Top 10 Small Towns in Tuscany
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Latest page update: 14 April 2025
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By: Dion Protani
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Tuscany is one of the most visited regions in Italy, known around the world for its rolling hills, vineyard landscapes, Renaissance cities, and beautiful hill towns.
While Florence, Siena, and Pisa often take the spotlight, the real character of the region is just as often found in its smaller towns — places with medieval centres, historic palaces, quiet piazzas and sweeping views over the countryside. These towns offer a slower pace, a chance to explore on foot, and a more personal connection with Tuscan life — shaped by local traditions, seasonal rhythms, and timeless scenery. |
Volterra, Tuscany
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Montepulciano
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Set in the hills of southern Tuscany, Montepulciano is known for its Renaissance architecture, panoramic views, and long association with wine — particularly the Vino Nobile di Montepulciano.
The town’s main street, the Corso, leads uphill through elegant palaces and artisan shops to Piazza Grande, one of the most impressive squares in Tuscany. From here, visitors can take in sweeping views over the Val di Chiana and Val d’Orcia. Montepulciano is also home to wine cellars carved into the rock beneath the town, making it a rewarding stop for anyone interested in history and viticulture. |
Montepulciano, Tuscany
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San Gimignano
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Often referred to as the “medieval Manhattan,” San Gimignano is famous for its skyline of stone towers that once symbolised the wealth of rival noble families.
Set on a hilltop in central Tuscany, the town is enclosed by well-preserved walls and filled with narrow streets, historic churches, and small squares. The heart of San Gimignano is Piazza della Cisterna, surrounded by medieval buildings. Despite its popularity, the town retains an authentic feel and offers unforgettable views over the surrounding countryside, especially at sunset. |
San Gimignano, Tuscany
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Pienza
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Pienza is a small town in southern Tuscany, completely redesigned in the 15th century by Pope Pius II. The result was one of Italy’s earliest examples of Renaissance town planning, centred around the harmonious Piazza Pio II.
The town’s key landmarks include the Duomo and Palazzo Piccolomini, both set against wide views of the Val d’Orcia. Narrow lanes like Via dell’Amore lead to panoramic terraces overlooking the countryside. Pienza is also known for its pecorino cheese, which is sold in shops throughout the centre. |
Palazzo Piccolomini, Pienza
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Volterra
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Volterra is one of Tuscany’s most atmospheric hill towns, with origins dating back to the Etruscan period. Its elevated position offers wide views and a distinct sense of isolation from the surrounding countryside.
The town is known for its ancient walls, narrow streets, and well-preserved medieval centre. Highlights include the Roman theatre, the Etruscan gate, and the alabaster workshops still in operation today. Volterra combines history with a strong local character and fewer crowds than more well-known towns. |
Piazza dei Priori, Volterra
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Cortona
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Cortona rises steeply from the Val di Chiana and offers sweeping views across the surrounding plain. It has roots in the Etruscan period and a long history reflected in its steep alleys and ancient stone walls.
The town became widely known after the book Under the Tuscan Sun was published, and still draws visitors for its scenery and relaxed atmosphere. Key sights include the Museo dell’Accademia Etrusca and the picturesque Piazza della Repubblica. Cortona’s position makes it a useful base for exploring eastern Tuscany and nearby Umbria. |
Cortona, Tuscany
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Montalcino
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Montalcino is a hill town in southern Tuscany, best known for producing Brunello di Montalcino, one of Italy’s most prestigious red wines. The town is surrounded by vineyards and olive groves, with a historic centre dominated by a medieval fortress.
Visitors can explore narrow streets lined with wine shops, climb the ramparts of the fortress for panoramic views, or visit the nearby Abbey of Sant’Antimo. Despite its fame, Montalcino retains a relaxed pace and local character. It’s a key destination for wine lovers and a natural stop on a Val d’Orcia itinerary. |
Montalcino, Tuscany
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Massa Marittima
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Massa Marittima lies in the hills of southern Tuscany, not far from the coast, and offers a striking mix of medieval architecture and quiet charm. Its historic centre is compact but rich in detail, with steep streets leading to a wide central square.
Piazza Garibaldi is home to the town’s most impressive landmark — a Romanesque cathedral that stands above the square on a grand staircase. Other highlights include the town hall, public fountain, and the nearby archaeological museum. Massa Marittima is less visited than other Tuscan towns, making it ideal for slower exploration. |
Massa Marittima
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Porto Santo Stefano
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Porto Santo Stefano is the main town on the Monte Argentario peninsula, set around a natural harbour on Tuscany’s southern coast. It’s known for its fishing heritage, coastal views, and links to nearby islands.
The seafront promenade is lined with cafés and restaurants, while uphill lanes lead to the Spanish Fortress with views across the bay. Ferries depart from the harbour to Giglio Island, making it a popular departure point in summer. Porto Santo Stefano offers a different side of Tuscany, with a stronger focus on the sea. |
Porto Santo Stefano, Tuscany
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Pietrasanta
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Pietrasanta sits close to the Tuscan coast in the province of Lucca and has long been associated with sculpture and marble work. Artists including Michelangelo sourced marble nearby, and the town still attracts creatives today.
Its centre features a spacious piazza, art galleries, and workshops that open directly onto the streets. The Duomo of San Martino and the adjoining cloister are key landmarks, while temporary exhibitions often appear in public spaces. Pietrasanta blends art, history and seaside proximity with a lively but relaxed atmosphere. |
Pietrasanta
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Pitigliano
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Pitigliano is one of the most visually striking towns in Tuscany, set on a ridge of volcanic rock with houses rising dramatically from the cliffs. Its long history includes Etruscan, Roman, and medieval layers, all visible in its winding streets.
The town is also known as “Little Jerusalem” for its historic Jewish quarter and synagogue, which remain open to visitors. Stone passageways, carved-out cellars, and arches built into the rock give the town a unique structure. Pitigliano feels remote, but it’s one of the most rewarding and atmospheric places to visit in southern Tuscany. |
Pitigliano, Tuscany
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Looking for more ideas? Browse our full list of destinations in Tuscany to find more small towns, cities and hidden places worth visiting.
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