Radda in Chianti

Travel Guide

A narrow street with stone buildings, a 'Zona traffico limitato' sign, and people walking.
A street lined with parked cars and historic buildings with stone facades and green shutters.
A liquor store with shelves of bottles and boxes.
A collection of wine bottles on a wooden surface.
A wooden wine rack filled with various bottles of wine.

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.

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
The price is CA $74 per night from Nov 26 to Nov 27
CA $74
CA $94 total
Nov 26 - Nov 27
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. ...
Plus Florence - Hostel
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is CA $160 per night from Nov 23 to Nov 24
CA $160
CA $195 total
Nov 23 - Nov 24
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! (1,004 reviews)
"Perfect location"

Reviewed on Oct 26, 2026

Hotel Paris
Hotel Albani Firenze

Hotel Albani Firenze

4 out of 5
Via Fiume 12 Florence FI
The price is CA $166 per night from Nov 15 to Nov 16
CA $166
CA $205 total
Nov 15 - Nov 16
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 ...
9.2/10 Wonderful! (1,008 reviews)
"Our stay was very pleasant. The staff was welcoming, very helpful and attentive. The room was very comfortable. Location was excellent. Overall a very good experience."

Reviewed on Oct 25, 2026

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.
Hu Firenze Camping In Town

Hu Firenze Camping In Town

Via Generale Dalla Chiesa, 1-3 Florence FI
Book a stay at this family-friendly campground in Florence. Enjoy free parking, an outdoor pool, and 3 poolside bars. Our guests praise the restaurant and the ...
Hu Firenze Camping In Town
Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione

Via Magenta 6 Florence FI
Book a stay at this luxury apartment in Florence. Enjoy free WiFi, a rooftop terrace, and a fitness center. Popular attractions Ponte Vecchio and Piazza del ...
9.8/10 Exceptional! (146 reviews)
"A great hotel for the price. Will stay here again"

Reviewed on Oct 25, 2026

Teatro Luxury Apartments Firenze - Starhotels Collezione
Forte16 View & Spa

Forte16 View & Spa

Viale Antonio Gramsci 16 Florence FI
Book a stay at this luxury aparthotel in Florence. Enjoy free WiFi, a full-service spa, and a rooftop terrace. Our guests praise the helpful staff and the clean ...
Forte16 View & Spa
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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