The Rocca Perugina is certainly one of the most significant monuments of the city with a long history of use maintained until the early 20th century. Today, carefully restored, it is part of the cultural and tourist circuit of the city. The visit, very suggestive, winds through rooms dedicated to local cultural enhancement, narrow tunnels, ancient prison cells, and some towers.

Following the repeated rebellions of Castel della Pieve, Perugia decided in December 1326 to build a fortress that would control the entire city and make the presence of its garrison safer. Already the previous year, Lorenzo Maitani, the architect of the facade of the Orvieto Cathedral, had been commissioned by the Perugian Municipality to supervise all the fortifications in the Trasimeno territories. In October 1326, his brother Ambrogio was present in Castel della Pieve to study the design of the fortification on site. The Rocca was erected next to the city walls, next to Porta Perugina, from which since 1296 the Via Pievaiola departed, built by Perugia for faster connections with Castel della Pieve, a center of vital strategic importance for its territorial dominion.

The triangular-shaped plan is reminiscent of the pointed forms typical of Gothic cathedrals, such as the facade of the Orvieto Cathedral designed by Lorenzo Maitani. The Rocca was originally surrounded by a deep moat and a wooden palisade. The fortification has five towers, some of which were accessible via a drawbridge. From all the towers, Perugia could be seen, allowing visual signals to request reinforcements if the Perugian garrison was in difficulty.

The military structure, built to maximum security standards, subsequently favored the settlement of Condottieri, such as Biordo Michelotti and Braccio Fortebraccio da Montone. From the 15th century, the Rocca underwent numerous renovations. In 1503, Cesare Borgia, while waiting to cross the Chiana to attack the Republic of Siena, settled in the Rocca and had Paolo Orsini and Francesco di Gravina strangled, guilty of participating in the "Conspiracy of Magione." Starting from 1529, with Cardinal Coppi known as il Tranense, the building lost its defensive functions and became the seat of the Perpetual Governors appointed by the Pope, who were always cardinals or nephews of pontiffs.