This essay introduces new evidence for an eschatological Phoenician motif that alludes to a final sailing and its perils, represented by a monstrous lion attacking or sinking a boat. The lion-and-boat motif was, so far, only documented in a Phoenician funerary stela from late classical Athens, the Antipatros/Shem stela. Excavations at the fifth-century BCE Tartessic site of Casas del Turuñuelo in southwestern Spain has revealed a set of ivory and bone panels that decorated a wooden box, bearing relevant iconography in the so-called orientalizing style. Additional comparanda from the Levant, Iberia, and Tunisia in various media (coins, ivories, amulets), add weight to this interpretation. Our analysis highlights how the artists behind the Athenian and Tartessic artifacts were innovative in their way of representing a theme that was not codified iconographically. Most remarkable is the use of an ivory-carving convention (the Phoenician palmette motif) to portray the stylized boat, a choice corroborated by a painted pottery sherd from Olympia. This “palmette-boat” depiction, in our view, is coherent with Egyptian Nilotic boats, but also with the use of flat or shallow river-boats in the Tagus and Guadiana region, illustrating mechanisms of local adaptation of Phoenician sailing and life-death “passing” symbolism. If, as we suggest, this representation can be added to that in the Athenian document, we now have testimonies of two different local adaptations of a Phoenician theme at the two ends of the Mediterranean oikoumene between the archaic and late classical periods.