Castellina in Chianti

Travel Guide

Castellina in Chianti which includes a church or cathedral, religious elements and heritage architecture
Castellina in Chianti featuring a city
Castellina in Chianti which includes farmland and animals
Buondonno Winery featuring a sunset
Castellina in Chianti which includes a statue or sculpture and heritage architecture

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.

Hotel Machiavelli Palace

Hotel Machiavelli Palace

3 out of 5
Via Nazionale 10 Florence FI
The price is ¥14,629 per night from Mar 29 to Mar 30
¥14,629
¥18,304 total
Mar 29 - Mar 30
includes taxes & fees
Stay at this hotel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (170 reviews)
was so perfect!

Reviewed on Mar 10, 2026

Hotel Machiavelli Palace
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88 Florence FI
The price is ¥25,971 per night from Mar 29 to Mar 30
¥25,971
¥31,148 total
Mar 29 - Mar 30
includes taxes & fees
Book a stay at this spa hotel in Florence. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the breakfast and the pool in our reviews. ...
9.6/10 Exceptional! (1,199 reviews)
Great location! Staff very helpful and food at hotel well priced and delicious! Loved the balcony with our room!!!

Reviewed on Mar 24, 2026

IQ Hotel Firenze
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is ¥19,616 per night from Mar 29 to Mar 30
¥19,616
¥24,158 total
Mar 29 - Mar 30
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! (1,317 reviews)
Property is very clean and new with a beautiful lounge area.

Reviewed on Mar 24, 2026

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.
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 Casa Vinicola Luigi Cecchi and Castellina ...
10/10 Exceptional! (152 reviews)
Incredible farmhouse. The views of the hills forests and vineyard was great. Good location for exploring Chianti and Tuscany region.

Reviewed on Mar 16, 2026

Farmhouse in the heart of the real chiantishire
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! (75 reviews)
Very quiet and nice place to stay. Host’s were great and easy to communicate with

Reviewed on Oct 28, 2025

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 ...
Riserva di Fizzano Residence
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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