Piazza Santa Maria delle Carceri is a place where Renaissance and medieval architecture blend in a suggestive harmony. Two of the most important city buildings overlook the square: the Basilica of Santa Maria delle Carceri and the Emperor's Castle, which come together in the view to create a single monument.

The square takes its name from the church of the same name which was built on the Stinche prison, on one wall of which a Madonna with Child was frescoed. On the 6th of July 1484, a miracle was claimed, when the Virgin's face changed expression as if she were alive, it was then decided to build the current church by assigning the task to Giuliano da Sangallo, Lawrence the Magnificent's favorite architect.

The other relevant structure is the Emperor's Castle, built by Frederick II of Swabia between 1247 and 1248 as a stronghold against "Guelph" Florence. The Castle represents the only example of Swabian Norman architecture in Central-Northern Italy.

On the opposite side of the square you can see the War Memorial by Antonio Maraini flanked by cypresses and the bell tower and apse garden of the Church of San Francesco, which houses a work of great artistic value by Salvatore Messina.