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 kilometers) 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
$60 nightly
The price is $84 total per night from Nov 8 to Nov 9
$84 total
Nov 8 - Nov 9
Total with taxes and 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. ...
8.6/10 Excellent! (1,004 reviews)
"Buena ubicacion, habitacion limpia. Desayuno bueno, delicioso y barato. El personal del hotel muy amable y siempre dispuesto a ayudar. Definotivamente lo recomiendo 100%.🌻"

Reviewed on Oct 8, 2026

Plus Florence - Hostel
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Viale Belfiore, 55 Florence FI
$80 nightly
The price is $104 total per night from Nov 8 to Nov 9
$104 total
Nov 8 - Nov 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Piazza del Duomo and ...
The Social Hub Florence Belfiore
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
$136 nightly
The price is $163 total per night from Nov 9 to Nov 10
$163 total
Nov 9 - Nov 10
Total with taxes and 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. ...
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
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 ...
8.8/10 Excellent! (1,783 reviews)
"Très agréable, offrant les avantages du camping et de la ville"

Reviewed on Oct 8, 2026

Hu Firenze Camping In Town
La Torre Del Cestello

La Torre Del Cestello

Via Borgo San Frediano, 8 Florence FI
Stay at this residence in Florence. Enjoy free WiFi, valet parking (surcharge), and daily housekeeping. Popular attractions Ponte Vecchio and Piazza del Duomo ...
9/10 Wonderful! (342 reviews)
"The location of the hotel was amazing and central with everything within walking distance. The checkin was smooth and the receptionist was warm. In terms of value for money, we thought the price was higher for the quality of the rooms. The hotel has a nice homely feel though I believe the showers ..."

Reviewed on Oct 8, 2026

La Torre Del Cestello
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 ...
Teatro Luxury Apartments Firenze - Starhotels Collezione
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 Radda in Chianti attractions

Things to do

Frequently asked questions

Is Radda in Chianti worth visiting?
Radda in Chianti is worth visiting for its delicious Italian and European dining, where travelers can enjoy local specialties like pasta and charcuterie. Travelers can also explore standout attractions such as Castello di Albola and the beautiful Borgo di Vescine - Tenute di Castelvecchi.
When is the best time to visit Radda in Chianti?
The best time to visit Radda in Chianti is from May through September, when travelers can enjoy warm, pleasant weather ideal for exploring the region. For fewer crowds and better value, the quieter months of November through February are a good option, offering a cooler experience perfect for a more relaxed trip.
What is Radda in Chianti known for?
Radda in Chianti is known for its historic estates, offering travelers a chance to explore places like Castello di Albola and Borgo di Vescine - Tenute di Castelvecchi. It is also home to Castello di Radda Winery, where travelers can experience the region's renowned winemaking.
What is a good itinerary length for Radda in Chianti?
A good itinerary length for Radda in Chianti is two to three days to explore local wineries like Castello di Albola and Castello di Radda Winery, enjoying a wine tasting. An extended stay of four to five days allows for deeper visits to multiple estates, such as Borgo di Vescine - Tenute di Castelvecchi, and a more comprehensive Chianti wine tour. See Radda in Chianti Activities.
What are the top things to do in and around Radda in Chianti?
In Radda in Chianti, travelers can explore historic landmarks and enjoy authentic wine experiences:


How do I plan a trip to Radda in Chianti?
To plan your trip to Radda in Chianti, search for places to stay on Expedia and book flights in advance. A rental car is helpful for exploring landmarks like Castello di Albola and Borgo di Vescine, and for visiting wineries. Plan wine tours and tastings, and remember to pair outdoor activities with indoor backups for weather flexibility.
What cuisines can you find in Radda in Chianti?
In Radda in Chianti you can find Italian cuisine, featuring classic dishes such as pasta, pizza, risotto, and tiramisu. Travelers can also enjoy European and Mediterranean flavors, alongside steakhouses and unique theme restaurants.
Can I book a refundable hotel in Radda in Chianti?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Radda in Chianti by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Radda in Chianti with Expedia?
Expedia makes it easier to plan your Radda in Chianti trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Radda in Chianti?
The best choice depends on your travel style. Hotels in Radda in Chianti can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Radda in Chianti trip on Expedia?
Once you've booked your Radda in Chianti trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Radda in Chianti trip?
Expedia offers customer support before, during, and after your Radda in Chianti trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Radda in Chianti?
If it's your first trip to Radda in Chianti, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
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