Along the southwestern side of Italy’s boot heel lies one of the prettiest baroque towns in the entire Puglia region. A 13th-century Byzantine fortress dominates Gallipoli’s compact historic center, set on a small island off the mainland surrounded by defensive walls and a superb beach. Admire the whitewashed buildings and elegant palazzi while wandering the town’s labyrinth of narrow alleyways, all of which lead to a wide, seafront promenade where you can watch the colorful fishing boats while sipping a limoncello. Must-sees include the Antica Fontana, an ornate Greek fountain dating from the 3rd century BC; and the imposing Cathedral of Sant’Agata, its elaborate façade decorated with marble statues and a finely carved, 32-panel wooden door depicting scenes from the life of the basilica’s eponymous saint. Below Palazzo Granafei lies the ancient Hypogeum Oil Mill, one of dozens of vast cellar-mills that once produced olive oil underground. A few miles inland lies the ancient town of Alezio, famous for its namesake wine produced from the heritage Negroamaro grape.