Tuscany offers many different things to do and places to see to its visitors. It is the reason why is so famous worldwide together with food and wine. Besides the main cities rich in history and art, and iconic hamlets, if you know where to look, you can find unusual Tuscany villages to restore your spirit and body.

In this article, we take you on a virtual tour of ten small Tuscany villages off the mass itineraries.

If not completely satisfied, We have other tips for you. You can reach the coast and the beaches of Versilia, the Etruscan Coast, and the Maremma. Or take a ferry and head to one of the seven beautiful islands of Tuscany. Coming during wintertime there are also nice ski resorts on the Apennines.

Top Ten unconventional Tuscany villages to see

We have already dedicated space to the most popular villages in Tuscany. To find out which ones we have included, we invite you to read this article:


Instead, starting from north to south here is our choice of ten alternative Tuscany villages to visit.

Villages on the Tuscany map

Top 10 Tuscany Villages


Pontremoli is a really nice village in Lunigiana at the feet of the Tuscan-Emilian Apennines. In the past, it was a stop along the pilgrim route of the Via Francigena. If you are a hiker you can walk it also nowadays.

Here are useful tips about the map and itinerary of Via Francigena

Pontremoli takes its name from the Latin Ponte Tremulus which means wobbly bridge. The biggest attraction is the Castle of Piagnaro which hosts the museum of the Statue Stele, ancient statues menhir, whose meaning is yet to be discovered. Do not miss a walk across the center and a tasting of the typical food as Testaroli and Sgabei.

Pontremoli Tuscany View from the castle
View of Pontremoli from the Castle – Photo Credits: Nicola Bandini My Travel in Tuscany

Castelnuovo Garfagnana

In the heart of the wild area of Garfagnana you find the hamlet of Castelnuovo Garfagnana. The symbol of the village is the Rocca Ariostea, an ancient fortress that, from 1522 to 1525, was the dwelling of the Governor, the famous Italian poet Ludovico Ariosto.

View of the Fortress Ariostesca in Castelnuovo Garfagnana Tuscany
Rocca Ariostea, Castelnuovo Garfagnana – Photo Credits: Nicola Bandini My Travel in Tuscany


Only 15 km (9 mi) away from Lucca, set on a hill overlooking the valley, Montecarlo lies. If delicious wines, both red and white, are good reasons to come, I am sure you will love it also for the beautiful scenery, the fortress and walls, and the smallest theatre in the world. Just outside the walls, look for the oak of witches, a wonderful centuries-old oak 24 m (78 feet) tall and 4 m (13 feet) in width.

The small Theatre of the Rassicurati – Photo Credits: Mongolo1984


The birthplace of the Renaissance Man Leonardo da Vinci is located on top of a hill in the province of Florence. The unique profile of Castello Guidi dominated the historical center. The castle is also named the Castle of the Ship for its shape which looks like a ship with a tower as a mast. The complex hosts the museum dedicated to Leonardo, which displays some of his drawings, machines, and inventions. Just a few miles out of the village you can visit the house of the Genius.

Vinci Tuscany village
View of Vinci – Photo Credits: BERND THALLER


Montescudaio is one of the Tuscany villages renowned for its red wine tradition and is considered one of the most beautiful hamlets in Italy. Or at least for me, because I spent so much time there and I still have dear friends. Set on the top of a hill, it is just a few miles away from the sea of the Etruscan Coast. On sunny days, from the panoramic terrace in front of the church, you can admire the amazing view of the valley with the Mediterranean Sea and the Islands as background.

Montescudaio Etruscan Coast


The tiny hamlet of Montefioralle is located in the municipality of Greve in Chianti. Its origins date back to 1100 and it seems to be one of the most ancient villages of Chianti. Montefioralle was built around the castle and it is still enclosed within the original fortified walls. Enjoy a walk along its narrow streets and visit the church of Santo Stefano. Before leaving, do not forget to taste some traditional food with a glass of Chianti Red.

Montefioralle Tuscany villages
Montefioralle – Photo Credits: GIUSEPPE MOSCATO

Massa Marittima

Massa Marittima is a splendid hamlet full of art and one of the best Tuscany villages for its unique architecture. Also in Massa, we find one of the typical characteristics of medieval cities. In fact, the main square of the old town gathers all the most important buildings. In just one place you find the Dome, the palace of the Podestà, the town hall, the loggia of the market, the mint, and the public spring. Instead, walking up to the new city, you will find the huge fortress with the Clock Tower.

Massa Marittima Tuscany Villages
Massa Marittima – Photo Credits: Paolo Trabattoni


We are in the middle of the spectacular lunar landscape of the Crete Senesi. DThe tiny burg of Buonconvento was born along the Via Francigena during the Middle Ages. Its name derives from the Latin Bonus Conventus which means lucky and happy place. There is only a main street, today called Via Soccini, that crosses the center from north to south, connecting the two entry doors of the fortified walls.

Buonconvento Tuscany Village
Buonconvento in black and white – Photo Credits: Pedro Albuquerque

San Quirico d’Orcia

San Quirico d’Orcia is one of the five Tuscany villages of Val d’Orcia. You may have heard about this wonderful valley because has been listed in 2004 in the UNESCO World Heritage Sites. The village has ancient Etruscan origins and medieval architecture. Narrow paved alleys and the Romanesque parish church of the Collegiata distinguish the picturesque historic center. Moreover, the splendid gardens of Horti Leonini deserve a visit.

The surroundings of San Quirico are the best photographic sceneries of the entire Val d’Orcia. Wheat fields and cypress in rows add color to the gently rolling hills. The little chapel of Vitaleta is the precious stone in the middle of an impressionist painting. The municipality of San Quirico d’Orcia includes also Bagno Vignoni. The hamlet is famous for its unique square and its natural hot springs.

San Quirico D'Orcia Tuscany villages
San Quirico d’Orcia – Phot Credits: Georg Weis


Monterchi is a medieval village on the top of the Monte Ercole (Mount of Hercules), located in the Valtiberina, at the border between the Tuscany and Umbria regions. One of the most important frescoes of the entire Renaissance made this place known. We talk about the Madonna del Parto, made by the famous Italian painter Piero della Francesca to honor his mother who was a native of Monterchi. Not too far from Monterchi, we find the town of Sansepolcro. Every first two weeks of September, the historic center hosts the traditional Crossbow Games, a reenactment of the festival born in 1594.

Monterchi Valtiberina Tuscany villages
Monterchi – Phot Credits: Claudio Biancucci

These 10 small Tuscany villages are only a short list of the many unconventional places scattered all around the region. Leave a comment below if you find other tiny villages that deserve to be discovered. But do not tell too many people.

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4 thoughts on “Here is The Top-10 Unconventional Tuscany Villages in Italy

  1. leelaurino says:

    why are ALL the wonderful places not on train lines? I visit and stay in Italy for long periods of time but only can visit towns that I can reach via train… may be time for a car hometoitaly.com

    • Nicola Bandini says:

      Hello Leelaurino, thanks for your question. All these villages, and mostly all little villages of Tuscany and Italy are on the the top of hills or mountains, while trains runs easily across the valleys. Usually, few buses link the main towns with the small hamlets around.
      Probably the best way to visit the countryside of Tuscany is by car. Driving along the country roads you can enjoy amazing landscapes and stop whenever you want. If you have any request for your next trip to Tuscany, feel free to contact me. 🙂

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