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 artefacts. 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.

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is €114 per night from 30 Aug to 31 Aug
€114
30 Aug - 31 Aug
includes taxes & fees
Stay at this business-friendly hotel in Florence. Enjoy free Wi-Fi, an outdoor pool and 2 bars/lounges. Our guests praise the breakfast and the pool in their ...
9/10 Wonderful! (1,517 reviews)
"I booked this place specifically for the pool & it was such a good idea! It is a short walk into the main attractions, and there is a tram stop right out front which will take you in or to the airport. As someone who finds public transport stressful I found it so easy. The walk is also nice for seeing ..."

Reviewed on 10 Aug 2026

The Social Hub Florence Lavagnini
Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
The price is €84 per night from 12 Aug to 13 Aug
€84
12 Aug - 13 Aug
includes taxes & fees
Stay at this hostel in Florence. Enjoy free Wi-Fi, an outdoor pool and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (1,010 reviews)
"The location is very nice; however, some of the amenities aren’t the best. You get what you pay for on this place."

Reviewed on 10 Aug 2026

Plus Florence - Hostel
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is €131 per night from 12 Aug to 13 Aug
€131
12 Aug - 13 Aug
includes taxes & fees
Stay at this hotel in Florence. Enjoy free Wi-Fi, breakfast (surcharge) and room service. Our guests praise the breakfast and the helpful staff in their reviews. ...
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.
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

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

Reviewed on 12 Jul 2026

Villa with large garden in the Chianti hills
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 7 Apr 2026

Private villa in the heart of chianti with view of siena
Beautiful house on Chianti hilltop with exceptional views.

Beautiful house on Chianti hilltop with exceptional views.

Siena Tuscany
Stay at this family-friendly holiday home in Castellina in Chianti. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lilliano Estate Winery ...
10/10 Exceptional! (77 reviews)
"Superbe villa toscane fleurie au milieu d’un hameau très calme. Très spacieuse et pleine de charme. Nous avons adoré les multiples ambiances possibles pour dîner (terrasse ou jardin). Vue et sunset spectaculaire sur les vignes et la vallée du Chianti. Piscine au delà de nos espérances parfaitement ..."

Reviewed on 9 Aug 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.

Stay near popular Castellina in Chianti attractions

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