Alessano lies at the foot of the Serra dei Cianci, a hill chain among the highest in the Salento sierras. Its municipal territory also includes the village of Montesardo, the peak of Salento, a natural fortress due to its position. According to tradition, but without written evidence to confirm, the town was probably founded the Byzantine Emperor Alexius the Comnenus. The Normans gave the city a prominent role over the entire Leuca Cape, so much so that it became the see of the Bishop of Leuca from the X century to 1818 and the centre of a County (XI-XV cent.). Some important noble families, including the Gonzaga, made of it the most important Seignory of southern Salento. Alessano was also an attractive place for Venetian and Jew families of traders.