about 350 km, 3 hours + 20 min

Founded by Elymians, the city is still an important fishing port and the main gateway to the nearby Egadi Islands. The city sits on a low-lying promontory jutting out into the Mediterranean Sea. It was originally named Drépanon from the Greekword for "sickle", because of the curving shape of its harbour.

Two ancient legends tell of mythical origins for the city. In the first legend, Trapani stemmed from the sickle which fell from the hands of the goddess Demeter while she was seeking for her daughter Persephone, who had been kidnapped by Hades. The second myth featuresSaturn, god of the sky, who eviscerated his father Cronus with a sickle which, falling into the sea, created the city. In ancient times Saturn was the god-protector of Trapani. Today Saturn's statue stands in a piazza in the centre of the city.

After the Roman, Vandal, Byzantine and (from the 9th century) Arab dominations, Trapani was conquered by the Normans of Roger I, flourishing under their dominations and having also a role in the Crusades as one of the most important ports in the Mediterranean Sea. In the 17th century the city decayed due to revolts, plagues and famines; however in the following century it grew from 16,000 to 30,000 inhabitants; commerce remained of local importance, while its military position in the Kingdom of Naples remained notable.

The city was badly damaged during World War II when it was subjected to intense Allied bombardments. It has grown greatly since the end of the war, sprawling out virtually to the foot of Monte San Giuliano. Tourism has grown in recent years due to the city's proximity to popular destinations such as Erice, Segesta and the Egadi Islands.

The city is renowned for its Easter related Holy Week activities and traditions, culminating between Good Friday and Holy Saturday in theProcessione dei Misteri di Trapani, colloquially simply the Misteri di Trapani (in English the Procession of the Mysteries of Trapani or the Mysteries of Trapani), a day long passion procession organized and sponsored by the the city's guilds, featuring twenty floats of lifelike wood, canvas and glue sculptures, mostly from the 17th and 18th centuries, of individual scenes of the events of the Passion.

The Misteri are amongst the oldest continuously running religious events in Europe, having been played every Good Friday since before the Easter of 1612. Running for at least 16 continuous hours, but occasionally well beyond the 24 hours, they are the longest religious festival in Sicily and in Italy.

From 28 September to 9 October 2005 Trapani was the location of Acts 8 and 9 of the Louis Vuitton Cup. This sailing race featured, among other entrants, all the boats that took part in the 2007 America's Cup.