Castellina in Chianti

Travel Guide

A stone building with a clock tower, steps leading up to it, and people walking around.
A historic town with medieval architecture, including a prominent tower and closely packed buildings.
A vineyard path with chickens and a white chicken.
A garden with a tree, a building, and a stone wall.
A statue of a clenched fist in front of a stone building with a flag.

High up on a hill in the Tuscan countryside sits this old town with an ancient castle, centuries-old churches and burial sites that date back to Etruscan times.

Castellina in Chianti is an ancient town of cobblestone streets and old buildings. Situated on a hilltop at the crossroads of three valleys, the town has commanding views of the surrounding countryside. Tour historical churches and fortifications, shop in medieval streets and visit burial sites that are more than 2,000 years old.

Discover Castellina's past in the many centuries-old buildings and ancient sites in and around the town. Explore the Rocca Comunale of Castellina, the old fortress that towers over the rest of the town. It houses an archeological museum featuring relics excavated from the local area. See Bronze Age and Etruscan finds, including an Etruscan chariot and medieval artefacts. While you are at the castle, head up the 14th-century tower for views over the town and the surrounding landscape.

Visit the neo-Romanesque Church of San Salvatore, which was rebuilt after the devastation of World War II. Inside is a 15th-century fresco depicting the Virgin Mary with Child. Walk down the Via delle Volte, a covered passageway that skirts the ancient walls and is lined with shops and restaurants.

A short walking distance from the town centre is Montecalvario, an Etruscan tomb with four burial chambers. Objects that were found here are now on display in the Museum of Archeology of Chianti Senese at Castellina’s Piazza del Comune. Uncover more history at the Etruscan Necropolis of Poggino, a few minutes’ drive from Castellina. The site features five Etruscan tombs that date back to the 6th century B.C.

Enjoy the town's hospitality in the restaurants on Via Ferruccio, the main street. There are also numerous shops along this street.

Reach Castellina in Chianti’s ancient streets, buildings and archeological sites by bus and train from several other Chianti destinations. Note that the train station is a few miles from the town. The nearest international airport is in FlorenceOpens in a new window, which is 31 miles (49.9 kilometres) north.

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
The price is €130 per night from 25 Oct to 26 Oct
€130
25 Oct - 26 Oct
includes taxes & fees
Stay at this hostel in Florence. Enjoy free Wi-Fi, an outdoor pool and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,002 reviews)
"The rooms were very clean and fresh towels were brought often! The common areas were clean and well maintained. The only thing I wish was there were hooks in both bathrooms (especially the shower) so I could hang my towel and clothes and not have to put them on the floor or the sink. Other than that ..."

Reviewed on 24 Sept 2026

Plus Florence - Hostel
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Viale Belfiore, 55 Florence FI
The price is €169 per night from 25 Oct to 26 Oct
€169
25 Oct - 26 Oct
includes taxes & fees
Stay at this business-friendly hotel in Florence. Enjoy free Wi-Fi, an outdoor pool and breakfast (surcharge). Popular attractions Cathedral of Santa Maria del ...
The Social Hub Florence Belfiore
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is €169 per night from 25 Oct to 26 Oct
€169
25 Oct - 26 Oct
includes taxes & fees
Stay at this business-friendly hotel in Florence. Enjoy free Wi-Fi, an outdoor pool and 2 bars/lounges. Our guests praise the breakfast and the pool in their ...
The Social Hub Florence Lavagnini
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena Tuscany
Stay at this family-friendly holiday home in Castellina in Chianti. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lilliano Estate Winery ...
9.6/10 Exceptional! (82 reviews)
"Wir waren als Familie mit 2 Teenager-Kindern eine gute Woche hier und fanden es super! Das Haus und vorallem der Garten sind traumhaft. Der Pool ist ein paar Schritte entfernt und wird mit anderen geteilt, was völlig okay war. Zum Haus gehört eine Katze, die jeden Morgen an der Terrassentür wartet, ..."

Reviewed on 31 Aug 2026

Villa with large garden in the Chianti hills
Riserva di Fizzano Residence

Riserva di Fizzano Residence

3 out of 5
Localita Fizzano Castellina in Chianti SI
Stay at this family-friendly residence in Castellina in Chianti. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Lilliano Estate Winery ...
Riserva di Fizzano Residence
Beautiful house on Chianti hilltop with exceptional views.

Beautiful house on Chianti hilltop with exceptional views.

Siena Tuscany
Stay at this family-friendly holiday home in Castellina in Chianti. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lilliano Estate Winery ...
10/10 Exceptional! (79 reviews)
"We've stayed on two previous occasions at La Bagnaie, but not at this particular villa. The reviews don't really do it justice. It was well furnished, fanatically located with views across Tuscany to San Gimignano, and with every necessary bit of information provided in advance. Jacky, the manager ..."

Reviewed on 20 Sept 2026

Beautiful house on Chianti hilltop with exceptional views.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Castellina in Chianti attractions

Things to do