The first historical evidence concerning Leghorn dates back to the 9th century, when the settlement was only a part of the port of Pisa. Its development began at the end of the 12th century, when, with the Pisa Statutes of 1284, it was decided that the captain of the port had to live in Leghorn. Those same statutes, in order to people the harbour village, provided special custom facilities and advantages to all those who decided within the following ten years to live and work in Leghorn were attacked by the inhabitants of Genoa and Lucca, which caused a lot of damage to the towers and to the Castle of Leghorn. After having signed the peace treaty in 1299, a period of reconstruction began that finished with the fortification of the port of Leghorn.

Indissolubly bound to Pisa, Leghorn lived its same destiny. After the murder of Pietro Gambacorta in 1392, who had been Lord of Pisa since 1370, the village and its port were for some years under the domination of the Duke of Milan, Gian Galeazzo Visconti. In 1405 Pisa rose against the Visconti domination, but the year after it had to surrender to a new enemy:Florence. In the meantime, Leghorn had passed under the rule of Genoa, and this lasted until 1421, when the inhabitants of Genoa made up their minds to consent to the repeated request of Florence wich wanted to buy Leghorn.

The Doge, Tommaso Fregoso, being short of money to defend the Republic of Genoa from the armed forces of Milan, sold Leghorn to Florence in June 1421 at the price of of 100, 000 golden florins. For the Florentine Republic thi meant having its own port available for that international trade that had produced its fame. Exactly as Pisa had done in 1284, Florence too decided to facilitate the populating of Leghorn. Several Florentine artisans settled there to built the galleys ordered by the Republic for the transportation of goods. 1200 florins were allocated each year for the construction of a galley every six months.

The Republic decided moreover to maintain a certain number of tax facilities at Leghorn, to permit development of the harbour town, which after the silting up of the port of Pisa soon became the most important Tuscan seaport. But it was thanks to the rise to power of the Medici's that the history of Leghorn knew a real turning point. Already at the beginning of the sixteenth century, Cardinal Giulio de' Medici, whothen ascended to the papal throne in 1523 with the name of Pope Clemente VII , commissioned of Antonio da Sangallo the Elder the design for a defensive fortress. The dates of the construction of what is nowadays called Fortezza Vecchia are not certain.

According to some historians in fact, the defensive building was constructed between 1521 and 1524, while according to others, the works progressed until and even after 1530. What is certain is that Sangallo included in the fortress some of the pre-existing structures such as Matilde's Tower and the "Pisans' Perspective".

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