Rolling hills, rows of cypress, and golden stone fill the heart of Tuscany. Most travelers rush to Florence, Siena, and Pisa. Yet, the region’s real soul lives in its small towns.
These places kept their old walls, towers, and traditions while time moved on.
In this article, we’ll explore 27 of the best small towns in Tuscany, Italy. You’ll find hillside fortresses and cliff-top villages.
Some streets smell like fresh bread drifting from family bakeries. A handful of towns guard world-famous wines.
Others offer hot springs first used by the Romans. There are even a few places that still echo with legends of poets, popes, and explorers.
Use the list to plan day trips or a full road journey.
Taste pecorino in Pienza. Walk the ancient Etruscan lanes of Sorano. Watch the sun set behind the towers of San Gimignano.
Each stop adds a new layer to your Tuscan memory. Let’s begin!
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1. Volterra, Pisa
(Photo by Moira Nazzari)
Volterra rises on a high ridge, its ancient Etruscan walls tracing the horizon. The Roman theater still stands, a stubborn reminder of centuries gone by.
People know Volterra for its smooth alabaster carvings. Local artisans shape these pieces by hand and send them all over the world.
2. Barga, Lucca
(Photo by Michael Kroul)
Barga sits up in the Garfagnana hills. The Romanesque Duomo di San Cristoforo looks out over the Serchio Valley.
This town’s pretty famous for its summer jazz festival, which has been running for ages. You’ll also spot a unique Scottish-Italian style in the local cafés and events, kind of unexpected, right?
3. San Quirico d’Orcia, Siena
(Photo by James Obernesser)
San Quirico d’Orcia sits right in the heart of the UNESCO-listed Val d’Orcia. The town holds onto a rare Renaissance garden called Horti Leonini.
You’ll also spot its sturdy medieval walls. People know San Quirico d’Orcia for the Via Francigena, which winds through town, and for the Romanesque Collegiate Church of Saints Quirico and Giulitta.
4. Castellina in Chianti, Siena
(Photo by Rich Martello)
Castellina in Chianti holds onto a 15th-century stone fortress. There’s also this underground street, Via delle Volte, which once offered protection to soldiers.
Castellina in Chianti is known for its Chianti Classico red wine and for an ancient Etruscan burial mound called Monte Calvario.
5. Monteriggioni, Siena
(Photo by Shalev Cohen)
Monteriggioni still has its round wall, lined with 14 stone towers. They look pretty much like they did 800 years back.
Monteriggioni is famous because visitors can walk on the walls and enjoy a large medieval fair held every July.
6. Sorano, Grosseto
(Photo by Mauro Gigli)
Sorano clings to a tall tufa cliff above the Lente River. The Masso Leopoldino fortress keeps watch over the town.
Locals sometimes call Sorano the “Matera of Tuscany.” It’s got cave homes and medieval lanes carved right into the soft rock.
7. Cortona, Arezzo
Cortona sits on a ridge above the Val di Chiana. Etruscan walls wrap around the town, and there’s a medieval town hall topped with a clock tower.
After “Under the Tuscan Sun” hit bookshelves and movie screens, people everywhere started talking about Cortona. From up here, you get these sweeping views stretching all the way to Lake Trasimeno.
8. Massa Marittima, Grosseto
Massa Marittima has this rare, star-shaped Piazza Garibaldi. The Romanesque-Gothic Cathedral of San Cerbone sits right at the top.
People know Massa Marittima for its long mining history. Every spring and summer, the town hosts the Balestro del Girifalco crossbow contest: something you really shouldn’t miss if you’re in the area.
9. Pontremoli, Massa-Carrara
Pontremoli is located at the meeting point of two rivers. Piagnaro Castle towers above, home to the Statue Stele Museum.
Every summer, the town buzzes with the Medievalis fair. Its old stone bridges once led countless pilgrims along the Via Francigena.
10. Buonconvento, Siena
Buonconvento is behind tall red-brick walls from the 1300s. There’s a single straight main street, which used to be guarded by two gates.
People know Buonconvento for the Museo della Mezzadria. This museum dives into Tuscan farm life.
It’s also a key stop on the Via Francigena pilgrimage route.
11. Colle di Val d’Elsa, Siena
Colle di Val d’Elsa rises on a ridge. The medieval Colle Alta quarter welcomes you through the stout stone gate of Porta Nuova.
Locals call Colle di Val d’Elsa Italy’s “City of Crystal.” The town has crafted fine lead-crystal glass for centuries and even has a Crystal Museum.
12. Lucignano, Arezzo
Lucignano has this rare oval street plan that winds inward, almost like a snail curling up. That’s why folks call it the “town of circles”.
People know Lucignano for the golden Tree of Life, which you’ll find in the Museo Comunale. The town also bursts to life during the May Maggiolata flower parade, definitely worth seeing if you can.
13. Bagno Vignoni, Siena
Bagno Vignoni has this broad stone pool filled with hot spring water, right in the spot where most towns would put a square.
People know Bagno Vignoni for its Roman-era thermal baths. Pilgrims on the old Via Francigena route stopped here to soak and recover.
14. Campiglia Marittima, Livorno
Campiglia Marittima sits on a hill close to the Tyrrhenian Sea. The medieval Rocca fortress rises above, keeping an eye on the Val di Cornia.
Campiglia Marittima is renowned for the Archaeological-Mineral Park of San Silvestro. Here, a mine train runs through old copper and silver tunnels, pretty unforgettable if you ask me.
15. Pitigliano, Grosseto
Pitigliano rises on these tall tufa cliffs, with stone houses that almost look like they’re sprouting right out of the rock.
Locals call it “Little Jerusalem” because of the old Jewish quarter. There’s a 16th-century synagogue tucked away here, along with a kosher bakery that still draws curious visitors.
16. Radda in Chianti, Siena
Radda in Chianti sits high up between Siena and Florence. Stone walls surround the town, and the 16th-century Palazzo del Podestà shows off colorful coats of arms.
People know Radda in Chianti for its Chianti Classico wineries. Every June, the “Radda nel Bicchiere” tasting event lets local estates pour their best bottles.
17. Suvereto, Livorno
Suvereto still has thick medieval walls, first recorded way back in 973. There’s also a Palazzo Comunale with a tall clock tower standing above it.
Suvereto is known for cork-oak forests, which actually inspired the town’s name. Every summer, locals get together for the high-energy barrel-rolling race called Corsa delle Botti.
18. Greve in Chianti, Florence
Greve in Chianti has this broad, triangular Piazza Matteotti. Arcades line the square, and there’s a statue of the explorer Giovanni da Verrazzano right in the middle of it all.
People call Greve the gateway to Chianti Classico wine country. Every September, the town throws a big wine festival that packs the square with tasting stands.
19. Montepulciano, Siena
Montepulciano sits on a hill, in the Val d’Orcia. Its Piazza Grande stretches wide and shows off Renaissance palaces on every side.
Montepulciano is famous for Vino Nobile red wine. Locals age this wine in long, brick cellars hidden beneath the old houses.
20. Anghiari, Arezzo
Anghiari rises above the Tiber Valley, tucked behind thick stone walls. Those walls have watched over its streets since the Middle Ages.
Anghiari is famous for the 1440 Battle of Anghiari, which Leonardo da Vinci sketched later. The Museum of the Battle shares that story in detail.
21. San Gimignano, Siena
San Gimignano is located in the Elsa Valley and has 14 stone towers. That’s actually why people call it the “Medieval Manhattan.”
It’s famous for its UNESCO-listed old center. Oh, and Vernaccia di San Gimignano, the first Italian white wine to snag DOCG status, comes from here too.
22. Montalcino, Siena
Montalcino stands on a hill with its 14th-century pentagon fortress quietly watching over the Val d’Orcia.
People everywhere know Montalcino for Brunello di Montalcino, a red wine that ages at least five years in oak barrels.
Read also: 15 Must-See Castles in Northern Italy: High-Res Photos & Interesting Facts
23. Castiglione di Garfagnana, Lucca
Castiglione di Garfagnana holds onto its 15th-century stone walls and round towers. These old defenses still watch over the hilltop Rocca fortress.
You’ll also find the town on the list of “The Most Beautiful Villages of Italy.” There’s a 13th-century bridge here, built by Spinetta Malaspina, that’s worth a look.
24. Certaldo, Florence
Certaldo sits on a red-brick hilltop, watched over by the 12th-century Palazzo Pretorio. Medieval walls still wrap around the town, and they’re impressively well-kept.
People know Certaldo as the birthplace of Giovanni Boccaccio. Every July, the Mercantia street-theater festival brings the place to life.
25. Montefioralle, Florence
Montefioralle crowns a hill above Greve in Chianti. Its stone lanes wind in a near-perfect ring of medieval walls.
It’s listed among Italy’s “Most Beautiful Villages.” Some locals even claim explorer Amerigo Vespucci was born here.
26. Pienza, Siena
Pienza sits on a ridge above the Val d’Orcia. Pope Pius II rebuilt it between 1459 and 1462, dreaming up the first “ideal” Renaissance town.
Everything centers on the perfectly proportioned Piazza Pio II, with its striking cathedral and the Piccolomini Palace. People flock here for the UNESCO status, sure, but also for the tangy Pecorino di Pienza.
Each September, the Fiera del Cacio celebrates this cheese with gusto. Pienza even inspired humanist city-planning all over Europe: pretty impressive for such a small place.
27. Sovana, Grosseto
Sovana winds its way down a single medieval lane, leading to Piazza del Pretorio. The Rocca Aldobrandesca keeps watch nearby, along with the Romanesque Cathedral of SS. Pietro e Paolo.
People know Sovana for its striking Etruscan tombs in the Parco Archeologico Città del Tufo. It’s also the birthplace of the reformer Pope Gregory VII, something locals seem quietly proud of.