Castiglion Fiorentino, located along the itinerary leading from Arezzo to Cortona, is another village of the Chiana Valley. 

Recent archaeological finds witness the extremely ancient origins of this Etruscan and mediaeval settlement.

Many are the itineraries to be followed starting from the square of the Town Hall, from which one can enjoy a panoramic view of the Chio Valley, standing under the airy Loggia planned by Vasari, opposite to which one can admire the Town Hall Palace. Located along the uphill walkway towards the Cassero (castle keep), the Municipal Archaeological Museum contains witnesses of the Etruscan civilization and the nearby Pinacoteca (Municipal Art Gallery) houses notable figurative and sacred art works, including, among others, works by Margarito d'Arezzo and Bartolomeo della Gatta.

Other praiseworthy works of art can be seen within the Museum of the Collegiate church, among which is the precious “Deposition” by Luca Signorelli.