There are many testimonies of Castellina in Chianti dating back to medieval times. The first certain documents date back to the 11th century, when the area was a fief of the nobles of the Castello del Trebbio, a family related to the Guidi counts. In the twelfth century, Castellina in Chianti came under the influence of Florence and in 1193 an agreement was signed between the lords of Trebbio and Florence in which the Florentines were granted the task of militarily guarding the castles of Trebbio and Castiglione (now Castellina in Chianti ). After the Lodo di Poggibonsi of 1203, an act in which the Chianti borders between Florence and Siena were sanctioned, Castellina found itself to be one of the most important Florentine outposts since it was placed on the most direct road connecting the two rival cities.
In the 14th century, Castellina in Chianti became one of the cornerstones of the Lega del Chianti, so much so that it was at the head of one of the contractors in which it was divided. The Terziere of Castellina administered the part of the Chianti that slopes down towards the Valdelsa. In 1397 it was sacked and completely burned by the troops of the Duke of Milan Gian Galeazzo Visconti commanded by Alberico da Barbiano. In 1400 it was then decided to fortify the town. Today you can stroll among the medieval streets teeming with shops and food and wine specialties; don’t miss the covered walkway from whose windows you can admire one of the most beautiful landscapes of the whole Tuscany. A stop in Castellina in Chianti can not be separated from a visit to some of the numerous wine bars in the area, for a wine tasting accompanied by a nice cut of cold cuts: the area is in fact known for the great Norcina art of Chianti, capable of offering cold cuts with an unforgettable taste.