The Medieval Fortress of Castiglione del Lago, better known as Rocca del Leone, is characterized by an irregular pentagonal shape. It stands on the remains of an Etruscan acropolis, of which a stretch of wall remains visible and is composed of a triangular tower 39 m. high and four towers that fortify the crenellated walls. Two of these, built in the first half of the 16th century, are circular in shape, as the round structure was more resistant to attacks by cannons. The town of Castiglione was most probably already inhabited in Etruscan times – several finds of this civilization have been found in the territory – and almost certainly in Roman times. After all, it was a position that favoured, one might say required, a settlement.
The wording "Rocca del Leone", with which this architectural complex is often referred to, is not attested in any document of the time or later. The fortress of Leone, considered practically impregnable at the time, was one of the largest military buildings in Europe. Visiting it, the writer Nicolò Machiavelli (1469 – 1527) was struck by its threatening appearance, which visually expressed the strength of authority. He seemed to him a dumb stone witness to those processes of power, which he later began to lay bare, giving dignity of scientific study to his observations on the political cynicism of principles, their methods and their deceptions.