Etruscan times the Castiglione area, ruled by Chiusi, was primarily dedicated to the production of wheat. Around the 7th century A.D. the promontory proved to be a formidable defensive outpost for the Byzantine Duchy of Perugia against the neighbouring Longobard territory of Tuscany.
Later Arezzo, Cortona and Perugia fought for the possession of Castiglione, which was finally subjected by Perugia.In the 1617 Castiglione became a duchy until 1648, when the area was taken over by the Apostolic Chamber of the Papal States.
Rocca del Leone
This fortress, probably designed by Frate Elia Coppi, was built in 1247.
The Pentagonal walls are sectioned off by four square and one triangular towers.
Palazzo della Corgna
The 16th-century architect Jacopo Barozzi, called "Il Vignola", built this structure incorporanting the ancient houses of the formerly-powerful Baglioni family and the existing defensive walls. The covered battlements that connect the Palace to the Fortress add to the typically feudal atmosphere of the place.
The Niccolò Circignani, called "il Pomarancio", began painting in 1574 in the "Hall of the Feats of Ascanio della Corgna" and continued in the "Hall of the Feats of Ascanio della Corgna" and continued in the "Hall of the Judgements of Paris" and in the "Hall of the Fall of Phaeton".
He and Giovanni Antonio Pandolfi painted the "Room of the Aeneid". The bizarre decoration of the "Room of the Metamorphoses" are particularly interesting.