Castiglion Fiorentino is an important town in the Val di Chiana situated on a hill 345 meters high, between Arezzo and Cortona.

The village has remote Etruscan origins, it is shown by the remains of Etruscan walls found at the Cassero. The actual town began to form in the eleventh century, first as a fief of the Bourbon del Monte, then, from the thirteenth century, as a possession of Arezzo, with the name of Castiglion Aretino. Arezzo fortified the village with a mighty wall. Between 1345 and 1369 Castiglion Fiorentino came under the control of Perugia. In 1384 it became a permanent possession of the republic of Florence, which changed its name to Castiglion Fiorentino. 

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