Castellina in Chianti is a small town in the heart of the Chianti region in Tuscany that boasts an atmospheric Medieval closed walkway. It’s the perfect setting for a romantic dinner or some serious wine tasting.

A bit bigger and busier than Radda in Chianti, Castellina is one of the main destinations in the Senese Chianti. Here you’ll find of opportunities sample food and wine, and do a little shopping. It’s located 18 km. from Siena and 35 km. from Siena, in an area of great beauty and gorgeous vies. The drive to reach the town is in itself a gorgeous sight. Being based in or in some agriturismo near Castellina is perfect to explore this region and visit Siena easily for some top quality sightseeing.

What to see in Castellina in Chianti:

The impressive “Rocca” (fortress) that dominates the town with its crenellated tower is today home to the Museo Archeologico del Chianti senese, which showcases the Chianti’s Etruscan’s roots.

Castellina in Chianti, the Fortress

Castellina in Chianti, the Fortress

The other highlight of the town is Via delle Volte, a tunnel-like medieval street. Once used for defensive reasons, today it’s a perfect spot for a romantic meal. From the small holes in the wall you can have some stunning glimpses of the surrounding countryside.

Along with Radda and Gaiole in Chianti, Castellina was part of the “Lega del Chianti”, a military-administrative league through which Florence kept control over its lands and property, something which gave the town an important role throughout the Medieval period.


Don’t miss:

The Archeological Museum of the Senese Chianti – The museum uses interactive technology to highlight finds from archeological digs around Castellina, Gaiole, Radda and Castelnuovo Berardenga.

Find out all the best destinations of the Chianti region.

Wine tasting:

Castellina has got some renowned enoteche dotting its streets, so you’ve got plenty of choice if you’re here for some wine tasting and buying. In this area some of the best Tuscan wines are produced, we are in the heart of the Chianti Classico region, where wine is produced following strict rules that assure the top quality and extremely high standard of product. Visiting one of the enoteche of the area, a paradise for wine lovers, is also a way to better appreciate the history and traditions of this area, that has been shaped by wine making for centuries.

Tourist Office: Via Ferruccio 40


For a complete Chianti exploration, head to Radda in Chianti, 10 km. away. Scenic drive amongst vineyards and woods. Check out our detailed driving itinerary dedicated to the Chianti region.

Monteriggioni – One of the best Medieval hilltop towns in Tuscany is within half an hour drive, 20 km. away