Radda in Chianti is a quaint, cobblestone-covered comune in the heart of Tuscany. Situated in the Chianti Classico wine zone, it is known for producing some of the best wines in the world. Some of Italy’s richest history is also woven into this Etruscan town and its neighboring landscapes.

Nestled between the valleys of Arbia and Pesa, this Italian medieval gem is waiting to be explored. Here, visitors can stroll by the historic town walls and charming ice house, taste sophisticated local wines, or feast upon classic Tuscan cuisine. With the additional option to cycle or hike around the region’s breathtaking nature, there is something here for every kind of traveler. Because of its convenient placement within Chianti, tourists can also stop by nearby towns such as Castellina, Greve, and San Gimignano.

Charm oozes from every corner of this quaint town. Its medieval streets are filled to the brim with endearing squares, ancient cathedrals, and vibrant coffee shops. We highly suggest that you pay a visit to the other towns in the Chianti area, which are sure to charm you just as much. Now, we will outline all the best experiences you won’t want to miss in this heavenly Italian destination.

Where is Radda in Chianti?

Radda in Chianti is a picturesque town located in the heart of the Chianti Classico region in Tuscany, Italy. Positioned approximately 30 kilometers southeast of Florence, Radda is situated on a hilltop, offering stunning panoramic views of the surrounding vineyards and olive groves. As one of the prominent communes in the Chianti wine-producing area, Radda boasts a rich history dating back to the medieval era. The town is characterized by its well-preserved medieval architecture, including the defensive walls and the Palazzo del Podestà. Visitors to Radda can immerse themselves in the authentic Tuscan atmosphere, explore the narrow cobblestone streets, and savor the renowned Chianti wines produced in this renowned viticultural region.

What to Do and See in Radda in Chianti

This town is a delightful Tuscan treasure that provides numerous sightseeing and recreational opportunities. Below are some of the notable tourist spots and leisure pursuits within the area.

1. Piazza Ferrucci

The overview of Piazza Ferrucci, in Radda in Chianti
Piazza Ferrucci, Radda in Chianti – “Radda in Chianti” by Rutger van der Maar is licensed under CC BY 2.0.

This is the main square in Radda, surrounded by lively cafes and beautiful buildings. Among them are the Town Hall and the Palazzo Pretorio, which is now home to the Museo del Chianti. This plaza is a popular gathering place for locals and visitors alike.

2. Town Walls

The city walls seen from above, via a drone
The town walls seen from a drone – Kasa Fue, CC BY-SA 4.0, via Wikimedia Commons

Radda’s defensive walls are well-preserved and offer a glimpse into the town’s medieval past. Because Radda in Chianti was once the capital of the Chianti region, its defensive walls provided protection against the crossfires of the Florence and Siena wars. Feel free to walk along these walls to sample the rich history of the town.

3. Santa Maria al Prato

The entrance to the church of Santa Maria al Prato, in the Radda in Chianti
The Church of Santa Maria al Prato, in Radda in Chianti – Vignaccia76, CC BY-SA 3.0, via Wikimedia Commons

Still acting as a pivotal place of worship for the locals of the town, Santa Maria al Prato is an active church that has truly ancient origins. With a gabled facade and recently restored medieval art, this church is a seamless conjunction of art, culture, and history. The monastery next to it has been converted into “Casa del Chianti Classico” after an extensive and careful renovation. A small sensory museum about the Chianti Classico is also available there.

4. The City Hall

Now open to the public for guided tours, this architecturally astonishing building was originally constructed to be a palace in the 16th century. Today, the City Hall is a bustling area in town that is sure to keep visitors entertained with concerts, exhibitions, and other cultural events throughout the year.

5. Propositura di San Niccolò

The first floor of the facade of the historic Church of San Niccolò
Radda in Chianti, church Propositura di San Niccolò

One of the oldest churches in Radda, this ancient building is home to fascinating frescoes and artwork. The Propositura di San Niccolò is also known for its captivating bell tower. Visitors can climb to the top of the tower and enjoy the lush scenery from an unforgettable perspective.

6. The Ice House of the Grand Duke

Believe it or not, this structure was once used to store ice in hot summer months so that the comune could store its food properly. Tourists can tour the inside of the house in order to learn about the original tools and equipment used for these food storage practices.

7. Ancient Medieval Walkways

Enjoy the quiet and evocative atmosphere of the  “camminamento medievale” to get a taste of Italy’s authentic medieval architecture. Radda has successfully restored a significant portion of the town to its original stone-built simplicity. Notably, the tunnels contain a restaurant (al Bacco) and a delightful little nook with tables and chairs from the enoteca Casa Poriciati.

Best Places to Stay in Radda in Chianti

With so much to see, you will need an optimal place to stay during your exploration of Radda in Chianti. Below is a list of prime accommodation within close proximity to the town center.

Centrally-located, Luxurious Hotel

Swimming pool inside the Palazzo Leopoldo Dimora Storica & Spa
Photo Credit: Booking.com – Palazzo Leopoldo Dimora Storica & Spa

The Palazzo Leopoldo is a lavish hotel that is located in the center of Radda. It features beautifully appointed rooms, a spa, and a rooftop restaurant with sweeping views. You can even enjoy massages, a sauna, a Turkish bath, and a heated indoor swimming pool with hydromassage area.

Location: Via Roma 33, 53017 Radda in Chianti, Italy

Stars: 4

Features: City view, Swimming pool no. 1 (covered), Pets Allowed

Reviews: 8.4/10

Adorable, Serene B&B

Elegant living room in Relais Vignale & Spa
Photo Credit: Booking.com – Relais Vignale & Spa

For a more peaceful stay within the Italian greenery, book the Relais Vignale. This lovely bed and breakfast is situated in a restored villa just outside of Radda and offers spacious rooms, a swimming pool, and a restaurant serving local cuisine. The building was renovated according to the original architecture, and offers the standards of a 4-star hotel.

Location: Via Pianigiani 9, 53017 Radda in Chianti, Italy

Stars: 4

Features: Outdoor pool, Spa & wellness centre, Bar

Reviews: 8.4/10

Authentic, Historical Hotel in Town Center

Authentic luxury bed room in Hotel Palazzo San Niccolò & Spa
Photo Credit: Booking.com – Hotel Palazzo San Niccolò & Spa

Are you seeking a stay teeming with ancient history? If so, the Palazzo San Niccolò & Spa is the spot for you. It is a mesmerizing boutique hotel located in the historic center of town. It has 15 rooms and suites, each uniquely decorated with antique furnishings and modern amenities.

Location: Via Roma 16, 53017 Radda in Chianti, Italy

Stars: 4

Features: City view, Garden, Swimming pool no. 1 (covered)

Reviews: 8.3/10

Elevated Farm Stay Close to Town

Aesthetic room in Tenuta Cortedomina
Photo Credit: Booking.com – Tenuta Cortedomina

Providing mountain views, the Tenuta Cortedomina is a soothing farm stay that will enhance your relaxation. The location features a garden, shared lounge, terrace, and restaurant. A buffet breakfast, including continental or Italian options, is served daily at the property. Guests can enjoy ping pong or cycling in the surrounding areas during their stay. Couples have particularly praised the location, rating it 9.6 out of 10 for a two-person trip.

Location: Case Sparse Lo Spicchio, 53017 Radda in Chianti, Italy

Stars: 4

Features: Restaurant, Excellent breakfast, tea kettle / coffee machine in all rooms

Reviews: 9.6/10

Restaurants and Wine Bars in Radda, Italy

As a popular tourist destination, the town offers a wide range of dining options to cater to different tastes and budgets. From traditional Tuscan trattorias to upscale fine-dining establishments, visitors can find plenty of choices for breakfast, lunch, and dinner.

La Bottega di Giovannino

Pasta dish served by the La Bottega di Giovannino
Photo Credit: residenciaartefelismina.oficia

La Bottega di Giovannino is a popular artisanal food shop located in the comune’s historic center. If you’re searching for a cozy family atmosphere, this is the place for you. Here, you can feast on homemade pastas, superb meat dishes, and meals that are known to taste like your nonna cooked it for you. Make sure to stop by this pasta heaven with locally sourced ingredients and stellar service.

Official Website: La Bottega di Giovannino

Location: Via Roma, 6, 53017 Radda in Chianti SI

Reviews: 4.6/5

Insider Tip: Exquisite local cuisine

La Vin’Osteria

Delicious steaks prepared by the La Vin’Osteria
Photo Credit: La Vin’Osteria

This venue is known for its wide selection of Chianti wines and its Tuscan flavors and aromas. A lovely mix of cheeses, meats, pastas, salads, side dishes, and desserts are also available on the menu. La Vin’Osteria even has vegetarian and gluten-free options for its guests. Its rustic decor and friendly staff makes for a homely and welcoming atmosphere. Make sure to unwind here with a glass of Chianti wine and a delicious meal after a long day of wandering through Tuscany.

Official Website: La Vin’Osteria

Location: La, Via Villa di Sotto, 16, 53017 Radda in Chianti SI

Reviews: 4.7/5

Insider Tip: Stunning location

Taverna Le Cose Buone

Seafood dish with pasta cooked by the Taverna Le Cose Buone
Photo Credit: chopstix travel

The Taverna Le Cose Buone includes a snug dining room and outdoor terrace in the historical center of Radda. Serving a plethora of traditional Tuscan dishes, this little place with red and white checkered tablecloths provides the authentic Italian experience. Come try the tasty tagliata – it will melt in your mouth!

Official Website: Taverna Le Cose Buone

Location: Via Bettino Ricasoli, 71, 53013 Gaiole in Chianti SI

Reviews: 4.4/5

Insider Tip: Delicious Fish Dishes

La Perla del Palazzo

Elegant outdoor dining area in La Perla del Palazzo
Photo Credit: La Perla del Palazzo

La Perla del Palazzo is popularly revered for its “exquisitely Tuscan menu.” Try the antipasto, pici cacio e pepe, stewed wild boar, tiramisu, or the house cantucci. Also centrally located, this restaurant provides an elegant environment for a more lavish culinary experience. Enjoy the venue’s extensive wine list to blend perfectly with your meal!

Official Website: La Perla del Palazzo

Location: Chiasso dei Portici, 8, 53017 Radda in Chianti SI

Reviews: 4.2/5

Insider Tip: Affordable Price

Places Not to be Missed Around Radda in Tuscany

Countryside near Radda in Chianti
Countryside near Radda in ChiantiPhoto by Giorgio Rodano CC BY-NC 2.0

Based in the center of Tuscany, Radda in Chianti acts as the perfect foundation for your adventures throughout the region. From the many captivating places to experience, we have compiled a list of the most intriguing and entertaining destinations nearby.

Castellina in Chianti

A cute nearby town only 15 km away, Castellina in Chianti is a historical town that played a vital role in the battles between Florence and Siena. Not only that, but it also acts as the perfect destination for foodies and wine connoisseurs. Here, you can check out several attractions including the large stone fortress, the Church of San Salvatore, a medieval tunnel, and several refined wine tastings.

Greve in Chianti

Greve in Chianti is another enchanting getaway located about 20 km away. Here, you can check out the town’s distinctive triangular-shaped plaza, its notorious wine museum, the Parish of Santa Croce, or its bike tours. End your adventures off with a wine tasting on the whimsical hills of Greve– there’s a reason why Chianti’s wine is so well-known.

San Gimignano

About 40km away from Radda, San Gimignano is the epitome of the Tuscan hill town. Visually striking and perfectly preserved, this town’s pointy skyline gets all the attention from visiting tourists. Among this medieval skyline of 14 towers lies one which can actually be climbed! If you’re not a fan of heights, sample some typical Tuscan home cooking such as cinghiale (wild boar) in this town’s top-rated restaurants.

Gaiole in Chianti

Tourists from all over the world flock to Gaiole in Chianti’s famous wine tastings, historical landmarks, and scenic landscapes. Situated around 15 km away, this bewitching town is home to Church of San Sigismondo, Ricasoli Square, and several spectacular castles. Explore them all through a riveting bike tour!

Casa del Chianti Classico

The Casa del Chianti Classico is a museum dedicated to Greve in Chianti’s wine history. Visitors can learn about the region’s winemaking traditions, trek through the vineyards, and taste a variety of local wines.


A medieval hilltop town located around 50 km away from Radda, this site offers stunning views and a charming atmosphere. Tourists can explore historic buildings and narrow streets, savor a variety of local cuisine and wines, and visit the Palazzo Pretorio, which features a collection of medieval and Renaissance art.

How to Get to Radda in Chianti

A couple enjoys the sunset with a panoramic view of the walls of Radda in Chianti
Sunset view from the town walls of Radda in Chianti

By Car

The easiest way to get there is by car. If you’re traveling from Siena to Radda in Chianti, you have two route options: 

  1. Use the Florence-Siena freeway.  Take the Badesse exit and head to Castellina before continuing on to Radda in Chianti.
  2. As an alternative, you can travel to Radda by taking the SR222 Chiantigiana in the direction of Castellina in Chianti.

The town doesn’t have a train station. As a result, a combination of rail and bus routes is the most convenient way to get to Radda using public transit.

By Train and Bus

Here’s how to get there by train and bus:

  • The main train station in Florence, Santa Maria Novella, serves as an Italian transportation center and provides easy connections to neighboring cities. You can check train schedules and purchase tickets on Trenitalia’s website or on Italo’s website.
  • From Florence, take a bus to the Radda in Chianti bus stop. The name of the bus company that runs this route is Tiemme SpA. The Santa Maria Novella train station is close to the Florence bus terminal, where the bus departs from.

On the Tiemme website, you may check the bus timetable and buy tickets, or you can buy them in person at the Florence bus station.

You could also take the train from Florence to Siena and then a bus from Siena to the Radda station. The name of the bus company that runs this route is Siena Mobilità. About 45 minutes pass on the bus from Siena.

Why Visit Radda in Chianti?

The vineyards in the countryside of Radda in Chianti
Vineyards around Radda in Chianti – Photo by Chris Ford CC BY 2.0

A quintessential contributor to the famous Tuscan paradise, this town should definitely be added to your “to-visit” list.

Perched on a hilltop, this comune is surrounded by picturesque rolling hills, olive groves, and vineyards. The surrounding nature around the town is an ideal place to experience astonishing scenery.

Famous for its world-class wines, this is the perfect place to order a glass with your dinner as well. Visitors can sample the local wines and enjoy traditional Tuscan cuisine in the comune’s many restaurants and cafes.

The town is also home to several historic landmarks, including the Santa Maria al Prato and the Church of San Niccolo. The comune also hosts cultural events throughout the year, including music and food festivals.

Lastly, the rural greenery beside the town is perfect for outdoor activities like hiking, cycling, and horseback riding. Visitors can also take leisurely walks through narrow streets and enjoy the relaxed pace of life in this small Tuscan village. With so much to experience, this seemingly modest comune is a stop on your Italian adventures that you won’t want to miss!