Radda in Chianti has always played a leading role in the history of this corner of Tuscany. In 1100 Radda was the most important and populated centre, also due to its central position and to the hugeness of the lands it could control. After the birth of the municipalities and till 1500, the conflicts between Siena and Florence were continuous and always very strong. Radda was in the middle of everything, so that the Castle of Radda became the headquarter of the Chianti League under the Republic of Florence and house of the Podestà. The 17th century can be defined as the age of Chianti because it’s since then that it starts to be known for its wine, exported to England already from the half of 16th century. In that period also a lot of farms and genteel villas, where owners came to spend the summer holidays, sprang up, it’s sufficient to remember the family Strozzi or Pazzi of Florence.
Today Radda holds within its walls the old medieval hamlet completely intact. It is still possible to admire the Palazzo of Podestà, in the middle of the village, built in the '400 with a beautiful wall-painting inside dated to the 1500. Of great interest are also the crests on the Palazzo’s external wall. In front of the Palazzo Comunale the Church of San Niccolò with a wooden Crucifix inside of the 16th century, venerated by the local inhabitants. Very interesting are also the Piazzetta del Castello, the Medioeval Walking, the Ghiacciaia Granducale and the walking around the walls. Nearby the Franciscan Convent of S. Maria in Prato, whose history starts in the Medioevo, restored in the 18th century, which hosts a very prestigious work "Madonna con bambino" by Neri di Bicci dated 1474, the medioeval hamlet of Volpaia where is placed a very unusual religious building, theChurch of Sant'Eufrosino also called the "Commenda" (1443), and the castles of Albola and Monterinaldi, the Hamlet of Badia Montemuro also named the "Badiaccia". A significant testimony af the ancient religious organization is represented by the Pieve di S. Maria Novella that, even if completely renovated in the last century, still shows the original structure, as demonstrated by the rich romanical domes, interesting the baptismal font with majolica tiles of robbiana school.