Trapani was founded by the Elymians to serve as a port to the near city of Erice.

It was originally named Drépanon from the Greek word for "sickle", because of the curving shape of its harbour. In fact, according to the legend, the city was created by Saturn, who eviscerated his father Uranus, god of the sky, with a sickle which, falling into the sea, created the city.

Over the centuries, the city was colonized by Romans, Vandals, Byzantines, Arabs and Normans, taking also part in the Crusades as the most important harbor in the Mediterranean Sea. 

Much of the old city of Trapani dates from the later medieval or early modern periods.

Notable monuments, mostly in the Baroque style, include:

- The magnificent Basilica-Sanctuary of Maria Santissima Annunziata (also called "Madonna di Trapani") originally built in 1315–1332 and rebuilt in 1760. It houses a marble statue of the Madonna of Trapani, which might be the work of Nino Pisano, and with the museum Agostino Pepoli.
The Church of Sant'Agostino (14th century)

- The Church of Santa Maria di Gesù (15th-16th centuries)

- The Baroque Palazzo della Giudecca or Casa Ciambra.

- The Cathedral (built in 1421, but restored to the current appearance in the 18th century)

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