Tuscany often evokes images of Florence’s Duomo, the Leaning Tower of Pisa, or the vineyards of Chianti. Yet, the region hides lesser-known gems that deserve a spotlight. These small cities offer Tuscany’s beauty, history, and charm without the crowds. Explore these underrated destinations for an authentic, quieter slice of Tuscan life.
1. Cortona: Ancient Charm and Breathtaking Views
Nestled on a hillside, Cortona combines history and scenery with a quaint, small-town atmosphere. This ancient city dates back to the Etruscan civilization and offers visitors a deep historical experience. Wander through narrow stone-paved streets and enjoy panoramic views stretching over Lake Trasimeno and the Val di Chiana.
Start at Piazza della Repubblica, where a medieval clock tower and 13th-century buildings set a stunning scene. From there, visit the Diocesan Museum, home to religious artifacts, including works by Fra Angelico. For a more expansive look into history, head to the Museo dell’Accademia Etrusca, showcasing an impressive collection of Etruscan relics.
Hiking enthusiasts can explore nearby trails leading to the Basilica of Santa Margherita or the Hermitage of Le Celle, a peaceful Franciscan monastery. Cortona’s elevated position ensures that every corner offers spectacular views, perfect for unwinding after a day of exploring.
2. Pistoia: Art, Architecture, and Hidden History
Pistoia may not have the renown of Florence, but it rivals its art and architecture. Known for its Romanesque churches, Pistoia is a dream for lovers of medieval and Renaissance structures. Begin at the Piazza del Duomo, surrounded by impressive buildings like the Cathedral of San Zeno, a marvel of medieval architecture with a beautiful silver altar.
The Baptistery of San Giovanni in Corte, an octagonal marble masterpiece, sits nearby. Step inside to appreciate intricate details that transport you back to Pistoia’s prosperous past. Art lovers should visit the Museo Civico for its collection of Renaissance paintings and sculptures.
Venture into Pistoia’s underground passages, a maze of tunnels that run beneath the city. These hidden routes, known as Pistoia Sotterranea, give insight into ancient Pistoia and its intricate water systems. The tunnels add an element of mystery to your visit and offer a unique perspective on the city’s history.
3. Volterra: Etruscan Relics and Twilight Beauty
For those drawn to history and mystery, Volterra is an extraordinary destination. This small, fortified city stands on a hill and reveals layers of Etruscan, Roman, and medieval history. Walk through ancient gates, like the Porta all’Arco, a striking Etruscan arch that has stood for over 2,000 years.
The Roman Theatre, built in the 1st century BCE, remains well-preserved and offers a glimpse into ancient Roman entertainment. For more artifacts, visit the Guarnacci Etruscan Museum, which houses one of Italy’s most comprehensive Etruscan collections.
While wandering the city, visit the Palazzo dei Priori, Italy’s oldest town hall, dating back to 1208. Its facade and frescoed interiors are a delight to explore. Volterra’s quiet, cobblestone streets make it ideal for leisurely exploration, and the views from the city walls are breathtaking, especially at twilight.
4. San Miniato: Truffles, Towers, and Medieval Festivals
Perched along the Arno River, San Miniato is best known for its truffles, but it offers much more. The city has a charming medieval feel, with historic towers, churches, and panoramic views.
Start at Rocca di Federico II, a fortress tower dating back to the 13th century. Climb to the top for views of the Arno Valley, with vineyards and olive groves stretching far into the distance. Below, the Cathedral of Santa Maria Assunta and San Genesio is worth visiting for its Romanesque-Gothic architecture and beautifully painted interiors.
If you visit in November, experience the San Miniato Truffle Festival, a lively event celebrating the region’s prized white truffles. During the festival, the city bursts with vendors, live music, and medieval costumes, offering a unique way to experience San Miniato’s culture.
5. Massa Marittima: Medieval Mines and Majestic Plazas
Massa Marittima, located near the Maremma hills, offers an intriguing mix of medieval architecture and mining history. Known as “Tuscany’s Medieval Jewel,” the city centers around Piazza Garibaldi, a grand square lined with historic buildings and a striking cathedral.
The Cathedral of San Cerbone, a Romanesque structure with an elegant facade, dominates the piazza. Inside, you’ll find remarkable frescoes and ancient relics that showcase the city’s rich past. Next, visit the Museo della Miniera, a fascinating museum dedicated to the city’s mining history. This underground museum allows visitors to walk through recreated tunnels, revealing the hard lives of miners in centuries past.
For sweeping views, hike up to the Fortezza Senese, a 14th-century fortress with walls that encircle the town. Massa Marittima also offers trails through the surrounding hills, perfect for nature lovers looking to enjoy the Tuscan countryside.
