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 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 CA $76 per night from Nov 8 to Nov 9
CA $76
CA $96 total
Nov 8 - Nov 9
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. ...
8.6/10 Excellent! (1,003 reviews)
"The place is clean and the city centre is walkable."

Reviewed on Oct 15, 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 CA $92 per night from Nov 15 to Nov 16
CA $92
CA $124 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Piazza del Duomo and ...
9.4/10 Exceptional! (787 reviews)
"Great space to regroup after jumping around in multiple places. Truly is a one-stop-shop with everything you need right there. Easy to walk to main attractions"

Reviewed on Oct 14, 2026

The Social Hub Florence Belfiore
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is CA $181 per night from Nov 15 to Nov 16
CA $181
CA $218 total
Nov 15 - Nov 16
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! (1,000 reviews)
"Old, unique hotel with a lot of stairs and a small, slow elevator. Our room was huge, but the laminate floor near the bathroom gave when we waled on it, felt like we might fall through. Location is great, between Santa Maria and the Duomo. Very easy to navigate from."

Reviewed on Oct 15, 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! (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! (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
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 Montecalvario and Castellina Fortress ...
10/10 Exceptional! (159 reviews)
"Sehr schöne Zeit in dem Farmhaus verbracht.Es ist Alles da was man braucht, wunderschöne Lage ,gutAusgangspunkt um die Chianti erkunden"

Reviewed on Sep 28, 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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