The most beautiful villages in Tuscany to fall in love with

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Last Updated on April 3, 2024 by Laura Teso

The most beautiful villages in Tuscany? Well, I haven’t visited all the Tuscan villages (yet). And some of those I have visited, I haven’t explored properly, as they deserved, due to lack of time. Consequently, this list is to be considered a work in progress. I hope to update it from time to time to add other wonderful Tuscan villages that I will visit in the future, and hopefully, with more time.

The most beautiful villages in Tuscany

Siena area

San Gimignano 

San Gimignano is one of the most beautiful villages in Tuscany, loved by everyone for its splendid medieval towers. Just think that today only 13 of the original 72 remain standing. How cool must it have been with all 72! One of them can be visited thanks to the FAI, Torre e Casa Campatelli, and it allows you to get an idea of life in the village during the Middle Ages. In Piazza della Cisterna, two ice cream parlors compete for the title of the best in the town: Dell’Olmo and Dondoli, the latter winner of the World Gelato Championship twice. Also worth seeing is the Duomo which houses a series of stunning frescoes. You can learn more about it here: San Gimignano.

San Gimignano view - most beautiful villages in Tuscany
San Gimignano view

Monteriggioni 

Monteriggioni is really tiny but I adore it. Probably because the first time I visited it I ended up there by pure chance. So I was astonished by its round city walls (now partly walkable), the picturesque square and the (just 2) streets with elegant/decadent shops and portals. Some scenes from famous films were filmed here, such as Stealing Beauty, The English Patient and The Gladiator. Here’s my article about Monteriggioni.

San Gusmè

I visited the minuscule San Gusmé years ago following the advice of the Routard Guide to have dinner in a cheap and simple restaurant in the center, Sira and Remino, after having traveled a rather tortuous road to reach it. It only takes a few minutes to visit San Gusmé. There are no shops, only two restaurants, or maybe three. The first time I went there it was summer and there was an open-air cinema for about thirty inhabitants in the small main square. Super cute! Trivia: at the entrance to the town there is a peculiar statue (to say the least). A man in the act of pooping with the writing: “King, emperor, pope, philosopher, poet, farmer and worker: man in his daily functions. Don’t laugh, think of yourself”. 

Me in San Gusmè
Me in San Gusmè

Sarteano 

It is a small village in Val di Chiana. Once you enter through the main door, you find yourself in the main Renaissance square. Small side streets branch off from it. With a slight slope, they lead towards the Castle. The village is very lively. Just think that with less than 5000 inhabitants it has 30 associations. The surrounding area is dotted with thermal springs and Etruscan necropolises (the finds are in the Civic Museum). Don’t miss a lunch at Da Gagliano, a tiny restaurant a stone’s throw from the square. And a dinner at Santa Chiara Restaurant: in summer you dine in the romantic garden, among the hydrangeas in bloom. Climb the ladder of the surrounding wall to admire a spectacular sunset over the countryside. Read the full article here: Sarteano.

Montepulciano 

It enchanted me. From the lower part, you walk up to the main square, Piazza Grande, overlooked by the Duomo and the Palazzo Comunale. A stone’s throw away are the entrances to two of the town’s historic wineries, Contucci and de’ Ricci. Here you can admire the gigantic barrels that hold the prized Vino Nobile di Montepulciano DOCG.

San Biagio, Montepulciano
San Biagio, Montepulciano

Cetona 

Cetona has a huge Renaissance square, Piazza Garibaldi, from which some streets branch off leading to the upper part, dominated by the Fortress. Of the three circles of walls that once surrounded it (impressive for a town of 3000 inhabitants) only the Rivellino tower remains standing. Here there is also the Villa, called Vignola, owned by the fashion designer Valentino.

Piazza di Cetona
Piazza di Cetona

Montalcino 

Montalcino is a village with a military structure, equipped with powerful walls and steep, narrow streets. Worth seeing are the Castle, the Duomo and Palazzo dei Priori with its very high tower. But above all you must stop to taste the famous Brunello.

most beautiful villages in Tuscany

Pienza

It was once called Corsignano. Then, Pope Pius II, who was born here, decided to renovate the entire town and transform it into the ideal city with the help of the architect Rossellino, who followed the dictates of Leon Battista Alberti. So the village changed its name, in honor of the pope. The main street is Corso Rossellino, which is overlooked by a line of boutiques, restaurants and shops. Many of these sell leather products or forms of pecorino cheese. That’s why the smell of both hangs in the air. The main square, Piazza Pio II, overlooks the Cathedral of Santa Maria Assunta, the Town Hall, Palazzo Piccolomini and Palazzo Vescovile. Overlooking the splendid panorama of the Val d’Orcia you find the Belvedere, crossing streets with lovely names: via del Bacio, via dell’Amore and via della Fortuna (Kiss, Love and Fortune street). Pienza is definitely one of my favorite villages.

Monticchiello 

It is a small hamlet close to Pienza, with surrounding walls and a defense tower. The citizens organize every year the so-called poor theater. Meaning that all inhabitants participate with different tasks: authors, actors, helpers.

Castelmuzio 

It is a little-known little village. Even Claude Monet fell in love with it and painted the landscape from its Belvedere. I was there alone, one afternoon in July. During my walk through the streets of the village I didn’t meet anyone. Everyone was at the town restaurant celebrating a grandfather’s birthday. The village of Castelmuzio is enchanting and silent, truly a place from another era.

Castiglione d’Orcia 

It is a pretty village, perched on a hill and dominated by a fortress, on the slopes of Mount Amiata. Its center is a labyrinth of cobbled streets, which emerge into the main square.

most beautiful villages in Tuscany

Radicofani

All roads lead to Radicofani, at least in Val d’Orcia. This is what I say every time I’m over there because, wherever you are in the surroundings, you can spot the Fortress of Radicofani. The village was an important milestone along the Via Francigena and therefore it hosted pilgrims from every European nation, including well-known figures such as Mozart and Dickens. But it is also the town of Ghino di Tacco. Exiled from Siena for political reasons, he became a brigand, a sort of Robin Hood of the area. Following a very curious story, told in the Decameron, he was pardoned and knighted by the Pope. In Radicofani, don’t miss a sandwich from Pane e Companatico, sitting in the delightful flowered square.

Casole d’Elsa

It is a medieval village that boasts a fascinating history. It was in fact disputed between Volterra, Siena and Florence. Its castle, dating back to the 11th century, dominates the village surrounded by walls. Inside you can admire the Romanesque Collegiate Church and the Praetorian Palace. The Museum of Sacred Art houses valuable works. The beauty of the place, the tranquility and the welcoming atmosphere have created an ideal environment for creativity. In fact, the village hosts several artists from all over the world and various cultural initiatives.

Bagno Vignoni 

Bagno Vignoni is a microscopic village (30 inhabitants). Since Roman times it was a destination for pilgrims who stopped along the Via Francigena to refresh themselves and bathe in its thermal waters. Lorenzo de’ Medici was often there. One immediately realizes the central role of the thermal waters here as soon as he/she sees that the main square is essentially occupied by a pool of steaming water. The village is very touristy, with spa hotels, shops, bars and restaurants. It also appeared in an episode of Succession (the Tuscany wedding one). 

most beautiful villages in Tuscany
Bagno Vignoni – most beautiful villages in Tuscany

Chiusdino 

I visited Chiusdino by chance and I really liked it. After parking, we went up a staircase towards the center, among clothes hanging on the windowsills, cats sleeping on doormats and pots of geraniums. No souvenir shops. Very untouristy. We stopped for lunch at the Tiburzi Cave, whose name is inspired by the most famous Maremma brigand, loved by the common people because he defended them from the abuses perpetrated by the landowners. Here there is also the birthplace of San Galgano, knight and hermit, famous for the roofless abbey 15 minutes from here.

Chiusdino, most beautiful villages in Tuscany
Chiusdino – most beautiful villages in Tuscany

Radicondoli

It stands on a hill offering breathtaking views. Its walls enclose a historic center full of charm, with the Collegiate Church of Saints Simon and Jude and the Praetorian Palace. The village boasts an important artisan tradition, with the production of ceramics and terracottas. The surrounding area is rich in woods and paths ideal for trekking and mountain biking.

Murlo

It is a very small and isolated medieval village, located on a hill and surrounded by 12th century walls. Worth a visit if you are nearby.

Most beautiful villages in Tuscany: Florence area

Certaldo 

It is the village where writer Boccaccio was born. In fact, his birthplace can still be visited. The highlight of the village is Palazzo Pretorio, with its coats of arms in glazed terracotta. Sadly, I visited it a long, long time ago and I have no pics.

Montefioralle

Part of the municipality of Greve in Chianti, it is a medieval village included among the most beautiful villages in Italy made up of cobbled streets, stone houses and ancient walls. Here you can find my article about Montefioralle

San Donato in Poggio

It is a small medieval village in Chianti and stands on a hill between Florence and Siena. Its walls enclose a picturesque historic center, with the Romanesque parish church of San Donato and Palazzo Malaspina. I absolutely recommend a stop at trattoria La Toppa.

Castellina in Chianti

Located in the heart of Chianti Classico, it has a circle of walls that enclose a charming historic center. Worth seeing are the Piazza del Comune, the Palazzo Pretorio and the Torre del Cassero.

Barberino Val d’Elsa

Its historic center develops along the main street (via Francesco da Barberino) which can be accessed by passing Porta Fiorentina to the north or Porta Senese to the south. The street is lined with interesting buildings with beautiful wooden doors. Halfway we find the main square, Piazza Barberini, while on a street parallel to the main road overlooks the main church which is dedicated to San Bartolomeo.

Most beautiful villages in Tuscany: Arezzo area

Anghiari

The village area was the spot of the famous battle (1440) between Milan and Florence, which decreed the supremacy of the latter in this territory. Following the victory, a fresco was commissioned from Leonardo da Vinci to decorate the Council Hall of Palazzo Vecchi in Florence Unfortunately Leonardo experimented with a technique that was a little too innovative. So the paint quickly faded and Vasari was commissioned to paint over it. Here in Anghiari there is the Museum dedicated to the Battle, with a room focused on the issue of Leonardo’s frescoes. It is a delightful village, surrounded by medieval walls (don’t miss the view from via Garibaldi) and made up of winding streets. Read my post about Anghiari.

Anghiari (tiny garden view)
Anghiari (tiny garden view)

Lucignano

Lucignano is a small village located on top of a hill and protected by oval walls. The main street (Matteotti) was once called via dell’Amore (Love street, to seal the link with Siena) or Borgo Ricco (Rich borough), because the noble palaces were located here. As opposed to via Povera (Poor Street, now via Roma), where the lower classes lived. The church of San Francesco houses prestigious frescoes, including the Triumph of Death, defined by art critics as the first comic strip in history. The Civic Museum houses a reliquary called The Tree of Love, a symbol of devotion and metaphor of eternal love. Precisely for this reason it is considered a good omen to get married or renew promises here. 

Wonderful Lucignano - most beautiful villages in Tuscany
Wonderful Lucignano

Cortona

Perched on a hill, Cortona is a jewel set in the Val di Chiana. Worth seeing are the MAEC (Museum of the Etruscan Academy), the Diocesan Museum, the Girifalco Fortress and the Basilica of Santa Margherita. Unfortunately I visited it well before opening the blog so I don’t have decent photos.

Lovely villages in the Grosseto area

Pitigliano, Sorano and Sovana are among the most beautiful villages in Tuscany. They are the so-called Tuff Cities, an area of extreme archaeological interest for the Etruscan necropolises, connected to each other by the suggestive and mysterious Vie Cave, paths dug into the rock, in the open air (therefore not tunnels).

Sovana 

It is a tiny village built on a tuff cliff, elegant and linear. In fact, it essentially develops along a single street, which goes from the Aldobrandesca Fortress to the Duomo, a little detached from the center. Only at the Town Hall (the lovely building with the turret and the bell) is there a short fork in the road. The nearby Palazzo Pretorio is also picturesque. In any case, my favorite thing about Sovana are the houses’ facades, full of vases with plants and flowers. Read my post about Sovana.

Cats in Sovana - most beautiful villages in Tuscany
Cats in Sovana

Sorano 

Situated on a high rock and dominated by the Orsini Fortress (which is also a hotel), this village of Etruscan origin is a succession of stairways, alleys, alleys and small squares full of shops, flowers and hanging clothes. 

Pitigliano

Arriving in Pitigliano (cover photo of the article) for the first time is an extraordinary emotion. It’s crazy to see the houses on the edge of the tuff promontory. The village is also called the Little Jerusalem due to the presence of a Jewish community, unfortunately deported (or fled) during the Second World War. You can still visit the Synagogue and buy the town’s typical dessert, Sfratto, in the adjacent shop. My nephew and I ate very well at the Hostaria del Ceccottino. The festival Settembre DiVino is also spectacular, with the celebration of all the local wineries in the streets of the village. Learn more in my article about Pitigliano. Where to sleep? At the lovely Locanda Pantanello.

Montemerano 

It was a pleasant surprise a short distance from the super famous Cascate del Mulino. Montemerano is a very small village, surrounded by medieval walls. The main square, Piazza del Castello, takes your breath away with its beauty as soon as you approach the entrance arch. From there it’s a succession of small squares, narrow streets, little corners full of plants and flowers. The village is also home to a 2 Michelin star restaurant, Da Caino. However, we ate a simple platter sitting at the outside tables of a grocery store. The Church of San Giorgio is worth seeing for a curious peculiarity, the painting of the Madonna della Gattaiola, i.e. Cat-flap Virgin. Basically there’s a hole at the base of the picture. It was made by the priest (centuries ago) to allow his cat to pass inside the pantry and get rid of the mice.

Montemerano - most beautiful villages in Tuscany
Montemerano – most beautiful villages in Tuscany

Did you enjoy my list of the most beautiful villages in Tuscany? I hope of adding other gorgeous villages in the future!

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