Radda was the capital of the League of Chianti, including Radda, Gaiole and Castellina. Since the end of the thirteenth century it became the seat of a mayor appointed by the Florentines and in 1415 was confirmed as the capital of the League. Among the mayors of Radda is to report Francesco Ferrucci.

In the seventeenth century, with the end of the conflict, the castles were transformed into mansions and its owners were engaged in the production of wine. During the 1860 plebiscite for the annexation of Tuscany to Sardinia, Radda voted against. In the fifties, even here there was the phenomenon of depopulation. In the seventies began the rediscovery of these places and all the castles, villas and farmhouses have been restored and are now home to cottages and farms.

Monuments and places of interest:
 

The Walls

Radda in Chianti, in the fifteenth century, had great strategic importance, and this led the republic of Florence to build defensive structures in masonry. A first set of walls was built in the fourteenth century but it was after the Aragonese wars that the defensive structures were intensfied, especially after 1478, when Radda was conquered and sacked . Of the walls remain today some towers, the best preserved is the one that dominates the public gardens.

Palace of the Podesta

The palace was built in the fifteenth century and was almost completely destroyed in 1478 during the War of Aragon. To the primitive building belongs to the porch of the minor Florentine architecture of the early fifteenth century. The building was enlarged in the XVIII century when a second floor and prisons were built. This building, for four centuries, was the site of the Captain of the League of Chianti. On the main façade are bricked up coats of arms of the podesta that have occurred over the time. The coats of arms are 51. Under the portico is kept the coat of arms of Francesco Ferrucci, podesta in 1527, and a fresco of the Florentine school that dates back to the sixteenth century.

The Grand Duke's Ice house

In Tuscany during the Grand Duchy were built many ice houses. Many had the pyramidal shape, while others, like the one of Radda were made in the shape of a truncated cone and basements. In the Ice house was accumulated the snow of the winter, pressed and turned into blocks of ice. The Ice houses of Radda in Chianti are situated outside the medieval village, close to the communal gardens.
 

In addition to the numerous chapels and churches, typical of these places, it is worth mentioning the Museum of sacred art of Chianti, which has its headquarters in Radda in Chianti. The main paintings housed in the museum are the Madonna and Child, between St. Lucia, Zenobius, and Mary Magdalene, polyptych attributed to Bernardo Daddi, The Annunciation with Saints Peter and Jerome, attributed to an anonymous Florentine painter of the fifteenth century; Martyrdom of St. Stephen, painting on canvas of a Florentine painter of the early seventeenth century; Mystic Marriage of Saint Catherine of Alexandria, by Francesco Curradi on canvas signed by the artist himself.

The museum houses also many sculptures as St. Anthony of Padua, polychrome terracotta of the eighteenth century and Our Lady of Consolation, by an anonymous author, eighteenth century.

The museum also houses vestments and Gold: silver chalices, made between 1700 and 1800, numerous shrines in carved and gilded wood made between the 600 and the 800.