Arrival in Lecce. City tour; 1 hour, easy. Frassanito to Torre Sant’Andrea; 2 miles, easy. Transfer to Otranto

You meet in the historic center of Lecce and commence with a guided tour on foot. Dubbed “the Florence of the South” for its decorative Baroque architecture, the area is known for its medieval castles, Baroque churches, and ancient frescoes. Once the center of the Messapi settlement, Lecce became an important Roman scholarly hub in the Middle Ages.

Your tour of this appealing city begins in Piazza Sant’Oronzo, the heart of the old town, named after the 1st-century bishop and patron saint of Lecce. His copper-coated wooden statue sits atop the Colonna di Sant’Oronzo, one of a pair of columns that marked the end of the Appian Way, the main road between Rome and southern Italy. It was given to Lecce in 1666 by the city of Brindisi, because Saint Oronzo was said to have cured the plague ten years earlier in Brindisi. On the south side of the piazza (square) you view the half-buried Roman Amphitheater, built in the 2nd century and once seating up to 25,000 people. From here, you make your way to the finest and most ornate of Lecce’s Baroque churches, the Basilica di Santa Croce, whose elaborate façade is decorated with animals, bizarre figures, vegetables, garlands and flowers, and a large, central rose window. You have time on your own to soak in the city’s youthful cultural ambiance before heading south to the seaside village of Otranto, situated at the tip of the Salentine Peninsula.

Along the way, you begin noticing Puglia’s signature natural features—seas of sprawling, centuries-old olive groves with gnarled, twisted trunks. Survivors of frosts that stunted olive groves in other nearby regions, the enormous trees lend an untamed, ancient air to the journey. Your route follows the Adriatic Sea, characterized by a rocky shoreline reminiscent of Greece, with its rugged coves and caves. Just north of Otranto, you stretch your legs on an approximate two-hour walk through a pinewood forest sloping down to a rocky beach. Following an optional swim, you resume walking along a dramatic cliffside trail offering sweeping views of the Adriatic Sea to Torre Sant’Andrea, one of the many ancient watchtowers crowning these coastal cliffs—evidence of the defenses erected against Turkish invasions.

After a brief refreshment, you board your coach for a 20-minute drive to the charming medieval village of Otranto, where you check into your elegant 19th-century hotel—a family-run, white-washed masseria (former fortified farmhouse), set amidst manicured grounds boasting organic gardens, fruit orchards, olive trees, and an inviting infinity swimming pool. Dinner tonight is a welcome feast, perhaps featuring the region’s favorite riso cozze e patate (rice, mussels, and potatoes) at a welcoming restaurant in town.

Porto Badisco; 4.6 miles, easy to moderate. Red Lake; 4 miles, easy to moderate with some more moderate sections. Otranto; 2 miles, easy village walking

After a satisfying breakfast, you depart the hotel on foot for the morning’s exploration. Mediterranean macchia (wild brush) lines the country road to the coast, sometimes following rocky slopes with steep sections. You are soon rewarded with sweeping views of the sea. The path eventually leads to nearby Porto Badisco, a charming bay whose clear turquoise waters and white sand bottom invite a swim before lunch.

This afternoon you may choose to return “home” to indulge in your hotel’s amenities, or you may opt to take part in an invigorating afternoon walk. The route this afternoon takes you through a stark rocky landscape within view of both the Adriatic and Ionian Seas en route to a fascinating abandoned bauxite quarry where the mineral was once mined and ferried as far away as Venice. Resembling a steep-sided crater lake, the quarry has walls of deep red—hence its local name, Red Lake.

The latter part of the afternoon is spent walking in and around Otranto, a small, friendly medieval port virtually surrounded by the sea. Returning to your hotel, there is time to unwind before gathering beneath the masseria’s wisteria-covered pergola for a special aperitivo of organic Salentinian delights and regional wine. Tonight’s dinner, served in your hotel’s elegant dining room, may feature a secondo of local prawns cooked in lemon sauce or fresh lamb sautéed with artichokes. A lively participatory pizzica folk music dance show caps off the evening.

Parco Regionale Porto Selvaggio; 4 miles, easy with moderate sections. Transfer to Matera

This morning you transfer westward to the Ionian coast of the Salentine Peninsula—the other side of the heel. Your walk is within the boundaries of Parco Regionale Porto Selvaggio (“Wild Harbor” Regional Park), a protected area of rocky coastline covered with umbrella pine, eucalyptus, and olive trees. Located in one of the most important prehistoric areas in all of Italy, the park is home to crumbling watchtowers, numerous caves, and natural shelters which have been used by humans since the Paleolithic Era. You begin your walk at Torre Dell’Alto, built in the 16th century to defend against Turkish invasions. With wild orchids, myrtle, and thyme underfoot, the trail leads through a pineforest before opening up to the coast and a beautiful little beach. A short climb up a steep staircase rewards you with spectacular coastal views before you circle back to Torre Dell’Alto.

Following your morning walk, you depart on a 3-hour journey (with a stop en route for lunch) to Matera, a UNESCO World Heritage site and your home for the next two nights in the neighboring region of Basilicata. Interestingly, Basilicata is the only Italian region with two names. Basilicata has been the official name since 1945; however, the region’s original name, Lucania, is still popular and commonly referred to—most residents still consider themselves Lucanians rather than Basilicatans and the regional cuisine is still known as Lucanian cuisine. Approaching the striking landscape of Matera, the sassi dwellings, cathedrals, and other cavernous edifices that were scooped from the rocky earth rise from the horizon. The area’s stark appearance inspired Mel Gibson to film “The Passion of the Christ” here for its resemblance to ancient Jerusalem.

You soon arrive at your family-run hotel, a unique eco-chic property, ideally located in the heart of the cobblestoned Sasso Caveoso district. Your gracious hosts welcome you to enjoy an aperitivo on the hotel’s terrace, taking in the sassi’s incomparable architectural profile. A special dinner based on the bounty of the season is prepared by the chef-owner.

Parco Regionale delle Chiese Rupestri; 3-4 miles, easy to moderate. City tour of Matera; 1 hour, easy

Following an enticing breakfast of homemade baked goods and preserves, cured meats, and cheeses from Basilicata, a short transfer delivers you to the Belvedere, the location of the crucifixion in “The Passion of the Christ,” as well as a fantastic viewpoint of Matera and the plunging ravine upon whose edge it is built. Accompanied by a local guide, you venture on foot into the remarkably diverse terrain of the Parco Regionale delle Chiese Rupestri. The “Park of the Rock Churches” is a protected nature sanctuary comprised of dramatic cliffs, ravines, gorges, and prehistoric caves—and some 923 plant species. The area was also once home to ancient civilizations. While the footing can be rocky in places, the walking is superb amidst rare orchids and the wild herbs of the Mediterranean macchia (thyme, oregano, wild mint, and sage), and along trails flanked by oak trees.

By late morning, you return to Matera for a delicious lunch of Lucanian cuisine. Platters of sausages, colorful vegetables, and local cheeses—such as the exceptionally flavorful Lucanian pecorino or creamy burrata cheese—are accompanied by the famous Matera bread and pitchers of vino rosso. Following lunch, your adventure continues with a guided walking tour of Matera. The labyrinthine streets combine ancient stone sassi structures with buildings of later eras—a fascinating blend of old and new. Highlights are the charming Piazza Duomo, humble sassi dwellings, and such monumental edifices as the cathedral of San Pietro Caveoso and the 13th-century Romanesque cathedral. You learn about the intriguing caves and lifestyle of the former cave residents. At one time an “open door” attitude prevailed; sassi entryways were always open, extending a welcome to neighbors and visitors, no matter the weather.

The late afternoon is yours to explore Matera’s maze of narrow alleyways. By day’s end you will undoubtedly agree with the famous Italian writer, Carlo Levi, who wrote in 1952: “the peasant’s culture is hidden in the caves of Sassi, an ancient heart tucked away from all. Whoever visits Matera will be taken aback by how expressive and touching its aching beauty is.” You dine this evening at a restaurant of your choosing in Matera.

Transfer to Valle d’Itria. Barsento to Alberobello; 4-5 miles, easy

Today you leave the cultural mysteries of Matera and travel to the lush Valle d’Itria in central Puglia. Blanketed with vineyards and olive groves, the valley is dotted with hundreds of trulli, curious stone structures once used by Apulian farmers of centuries past. The buildings feature circular, whitewashed walls and cone-shaped roofs that were originally made without mortar so as to make the structures temporary (an ancient tax loophole!). These “beehives” compel close examination—notably the Paleo-Christian good-luck symbols painted on the roofs.

You reach your trailhead near the 6th-century church of San Pietro in Barsento, a neighboring town of Alberobello. A picturesque afternoon walk leads through green pastures, woodland, and along country lanes flanked by stone walls and seemingly endless olive groves and trulli. Once you reach the village of Alberobello, a UNESCO World Heritage site whose streets are literally packed with trulli, you are free to roam this fairy-tale town and have lunch on your own—perhaps a plate of the region’s favorite homemade orecchiette pasta with turnip tops—in the town’s Piazza del Popolo (People’s Square).

By late afternoon, you transfer to the tiny hamlet of Savelletri di Fasano, your home for the two final nights—back on the Adriatic coast. Situated on a tranquil countryside estate with views of the sea in the distance, your luxurious masseria offers a range of five-star amenities for your enjoyment, including a solar-heated swimming pool, nine-hole golf course, Aveda spa, and access to a private beach club. Dinner at your hotel is a sumptuous feast of seafood from the neighboring fishing village of Savelletri—red tuna grilled to perfection or swordfish in a fresh tomato and caper sauce.

Village of Ostuni and surrounding countryside; 4-5 miles, easy to moderate

This morning you explore the nearby historical village of Ostuni. Known as the “white city” for its whitewashed walls, Ostuni overlooks the Adriatic and boasts a captivating medieval center that features a dramatic 15th-century cathedral.

Transitioning from the city to the country, you enter the lush countryside surrounding Ostuni. Home to an abundance of oak, cork, and carob trees, this region is thick with shrub vegetation such as wild broom and bay laurel spilling across the trail. The ancient farmer’s path, bordered along the way by sturdy stone walls, winds through a sea of secular olive trees.

By early afternoon, you arrive amidst the olive groves at a whitewashed masseria for an exclusive private tour of the ancient underground olive mill, followed by a tasting of the masseria’s DOC (Denominazione D’Origine Controllata) olive oil produced from their centuries-old olive trees. A hearty "farewell lunch" is served of the masseria’s organic farm products—fresh pasta, cheese, and meats, tangy greens, wild aromatic herbs, and freshly baked bread.

Late afternoon offers time simply to relax at your beautiful hotel, to indulge in a spa treatment, or perhaps cycle to the nearby beach. For tonight’s dinner, you enjoy a taste of the local life at an authentic pizzeria in the neighboring village of Selva di Fasano; a perfect venue for toasting Apulian traditions and new friends.

Transfer to Brindisi. Departure

After a bountiful breakfast you transfer to Brindisi, where you bid one another a fond “arrivederci!”