From Rome, you can fly directly to the small airport in Brindisi, about halfway down the “heel” of Italy. From there, it’s a short drive to the baroque city of Lecce, Puglia’s crown jewel. Less than an hour from the airport, La Fiermontina Palazzo Bozzi Corso stands behind an unmarked door on a narrow street in the heart of the city. Check in to one of the hotel’s Deluxe Suites, named for illustrious friends and family of the owners.

While in Lecce, give yourself at least two full days to explore the city, marveling at architectural wonders such as the Basilica of the Holy Cross and the Piazza del Duomo, where you’ll discover elaborately carved limestone façades. The city is also home to an excavated Roman amphitheater that lies beneath Piazza Sant’Oronzo, the city’s main square.

Lecce’s winding streets are lined with local boutiques and restaurants. After a day of exploring, take a relaxing afternoon break at the famous Caffè Alvino, where you can sip coffee and snack on pasticciotto, an indulgent pastry filled with vanilla custard.

In the evenings, return to Palazzo Bozzi Corso for apertivo hour on the roof, watching the sunset behind the towers and rooftops of the city. Reserve ahead for a table at Primo, a sophisticated one-star restaurant in a minimalist setting offering a tasting menu highlighting the region’s fresh produce and specialties, like tomatoes, eggplant and burrata, along with fine Pugliese wines from small-scale producers.

With Lecce as your headquarters, embark on day trips to explore the southern portion of Puglia. Spend an afternoon in the seaside town of Otranto or visit Santa Maria di Leuca, at the tip of the heel, for sea views from Punta Meliso.

If you’re visiting from May to September, we recommend planning a beach day at one of the clubs along the Ionian Coast. For example, Porto Cesareo, less than an hour from Lecce, has shallow turquoise waters and soft sand.

The small towns and countryside surrounding the city are also home to restaurants that merit making a special trip. Bros’ Trattoria, helmed by the chefs behind the Michelin-starred Bros’, serves simple and comforting dishes in a romantic farm setting. For lunch by the sea, Lo Scalo has tables perched above a rocky coastline. Since 1968, the restaurant has served refined dishes made with fresh local fish and lobster.

After exploring southern Puglia, make your way to the white city of Ostuni, perched on a hill overlooking the countryside with views to the Adriatic Sea. Right outside the swirling pedestrian-only streets of the old town, Paragon 700 is a boutique mini-resort in a former palazzo with a spa, pool and commendable restaurant.

Check in to the Paragon Suite, a room with a sprawling terrace, a large sunken tub and original frescoes that practically glow in the afternoon sun.

While Ostuni can feel overrun with tourists during the day, in the afternoon the city becomes quiet again. Climb the narrow pedestrian streets until you reach Bar Perso, where you can settle in for a Negroni or an Aperol spritz as you watch the sky turn cotton-candy pink at sunset. For dinner, make a reservation at cozy Casa San Giacomo, where you can dine on simple and fresh Pugliese cuisine, like orecchiette with zucchini and burrata, or a perfectly grilled steak.

Take advantage of Paragon 700’s prime location to do a bit of exploring. Our Travel Office can arrange for a guide to pick you up in the morning and take you on a tour of the surrounding countryside. Start off in the baroque village of Martina Franca before stopping for lunch at a local restaurant in Locorotondo, a charming hilltop village with views of the Itria Valley. In the afternoon, you’ll visit Alberobello. Your guide will lead you through the ancient city known for its more than 1,600 trulli, Hobbit-like structures with conical roofs built without mortar so they could be easily disassembled to avoid paying taxes.

If you’re looking for something a little more adventurous, the Travel Office can arrange hiking, biking and self-driving tours throughout the valley. For the ultimate Italian experience, you can hop in a vintage Fiat 500 for a tour of Pugliese farms and other food producers to put together a picnic.

Back at Paragon 700, perhaps indulge in a treatment at the cool subterranean spa, located in an old water cistern under the hotel. You can venture into town for dinner, but the best restaurant in Ostuni is in your hotel. Dine under the pergola or in the atelier-like dining room, where you can enjoy a multicourse dinner of exquisitely executed seafood and pasta dishes.

After a few days in the countryside, it’s time to visit Puglia’s Adriatic coast and enjoy one of the chicest hotels in the region. Start your day with a drive to Polignano a Mare, a cinematic village on a rocky cliff overlooking the sea. There, you’ll board a private boat for a tour of the town’s underground caves as your guide regales you with the fascinating history of the grottoes once used by smugglers.

After your morning on the water, climb the bridge into town and make your way to the famous Grotta Palazzese, a restaurant in a dramatic cave. Reserve far in advance for a table next to the sea, where you can spot swimmers and kayakers while you dine on a tasting menu of delicacies like lobster, truffles and caviar.

In the afternoon, check into Rocco Forte’s Masseria Torre Maizza, a low-key yet luxurious 40-room resort situated in a former olive plantation. Spend the rest of the afternoon lounging under the wisteria near the pool or relaxing with a facial or massage at the Irene Forte spa.

Start your evening with cocktails at the bar before moving on to the elegant but homey dining room, where you can choose from the many traditional Pugliese menu items.

Spend your last few days in Puglia luxuriating at Masseria Torre Maizza. Visit the stylish Lido Bambù, the Masseria Torre Maizza’s beach club just a short drive from the property, and dine at the seafood-focused restaurant there. Or visit one of the local swimming spots along the coast, like Lama Monachile, the tiny beach nestled between two cliffs in Polignano a Mare, or the grottoes between Lido Bambù and Monopoli. Keep in mind that the beach is free to visit and has no services, so you’ll need to bring your own towel (and perhaps water shoes to manage the rocky shore). If you’re feeling adventurous, you can embark on a food tour of Bari’s old town, a once-rough neighborhood that’s become a tourist hot spot in recent years. Sample street foods like sgagliozze (deep-fried polenta squares), or sharpen your culinary skills at a pasta-making class.

In the evenings, it’s hard to beat the magical setting of Masseria Torre Maizza, but it’s worth a visit to the fishing village of Monopoli for a sunset stroll through the lanes lining the port. Dine streetside at the lively La Locanda dei Pescatori, a popular seafood restaurant with an extensive menu.

On your last day, ideally leave room in the schedule for one last dip in the sea before flying back to Rome from Bari.