As the only major Philistine city directly on the sea, Iron Age Ashkelon was uniquely involved in the changing trade patterns of the eastern Mediterranean. The Leon Levy Expedition to Ashkelon has uncovered a stratified sequence from the late thirteenth-early twelfth century BCE which provides evidence for the transformation of Ashkelon from a Canaanite seaport to a Philistine stronghold. The earliest Philistine settlement appears as a completely new architectural phase accompanied by distinct ceramic forms with no predecessors in earlier phases. All of the available evidence from Ashkelon, including epigraphic finds and ceramic forms with close parallels to the nearby site of Lachish, support a traditional chronology in which the earliest Philistine settlement occurred in the first half of the twelfth century BCE. But more than the date of the settlement, a diachronic study of Ashkelon’s imports through the Iron Age, from the first arrival of the Sea Peoples to the final destruction of the city by Nebuchadnezzar, reveals the important role of maritime economy in the development of the southern Levant. This study will argue that maritime trade played an important role in the development of Ashkelon, even from the twelfth century. Throughout the Iron Age, Ashkelon’s varying relationships with Phoenician, Cyprus, N. Syria, and Egypt created an unmatched mercantile spirit in this Philistine sailing town.