Gargano Peninsula, Apulia

Gargano Peninsula, Apulia

Some of the most beautiful patches of aquamarine sea and white sand on the whole Italian peninsula are within sight of the watchtowers, castles, and stone villages of Puglia’s coast, which defines the heel of Italy’s boot. The region also provides a powerful visual history of each wave of invaders, from the Greeks to the Normans to the Turks. The finest stretch of beaches curls around the southernmost tip, between Otranto and Gallipoli—which happen to be two of the most atmospheric cities in Puglia.

Santa Maria di Leuca, Apulia

Santa Maria di Leuca, Apulia

Start in Otranto, with its eleventh-century cathedral, and head a mile south to the ruins of the Basilian abbey of San Nicola di Casole—on a clear day, you can see Albania and Corfu in the distance. Continue past Paleolithic grottoes and coves of powder-white sand and turquoise sea until you reach the cape of Santa Maria di Leuca, the very bottom of Italy’s stiletto, where the Adriatic and Ionian seas meet. Nearby, at the Fiordo del Ciolo, bold divers leap from cliffs into the brilliant blue bay. Up the Ionian coast, landscapes become more African as you approach the ancient port of Gallipoli, a tangle of alleys and piazzas that juts into the sea. While many of the beaches near Gallipoli have a nightclub-on-the-sand feel (though not as much as Cocoloco, to the north of Torre San Giovanni), the quiet reserve of Porto Selvaggio has a sublime setting: a half-moon bay with azure water and a backdrop of rock.

On the Adriatic side, the Gargano Peninsula (the spur to Italy’s boot), with its limestone cliffs and seafront monasteries, is the jumping-off point for the small Tremiti Islands, famous for their crystal waters but overrun in summer. Near the whitewashed Greek-style city of Ostuni, an old Aragonese tower dating from the fifteenth century, Torre Guaceto, overlooks one of the most pristine World Wildlife Fund parks in Italy, while between Lecce and Otranto, castles are almost as common as holidaymakers.

Puglia’s hotel scene has exploded in recent years, but prices (except in July and August) are still a fraction of what you’ll pay in other Italian enclaves. Near a fishing village between Santa Maria di Leuca and Otranto, the luxurious Convento di Santa Maria di Costantinopoli is in a former nunnery well located for day-trips to both coasts (44-773-636-2328; doubles, $481, including breakfast, lunch, and drinks). Gallipoli’s historic center has two stylish hotels: the Relais Corte Palmieri, in an eighteenth-century town house with particularly nice terrace rooms (39-0833-265-318; doubles, $193-$227), and the Palazzo Mosco Inn, which has a great rooftop solarium (39-0833-266-562; doubles, $194-$227). Other options include contacting the outfitter Flavours Holidays, which organizes weeklong cooking classes at Casino Pisanelli, near Santa Maria di Leuca, which is an easy drive from Otranto and Gallipoli (44-131-343-2500; 7 nights, $2,500), or renting the eighteenth-century villa directly (39-33-523-1626; 7 nights, $5,500). Far less expensive are the renovated masserie, or fortified farmhouses: Masseria Bernadini has a great location, close to both Porto Selvaggio and Gallipoli (39-0833-570-408; suites, $275-$344), and south of Gallipoli, Masseria Don Cirillo will help to organize boat trips to explore the coast (39-0833-931-432; doubles, $206-$344).