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 ¥8,893 per night from Nov 24 to Nov 25
¥8,893
¥11,194 total
Nov 24 - Nov 25
includes taxes & fees
Stay at this hostel in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
Plus Florence - Hostel
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is ¥17,538 per night from Nov 30 to Dec 1
¥17,538
¥21,403 total
Nov 30 - Dec 1
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. ...
Hotel Paris
Hotel Albani Firenze

Hotel Albani Firenze

4 out of 5
Via Fiume 12 Florence FI
The price is ¥18,263 per night from Nov 29 to Nov 30
¥18,263
¥22,559 total
Nov 29 - Nov 30
includes taxes & fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful ...
Hotel Albani Firenze
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! (42 reviews)
"Had a wonderful time here over 3 days in mid-September. The room was rustic but it fit the surroundings, with the only issue being the air conditioning did not keep up with the heat at night. Their dinners were fabulous, with some of the best food and service we had in 5 weeks across Italy. Breakfast ..."

Reviewed on Oct 5, 2026

Riserva di Fizzano Residence
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! (83 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
Beautiful house on Chianti hilltop with exceptional views.

Beautiful house on Chianti hilltop with exceptional views.

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 ...
10/10 Exceptional! (80 reviews)
"The pictures do not even come close to showing the beauty of this property. Incredible views, large bedrooms, a fabulous kitchen ready for you to cook your own Italian meal. I can’t wait to return. Reserve now, you will not be disappointed!"

Reviewed on Oct 30, 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.

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