Milazzo area, the site of a very ancient Neolithic and Siculo settlement (4000 BC), between IX and VIII centuries BC suffered a progressive Greek domination. In 716 BC, Greek settlers founded the site of Mylai, in an area on the first grafting peninsular with the mainland, that was distinguishable in the first hill and its southern slopes to the lowlands. The imperial age, with the Byzantines and the Arabic following domain, confirmed the Greek site. Then the Normans built here a fort, which remains a tower with a square plan. The work of building a real castle, however, was organized by Frederick II of Svevia in the first half of XIII century. 

At the end of that century James of Aragon widened the walls beginning to close the village (Borgo), built on the closest southern slopes.
By mid-century XIV, in the south area outside these walls stood the Casali, originated by Angioini buildings during a long siege. In the XV century Alfonso of Aragon - while settlements were initiated in the low area around the Casali – made stronger the castle defence by a mighty wall and other advanced works. Along the XVI century Milazzo reached its triple morphological configuration: walled city, village, lower city. It’s still distinguishable nowadays: since the Thirties of the century was built a great wall surrounding the upper city settled out of the Aragonese wall. This wall distinguished the city from the village, cut off on hill slopes. In turn, the village was separated from the lower city with the building of the Spanish Quarter, whose work was begun in 1585 to close the access to the peninsula. Although in the XVII century there were many settlements inside the village, the flat vocation of the urban development increased more and more.

 In the XVIII century, in fact, not only the most significant building initiatives spread out in plain, but also the residential interests for the walled city were definitively abandoned and those for the village reduced. The XIX century opened the city to new urban criteria: further flat development of the city started in the southern and western areas, and the Cumbo Borgia plan (1893) gave the indications for a new road in the heart of the city. But this project was delayed until 1936, when the Savoy plan began to be operating, inheriting the directives of the previous plan. It bends left in Colonel Magistri Street, and soon right in Rizzo. By the first street on the right (Birago), it reaches the coast in Mille Street, and from here to the left: right here there is the port, protected by the wide peninsula and the first hill on which the castle and the old cathedral are located. Leaving behind and left the urban development of the XX century, one can reach - in Mille Square - the first boundary of the XVI century walled city: in the square was located the old-XVI century Messina door, that defined the entrance to the city by establishing an urban and territorial limit.