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19 Best Tuscan Towns to Visit in Italy

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 town to town is a highlight in itself.

With so many beautiful towns to visit in Tuscany, how do you choose which ones to visit?

Here are the best small towns in Tuscany to visit. Some you’ll recognize from other ‘Best Tuscan 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.

So, let’s go!

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Best Tuscan Towns

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

Tuscany is a part of Italy where life gets a little slower and much simpler. Let your passions be your guide when planning your trip.

Whether you’re a foodie and appreciate great food and wine. Maybe you love art history and architecture and want to see where the Italian Renaissance started. Enjoy cycling or maybe you are a sun worshipper and want to experience the Tuscan coastline.

Whatever the reason, you’ll find it all in Tuscany, plus a whole lot more.

Get out your map, and let’s start to plot the most beautiful towns in Tuscany to add to your road trip.

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Provinces in Tuscany

cypress trees, road and valley in tuscany

There are 10 provinces that make up the region of Tuscany. As you start to do your trip planning, choose only a couple of provinces that are in close proximity to each other to focus on. The region is larger than you think!

From the list of # Best Tuscan Towns- here is the list of provinces, and the recommended towns found in this article.

  • The province of Arezzo: Arezzo, Cortona, Lucignano
  • The province of Siena: Montalcino, Montepulciano, Monteriggioni, Pienza, San Gimignano, Siena,
  • The province of Florence the city of Florence
  • The province of Lucca: Barga, Lucca
  • The province of Pisa: Pisa, Volterra

Other provinces in Tuscany, but not the focus here are Grosseto, Livorno, Massa and Carrara; and Pistoia.

#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! 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 the movie Life is Beautiful. 

Things to do in Arezzo:

  • Shop! Visit the chic boutique shops and the well-known monthly antique market held on the first weekend of every month
  • Explore the old historic centre, with notable landmarks of San Francesco Basilica (seen in the movie The English Patient), the stained glass windows of the Cathedral of San Donato
  • Recommend restaurants Caffe Vasari or Chiave D’Oro
  • Market day is 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. Under the Tuscan Sun, first, the book and then the movie put this town on the map. It’s definitely one of the towns to visit in Tuscany.

Things to do in Cortona:  

  • Admire the Etruscan walls and the noteworthy Church of San Francesco and the Museo dell’Accademia Etrusca
  • Shop for local artisanal products like ceramics, leather goods, and wine
  • Recommended restaurants La Buccaccia or Osteria del Teatro or 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 a very authentic Tuscan town.

Things to do in Lucignano:

  • Grab an ice cream at Gelateria Snoopy and wander the town
  • Admire the scenic views of the beautiful countryside
  • Recommended restaurant is Zenzero
  • 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 a picturesque hilltop village with 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. 

Things to do in Montalcino:

  • Do a wine-tasting in the fortress of Montalcino where you can sample most of the nearby producers at once
  • Explore the historic centre including the church of Sant’Agostino
  • Market day is Friday

#5 Montefollonico is off the beaten path

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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.

Things to do in 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
  • Recommended restaurant is La Botte Piena
  • 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. Wine enthusiasts will love sampling the latest vintage 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.

Things to do in 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
  • Recommended restaurant is Osteria l’Aquachetta and La Grotta
  • 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. Monteriggioni is considered one of the oldest towns in Italy. Records show that it has been inhabited since the 8th century. History lovers, add this one to your list!

Things to do in 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 their theatre

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.

Things to do in Monticchiello:

  • Attend the annual Teatro Povero di Monticchiello, a unique outdoor theatre festival
  • Explore the castle and walls of Monticchiello and admire the scenic views
  • Relax at the nearby thermal baths of Bagno Vignoni
  • Recommended restaurant is La Porta

#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.

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.

Things to do in 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
  • Recommended restaurant is 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.

Things to do in 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.

Things to do in 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. It’s a very popular, and tourist favourite. The well-preserved architecture makes you feel like you are stepping back in time, to 1300 in fact. There are so many historic sites that this city needs to be explored for an entire day, if not more. The impressive historic city centre has many streets to simply get lost in.

Things to do in 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
  • Market day is Wednesday

#13 Torrita di Siena is for history lovers

Torrita di Siena is a charming and picturesque town with a rich history and cultural heritage. The origins date back to the Etruscan and Roman periods, with many historical landmarks waiting to be explored. The historic centre makes you feel like you’ve stepped back in time as you access it through four medieval gates.

  • 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. This Renaissance has it all! From art, architecture, food, shopping, historical sites and even the most incredible sunsets. This Tuscan city is chock full of important landmarks and has UNESCO-designated status.

Things to do in Florence:

  • Visit the well-known sites of the cathedrals of Santa Maria del Fiore, Campanile di Giotto, and Basilica Santa Croce, the lively piazzas of della Repubblica, Signoria, and Annunziata, and the palaces of Palazzo Vecchio, Strozzi, and Pitti & Boboli Garden
  • 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, Ponte Santa Trinita
  • Recommended restaurants include Vini E Vecchi Sapori, Osteria dell’Enoteca, Trattoria Cibreo and the lively 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 is a Tuscan town you’ll want to visit. So much so, it’s been rated as one of the most beautiful villages in Italy.

Things to do in 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.

Things to do in Lucca:

  • Visit the fortified wall of 4 km and features 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
  • Recommended restaurants include 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, its been nicknamed ‘Little Athens’ due to the high concentration of artists who live and create here.

Things to do in 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.

Things to do in 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
  • Recommended restaurants include Trattoria Sant’Omobono, La Pergoletta, 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.

Things to do in 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 the three museums, and one dedicated specifically to alabaster
  • Market day is Saturday

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.

Check prices and book your dates for Siena House

As a holidaymaker

As far as destinations go, Tuscany is the perfect one. It’s not easy to know where to go when an entire region is so incredible. Hopefully, this list of the most beautiful towns in Tuscany has inspired your trip planning. I hope you love these Tuscan towns as much as I do!

Other Italy inspiration can be found here…

Ciao

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