Sicilia!

This nine-day itinerary traces a south-by-southwest arc through Italy that most student tours never attempt — from Rome down the Amalfi coast to Sorrento, then across by ferry to the island itself, stopping in Taormina before finishing in Palermo. Sicily is the point. The island has been fought over, settled, and reinvented by Greeks, Romans, Arabs, Normans, and Spaniards, and that layered past is visible in the architecture, the dialect, and the street food on every corner. Your group arrives in Rome first, shakes off the flight, and gets a full day in the city before the tour pivots south toward the coast and then the island.