A baroque jewel in Italy’s southeastern heel, Lecce flourishes with the carved sandstone of its cathedrals and piazzas. Atmosphere and cuisine are the main attractions here, with rustic Apulian cuisine on offer at the countless wine bars and cafes spilling onto the city's cobblestone lanes.

Gallipoli may be best known for its wartime history, but Apulia’s island-like fortress retains a southern Italian charm all its own. Colorful fishing boats dart around the old city walls, while resilient stone churches peer across a medieval bridge to the mainland port.

A patchwork of vineyards and olive groves, dotted with whitewashed hill towns and sun-bronzed beaches—Italy’s southern heel has no shortage of photogenic landscapes. There are a few surprises, too, including the baroque city of Lecce and the Itria Valley, with its UNESCO-listed trulli houses.