Radda in Chianti

Radda in Chianti is the heart of Tuscany's wine country, making it an ideal base for exploring the region. Strategically located between Gaiole in Chianti and Castellina in Chianti, Radda has a rich history as the headquarters of the Chianti League. The town's hilltop position and defensive walls made it a stronghold against Sienese attacks until Siena joined the Republic of Florence in 1559. This change shifted Radda's role from a military stronghold to a peaceful town, with many fortifications transformed into villas and residences. 

Today, Radda retains its medieval street layout. Highlights include the 16th-century Palazzo del Podestà, with its heraldic shields, and the town's cobbled streets lined with shops, restaurants, and bars, offering an authentic Tuscan atmosphere. Wine enthusiasts will find numerous enotecas and local wineries to sample Chianti Classico wines, plus the annual Chianti Classico wine festival, Radda nel Bicchiere, is a must-visit.

If you want to base yourself close in the heart of Chianti Classico with easy access to other towns in the region explore our collection of villas near Radda in Chianti.

Despite its small size, Radda in Chianti is the perfect addition to a day trip exploring the Chianti. Renowned for its stunning landscapes, historic architecture, and world-class wineries, Radda in Chianti provides an authentic Tuscan experience. Wander the town's cobbled streets, passing shops, trattorias, bars and charming piazzas, all waiting for you to explore at your own pace. Dive into the history of Chianti Classico wines at some of the local wineries or enotecas for a wine tasting, not before visiting the famous black rooster itself, standing proudly along the town walls.

A walk through the cobbled streets of Radda in Chianti will bring you to Piazza Ferrucci. The square is home to the historic Palazzo del Podestà, named after the renowned Francesco Ferrucci and the historic seat of the municipality. The Town Hall's facade showcases coats of arms from successive podestas during Radda's time as the capital of the Lega del Chianti. Opposite, above the main street, is the Chiesa di San Niccolò. The church features a monumental facade, featuring a large arch with two pairs of lions at its base, built-in 1926 by Carlo Coppedè, who designed the square's layout and semicircular fountain. Thanks to its central location, visitors can easily wander upon historic workshops, restaurants and wine shops from the square.

When thinking of Tuscany, many visitors think of the Chianti, and when thinking of the Chianti, the Black Rooster is the area's most recognisable symbol. Therefore, a stop at Gallo Nere, or Black Rooster, is a must when visiting Radda in Chianti. Sitting proudly on its platform along Via XX Settembre, the rooster commands one of the village's best viewing points over the Chianti countryside, making for the perfect photo opportunity. 

The legend of the Chianti Black Rooster dates back to the medieval rivalry between Siena and Florence. The two towns, battling over territory, took an unusual yet diplomatic approach to solve their dispute. A knight from each faction would start walking towards the rival's wall at the singing of the rooster's crow, and their meeting point would mark the border. Siena chose a well-fed white rooster, while Florence chose a starving black rooster. The black rooster crowed earlier due to hunger, giving the Florentine knight a significant advantage. The two met near Castellina in Chianti, and since this meeting, the legend of the Black Rooster has become the symbol of the Chianti area.

One of Tuscany’s most famous wine festivals takes place in Radda in Chianti, the Radda nel Bicchiere (Radda in a glass). Radda nel Bicchiere is an initiative of the Proloco of Radda in Chianti, which brings the whole village to life, offering visitors and tourists a unique tasting experience of the wine produced in this charming Chianti village.

Best of all there is no reservation or online pre-sale to attend the event! Simply make your way to the dedicated wine glass sale point where you will receive a wine glass and can taste more than 80 wines at the stands. Restaurants and wine bars in the village also participate in the event, offering special menus for the occasion.

https://www.raddanelbicchiere.net/ 

If you want to learn more about Tuscan wines, including Chianti Classico, the most popular wineries in Tuscany and wine festivals across the region visit our Tuscan wines page.

If you’ve got young children in tow or are simply tired of wine estates, then visit the quirky Chianti Cashmere Goat Farm, northeast of Radda’s town centre, the first and largest Cashmere Goat farm in Italy. Founder Nora Kravis left New York’s Long Island for Italy long ago and never looked back. The farm offers a wide range of activities for all to get involved from meet and greets with the goats and guardian dogs, lunch under the pergola, and even becoming a Shepard for a day.

After getting your fill of cute goats and puppies, turn your attention to the cashmere itself. In colour, the superior cashmere goats are shades of cream, hazelnut, brown, grey and charcoal so the yarn can be used undyed in its original shade. Knitters can choose some lovely fibres and sustainable cashmere yarn. You can also buy home textiles hand-made in Tuscany as well as hand-woven, scarves, shawls, throws, hats, socks and baby blankets.


Web: www.chianticashmere.com

Radda in Chianti is a haven for food enthusiasts, offering an impressive selection of restaurants and bars. From cosy trattorias serving traditional dishes, such as the t-bone steak and ribbolita soup, to elegant restaurants offering gourmet experiences, visitors will not be short of locations to refuel and enjoy the local culture.  

The village is also well-known for its wine scene, sitting in the heart of the renowned Chianti Classico area. As you wander the streets, you will find many wine bars where you can sample renowned wines. Many of these bars offer tasting sessions, such as Casa Chianti Classico, allowing you to learn about the winemaking process and discover the unique flavours of the local vintages. 

Whether you're a connoisseur of fine dining or simply looking to enjoy a casual meal with a view, Radda in Chianti provides an unforgettable gastronomic experience.

Casa Porciatti
Deli and butchery
Address: Piazza Quattro Novembre, 1 - 53017 Radda in Chianti, Siena – Tuscany
Tel: +39 0577 738055

Wine shop and wine bar
Address: Camminamento Medievale - Via Roma 51 - 53017 Radda in Chianti, Siena - Tuscany
Tel: +39 0577 738234

Web: https://casaporciatti.it/ 

La Vin’Osteria
Address: Radda in Chianti, La Villa di Sotto, 16 - 53017 (SI)
Tel: +39 0577 735604 / 328 4234702
Web: https://www.lavinosteria.com/

Chianti Brew Fighters
Address: Via G.Rossa 10/C – 53017 – Radda in Chianti (SI) – Italy
Tel: 366 837 0024
Web: https://chiantibrewfighters.it/

Macelleria Rocchigiani Fino & Figlio
Address: Via Roma 4 - 53017 Radda in Chianti (SI)
Tel: +39 0577 738178
Web: https://www.macelleriarocchigiani.it/

Bar Dante Alighieri
Address: Piazza Dante Alighieri, 1, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738815
Web: https://www.bardanteradda.com/

Pizza Pie
Address: Via XX Settembre, 3, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738758

La Loggia Del Chianti
Address: Via degli Ulivi, 1, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738491
Web: www.laloggiadelchianti.it 

Enoteca e Wine Bar Casa Porciatti
Address: Camminamento medievale, Via Roma, 51, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738234
Web: www.casaporciatti.it 

Olinto wine & food
Address: Piazza IV Novembre, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738291
Web: https://www.instagram.com/olintovinoecucina/?hl=en-gb 

Pasticceria Gelateria Sampoli & Lapis
Address: Viale XI Febbraio, 2, 53017 Radda in Chianti SI, Italy
Tel: +39 0577 738711
Web: www.barsampoli.it 

Lo Sdrucciolo Bar Gelateria
Address: Via XX Settembre, 15/C, 53017 Radda in Chianti SI, Italy
Tel: +39 0577738401
Web: https://www.instagram.com/losdrucciolo/?hl=en

When visiting Radda in Chianti, there is space for parking around the town's walls. Most spaces are outlined by a blue line, indicating they are paid parking spaces. However, there are also two designated car parks for the town. 

Parcheggio Cimitero – sits just outside the town walls and can be found next to the public park area with a play area for children. 
Radda Parkplatz – is just below the town, where you will need to go up some steps to the Gallo Nero viewpoint sitting along Via XX Settembre. 

Like most Chianti towns, Radda in Chianti operates a strict ZTL system, which means the town is essentially closed to traffic, particularly for non-residents. 

Visitors can find the tourist information centre in the Piazza del Castello. 

For more information regarding driving in Tuscany, where you can learn more about the ZTL system and parking across the region, visit our driving in Tuscany page.

Road distances from Radda in Chianti

Volpaia – 7.1km
Lecchi in Chianti – 9km
Gaiole in Chianti – 10.7km
Castellina in Chianti – 11.4km
San Sano – 11.9km 
Siena – 26.8km 
Florence – 57.4km

A day trip from Radda in Chianti offers the perfect opportunity to explore the heart of the Tuscan countryside. Visitors based in the area have easy access to the other charming Chianti towns, such as Castellina in Chianti, Gaiole in Chianti, and Lecchi in Chianti, ideal for those seeking to experience the quintessential beauty of Tuscany. The journey between the towns also makes for a leisurely drive through picturesque landscapes filled with olive groves and vineyards dotted with castles to visit along the way. The Chianti is renowned for its Chianti Classico wines, so why not take a trip to a local winery where you can indulge in tastings and tours of some of the best vineyards in Italy.

Volpaia, a medieval hamlet just north of Radda, is reached along a scenic winding road. Framed by walls and towers, this fortified hamlet has retained its medieval layout and defensive character. This small town offers visitors a quintessential Tuscan experience with its historic architecture and picturesque landscapes. Visit the famous Castello di Volpaia, for a wine tasting of local wines and olive oil produced at the winery. Or stop for a bite to eat at Bar-Ucci, a favourite with our Villa Specialists. 

For more information, see our guide to Volpaia.

Visit neighbouring Castellina in Chianti, a charming town just west of Radda. Wander down Via delle Volte, a covered walkway taking visitors on a walk back in time, lined with taverns and panoramic views from the slits in the wall. Or visit the town's historic centre, home to the ancient Rocca di Castellina and archaeological museum. You won't go hungry during your visit with excellent dining options to experience local cuisine, not forgetting the numerous local wineries to explore. And for dessert? Visit Gelateria di Castellina for some delicious ice cream, hailed the best in the area!

For more information, see our guide to Castellina in Chianti.

Gaiole in Chianti, a charming village in the heart of Tuscany, offers the perfect day trip from Radda in Chianti. Renowned for its picturesque vineyards and historic castles, visitors can explore the iconic Castello di Brolio, where you can sample some of the iconic Chianti Classico wines produced by the famous Ricasoli family. Gaiole is also known for its cycling routes, famously hosting the annual L'Eroica race. Gaiole's rich history, culinary delights and breathtaking landscapes make the village the perfect addition to a day trip exploring the area.

For more information, see our guide to Gaiole in Chianti.

This former Benedictine abbey surveys gorgeous estate vineyards just north of Radda and Gaiole. Badia a Coltibuono has been linked to the Giuntini/Stucchi-Prinetti family since 1846, with six generations having succeeded one another in the property, continuing the passion and respect for their family's legacy being among the pioneers of Chianti. The family's estate is home to the production of Chianti Classico wines and organic oils, which visitors can experience first-hand.

During the summer, the estate opens to the public, offering access to the grounds and various experiences. Visitors can enjoy wine and oil tastings, cooking classes, and estate tours where visitors can learn more about the family and their locally produced products. The historic Badia a Coltibuono restaurant is on-site, a culinary experience of the estate's local produce, using 'chilometro zero' products.

Address: Badia a Coltibuono 53013 Gaiole in Chianti (SI)
Tel: (+39) 0577 74481
Web: www.coltibuono.com

As one of the leading Chianti Classico producers, this working wine estate just south of Radda is known for its superb, full-bodied reds. Castello di Ama dates to 1976, managing 75 hectares of vineyards and 40 hectares of olive groves in Gaiole in Chianti. The valleys from which Castello di Ama wines come from are within 1.5km of the winemaking cellar, annually producing about 320,000 bottles of wines. Ama is also well-known for its art installations, a project that began in 2000, with installation occurring annually across the property's estate.  

Book a wine tour and tasting, come for lunch, visit the estate's grounds exploring the current art installations, or visit the estate's Enoteca to sample and buy the wines, olive oil and nature-inspired home fragrances.

Address: Castello di Ama, Localita Ama 53013 Gaiole in Chianti
Tel: (+39) 0577 746069
Web: www.castellodiama.com

Radda in Chianti has held a special place in my heart since visiting the town on one of our biannual villa visits. During our week in Radda, we always got our breakfast from Bar Dante Alighieri, where it seemed the locals also liked to get their breakfast and lunch. Each morning, we had the same lovely man behind the counter, who was always smiling and chatting with us, no matter how busy he was. He told us of his travels, even visiting the UK close to our office. On our last morning of the stay, we came across a villa owner along with Lies Robbertsen from Studio Radianza in Lecchi, which made us feel so connected to the Tuscan community!

~ Lindsy, Villa Specialist

Escape to the captivating region of the Chianti, staying in one of our handpicked villas near Radda in Chianti. Nestled in the heart of Tuscany, our villas near Radda provide the perfect base for exploring historic wineries, strolling through medieval villages and savouring local delicacies whilst offering a tranquil retreat amidst the Tuscan countryside. Whether you're planning a romantic getaway, a family holiday, or looking for a town apartment, our collection ensures you can enjoy the beauty of Radda in Chianti and its surroundings in comfort and style.

Explore our Siena and Chianti villas or speak to one of our Villa Specialists to start planning your Tuscan holiday today.