Tuscany is known for its beautiful hills, stone buildings, and tall cypress trees.
While cities like Florence and Pisa get most of the attention, the real charm is found in many small towns across the region. These towns have kept their old walls and traditions alive through the years.
You can explore places with ancient streets, castles on hills, and villages by cliffs. Some towns are famous for their wines, others for hot springs used since Roman times.
Whether you want to taste local cheese or walk through historic lanes, these towns offer many ways to experience the true heart of Tuscany.
Read also: 12 Best Towns on the Amalfi Coast (Italy) that You Should Visit
1. Volterra, Pisa Area
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Volterra is perched on a tall ridge, surrounded by old Etruscan walls. The Roman theater there is still visible, showing the town’s long history. Volterra is famous for its smooth alabaster, carefully carved by local artisans and shipped worldwide.
2. Barga, Lucca
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You’ll find Barga nestled in the hills of Garfagnana, overlooking the Serchio Valley. The town is known for the Romanesque Duomo di San Cristoforo, a key landmark. Each summer, you can enjoy a long-running jazz festival. In the cafés and events, you might notice a mix of Scottish and Italian influences.
3. San Quirico d’Orcia, Siena
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In San Quirico d’Orcia, you will find the rare Renaissance Horti Leonini garden. The town is surrounded by strong medieval walls that show its old history. You can walk along the Via Francigena, a famous ancient route that passes through. Don’t miss the Romanesque Collegiate Church of Saints Quirico and Giulitta for its simple, historic design.
4. Castellina in Chianti, Siena
You can explore a stone fortress from the 1400s here. Walk through Via delle Volte, an underground street built to protect soldiers. Don’t miss tasting the local Chianti Classico red wine. Nearby, the ancient Etruscan burial site Monte Calvario is worth a visit.
5. Cortona, Arezzo
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You’ll find Cortona perched on a high ridge overlooking the Val di Chiana. The town is surrounded by ancient Etruscan walls and features a medieval town hall with a clock tower. From Cortona, enjoy wide views stretching to Lake Trasimeno, offering a peaceful, historic setting to explore.
6. Buonconvento, Siena
Buonconvento is surrounded by tall red-brick walls from the 1300s. The town has one main street that runs straight through, once protected by two gates. Be sure to visit the Museo della Mezzadria, which shows traditional Tuscan farm life. Buonconvento is also part of the Via Francigena pilgrimage path.
7. Lucignano, Arezzo
You will notice Lucignano’s unusual oval layout, with streets curving tightly inward like a spiral. This design gives the town its nickname, the town of circles. Inside the Museo Comunale, you can see the famous golden Tree of Life artwork. If you visit in May, the Maggiolata flower parade offers a vibrant and colorful event to enjoy.
8. Campiglia Marittima, Livorno
You will find Campiglia Marittima on a hill near the Tyrrhenian Sea. The old Rocca fortress stands tall, watching over the Val di Cornia valley.
At the Archaeological-Mineral Park of San Silvestro, you can ride a mine train through historic copper and silver tunnels for a unique experience.
9. Pitigliano, Grosseto
Pitigliano is perched on high tufa cliffs, with stone houses that seem to grow from the rock itself. The town is known as Little Jerusalem because of its historic Jewish area. Here, you can visit a 16th-century synagogue and a kosher bakery that attracts visitors.
10. Radda in Chianti Near Siena
Radda in Chianti is located perched between Siena and Florence, enclosed by old stone walls. The 16th-century Palazzo del Podestà stands out with its bright coats of arms.
If you enjoy wine, don’t miss the Chianti Classico wineries here. In June, the “Radda nel Bicchiere” event offers a chance to taste top local wines.
11. Suvereto, Livorno
Suvereto is surrounded by thick medieval walls that date back many centuries. Its notable landmark is the town hall, topped with a tall clock tower. The area is rich with cork-oak forests, which inspired the town’s name. Each summer, you can join locals in the lively barrel-rolling race called Corsa delle Botti.
12. Greve in Chianti Near Florence
You’ll find a wide, triangular square called Piazza Matteotti in Greve in Chianti. The square is surrounded by covered walkways with shops. In the center stands a statue of explorer Giovanni da Verrazzano.
Key points:
- Known as the entrance to Chianti Classico wine area
- Hosts a large wine festival each September
- The festival includes many wine tasting booths
13. Montepulciano, Siena
Montepulciano is located on a hill within the Val d’Orcia. Its wide central square, Piazza Grande, is lined with elegant Renaissance buildings. Don’t miss tasting Vino Nobile, a red wine aged in long brick cellars beneath the town’s old homes.
14. San Gimignano, Siena
When you visit San Gimignano, you’ll see 14 tall stone towers that stand out in the Elsa Valley. This unique skyline earned it the nickname Medieval Manhattan. You can explore its well-preserved old town, which is protected by UNESCO. Don’t forget to try Vernaccia, a local white wine with a special DOCG status.
15. Montalcino, Siena
You will find Montalcino on a hill, surrounded by the scenic Val d’Orcia. Its old 14th-century fortress shapes the town’s skyline. You can also experience the famous Brunello di Montalcino wine, known for aging at least five years in oak barrels.