Piazza Terrazza dei Due Mari

This anchorage sits at the very tip of Sicily's southeastern heel, where the Mediterranean and Ionian seas meet—one of the most geographically dramatic spots on the island. You drop anchor off Portopalo di Capo Passero, a small fishing town with a ruined island fortress visible just offshore. The light here is something else, and on a clear day you can make out Malta on the horizon.