10 Best Small Hill Towns in Tuscany

October 4, 2022

Tuscany, Italy, is one of the most beautiful regions in Europe. The rolling hills, picturesque towns, and winding roads are just a few things that draw travelers to this beloved destination year after year. Whether you’re looking for a romantic getaway or simply hoping to explore the area’s rich history and culture, there’s no denying that Tuscany holds something special for everyone. But what happens when your plan is to take an extended road trip? Visiting top cities like Florence can be exciting, but chances are, you’ll also want to find some off-the-beaten-path adventures as well. Fear not! Here we have put together our top 10 list of small hill towns in Tuscany worth visiting on your next vacation!

San Gimignano

San Gimignano, Tuscany, Italy

Passing through the province of Siena is another of the most famous Tuscany towns, especially for the state of conservation of its historical monuments that make the city profile genuinely unique. If there is a medieval town in Tuscany not to be missed, which attracts thousands and thousands of tourists every day of the year, this is San Gimignano. It is a special place as soon as you see its profile in the distance with its numerous towers, which seem to lie on the top of the hill on which the town stands. This small town is known for its sixteen towers, which rise on top of the hill on which it stands and is declared one of the UNESCO World Heritage sites in Tuscany.


Torre Volterra, Tuscany, Italy

One of the best hill towns in Tuscany is Volterra. Unique and unrepeatable, it is presented in all the guides of Tuscany as a city of art. Built-in a resplendent territory, it is imbued with an aura of mystery that adds charm to an already magnificent place. Performances, tradespeople, artisans, musicians, jugglers, peasants, and noblemen transform.

Volterra into a medieval city. Its streets, buildings, and towers are built entirely of stone, as are its walls. But the stone that made the richness of this place is “alabaster.” This white stone, exceptionally soft, lends itself perfectly to being worked to create objects and sculptures, which have been handled in Volterra since the time of the Etruscans. The Cooperative Artieri Alabastro, established in 1895, brings together the alabaster artisans of the city. In their headquarters, you can find the works produced by over 20 local artisans and therefore know.

Volterra’s most important archaeological find is its Roman theater, built in the Augustan age by the Caecina family. It is based on the type of the Greek odeons and, today, instead well preserved.

Around Volterra is the splendid Tuscan countryside, with its hills and valleys representing an always pleasant panorama. A red sculpture between the city and San Gimignano marks a beautiful panoramic point. The nearby archaeological park gets the same treatment, inviting you to experience the countryside as it was in the 14th century with farmers, shepherds, monks, military camps, and animals.


Fountain, Lucca, Tuscany

Lucca is another hill town city in Tuscany. The city of hundred churches is known for its perfectly preserved sixteenth-century walls, which are about 2.5 miles long, 40 feet high, and 100 feet wide. The six doors that allow access to the city still exist today. Once a stop along the silk roads, Lucca has been the backdrop for films and TV programs such as “Top Gear” and “Portrait of a lady.”

Lucca is an extraordinary center for culture and gastronomy in Tuscany. We recommend eating egg pasta with rabbit ragout and Buccellato, a simple dessert that ennobles bread and which is in the dough with the addition of raisins and anise. Don’t forget to taste pasta filled with a meat filling, shaped in a semicircle of large dimensions called the Tordelli from Lucca. Try the ice cream of the Cremeria Opera or the spritz-based aperitifs in Piazza San Michele, in front of the church of San Michele in Foro.

Lucca is the birthplace of Giacomo Puccini. He is a famous leading Italian composer of his generation.

Colle di Val d’Elsa

Colle di Val D'elsa, Tuscany, Italy

Colle Val d’Elsa is a town in the heart of Tuscany in a strategically favorable position near the cities of Siena, Florence, and Volterra. The town has a beautiful historic center on top of a hill. The town’s upper part is the oldest part, where you can admire the Porta Nova, one of the doors that allows access to the medieval village that now houses a beautiful restaurant where you can taste typical dishes of Tuscan cuisine and also offers excellent views of Tuscany, a medieval atmosphere, and a beautiful Duomo. There are exciting monuments, magnificent museums, and above all, as is the norm in this area of Italy, splendid surroundings to get lost amid nature and the countryside. Don’t forget to visit the Archeological Museum and the Civic and Diocesan Museum, both located in the historical center.

Colle Val d’Elsa, a centuries-old tradition, has one of the leading Italian production centers of the extraordinary material, crystal. As evidence of this fact, in addition to the numerous shops, there is also the beautiful crystal museum, all to be visited.


Montepulciano, Tuscany, Italy

Montepulciano is a charming medieval village in Tuscany. Among the alleys, streets, and squares of the historical center of Montepulciano are hidden wonderful palaces and sumptuous residences, the testimony of the great power noble families, had during the fourteenth and fifteenth centuries.

Their origins date back to the Etruscan era when you could stroll among Renaissance palaces, enchanting squares, ancient churches, and panoramic views of the Tuscan hills covered with vineyards. This small town is remembered as the birthplace of the great Renaissance poet Agnolo Ambrogini, the Poliziano. But the town is also famous for the Nobile wine, one of the finest Italian reds with a controlled and guaranteed designation of origin. The Vino Nobile di Montepulciano, one of the most famous in Tuscany, is produced with the grapes of a Sangiovese clone known as Prugnolo Gentile. Its name derives from the plum scent it transmits to the wine.

October brings the harvest of oil-rich olives to make the highest quality extra virgin olive oil. Celebrate the annual harvest with the Olive Oil and Autumn Flavors Festival.


Montalcino Wines, Tuscany, Italy

Montalcino is the largest municipality in the province of Siena. This charming village full of history is located south of Grosseto and is surrounded by a mighty city wall and has an art museum and, among the olive groves outside town, a perfect 12th-century abbey. The historic center grows around Piazza del Popolo, with a slender-looking 12th-century Palazzo dei Priori. The atmospheric streets of the town center are perfect for a stroll. You can visit the Fortress and walk its ramparts. There’s a splendid view from the top and an Enoteca for more wine-tasting opportunities.

The town, immersed in the splendid landscape of the Vall’Orcia Natural Park, is renowned worldwide for producing the precious Brunello di Montalcino. The Consortia del Vino Brunello di Montalcino was founded in 1967 as a free association between producers to protect their wine, whose prestige was growing increasingly.

Montalcino is known for its white dessert wine, Moscadello, pecorino cheese, and various Tuscan “salumi.”


Montecatini, Tuscany, Italy

Montecatini is famous for its thermal waters and is called “Spa Town.” It is an easily accessible city worth a visit; it’s a perfectly maintained historic center with parks, gardens, and Art Nouveau villas and the possibility of making some exciting excursions in the surrounding area. Montecatini Terme is protected by UNESCO, being part of the World Heritage Site that reached the Great Spa Towns of Europe. In recent years the number of hotels started growing, and by staying in this lovely town, you can enjoy the tranquility of a spa town while having unspoiled nature and beautiful works of art close by.

The concerts of the Toscana Music Festivals are arranged in the classy ambiance of the Spa of Montecatini and the Basilica Santa Maria Assunta.

San Miniato

San Miniato, Tuscany, Italy

San Miniato is in the heart of Tuscany, belonging to the province of Pisa, but practically equidistant from this region’s main artistic, historical, and landscape cities such as Florence, Pistoia, Lucca, Pisa, Volterra, and Siena.

Among the numerous hamlets of the municipality of San Miniato, some deserve a particular mention, above all, for their historical events and artistic interest. The town is famous for its medieval German castle, open-air theatre & the Tartufo Bianco, a gastronomic treasure. San Miniato hulking Rocca Castle got a severe upgrade under Frederick II, Holy Roman Emperor and Duke of Swabia, at the high point above the town’s narrow and winding streets. A must-see is Piazza della Repubblica, where you can admire the fantastic 17th-century graffiti painted on the facade of the seminary and the scarce and very few shops fourteenth centuries wholly restored.

Enjoy white truffle festival was first organized in 1969 and took place over the 2nd to 4th weekends of November in the historic center of San Miniato.


Street of Pienza, Tuscany, Italy

Pienza is a city of infinite beauty, rich in history and charm, the village overlooking the rolling hills of the Val d’Orcio. This small town is world famous for being known as “the ideal city” wanted by Pope Pius II, and its historic center has been declared a World Heritage Site by UNESCO. It is located within the Val d’Orcia Park, a World Heritage Site. The center of the city is the square dedicated to Pius II, built by Bernardo Rossellino, with a particular trapezoidal shape with a herringbone brick pavement, overlooked by the Cathedral and the Borgia, Piccolomini, and Palazzo Comunale buildings.

Pienza also is famous for its cheese called Pecorino di Pienza. Along the tiny streets, you feel the scent of Pecorino fills the air, and you find many shops to taste and buy. Pienza’s major festival celebrates its famous cheese in early September. Gioco del Cacio al Fuso features cheese rolling and plenty of good eating.


Cortona, Tuscany, Italy

Cortona is a small, charming town in the province of Arezzo in southern Tuscany. The city sits on the top of a hill about 2000 feet above sea level and is enclosed by stone walls constructed by Etruscans and Romans. The town dominates a valley and offers a spectacular view from all over the place.

The tiny city offers many exciting places to visit, including the Diocesan Museum, The Etruscan Academy Museum of the City of Cortona, the Santa Margherita Sanctuary, and the Girifalco Fortress.

Don’t forget to admire a beautiful panel painting of the Annunciation by Beato Angelico in the Diocesan Museum.

You’ll find many small shops on the main streets that offer local handmade objects and gastronomical products in town. Also, many beautiful and traditional local restaurants offer Tuscany cuisine to their customers. One of the famous Tuscan plates is the Chianina cattle, one of Italy’s oldest, high-quality bovine breeds bred in Valdichiana.

The local restaurants offer a wide selection of local wines that are delicious and tasteful because Montalcino and Montepulciano are close to Cortona.

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