The village sits on top of a hill and archaeological excavations have ascertained that it has been inhabited as early as the eighth century B.C. At the highest point of the town, we find the Cassero area, an original Etruscan settlement and the location of the main fortress during the Middle Ages. Castiglion Fiorentino boasts the works of numerous artists, including those of Bartolomeo della Gatta as well as the gorgeous loggia restored by Giorgio Vasari.

The agricultural vocation in Valdichiana has always been very strong; for this reason Castiglion Fiorentino has earned the epithet "City of Olive Oil" due to its strong historical tradition from ages past. There are many excellent businesses operating in this sector that continue to maintain a strong bond with tradition.