Situated in the upper part of the town, the Cassero complex towers over the whole Valdichiana valley and still maintains its medieval defensive structure. Its unmistakable profile makes it the main reference point and symbol of Castiglion Fiorentino.
In the eighth century B.C., a village of huts occupied the entire hillside, which was later enclosed with a wall to defend the Etruscan acropolis; the present-day appearance of the Cassero is the product of changes made from the eleventh century onwards, when the area became a castle to guard the more important roads, away from the wetlands.
In the Hellenistic period, the populated area also extended to Casseretto (the last defensive bulwark of medieval Castiglione), as indicated by the discovery of the Etruscan walls on the north side and the remains of an Hellenistic dwelling.
In the courtyard of the Cassero, stands majestically the Tower: it was built under Perugian rule in the 14th century. The characteristic sail-shaped bell tower, which tops the tower and supports the “Campana Grossa” (large bell) appears to be more recent. On the southern side of the Casseretto, an entrance to the inner courtyard opens up with a round arch, and the 18th century staircase leads to the raised level of the tower. Today’s visitors can climb up to the top of the tower (about 35 meters) and enjoy the suggestive view over the old village and the scenery of the Valdichiana and Val di Chio.
Next to the south wall of the Casseretto is the Gate known as the Perugina or "Caditoia", made of sandstone drafts with a round arch. Three old shields are found on the exterior of the Gate, commemorating the three old dominations over Castiglion Fiorentino.
From the northwest corner of the Casseretto, via the "Wing Wall" (Muro dell’Ala), a corridor starts that connects the fortress to the outermost walls where the Gate and the Relief Tower were located.
A giant bench was installed under the Cassero Tower in 2022. The original tricolor "seat" was donated by a company to the Municipality of Castiglion Fiorentino at the end of the pandemic, as a symbol of restart. Sitting comfortably, you can admire all the colors of the valley. And take unforgettable photos!