The Chianti area is Tuscany’s main wine region. Located south of Florence, it’s remarkable for its rolling hills and sun-drenched vineyards. With scenic towns like Radda, Castellina and Castelnuovo Berardenga within its borders, it makes a perfect destination for those looking to enjoy countryside views, exceptional food and wine, and a traditional way of life. These are our top 10 small towns in the Chianti to help you organise your trip.

Chianti 10 Top Towns to visit

1. Radda in chianti

The hilltop town of Radda in Chianti was once the Capital of the ‘Chianti League’. In a way, this is still true today as few towns in the Chianti can match Radda’s charming Medieval layout. And its expansive views over the vineyards are quite remarkable. In Radda, Chianti Classico wine is king, the ruling tipple in all the town’s rustic enoteche, gorgeous shops and seasonal festivals. For a full immersion in Chianti Classico world visit during the Radda nel bicchiere wine festival in Spring, busy but definitely a must for all wine passionate.


LOCATION: Radda in Chianti is halfway between Florence and Siena – 50 kms. from Florence, and 40 kms from Siena. Best way to get there: by car. No direct buses/train from Florence. There’s a direct bus from Siena.

Experience a Chianti Wine Tour leaving from Florence. Book yourself on this Classic half-day wine tour that immerses you in the vineyards of the Chianti. You’ll stop at a well-known vineyard, take a tour of the cellar and enjoy a guided wine tasting featuring the famous Chianti Classico’s and the Riservas amongst others.

radda in chianti
Radda in Chianti, the main square – photo: @lovefromtuscany

2. Castellina in Chianti

The ‘sister’ of Radda, Castellina lies 16 kms from Radda and features the intriguing Vie delle Volte, a Medieval cover passageway today dedicated to locally produced wine and food. Wooden barrels, the scent of grapes, inviting cellars to explore. Everything here is about enjoying Chianti wine. There’s a small Archeological Museum of the Chianti Senese hosted inside the impressive Medieval fortress that is well worth a visit.


LOCATION: 27 Kms. from Siena, 47 Kms. from Florence – Best way to get there: by car. There’s a direct bus from Siena, no direct bus/train from Florence.

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3. Greve in Chianti

Greve’s welcoming main square is surrounded by loggia on all sides and hosts a statue of the town’s most famous son, the explorer Giovanni da Verrazzano. The square is a great space for markets that Greve in Chianti has been putting on for literally centuries.

Each Easter Monday there’s the popular antique market, plus you find the weekly market every Saturday, several festivals throughout the year including a music Spring Festival and the annual Chianti Classico Exposition. Check out the food mecca Macelleria Falorni and the Museo del Vino, a museum completely dedicated to wine.


LOCATION: 30 kms. south of Florence, 43 kms. north of Siena – There’s a direct bus service from Florence.

=> Discover the Best Chianti Wine Festivals in September

Small towns in the Chianti
Greve in Chianti –
By VelvetOwn work, CC BY-SA 3.0, Link

4. Montefioralle

This diminutive hamlet and former castle is perched on the top of a steep hill above Greve in Chianti. You can walk there if you have the stamina (2 kms uphill!). Montefioralle is a delightful stone hamlet with a couple of restaurants and plenty of picturesque corners that make for great photos.


LOCATION: 2 kms. from Greve in Chianti – Best way to get there: car. No public transport.

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small towns in the chianti

5. San Casciano in Val di pesa

San Casciano is one of the gates to the Chianti region, very close to Florence that is perfect for a day trip or even as a base from which to visit the city for those who want an authentic – and not overrun with tourists – small Tuscan town. Its charm lies in the authenticity. It’s lively despite its size, and can keep you entertained for a few hours; it has some nice shops, gorgeous trattorias and even a Sacred Art museum.


LOCATION: 20 Kms. from Florence – Best way to bet there: car or direct bus from Florence.

6. Panzano

There’s a reason Panzano is one of Chianti’s most appreciated food capitals. The poet-butcher (now TV celebrity) Dario Cecchini has his butcher shop here; a kind of Tuscan style fast food, done really well. Here you can have an incredible burger, or tuck into a juicy bistecca in front of an open fire. It’s the real thing. Meat lovers should book a table at Solociccia the restaurant just in front of the shop. Try the lardo, spread on toasted warm bread – a real meat eater’s delicacy. Then climb to the top of the hill to see the Church of Santa Maria. Definitely one of the top towns to visit in Chianti for foodies.


LOCATION: 40 kms. from Florence, 48 kms. from Siena – close to Greve in Chianti. Best way to get there: car. There’s a direct bus from Florence and from Greve in Chianti.

=> Check out this scenic Chianti Road trip with a lunch stop in Panzano.

=> Discover the 8 Top Experiences to have in the Chianti region!

small towns in the Chianti
Panzano, the Church of Santa Maria
By Peter K BurianOwn work, CC BY-SA 4.0, Link

7. Volpaia

Volpaia is not a town, but a tiny hamlet, with ancient stone walls and doorways framed by climbing flowers. Here you can discover, in a few square meters, what the Chianti is all about. The former castle today hosts a informal wine tasting spot in the Medieval tower, a couple of eateries and a lovely restaurant with views over the vineyards that have made this part of the world so famous. There are two little churches , plenty of picturesque doors and flowery corners to capture with the camera.


LOCATION: 5 Kms. from Radda in Chianti. Best way to get there: car. No public transport.

best chianti town to visit

8. Castelnuovo Berardenga

Very close to Siena and the scenic Crete Senesi, in the southern part of the Chianti region, Castelnuovo Berardenga is surrounded by a charming landscape and a few villas. The town used to serve as a defence for Siena in the 14th century, and the atmospheric Vicolo dell’Arco still speaks of its Medieval past. You can visit the parish churches and see (or even stay) in one of the splendid architectural complexes in the area, like Villa Chigi Saracini, Montalto Castle, or the Certosa di Pontignano. And enjoy the relaxed pace of life of this town that has joined the Slow City movement.


LOCATION: 25 Kms. from Siena – Best way to get there: by car. There’s a direct bus from Siena.

small towns in the Chianti
A view of the Certosa di Pontignano –
By LigaDueOwn work, CC BY-SA 4.0, Link

9. San Gusmè

Very close to Castlenuovo, this is a miniature walled village surrounded by vineyards and more vineyards! Here you’ll find one tiny square, 100 inhabitants, one bar and two good restaurants. A beautiful village that seems to have been forgotten by history and the passing of time.


LOCATION: 5 Kms. from Castelnuovo Berardenga – Best way to get there: car.

=> 3 Magical Places immersed in the Chianti vineyards

San Gusmè
Photo by Vignaccia76Opera propria, CC BY 3.0, Collegamento

10. Gaiole in Chianti

Located on the road that leads from Chianti to the Valdarno area, east of Radda, its buildings don’t tell us much about Gaiole’s past, as the town has been reconstructed many times. A market town for centuries, it has a triangular main square that hosts markets and various events during the Summer, mainly dedicated to wine and local food. If Gaiole in Chianti itself cannot be said to be pretty or picturesque, nearby you find some of the most impressive castles of the Chianti region, like Brolio, Meleto and Vertine.


LOCATION: 30 Kms. from Siena – Best way to get there: car. There’s a direct bus from Siena.

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