Radda in Chianti

Travel Guide

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

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
The price is €467 per night from 1 Apr to 2 Apr
€467
1 Apr - 2 Apr
includes taxes & fees
Stay at this luxury hotel in Radda in Chianti. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (244 reviews)
You are paying for the view!!!! This hotel was not worth the money spent in my opinion. The hotel staff was not very accommodating, though the restaurant staff was lovely. We had to bring our luggage up to our room and back down during check in and check out — no one even offered and trust me it ...

Reviewed on 5 Oct 2025

Borgo Vescine
Hotel Machiavelli Palace

Hotel Machiavelli Palace

3 out of 5
Via Nazionale 10 Florence FI
The price is €92 per night from 22 Mar to 23 Mar
€92
22 Mar - 23 Mar
includes taxes & fees
Stay at this hotel in Florence. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the helpful staff in their reviews. Popular ...
8.4/10 Very Good! (170 reviews)
was so perfect!

Reviewed on 10 Mar 2026

Hotel Machiavelli Palace
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88 Florence FI
The price is €124 per night from 22 Mar to 23 Mar
€124
22 Mar - 23 Mar
includes taxes & fees
Stay at this spa hotel in Florence. Enjoy free Wi-Fi, an outdoor pool and a full-service spa. Our guests praise the breakfast and the pool in their reviews. ...
9.6/10 Exceptional! (1,192 reviews)
Wonderful!

Reviewed on 20 Mar 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 Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the breakfast and the helpful staff in their ...
9.4/10 Exceptional! (483 reviews)
The hotel was in the perfect location, walkable to everything. Staff was friendly, breakfast was great! Our room was spacious and super clean. Quiet! We had dinner in the hotel restaurant the first night, so good! Walkable to the train station, Duomo and bell tower attractions. Lots of shops and ...

Reviewed on 20 Mar 2026

Il Rivalta - Place of Charme
Palazzo Alfieri Residenza d’epoca

Palazzo Alfieri Residenza d’epoca

Lungarno Corsini 2 Florence FI
Stay at this luxury residence in Florence. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (751 reviews)
Clean, beautiful view from suite River View room.

Reviewed on 20 Mar 2026

Palazzo Alfieri Residenza d’epoca
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Via Generale Dalla Chiesa, 1-3 Florence FI
Stay at this family-friendly campsite in Florence. Enjoy free parking, an outdoor pool and 3 poolside bars. Our guests praise the restaurant and the helpful ...
8.8/10 Excellent! (1,627 reviews)
Fantastic accommodations in Florence. Easy drive from any part of the city, also a 1-minute walk to the bus if you don't have your own car or just don't feel like driving. Would definitely stay here again, highly recommend!

Reviewed on 18 Mar 2026

Hu Firenze Camping In Town
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.

Popular places to visit

Things to do

Explore a world of travel with Expedia