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.

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
The price is S$161 per night from 26 Aug to 27 Aug
S$161
26 Aug - 27 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! (1,477 reviews)
"It was a great stay for us and the hotel has chic and modern vibe. View from the rooftop is breathtaking. This hotel has thought of everything you need and made it available. We enjoyed our stay and will definitely stay again."

Reviewed on 27 Jul, 2026

The Social Hub Florence Lavagnini
Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
The price is S$136 per night from 29 Jul to 30 Jul
S$136
29 Jul - 30 Jul
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! (1,006 reviews)
"Todo está muy limpio, tienen una piscina muy bonito con un restaurante que la comida estaba deliciosa y está situado en un lugar estratégico para caminar"

Reviewed on 15 Jul, 2026

Plus Florence - Hostel
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
The price is S$236 per night from 27 Aug to 28 Aug
S$236
27 Aug - 28 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. ...
9/10 Wonderful! (1,012 reviews)
"Great hotel in fantastic location. Very helpful and personable staff. Its an old building, but has so much charm."

Reviewed on 26 Jul, 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.
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 ...
Hu Firenze Camping In Town
Teatro Luxury Apartments Firenze - Starhotels Collezione

Teatro Luxury Apartments Firenze - Starhotels Collezione

Via Magenta 6 Florence FI
Stay at this luxury apartment in Florence. Enjoy free Wi-Fi, a rooftop terrace and a fitness centre. Popular attractions Ponte Vecchio and Cathedral of Santa ...
9.8/10 Exceptional! (99 reviews)
"Very nice staff and helpful. Convenient close to everywhere. Enjoy to stayed"

Reviewed on 27 Jul, 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 luxury residence in Florence. Enjoy free Wi-Fi, 2 bars/lounges and a rooftop terrace. Our guests praise the helpful staff in their reviews. Popular ...
9.2/10 Wonderful! (804 reviews)
"Our AC never got the room cooler than 80 degrees Fahrenheit, our jacuzzi tub didn’t work and ants in the room. Room itself was beautiful as was the location."

Reviewed on 24 Jul, 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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