The first settlements in Milazzo date back to the Neolithic age (4,000 BC). The city acquired prosperity between the seventh and sixth centuries BC, when, with the expansionist hegemony of the Greek populations of Zancle, Milazzo was also transformed into a fortified “Polis”. The submission to Messina lasted until 270 BC, the year in which, following a bloody battle, Milazzo was occupied by the Syracusan Gerone II. In the Roman period its waters were the scene of two important naval battles: in 260 BC. the Roman fleet commanded by the consul Caio Duilio triumphed over the Carthaginian (First Punic War); in 36 BC, the city, which became the naval base of Sesto Pompeo, was linked to the events of the war between them and Octavian who, supported by Milazzo, was leaded to victory. Following the victory, the city was given civic recognition by Octavian with the eagle and the motto “Aquila mari imposita – Sexto Pompeo surpassed“. Under the Eastern Empire, the town was part of an important defensive triangle and became one of the main Sicilian bishops. The Muslim domination began with the conquest of Milazzo by Fadhl Giafar (843 AD), and became chief town of a thriving agricultural and commercial center in the territorial district called “Tallo di Milazzo”. The construction of the large tower of the “Maschio”, referred to as “Saracen” and the introduction of tuna fishing, dates back to this period.

During the Napoleonic wars it became an English stronghold, hosting large fleets and garrisons. The 20th of July 1860 Milazzo was the scene of the famous battle between the Garibaldi’s troops and the fleets od Francesco II di Borbone. With the advent of the “Regno d’Italia” the city lost its importance. During the last World War, Milazzo suffered massive and bloody bombings. The city, together with Catania, Augusta and Palermo, was identified as a landing area in the English plan for the invasion of Sicily, called “Whipcord“, which was to take place on 9th December 1941, but was canceled on 30th October. During the “Husky” invasion planned in July 1943, the port of Milazzo was strengthened as an important maritime, railway and military center.

The History of Milazzo is lost in myth so much so that tradition recalls the Cave of Polyphemus located on the ridge of the Rocca, on which the Castle now stands. Legend tells that Polyphemus ruled the armaments of the Sun God, in this land (called Chersonese d’Oro) famous in Grece for its beauty, climate and fertility, when Ulysses landed there after a shipwreck.