1st: Castellina in Chianti

Set along the Chiantigiana road connecting Florence to Siena, this town has origins dating back to Etruscan times. It features an imposing fortress and a unique underground tunnel known as Via della Volte, which is lined with shops and restaurants. It is an important historical archive for Chianti Classico wine.
Highlights of this neighborhood: The fortress, Via della Volte (underground tunnel), Palazzo Squarcialupi, and the Enoteca Antiquaria wine shop.

2nd: Castelnuovo Berardenga

Located in the southern area of Chianti Classico near Siena, this town was built in 1366 as a strategic “new castle.” The historical center is known for the steep stone stairs of Vicolo dell Arco and its proximity to numerous villas and castles.
Highlights of this neighborhood: Vicolo dell Arco, Church of San Giusto and Clemente, the village of San Gusme, and the Castle of Montalto.

.

3rd: Gaiole in Chianti

Originating as a medieval marketplace, Gaiole lacks defensive walls but serves as a major gateway to the surrounding parish churches and wine estates. It is located along the river Massellone and is famous for the historic castles in its immediate vicinity.
Highlights of this neighborhood: Parish Church of Spaltenna, Castle of Vertine (medieval walled village), and the Abbey of Coltibuono.

.

.

4th: Monteriggioni

This town is one of the most important and best-preserved walled castles in Italy, sitting atop a rolling hill. At night, the hillside walls and 14 towers are lit from below, making the town appear to float above the valley.
Highlights of this neighborhood: The intact fortified walls and 14 towers, the medieval festival (every July), and the historic buildings within the castle walls.

.

.

5th: Poggibonsi

A settlement with roots in the Neolithic and Etruscan-Roman ages, Poggibonsi became an essential crossroad on the ancient Francigena Road. The inner old town reflects the ancient urban layout of Borgo Marturi and contains significant religious and historic sites.
Highlights of this neighborhood: Fonte delle Fate (fairies fountain), the unfinished 15th-century fortress, and the Convent of San Lucchese.

.

.

6th: Radda in Chianti

Enclosed in large defensive walls, Radda is a beautiful medieval town that served as the head of the League of Chianti starting in 1415. It maintains its medieval appearance with narrow streets and is home to the headquarters of the Chianti Classico consortium.
Highlights of this neighborhood: Palazzo Pretorio, Church of San Niccolo, the medieval Castle of Volpaia, and the Centro di Studi Chiantigiani.

.