The splendid village of Castellina boasts Etruscan and Roman origins, even if traces of this past are lost in time. It wasn't until the Middle Ages, when Castellina in Chianti became a very important military outpost. The history tells about Castellina dei Trebbiesi during the XI century – name given to the nobles of Trebbio (belonging to the political association of Counts Guidi), proprietors of a castle nearby the current village, whose faint ruins are visible from Badiola.

During the twelfth-century, Castellina became a Florentine garrison of considerable importance between the states of Florence and Siena. Main centre of the ancient Lega del Chianti along with Radda and Gaiole during the thirteenth century, later on, between the fourteenth and the fifteenth century, Castellina underwent incursions and sacks at the hand of the Senese state. These events forced the Florentines to make constant restorations and reinforcements of the boundary walls, committing the works to famous architects like Filippo Brunelleschi. In 1478, while Florence took part in the conspiracy of the Pazzi against the Medicean family, Giuliano Sangallo was sent to Castellina in order to reinforce once again the defence structures. In 1483 the war was over and Castellina went back to the Medici, but it definitely lost its strategical importance during the fifteenth century. Cosimo I de' Medici turned the old outpost into a rural centre, structured according to the sharecropping system.

In 1865 was born the commune of Castellina in Chianti, whose town hall was moved in 1927 to the restored medieval stronghold in Piazza del Comune,

One of the most interesting archaeological discovering of the whole Chianti region is the Tumulo of Mount Calvario – dated back to the sixth century before Christ – composed by four room-tombs with the entrances oriented towards the cardinal points.

As witness of a notable Etruscan presence in the area of Castellina, we must mention some other handmade articles, such as Pozzo di Casalvento, the big Necropolis of Poggino and a recently identified complex nearby Fonterutoli.

Castellina is nowadays a driving center for the production of Chianti wine. Do not miss the local events to taste some of the superb local products!

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