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 artifacts. 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 center 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 kilometers) north.

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is ¥16,042 per night from Aug 9 to Aug 10
¥16,042
¥20,257 total
Aug 9 - Aug 10
includes taxes & fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the breakfast and the pool in ...
9/10 Wonderful! (1,467 reviews)
"The room is spacious, though this is a block that houses students as well, so it could be a bit noisy. Pool has a stunning view, highly recommend. Located just outside the centre for some quiet, but easy enough to walk to everywhere."

Reviewed on Jul 23, 2026

The Social Hub Florence Lavagnini
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Viale Belfiore, 55 Florence FI
The price is ¥16,019 per night from Aug 23 to Aug 24
¥16,019
¥20,232 total
Aug 23 - Aug 24
includes taxes & fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Cathedral of Santa ...
9.4/10 Exceptional! (642 reviews)
"A"

Reviewed on Jul 23, 2026

The Social Hub Florence Belfiore
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is ¥25,247 per night from Jul 28 to Jul 29
¥25,247
¥30,005 total
Jul 28 - Jul 29
includes taxes & fees
Stay at this hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,008 reviews)
"We only stayed overnight but from what we experienced it was nice and close to town close to everything very nice"

Reviewed on Jul 20, 2026

Hotel Paris
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.
Riserva di Fizzano Residence

Riserva di Fizzano Residence

3 out of 5
Localita Fizzano Castellina in Chianti SI
Book a stay at this family-friendly residence in Castellina in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lilliano Estate ...
9.6/10 Exceptional! (35 reviews)
"The staff was SO helpful as soon as we checked it! We got great recommendations for dinner and small towns to visit in the area. Our room had the BEST view. The pool was so nice and the breakfast buffet was perfect! We loved our morning cappuccinos and all the fresh fruit and pastries. It was especially ..."

Reviewed on Jul 16, 2026

Riserva di Fizzano Residence
Private villa in the heart of chianti with view of siena

Private villa in the heart of chianti with view of siena

Fonterutoli Provincia di Siena
Stay at this villa in Castellina in Chianti. Enjoy a garden, laundry facilities, and air conditioning. Popular attractions Mazzei Winery and Walls of Monteriggioni ...
10/10 Exceptional! (5 reviews)
"We were a multi-generational family of 11 in town for a wedding. The location was central and easy to get to. There was plenty of room and lots of space for everyone to gather and to also have their own privacy. Would definitely return"

Reviewed on Apr 7, 2026

Private villa in the heart of chianti with view of siena
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena Tuscany
Book a stay at this family-friendly vacation home in Castellina in Chianti. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lilliano Estate ...
9.6/10 Exceptional! (81 reviews)
"Property had a pool and a big yard, very relaxing."

Reviewed on Jul 12, 2026

Villa with large garden in the Chianti hills
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.

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