The 10 most beautiful villages in Tuscany to visit once in a lifetime

Welcome to Tuscany. A region rich in history and culture. We are sure you will soon immerse yourself in this very special atmosphere that in some cases seems to take you back in time.

In Tuscany you can choose to dedicate your itinerary to visiting cities of art such as Florence, Pisa, Siena, to name but a few. Or, if you prefer to relax by the sea, you have kilometres of coast at your disposal, from Versilia to the Maremma.

A characteristic of Tuscany, then, are its mediaveli villages, authentic gems set in the countryside and among the hills: San Gimignano, Volterra, Pienza.

These are places that can still tell of a historical past and a culture that must be known. Visiting these villages you can taste the local gastronomy, which is truly varied, and the wines, such as Chianti Classico or Brunello di Montalcino.

You can admire the imposing Federiciana tower in San Miniato or tour the sites of the historic battle of Anghiari or even relax at the thermal baths of Bagno Vignoni. Ready to discover the 10 most beautiful villages in Tuscany?

Anghiari is one of the villages in Tuscany that must be part of your itinerary. It is famous for the historic Battle of Anghiari in 1440, when the Republic of Florence defeated the Republic of Milan. The village is built on a hill overlooking the Tiber valley, and its medieval fortifications are still well preserved. You can immerse yourself in the narrow streets, reliving some of that atmosphere. Not to be missed is the Museum of the Battle of Anghiari: where the famous battle and Leonardo da Vinci's lost attempt to paint it in Florence are recounted. It is said, in fact, that Leonardo's genius was commissioned by Cesare Borgia in 1505 to paint this battle on the wall of the Salone dei Cinquecento in Palazzo Vecchio. According to the story, Leonardo experimented with a new technique, which proved to be unsuccessful and so he gave up. The part was then covered by ‘The Battle of Scannagallo’, painted by Vasari in 1554. It is not certain whether Leonardo's painting ever really existed, but Vasari left a small trace that smacks of legend: ‘seek, find’, it says on the 1554 painting.

Returning to the village of Anghiari, the advice is to visit the historical centre with its narrow streets, walls and towers offer a fascinating walk through the Middle Ages. If you still have time left, visit the Church of Sant'Agostino: medieval in origin, with frescoes by local artists.

Among the typical dishes of this area are legume and cereal soups such as ribollita. Anghiari also produces excellent olive oil and homemade cold cuts.

Situated on a hill between Pisa and Florence, San Miniato has a very ancient history. Founded in Roman times, it became an important strategic centre in the Middle Ages due to its location along the Via Francigena, the ancient pilgrims' route. In the 13th century, it was disputed between Guelphs and Ghibellines, and was later dominated by the Medici.

As mentioned in the first paragraph, we recommend a visit to the Rocca di Federico II: an imposing tower with a spectacular view over the Valdarno.

Then there is the Cathedral of Santa Maria Assunta and San Genesio, a structure of medieval origin that contains various works of art and a fascinating cycle of frescoes. The Palazzo dei Vicari is also worth a visit. Seat of power during Florentine rule, it preserves coats of arms and frescoes from the Renaissance period.

The white truffle is the star ingredient. You can enjoy it with fresh pasta, such as tagliatelle, or in simpler dishes such as eggs and cheese. In addition, typical products include wine, extra virgin olive oil and local salami. Every year in November, the White Truffle Festival is held, one of the most important in Italy, attracting visitors from all over the world.

Certaldo is famous for being the birthplace of Giovanni Boccaccio, author of the ‘Decameron’, probably written between 1349 and 1351 or 1353. The oldest part is Certaldo Alto, a beautifully preserved medieval village with a history dating back to Etruscan and Roman times. During the Middle Ages it became a Florentine stronghold. From here you can admire the ancient walls.

The home of the famous writer," La Casa del Boccaccio", is one of the places to visit. Today it is a museum dedicated to his life and works. Then there is the Palazzo Pretorio, former seat of the podestà, with a façade decorated with terracotta coats of arms and frescoed rooms. The Church of Saints Jacopo and Filippo is where Boccaccio's tomb is located, with valuable medieval frescoes.

Every year in July, the Mercantia Festival is held, one of the most famous street theatre events in Italy, with artists, craftsmen and shows enlivening the streets of the village. Consider, if you happen to be there during this month, popping in.

This village, among the most beautiful in Tuscany, is renowned for the Certaldo onion, sweet and ideal both raw in salads and cooked in soups. Typical dishes include the ‘onion soup’, a local comfort food. Chianti wines and extra virgin olive oil complete the menu.

If you want to visit the most beautiful villages in Tuscany and want to relax with a regenerating thermal bath, you are in the right place!

A small thermal village located in the Val d'Orcia, Bagno Vignoni was already known in Roman times for its hot waters. In the Middle Ages it became a stopping place for pilgrims on the Via Francigena and was frequented by personalities such as Catherine of Siena and Lorenzo de' Medici.

The main feature of the hamlet is the large thermal pool that occupies the centre of Piazza delle Sorgenti, an evocative, almost magical place where the water flows naturally hot. Not far from the hamlet, you can visit ancient mills used in the past thanks to the power of the thermal water.

The thermal waters of the village are known for their beneficial properties, ideal for relaxation and regeneration. We therefore recommend relaxing at the Bagno Vignoni thermal baths.

Typical dishes in the Val d'Orcia area include panzanella, a sort of salad of stale bread with vegetables, and pappa al pomodoro. Here too, wine is the protagonist, with the famous Brunello di Montalcino dominating the scene.

Pienza has been a UNESCO World Heritage Site since 1996 and is considered to be one of the earliest urban realisations of the Renaissance.

This village is located in the Val d'Orcia, and is famous for being the ‘ideal city’ of the Renaissance, planned by Pope Pius II (Enea Silvio Piccolomini) in the 15th century. The pope wanted to transform his home village, Corsignano, into an example of a harmonious and well-designed Renaissance town. The heart of the village is Piazza Pio II, surrounded by Renaissance buildings such as the Duomo, the Palazzo Piccolomini and the Palazzo Borgia. The Palazzo Piccolomini is a former residence of the pope that offers a spectacular view of the Val d'Orcia and has beautiful Renaissance gardens.

The Cathedral of the Assunta is also a place worth visiting. It presents a mix of Gothic and Renaissance styles, with a bright interior rich in works of art.

You will be fascinated to stroll through the streets of the village centre, where you will also find shops offering ceramics, some of which are carved inside caves dug into the tuff dating back to the year 1000.

Pienza is famous for Pecorino di Pienza, a cheese made from sheep's milk, which can be eaten fresh, semi-matured or matured. Excellent with honey and jams, its taste is unmistakable.

Montalcino, located in the beautiful Val d'Orcia, has a long history dating back to Etruscan and Roman times. In the Middle Ages, it became an important stronghold, known for its loyalty to Siena during the wars with Florence. After the fall of the Republic of Siena in 1555, Montalcino resisted for another four years before being absorbed by the Grand Duchy of Tuscany.

The Fortress of Montalcino was built in the 14th century to protect the town and offers a breathtaking view of the surrounding vineyards and hills. Today it is a venue for cultural events and wine tastings. We recommend a visit to the Museum of this fine wine. 

Then there is the Duomo di San Salvatore, a neoclassical church built in the 19th century, but its origins date back to the 14th century. It is a symbol of the city's religious history. At the Museo Civico e Diocesano you can find sacred art, medieval and Renaissance sculptures and paintings, reflecting Montalcino's rich cultural heritage. While the Abbey of Sant'Antimo is located just outside the town, it is a Romanesque abbey dating back to the 8th century. Known for its architecture and mystical atmosphere, it is a perfect place for a spiritual break.

Montalcino is world famous for its fine wine, Brunello di Montalcino, one of Italy's most prized and expensive red wines. Brunello is made exclusively from Sangiovese grapes and must age for at least five years before being sold.

One of the oldest settlements in Tuscany is the village of Cortona. It was an important Etruscan and Roman city and in the Middle Ages became a Guelph stronghold. Its dominant position on a hill offers spectacular views over the Val di Chiana. An extensive collection of Etruscan artefacts, including the famous ‘Etruscan chandelier’ are on display at the Museo dell'Accademia Etrusca. While at the top of the hill you will find the Fortezza Medicea.

The Church of San Francesco, on the other hand, contains relics associated with St Francis of Assisi and some important paintings, a place to include in your itinerary.

A curiosity: Cortona became internationally famous thanks to the novel and film ‘Under the Tuscan Sun’, which tells the life story of an American writer who moves to the town.

As for the local gsotronomy, not to be missed is the Chianina steak, a prized beef from the nearby Val di Chiana. Other local dishes include Tuscan crostini, pici all'aglione and wines such as Syrah di Cortona DOC.

With origins dating back to the Etruscans, Volterra is famous for its archaeological remains and alabaster production. It became an important Roman city and, later, a powerful medieval city-state. One of the most impressive sights is the Roman Theatre. Here you will find the remains of an ancient theatre dating back to the 1st century B.C., one of the best preserved in Italy. The oldest municipal palace in Tuscany is located in Volterra and is the Palazzo dei Priori: with a tower dominating the panorama.

The Museo Etrusco Guarnacci is one of the most important Etruscan museums, with funerary urns and objects of great historical value, and you should take the opportunity of this trip to visit it.

Among the other things you can discover in this Tuscan village, Volterra is known for the working of alabaster, a stone used to create refined handcrafted objects, still sold in the shops of the historic centre.

The signature dish is the zuppa volterrana, made with stale bread and vegetables. Porcini mushrooms and wild boar are key ingredients in many local dishes, as are the local cured meats and cheeses. We recommend a stop in one of the village restaurants.

Monteriggioni is one of the best-preserved walled cities in Italy. Built by the Sienese in the 13th century, it served as a military outpost against Florence during the medieval wars.

The medieval walls completely surround the town and are dotted with towers. You can walk along parts of the walls and enjoy the view of the surrounding countryside. Even as you reach the village of Monteriggioni, you will notice the walls in the distance.

When you take a walk through the village's narrow streets, don't forget to stop in Piazza Roma, where you will find medieval buildings all around and a simple but charming Romanesque church.

Monteriggioni is mentioned by Dante in the ‘Divine Comedy ’ (Inferno, Canto XXXI) as an image of the walls of hell. Its towers are compared to giants watching over the abyss. ‘Come in su la cerchia tonda, Monteriggioni di torri si corona’.

Typical dishes include pici, rabbit alla senese and traditional sweets such as ricciarelli. Wines such as Chianti Colli Senesi accompany these dishes.

Known as the ‘Manhattan of the Middle Ages’ for its numerous towers (once some 72, today 14 remain), San Gimignano is a splendid example of medieval architecture. Its fortune derives from its location along the Via Francigena and the production of saffron.

As a first stop in this Tuscan village, we recommend a visit to the town's highest tower, the Torre Grossa, which offers an exceptional panoramic view. Then you could go to Piazza della Cisterna, the main square. It is surrounded by medieval buildings and the site of numerous events and markets. Then there is the Cathedral of San Gimignano: a Romanesque church with valuable frescoes depicting biblical scenes.

San Gimignano is a UNESCO World Heritage Site. Its towers, symbols of the wealth of medieval families, were built in competition with each other, leading to the village's unique skyline.

One of the most interesting events during the year is the carnival, when the town is transformed by going back in time. Papier-mâché floats parade along the streets of San Gimignano, accompanied by music, confetti and masked groups.

The most famous local wine is Vernaccia di San Gimignano, a DOCG white wine. Typical dishes include ribollita and wild boar specialities.