Hill Towns of Tuscany
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Latest page update: 20 February 2025
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By Dion Protani
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The hill towns of Tuscany are one of the most evocative attractions of the region. No other Italian region can match the depth of illustrious names in this genre offered by Tuscany.
Topping the list are two UNESCO World Heritage Sites in San Gimignano and Pienza; the former often referred to the Medieval Manhattan due to its extraordinary collection of towers and the latter simply a Renaissance marvel. Volterra, Montepulciano and Cortona are three further famous hill towns of Italy and mainstays of any serious Tuscan itineraries. |
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San Gimignano is a medieval hill town known for its iconic skyline of tower houses, the town sits atop a hill offering panoramic views of the surrounding vineyards and rolling hills.
Major sights include the Piazza del Duomo, home to the stunning Collegiate Church of Santa Maria Assunta, with its beautiful frescoes. San Gimignano's historical centre, a UNESCO World Heritage site, showcases well-preserved medieval architecture. The town flourished during the 12th and 13th centuries as a wealthy trade center, with many towers built by noble families to demonstrate their power and wealth. |
San Gimignano
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Pienza is a small town located in the heart of Tuscany, in the province of Siena. Known as the "Ideal Renaissance City," Pienza was redesigned in the 15th century by Pope Pius II. Major sights include the Piazza Pio II, where visitors can admire the cathedral, Palazzo Piccolomini, and the town hall.
The charming narrow streets, lined with Renaissance-era buildings, give Pienza its distinctive atmosphere. The town is famous for its Pecorino cheese, produced locally. Pienza's transformation was one of the earliest examples of urban planning during the Renaissance, aiming to reflect ideals of beauty, harmony, and humanism. |
Pienza
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Volterra is a historic town located in the central part of Tuscany, perched on a hilltop overlooking the surrounding countryside.
Known for its rich Etruscan heritage, Volterra boasts several ancient landmarks, like the Etruscan Arch and the Roman Theatre. The town is also home to the impressive Palazzo dei Priori, which houses a museum showcasing its medieval history. Volterra has long been known for its alabaster production, a tradition that dates back to ancient times. Once an important Etruscan and Roman centre, the town played a key role during the Middle Ages, and its preserved walls and gates reflect this storied past. |
Volterra
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Montepulciano is a picturesque hilltown located in southern Tuscany, famous for its stunning views and Vino Nobile wine. The town sits atop a ridge between the Val d'Orcia and Val di Chiana valleys.
Visitors can explore major sights such as the Piazza Grande, where the town hall and the beautiful Cathedral of Santa Maria Assunta are located. Montepulciano’s narrow streets are lined with Renaissance and medieval buildings. The town has a rich history, flourishing during the medieval period as a strategic stronghold. Its well-preserved fortifications and palaces are a testament to its cultural and political importance over the centuries. |
Montepulciano
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Cortona is a charming town in southern Tuscany, set on a hilltop overlooking the Val di Chiana. Known for its ancient Etruscan origins, the town offers a blend of historical sites and scenic beauty.
Notable attractions include the impressive Piazza della Repubblica, the 13th-century Church of San Francesco, and the Museo Diocesano, which houses art and religious artifacts. Cortona's history stretches back to Etruscan times, and it flourished during the Roman Empire and Middle Ages. Its medieval walls, narrow streets, and stone buildings reflect its rich past. The town is also famous for its annual art and cultural festivals. |
Cortona
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Montalcino is a hilltop town in southern Tuscany, renowned for its picturesque landscape and the world-famous Brunello di Montalcino wine. Located in the Val d'Orcia, the town offers stunning views of the surrounding vineyards and olive groves.
Major sights include the imposing 14th-century Fortress, which provides panoramic views, and the beautiful Abbey of Sant'Antimo, a Romanesque gem. Montalcino’s history dates back to the Etruscan and Roman periods, but it flourished in the Middle Ages as a fortified stronghold. The town has remained an important centre for wine production, and its medieval charm continues to attract visitors from around the world. |
Montalcino
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Monterchi is a small town located in the northeastern part of Tuscany, near the border with Umbria. Set on a hillside, it offers scenic views of the surrounding valleys.
The town is best known for housing the famous fresco by Piero della Francesca, "The Madonna del Parto," which is displayed in the Museo della Madonna del Parto. Monterchi also features a charming historical centre with medieval architecture, including its Romanesque church, Chiesa di San Sebastiano. The town's history is deeply rooted in the Middle Ages, when it was a strategic settlement. |
Monterchi
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Monteriggioni is a small walled town located in the heart of Tuscany, surrounded by rolling hills and vineyards. Its medieval walls, complete with 14 towers, give it a distinctive and charming appearance.
The town's main square, Piazza Roma, is home to the beautiful Church of Santa Maria Assunta. Monteriggioni has a rich history dating back to the 13th century, when it was built as a defensive outpost of the Republic of Siena. The town’s well-preserved fortifications and narrow streets evoke its medieval past. Today, Monteriggioni is a popular stop for visitors, offering a peaceful atmosphere and picturesque views of the Tuscan countryside. |
Monteriggioni
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Massa Marittima is a historic town located in southern Tuscany, nestled on a hilltop overlooking the Maremma region. Known for its well-preserved medieval charm, the town is home to several impressive sights, including the stunning Cathedral of San Cerbone, which dominates the main square.
The Piazza Giuseppe Garibaldi offers a picturesque setting with beautiful architecture, while the ancient city walls and the fortress of Torre del Candeliere reflect its strategic past. Massa Marittima has roots dating back to Etruscan times and flourished in the Middle Ages as an important center for mining and trade. Today, it attracts visitors with its rich history and scenic beauty. |
Massa Marittima
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San Miniato is a medieval town located in the heart of Tuscany, positioned between Florence and Pisa. It is renowned for its scenic hilltop location, offering breathtaking views of the surrounding countryside.
The town is famous for its impressive Cathedral of Santa Maria Assunta, which boasts beautiful artwork and historical significance. Visitors can also explore the Rocca di San Miniato, a fortress that provides panoramic vistas. In the Middle Ages, it became an important stop for pilgrims on their way to Rome. Today, it is celebrated for its truffle festivals. |
San Miniato
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Fiesole is a picturesque town located just north of Florence, perched on a hill offering sweeping views of the Arno Valley.
Known for its rich Etruscan and Roman history, Fiesole is home to several notable ancient ruins, including the Roman Theatre and the Temple of Minerva. The town also boasts a beautiful cathedral, the Duomo di Fiesole, and several charming piazzas. Fiesole was once a prominent Etruscan settlement, later becoming an important Roman outpost. Its strategic location made it a significant center of trade and culture. |
Fiesole
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Torrita di Siena is a charming town located in southern Tuscany, nestled between the rolling hills of the Valdichiana and the Crete Senesi. Known for its well-preserved medieval architecture, the town is surrounded by impressive defensive walls and watchtowers.
Key sights include the Church of San Rocco, with its beautiful frescoes, and the town’s central square, Piazza Matteotti, which offers a picturesque view of the surrounding countryside. Torrita di Siena has a rich history, with origins dating back to the Etruscan period. |
Torrita di Siena
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Roccatederighi is a small hilltop village in the Maremma region of Tuscany, located in the province of Grosseto.
Known for its medieval charm, the village offers breathtaking views of the surrounding hills and valleys. Its narrow streets are lined with stone houses and lead to the impressive remains of the Rocca, a castle that once guarded the area. The Church of San Sebastiano is another notable sight, offering a glimpse of local history and architecture. Roccatederighi has roots dating back to Etruscan times and flourished during the Middle Ages. |
Roccatederighi
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Seggiano is a charming village located in the province of Grosseto, nestled in the hills of the Monte Amiata area in southern Tuscany.
Known for its stunning views of the surrounding landscapes, Seggiano is surrounded by lush olive groves, making it a key area for olive oil production. Major sights include the Church of San Bartolomeo and the medieval centre, with its narrow streets and stone buildings. Today Seggiano is a peaceful destination, offering both natural beauty and cultural heritage. |
Seggiano
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Montegiovi is a small, picturesque village located in the province of Grosseto, nestled on the slopes of Monte Amiata in southern Tuscany. The village is known for its tranquility and stunning views of the surrounding forests and hills.
Among its main attractions is the Church of San Michele, which showcases simple yet charming architecture. The village’s history dates back to ancient times, with roots in both Etruscan and Roman cultures. In the Middle Ages, Montegiovi was an important settlement for local agriculture. Today, it is a serene retreat, offering visitors a peaceful escape. |
Montegiovi
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