History: Castiglion Fiorentino was previously believed to be of medieval origin, but recent excavations have found its far-older Etuscan base (.e.g the decorative Gorgon element from an Etruscan temple dating to the V century BC - on display in the Pal. Pretorio). The city has been closely associated with Arezzo and Cortona for most of its history (one of the legends is that it wasfounded by inhabitants originally from Cortona)

and was one of the pawns fought over and passed repeatedly among the city-states of Arezzo, Firenze, and Perugia in their many battles (called Castiglion Aretino for some time beginning in the XII century until ca. 1290, then Castiglion Perugino for a period and finally Castiglion Fiorentino since ca. 1384). Castiglion Fiorentino's architecture has a predominantly medieval character and includes a wall around the original city center.

Close by, but outside the walls, is the Castello di Montecchio. At one time this was given to the British mercenary Giovanni Acuto (it is rumored that a film is being made about Acuto & his services).