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 you plan 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. Fear not! Here we have compiled our top 10 list of small hill towns in Tuscany worth visiting on your next vacation!

San Gimignano

San Gimignano is a hill town in Tuscany, Italy
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. Sixteen towers are the top landmark of this small town. They rise on top of the hill it stands and is declared one of Tuscany’s UNESCO World Heritage sites.


Torre Volterra, Volterra is a hill town in Tuscany, Italy
Torre Volterra, Volterra is a hill town in Tuscany, Italy

One of the best hill towns in Tuscany is Volterra. Unique and unrepeatable, all the guides of Tuscany present it as a city of art. Built-in the splendid 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. They’ve 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.


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Lucca is another hill town city in Tuscany. 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.” the city of hundred churches has perfectly preserved sixteenth-century walls, about 2.5 miles long and 40 feet high. The six doors that allow access to the city still exist today.

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 Val d’Elsa

Colle di Val D'elsa is located in the province of Siena Tuscany, known for its crystal glass production.
Colle di Val D’elsa is located in the province of Siena Tuscany, known for its crystal glass production.

It is a town in the heart of Tuscany in a strategically favorable position near Siena, Florence, and Volterra. The city 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 Civic and Diocesan Museum 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.


The beautiful historic town of Tuscany, Montepulciano - Italy
The beautiful historic town of Tuscany, Montepulciano – 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 is one of the most famous in Tuscany. It is produced with the grapes of a Sangiovese clone, 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. A mighty city wall surrounds this charming village, which is located south of Grosseto and is full of history. It 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, has a worldwide popularity for producing the precious Brunello di Montalcino. Producers founded the Consortia del Vino Brunello di Montalcino in 1967 as a free association to protect their wine, which was experiencing a growing prestige.

White dessert wine, Moscadello, pecorino cheese, and various Tuscan “salumi” also make Montalcino famous.


Montecatini, Tuscany, Italy

Montecatini’s thermal waters are very popular. The city is also known as “Spa Town.” It is an easily accessible city worth a visit. The surrounding area offers the opportunity to make some exciting excursions in addition to parks, gardens, and Art Nouveau villas in a perfectly maintained historic center. Montecatini Terme is protected by UNESCO, 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 Toscana Music Festivals arrange their concerts in the classy ambiance of the Spa of Montecatini and the Basilica Santa Maria Assunta.

San Miniato

San Miniato, Tuscany, Italy

San Miniato is one of the best hill towns in Tuscany. It is in the heart of Tuscany and belongs to the province of Pisa. It is 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. Frederick II, Holy Roman Emperor and Duke of Swabia, upgraded San Miniato’s, Rocca Castle. Piazza della Repubblica is a must-see where you can admire the fantastic 17th-century graffiti painted on the facade of the seminary and the scarce and very few shops in the fourteenth century wholly restored.

The Enjoy white truffle festival was first organized in 1969. It 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 overlooks the rolling hills of the Val d’Orcio. This one of the best small hill towns is world-famous, also known as “the ideal city” wanted by Pope Pius II in Tuscany. UNESCO has declared its historic center a World Heritage Site. It is located within the Val d’Orcia Park, a World Heritage Site. The square dedicated to Pius II is the center of the city. Bernardo Rossellino built it with a particular trapezoidal shape and herringbone brick pavement. The Cathedral, Borgia, Piccolomini, and Palazzo Comunale buildings overlook the square.

The cheese called Pecorino di Pienza is also famous in Pienza. Along the tiny streets, you feel the scent of Pecorino fills the air. You also 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.


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Cortona is a small, charming town in the province of Arezzo in southern Tuscany. The town dominates a valley and offers a spectacular view from everywhere. The city sits atop a hill about 2000 feet above sea level. The Etruscans and Romans constructed stone walls that enclose it.

The tiny city has many exciting places to visit. These include 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. They are delicious and tasteful because Montalcino and Montepulciano are close to Cortona.

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