Picturesque squares and top wines await visitors to Radda in Chianti in Tuscany, an attractive small town with gorgeous views. It’s one of the most scenic and atmospheric destinations in the Chianti region in central Tuscany.

Together with Castellina, Radda is the most attractive of all Chianti‘s small towns and one of the best places to visit in this area. It had a glorious past that put it at the centre of the area’s tumultuous history. Radda in Chianti was in fact the headquarters of the Chianti League, the military-administrative league founded by Florence in the 13th century to protect these territories from Siena’s clutches.

It lost its centrality once Siena was made part of the Duchy of Florence in 1555. But the town recovered in the recent past, thanks to a rich tourist offering and its wine estates. Radda is still at the heart of the Chianti Classico territory, and a perfect place to taste one the region’s famous wines.

radda in chianti

What to see in Radda in Chianti Tuscany, Italy

You can get a glimpse of the town’s eventful past in the main square. Here you’ll find the impressive Palazzo dei Podestà, recognisable from the collection of coats of arms on the facade. ‘Podestà‘ was effectively the chief magistrate, the local authority and the head of the Chianti League. Each appointed podestà would add his family symbol to those that had ruled before him.

The Church of San Niccolò, set above the square, was damaged during World War 2 and was given a facade (1926) in Neo-Romanesque style. At that time the public fountain with the lion head was added to the square.

A short walk will allow you to see the whole town whose plan is typically Medieval. The walls, the pretty squares and the nicely restored old houses create a lovely atmosphere. If you’re looking for a bit of peace and quiet Radda is a perfect destination. There are attractive shops and enoteche that house an impressive selection of the local Chianti wine.

=> To 10 Towns to visit in the Chianti region

=> Best Things to do in the Chianti!

“Radda nel bicchiere” Wine Festival

During the summer a variety of festivals take over the town. Radda nel bicchiere (Radda in the glass) is a Chianti Classico wine tasting feast organised every year by local wine producers. It usually takes place at the end of May/beginning of June -> See official site for more info.

=> Planning a road trip in Tuscany? Check out our 1-day Driving Itinerary in the Chianti region.

chianti view

Don’t miss

The Museo d’Arte Sacra del Chianti – Situated inside the Franciscan convent of Santa Maria in Prato. Here you’ll find many different works of art that come from nearby churches amongst which is a polyptych of a Madonna depicted with child and saints, by Neri di Bicci 1474.

What to see and do near Radda in Chianti, Tuscany

Radda is right in the middle of Chianti Classico territory. Wineries for wine tasting abound, and so do the spectacular views over the vineyards. A good spot for wine tasting is the Medieval former monastery Badia a Coltibuono, one of the top things to do in Tuscany.

=> 3 Magical places in the midst of the Chianti vineyards.

=> Top 10 Experiences for Wine Lovers in Tuscany!

radda in chianti

Monterinaldi, 6 km. to the north. This is a picturesque stone hilltop hamlet where wines, oil and vinegar have been produced for centuries. Book a tour of the Monterinaldi Winery to taste some of their excellent Chianti wines and visit the ancient cellars. The private tour of the cellar is followed by a homemade lunch in the Villa and a guided tasting of four different wines, including Vinsanto, the traditional dessert wine.

Castellina in Chianti, the other main centre of the Chianti region, is 8 km. away. A combined visit to the two towns and a good lunch washed down with some of the best Tuscan red wine is a perfect way to spend a day immersed in the true Chianti spirit.