why I went here.

My recommended tips for visiting Lucignano:

  • Grab an ice cream at Gelateria Snoopy and wander the town
  • Admire the scenic views of the beautiful countryside
  • I ate at Zenzero, and think you should too
  • Market day is Thursday

4. Montalcino is famous for its wine

Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Montalcino is one of those beautiful villages near Siena that is worth visiting. With its hilltop views and a medieval town centre full of well-preserved buildings dating back to the 13th century.

This Tuscan village is famous for its delicious Brunello di Montalcino wine produced using grapes from the surrounding vineyards. 

My recommended tips for visiting Montalcino:

  • Do a wine-tasting in the fortress of Montalcino where you can sample most of the nearby producers at once, it’s an unbelievable experience you won’t want to miss
  • Explore the historic centre including the church of Sant’Agostino
  • Market day is Friday

5. Montefollonico is off the beaten path


This under-the-radar village is passed by most tourists en route to Pienza. But don’t.

If you want to see what a peaceful village life might be like, take a detour and go here. The pretty narrow streets in Montefollonico are impressive.

Red and yellow brick, shuttered windows and flower-filled iron balconies, this is a tranquil way of life.

My recommended tips for visiting Montefollonico:

  • Get lost in the tiny streets
  • Explore the fortified defence wall from the 6th century, the Romanesque church of San Leonardo, and the church of San Bartolomeo from the 12th century
  • I ate at La Botte Piena and it was delicious of course
  • Market day is Tuesday afternoons

6. Montepulciano is for wine lovers

Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Montepulciano is one of Tuscany’s prettiest towns and is known for its wine. It’s also one of the top Tuscany towns to stay in.

Wine enthusiasts will love sampling the latest vintage of Brunello wines in the cozy wine-tasting cellars.

The walls surrounding this medieval town date back to the 14th century and this is one of the best small towns in Tuscany to visit.

My recommended tips for visiting Montepulciano:

  • Admire the main square made of Travertine and the Duomo
  • Sip on some wine in a cozy wine-tasting cellar like La Gatta Vecchia (my fave)
  • I ate at Osteria l’Aquachetta and La Grotta and they were the highlights of my trip
  • Market day is Thursday

7. Monteriggioni is known as the stone crown

stone village with olive tree in one of the most beautiful towns to visit in tuscany

This hilltop village can be seen from afar. The stone wall that encircles the town resembles a stone crown. It’s one of those small towns near Siena Italy that can easily be added to your itinerary.

Monteriggioni is considered one of the oldest towns in Italy. Records show that it has been inhabited since the 8th century. History buffs, this is one of the best towns in Tuscany to add to your list.

My recommended tips for visiting Monteriggioni:

  • Tour the Monteriggioni castle, founded in 1220
  • Admire the views from the 14 towers found within the fortified wall

8. Monticchiello is known for its theatre

cypress trees, road and valley in tuscany

Monticcheillo is a hidden gem in Tuscany.

This small authentic village dates back to Etruscan and Roman times as a former crossroads connecting other nearby cities. You can still see the medieval wall and fortress protecting the city from afar.

My recommended tips for visiting Monticchiello:

  • Attend the annual Teatro Povero di Monticchiello, a unique outdoor theatre festival in August
  • Explore the castle and walls of Monticchiello and admire the scenic views
  • Relax at the nearby thermal baths of Bagno Vignoni
  • The restaurant that caught my was La Porta, but I didn’t eat there

9. Pienza is famous for its pecorino cheese

Pienza is a hilltop Tuscan town located in the region of Val d’Orcia of the province of Siena. This romantic town offers visitors panoramic views of the beautiful Tuscan countryside in Italy.

The hilltop town of Pienza is a well-preserved UNESCO-designated Renaissance town that has been virtually untouched since the 15th century.

As one of the most beautiful towns in Tuscany, the biggest draw is the scenic views of the Val d’Orcia countryside and the Pecorino di Pienza cheese.

My recommended tips for visiting Pienza:

  • Stroll the incredibly romantic streets with names Via dell’Amore (or Love Street) and Via del Bacio (or Kiss Street)
  • Visit the main square with the important landmarks of the three Palazzo and the Cathedral
  • I ate at the delicious La Bandita Town House Caffe
  • Market day is Friday 

10. San Gimignano is known for its towers

tower over walled city as one of the best tuscan towns in italy

San Gimignano is one of the most beautiful towns in Tuscany, and the most recognizable.

This UNESCO-designated hilltop town is famous for its towers that can be seen off in the distance. Dubbed the ‘Medieval Manhattan’ 13 of the 65 towers survive today making it one of the best towns near Siena Italy.

My recommended tips for visiting San Gimignano:

  • Visit the 15th-century Cathedral, considered one of the best in Tuscany
  • Climb the Torre Grosse, the tallest tower in San Gimignano, built in 1311
  • Wander the Palazzo Comunale, home to a museum and art gallery
  • Market day is Thursday and Saturday

11. San Quirico D’Orcia is famous for not being famous

rolling green hills in most beautiful town in tuscany

One of the best towns to visit is one that no one knows about.

San Quirico has one of the most beautiful countryside and the drive to visit this town is worth it. The historic centre is authentic and beautiful and you won’t find a tourist in sight.

My recommended tips for visiting San Quirico:

  • Get your cameras ready, as the scenic drive to the San Quirico area is sublime
  • Beautiful garden in the centre of town
  • Market day is the 1st and 4th Tuesday of every month

12. Siena is known for its impressive historic sites

Siena is a medieval walled city in Tuscany Italy. The best places to visit in Siena are Piazza del Campo, Siena Cathedral, historic city centre with its winding alleyways from the middle ages.

Siena is a large medieval Tuscan city that can’t be missed. As far as cities in Tuscany to visit, this is by far one of the most popular.

The impressive historic city centre has many streets to simply get lost in. Admiring the well-preserved architecture makes you feel like you are stepping back in time, to 1300.

While the other best Tuscany towns that appear on this list can be experienced in an hour or two, Siena needs a full day to be explored, if not more.

My recommended tips for visiting Siena:

  • Visit the Piazza del Campo, considered to be one of Europe’s greatest medieval squares
  • Climb the Torre del Mangia, the oldest and tallest tower in Italy
  • Admire Italy’s most important religious buildings, the Siena Cathedral
  • Watch the Palio di Siena festival, the world-famous horse race played out in the piazza in July and August
  • Market day is Wednesday

13. Torrita di Siena is for history lovers

Some of the most beautiful places in Tuscany. Hilltop towns like Montalcino, Pienza, Montepulciano, Cortona, Arezzo and Siena

Torrita di Siena, not to be confused with the much larger city of Siena, is a charming sleepy village to visit while in the Siena area.

The origins date back to the Etruscan and Roman periods, and the historic centre makes you feel like you’ve stepped back in time as you access it through four medieval gates.

My recommended tips for visiting Torrita di Siena:

  • Visit the medieval Torrita Castle from the 13th-century castle which also offers panoramic views of the surrounding countryside
  • The many churches, most notable being the Romanesque church of Sante Flora and Lucilla
  • Market day is every Friday

14. Florence is for art lovers

bridge with colourful buildings in the capity city of tuscany - florence

The capital city of Tuscany is one not to be missed! Florence in a day will be tough, but if that’s all you got, go for it! You don’t want to must one of the best cities in Tuscany!

This Renaissance Tuscan city has it all! From art, architecture, food, shopping, historical sites and even the most incredible sunsets. There are so many reasons to visit Florence.

It’s so chock full of important landmarks that it has earned UNESCO-designated status.

My recommended tips for visiting Florence:

  • Visit the well-known sites of the cathedrals like Santa Maria del Fiore, the lively piazzas like della Repubblica and the palaces like Palazzo Vecchio
  • Tour the Uffizi Gallery, Italy’s (and the world’s) greatest art museum where you can admire masterpieces by Michelangelo and Da Vinci, and Botticelli’s “Birth of Venus
  • Watch the sunset from the best vantage point of Ponte Santa Trinita
  • Eat at the food hall of Mercato Centrale

15. Barga is for nature lovers

view of houses with red clay rooftops with mountains in tuscan town of barga

Barga is nestled in the majestic Apuan Alps.

If you love the mountains, then this best town in Tuscany you’ll want to visit. So much so, that it has been rated as one of the most beautiful villages in Italy.

My recommended tips for visiting Barga:

  • Tour the medieval castle with three gates leading you to scenic views of the town
  • Get lost in the web of winding ancient streets leading you to different piazzas and notable churches, as well as the 15th-century Conservatorio di Santa Elisabetta used to educate young girls
  • Market day is Saturday

16. Lucca is known for its churches

white building and tower in the beautiful town in tuscany

Lucca is a popular city to visit in Tuscany and on most people’s list of unmissable towns in Tuscany.

Nicknamed a town of 100 churches, there is of course more to this beautiful fortified city. Tall houses and pretty squares, and lots of options for eating and drinking.

My recommended tips for visiting Lucca:

  • Visit the fortified wall of 4 km featuring 10 bastions that you can walk along the top for the best vantage point in the city
  • Go to Piazza dell’Anfiteatro which was once a Roman amphitheatre – this lively square is a great place for people watching
  • Dine at Antico Caffe Della Mura, Da Leo, and La Nina to name a few
  • Market day is Wednesday and Saturday

17. Pietrasanta is known as the city of marble

white marble church with white modern marble statue in tuscan town of pietrasanta

A medieval city is known for being the capital of marble production.

This white city is full of marble facades and sculptures. Pietrasanta acts like an open-air museum with marble works of art dotted around the town.

By artists, it has been nicknamed ‘Little Athens’ due to the high concentration of artists who live and create here.

My recommended tips for visiting Pietrasanta:

  • Tour a marble processing factory and learn how this centuries-old tradition continues
  • Wander through the town admiring the contemporary works of art on every street and square
  • Market day is Thursday

18. Pisa is famous for its leaning tower

leaning tower in pisa with white church and lawn

The Leaning Tower of Pisa is known worldwide and draws thousands of tourists just to take that iconic photo of the famous UNESCO site.

But the city of Pisa is so much more than that.

My recommended tips for visiting Pisa:

  • Admire the other important landmarks in Pisa like Santa Maria della Spina, Palazzo Blu, Camposanto Monumenale, Cathedral of Santa Maria Assunta
  • Visit the many Piazza including Piazza dei Cavalieri and del Miracoli
  • Walk along the fortified wall giving you a bird’s eye view of the city below
  • Relax and dine at Trattoria Sant’Omobono, La Pergoletta, or Pane e Vino

19. Volterra is a historic double-walled village

view from hilltop tuscan town of volterra with buildings and trees

The double walls that surround this medieval city from the 13th century create this cozy village feel.

Volterra is known for the manufacture of alabaster and that craftsmanship is still seen throughout the town today.

My recommended tips for visiting Volterra:

  • Wander the streets and admire the architecture and artistic heritage this town has including a Roman theatre, the cathedral of Santa Maria Assunta and the wide open piazzas
  • Visit a museum, I liked the one dedicated specifically to alabaster
  • Market day is Saturday

Where I Stayed to See Towns around Siena Italy

The Siena House is a large villa beautifully restored to accentuate the authentic Tuscan features with a modern twist.

Every window is strategically placed to highlight the mesmerizing panoramic views of the hilltop villages in the distance.

Siena House offers 4 large suites for guests with private quarters to living space, a mezzanine, an outdoor kitchen and a pool.

The hosts, Malvin and Amanda, are welcoming and make sure your stay is an experience to remember, and that includes a delicious breakfast.

As a Holidaymaker

As far as destinations go, Tuscany is perfect! It’s not easy to know where to go when an entire region is so incredible. Even if you are in Rome and want to visit Tuscany for the day you can!

I hope this list of the most beautiful towns in Tuscany has inspired your trip planning. I just know you’ll love all of these best villages in Tuscany as much as I did!