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.

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
The price is ¥21,466 per night from Sep 20 to Sep 21
¥21,466
¥25,046 total
Sep 20 - Sep 21
includes taxes & fees
Stay at this hostel in Florence. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Plus Florence - Hostel
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is ¥27,688 per night from Sep 13 to Sep 14
¥27,688
¥32,955 total
Sep 13 - Sep 14
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! (1,572 reviews)
"The staff were great and very friendly and helpful. But, the rooms were on the smaller side, and the bathroom setup wasn’t the best. taking a shower would often leave the bathroom floor and even the area around the toilet soaked due to the open shower concept. The AC struggled to keep the room temperature ..."

Reviewed on Sep 10, 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 ¥27,893 per night from Sep 13 to Sep 14
¥27,893
¥33,180 total
Sep 13 - Sep 14
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! (723 reviews)
"Great stay. I would go back."

Reviewed on Sep 9, 2026

The Social Hub Florence Belfiore
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
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! (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 Aug 31, 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
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! (37 reviews)
"I stayed here for my solo travels for my 40th birthday and I really enjoyed every moment. The staff was exceptional and took care of so many sweet details for me and really made me feel so special for my birthday wknd. Although I traveled solo, I was never lonely or alone here in the best ways possible! ..."

Reviewed on Sep 8, 2026

Riserva di Fizzano Residence
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Castellina in Chianti Tuscany
Stay at this vacation home in Castellina in Chianti. Enjoy a garden, laundry facilities, and patios. Popular attractions Castellina Fortress and Archaeological ...
10/10 Exceptional! (157 reviews)
"Amazing views across the valley. At night we watched the fireflies and sun set. Close to Castilla in Chianti, lovely places to eat and a Co-op for all your needs. Lots of Vineyards and hilltop villages to explore."

Reviewed on Jul 25, 2026

Farmhouse in the heart of the real chiantishire
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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