Narrowly situated between the sea and Mount Erice, the ancient Drepanon developed around its port. Originally it was a Sicanian village and it then became a small, fortified town where traders, fishermen and craftsmen from diverse populations lived for centuries, such as the Elyminians who populated Erice and a small group of Ionians. It was a small seaside town founded by the Phoenicians who sailed across the Mediterranean seas and made Trapani a trading Empire. From the IX Century BC the Phoenicians lost their independence and settled in the western Mediterranean. They founded Carthage and reinforced Trapani, transforming the latter into an important port for the control of various trading goods. In this period the history of Trapani is indissolubly linked to that of Carthage. The town assisted in the great naval battles between the Carthaginians and the Romans: the battle of 249 BC that witnessed the defeat of the Roman float, and the battle of the Egadi in 241 BC which allowed the Romans to occupy Trapani. The Roman period notably penalized the town which lost its political autonomy, land ownership and endured new taxes and impositions. In 395 Sicily, and Trapani itself, were taken over by the Western Roman Emperor. These were difficult years, also because of the numerous Barbaric invasions. The town was reborn under the domination of the Arabs who began their occupation of Sicily in 827.

The Arabs called Trapani Itrabinis, Tarabanis, Trapanesch and their presence significantly marked the town: in architecture, agriculture, art, language and culture. The port was enlarged, new districts were built and small ownership was reintroduced. The Arabs also introduced new productions; they built hydraulic-engineering works; revolutionised the fishing techniques, and brought the port back to its original splendour. In 1097 Trapani was conquered by the Norman Ruggero. This was yet another period of great prosperity for the land. The port enjoyed duty free trade, and the town began hosting consulates of the most important traders from Geneva, Pisa, Venice, Florence, Amalfi and Catalonia. The Roman Catholic religion became the official religion under the Normans. In the Suevian period, beginning from 1194, the importance of Trapani’s port was confirmed. Under the reign of Carlo d’Angio’, Trapani endured a period of difficulty due to heavy tax pressures. The Sicilian Vespri of 1282, in which numerous notables from Trapani participated, brought the Angionian domination in Sicily to an end. This is when the Aragonese domination began.

The town experienced a new urbanisation under Giacomo II of Aragon. Carlo V further developed the activities of traders and craftsmen. The Spanish domination ended in 1713. After the brief Sabaudian and Austrian dominations, from the second half of the seventh century, the Bourbonist reign began and governed Sicily until 1860. In this period the people of Trapani dedicated themselves to commerce and industry. Naval activity flourished, as well as the tuna and salt industries. While it proved to be disinterested in the 1820 insurrection, Trapani participated in the 1848 revolts. In 1899 King Umberto I bestowed the town with a gold medal for the events of 1848.