The name, Castelfiorentino, dating back to 1149, was given to Castelvecchio, which had been built on the Via Francigena, in the place of the Roman settlement of Timignano.
The fortified castle, on its hillside, enclosed the parish church of S. Ippolito (formerly named S. Biagio before the tenth century and the time of barbaric invasions) and, with a second circle of walls, Borgo d'Elsa and Borgo Nuovo. There were a total of five gates, along with towers, but there were only two roads which crossed in the single town square (today called Piazza del Popolo). Beginning as an estate of the Cadolingi family and then of the Counts Alberti, it was progressively acquired by the Bishop of Florence in the XIIth century. It was then to suffer the consequences of the conflicts between Church and Empire, the political factions of the Guelphs and the Ghibellines, and between Siena and the same Florence. For Florence, it was an important outpost, and thus obtained the seat of the chief magistrate, the privilege of Florence's symbolic red lily on its gonfalon, or banner, and the official integration of the name Castelfiorentino.
Do not miss to visit the Sanctuary of Santa Verdiana (XVIII century), the Church of St. Francis (XIII century) and the Collegiata Church of St. Lorenzo and St. Leonardo.