When you think of Tuscany, images of tall cypress trees, meticulously maintained vineyards, and fortified hilltowns on rolling hills come to mind. These picturesque villages, dating back to Medieval and even Etruscan times, bring history to life with their rich heritage and stunning architecture. Tuscany is like an open-air museum, and its hilltowns are perfect for experiencing the historic ambiance of the region.
Boccaccio talked about Certaldo in his Decameron, and Dante mentioned the grand walls of Monteriggioni in his Divine Comedy. The landscape and hilltowns are so poetic that it’s tough to narrow it down to just 10 spots, but here’s our attempt:
San Gimignano, known as the Manhattan of the Middle Ages, impresses as your car winds through the Tuscan hillside. Its tall, tower-like structures act as landmarks for hikers. By day, it’s bustling with visitors from Florence and Siena, but it’s most enchanting at night. Sitting in Piazza della Cisterna, surrounded by illuminated towers and a deep blue sky, while listening to the swallows, is a unique experience.
Volterra, often overshadowed by San Gimignano, is an Etruscan gem worth visiting. It has served as a backdrop for many movies and TV shows, including “Medici – Masters of Florence.” The heart of Volterra is the Palazzo dei Priori and the Piazza dei Priori. Its cultural soul can be found in the Etruscan Museum, Pinacoteca, and Civic Museum, which showcase its unique heritage and rich art history. The area south and east of Piazza dei Priori is great for dining, with numerous restaurants, cafés, and enotecas.
Just 20 minutes north of San Gimignano, Certaldo is the final resting place of the Italian poet Boccaccio and features in one of the stories in his Decameron. This small hilltown in the Val d’Elsa region was once home to wealthy and noble people, Boccaccio wrote. Even though Certaldo has expanded beyond its original walls, the fortified hilltop part is worth visiting. You can take a funicular for 1.5€ to avoid climbing the 50-meter incline. The village has a Boccaccio museum, town hall, Sacred Art museum, several churches, and a few restaurants. Despite its appeal, Certaldo hasn’t turned into a tourist haven, maintaining a charming, authentic atmosphere.
San Miniato, famous for its white truffles, is a must-visit hilltown between Florence and Pisa. In November, the town hosts the international Truffle Market, showcasing both truffles and other Tuscan produce. You can even join a truffle hunt with locals. The village itself sits on three small hills overlooking the lower Arno valley. Climbing the cobblestone streets to La Rocca castle offers stunning views. The Tourist Office provides free guided tours in the summer, allowing access to the beautiful rooms of the city hall and its Madonna di Loreto chapel. There’s plenty to see, do, and eat in San Miniato, so you might want to stay longer than planned.
Colle di Val d’Elsa, perched above the Elsa River, is another enchanting hilltown. Park in the valley below and walk up to the old town along the main street. The heart of the town is Piazza del Duomo, dominated by the cathedral and Palazzo dei Priori. A walk to the end of the old town brings you to Il Baluardo, offering panoramic views of the new town and countryside.
Monteriggioni, on the road between Florence and Siena, has been standing strong for over 800 years. This town was Siena’s front line of defense against Florence. Its ten-meter-high fortified walls are remarkably well-preserved. For 3€, you can walk along a stretch of the ancient wall, imagining how soldiers patrolled centuries ago. When Siena fell to Florence in 1555, Monteriggioni lost its military significance, leaving it untouched and perfect for today’s visitors.
Montepulciano is famous not just for its Rosso di Montepulciano wine, but also as a filming location for the “Twilight” series. The climb up the steep, cobblestone streets to the Palazzo Comunale is worth every step, with wine shops, ancient cellars, and artisan boutiques along the way. Be sure to save money for some local delicacies and full-bodied red wines.
Pienza, located between Montepulciano and Montalcino, is a beautifully preserved Renaissance town reimagined by Pope Pius II. The town sits proudly on a hill and offers stunning views. Easily accessible after parking outside the city walls, Pienza is a UNESCO World Heritage site and a must-visit.
Montalcino is known for its Brunello wine, attracting many tourists in the summer. Visit La Fortezza, a fortress from the 14th century, to taste and buy this exceptional wine. The Enoteca offers a range of Brunellos and other SuperTuscans to enjoy. Montalcino itself is a small town, but a 15-minute drive takes you to the Abbey of Sant’Antimo, a Carolingian monastery surrounded by hills and olive trees.
Cortona, the easternmost hilltown on our list, is famous for Frances Mayes’ “Under the Tuscan Sun” and the Museum of Etruscan Academy and of the City of Cortona (MAEC). This small village, nestled behind ancient walls, offers steep streets leading to the Town Hall and Palazzo Casali, which houses MAEC. Despite its size, Cortona offers plenty of charm, inviting you to sit down with an espresso and soak in the Tuscan atmosphere.
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