The Fortezza Vecchia was raised on demand of the Florentine Government that started to plan this building after buying Livorno from Genoa in 1481. The aim to build it is to protect the port that the Medicidestined to become the Florentine counter-attraction to the Pisa port of call. The works started in 1506, when the architect Antonio da Sangallo was called in Livorno to plan a fortification project that could include two pre-existent Pisan structures, the Mastio di Matilde and the Quadratura. The Cardinal Giulio de' Medici, the future Pope Clemens VIII, was given the task to follow the operations in a first time. Antonio da San Gallo planned the new fortress that should have included the Tower of the Quadratura inside on commission of the Cardinal himself.
Rich in history, the Old Fortress deserves to be visited by those who love the history and the culture.

Struttura a pianta pentagonale, la Fortezza Vecchia presenta possenti mura in laterizio, ed è circondata, se si esclude un lato, dai fossi medicei, canali navigabili che attraversano parzialmente il centro storico. Tra i vari episodi storici legati alla fortezza si può ricordare, ad esempio, la ristrutturazione dei bastioni durante l'era napoleonica.

A pentagunal layout structure, the Old Fortress presents imposing walls with bricks and is surrounded by the Medicis' moats, ship canals that cross thruogh the historical centre. Amongst the several historic events linked to this fortress, we can remember, for example, the restoretion of the bastions during the Napoleonic era.