Radda in Chianti

Travel Guide

Radda in Chianti which includes heritage architecture
Radda in Chianti which includes heritage architecture
Radda in Chianti showing a small town or village, heritage architecture and street scenes
Radda in Chianti featuring drinks or beverages and interior views
Radda in Chianti showing drinks or beverages

Embark on a tour of a medieval town that has changed little over the centuries, and learn about hundreds of years of winemaking heritage.

Radda in Chianti is nestled behind large defensive walls on a forested hilltop. With old narrow streets, towers, stone façades, small piazzas and fantastic views of the Tuscan countryside, there are many reasons to visit the medieval town. See ancient buildings and important religious relics or taste some of the region’s renowned wines.

The small town is filled with historical sites and can easily be explored on foot. In the main square, view the 15th-century Palazzo del Podestà, which serves as the town hall. The façade is adorned with numerous coats of arms. Across from the palazzo is the Church of San Niccolò (Propositura di San Niccolò). It is thought to date back to the 13th century, but much of the original building was destroyed during World War II. Explore the church’s interior to see an ancient wooden crucifix. In the square fronting the church is a beautiful old fountain.

Continue your tour of the hilltop town along medieval passageways, walking by the old defensive walls and through tunnels. Be sure to pause every now and then to take in the beautiful views of the surrounding countryside. One of the other principal attractions here is the Ice House of the Grand Duke. The structure was built toward the end of the 19th century to store ice.

The name Chianti is synonymous with Italian wines and you can learn about the region's winemaking heritage at the Convent of Santa Maria del Prato. This former Franciscan monastery is open to the public from April to October for wine courses. The venue also hosts cooking shows and concerts, as well as a wine shop and a museum.

Reach Radda in Chianti by flying into FlorenceOpens in a new window, which is 30 miles (48.2 kilometres) northwest. Connect to the town by bus, taxi or rental car to enjoy its culture, fascinating history and winemaking craft. Radda is also connected by bus to several other towns in the region.

Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
Book a stay at this luxury hotel in Radda in Chianti. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (242 reviews)
This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs ...

Reviewed on Sep 24, 2025

Borgo Vescine
c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3 Florence FI
The price is CA $122 per night from Feb 22 to Feb 23
CA $122
CA $157 total
Feb 22 - Feb 23
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 helpful staff and the ...
8.2/10 Very Good! (1,001 reviews)
Great location, short walk to the Duomo, museums and shopping. A clean quiet room awaited me.

Reviewed on Jan 21, 2026

c-hotels Ambasciatori
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88 Florence FI
The price is CA $137 per night from Feb 26 to Feb 27
CA $137
CA $173 total
Feb 26 - Feb 27
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! (1,134 reviews)
Fantastic service, exceptionallly clean room, free drink and minibar was a nice addition. Highly recommend. Lovely coming home after a day sightseeing.

Reviewed on Feb 1, 2026

IQ Hotel 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.
Il Rivalta - Place of Charme

Il Rivalta - Place of Charme

4 out of 5
Lungarno Corsini 2 Florence FI
Stay at this apartment in Florence. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (463 reviews)
Excellent place 👍

Reviewed on Feb 3, 2026

Il Rivalta - Place of Charme
Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione

Via Magenta 6 Florence FI
Stay at this apartment in Florence. Enjoy free WiFi, a rooftop terrace, and a 24-hour front desk. Popular attractions Ponte Vecchio and Pitti Palace are located ...
9.6/10 Exceptional! (58 reviews)
We had an incredible stay at this hotel in Florence! The room was absolutely amazing — spotless, beautifully designed, and felt brand new. Everything was extremely clean and comfortable, and you can tell the property is very well maintained. The concierge staff was especially kind, welcoming, and ...

Reviewed on Feb 6, 2026

Teatro Luxury Apartments Firenze - Starhotels Collezione
Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca

Lungarno Corsini 2 Florence FI
Stay at this residence in Florence. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
9/10 Wonderful! (735 reviews)
Excellent location, beautiful view of the Arno River from my room. Nice included breakfast every morning.

Reviewed on Feb 7, 2026

Palazzo Alfieri Residenza d’epoca
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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Reviews of Radda in Chianti

4.8
Top destination
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4/5 - Good

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Close to many great wineries

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