Hiking Puglia and Matera

Hilltop Villages, Shepherds’ Paths, and Turquoise Seas


The deep blue hues of the Adriatic and Ionian seas, heirloom olive orchards stretching to the horizon, whitewashed coastal towns gleaming in the sun—this is the “heel” of Italy, a world apart from the north and a magical place for a WT's style of adventure. We’ll make an arc across Puglia, savoring hikes across traditional tratturi (shepherds’ trails), through the ancient olive orchards, and along spectacular coastal paths where the sea and the sky seem to meet. This southernmost part of Italy has surprising layers of Greek, Roman, and Norman cultures, as we’ll see in the stunning hill town of Ostuni, once a Greco-Roman city, and Otranto, with its Aragonese city walls. We’ll also enjoy the Baroque exhuberance of Lecce and visit two unforgettable World Heritage Sites, Alberobello and Matera. As always, we'll eat locally and well—we’ll go olive-tasting in the Itria Valley, where the orchards are hundreds of years old, sample the deep red Primitivo wines at a cellar in Manduria, taste the bounty of the sea (fresh-caught octopus, swordfish, anchovies, sardines, and more), and sample Puglia’s signature handmade pasta, orecchiette ("little ears”). Join us to experience the mystique of the Italian south!

Itinerary at a Glance

Days 1-3
Bari / Alberobello / Ostuni / Lecce

We head across the orchards and vineyards of the Valle d’Itria, which holds some of Puglia’s most iconic landscapes. The orchards stretch as far as the eye can see here, dotted with trulli, the whitewashed, conical-roofed houses Puglia is known for. In Alberobello, we’ll visit the 17th century Trullo Sovrano, the largest of the trulli houses. After exploring stunning Ostuni, with its tumble of alabaster buildings, we’ll taste olive oils at a farmstead and enjoy the opulent Baroque buildings of Lecce, with architectural surprises at every turn.

Borgo Canonica
Cisternino, Italy
Days 1 to 2 (2 nights)
Hotel Corte di Nettuno
Otranto, Italy
Days 3 to 4 (2 nights)
Days 4-6
Otranto / Santa Maria di Leuca

Otranto was first a Greek port, then a Roman one, and was later ruled by the Byzantines. We explore the town, hike past the Punta Palascia lighthouse to lovely Santa Maria di Leuca, where the Adriatic and Ionian seas meet, and cruise the coast to visit cave grottos that were ancient sanctuaries.

Hotel Corte di Nettuno
Otranto, Italy
Days 3 to 4 (2 nights)
Hotel Terminal
Castrignano del Capo, Italy
Days 5 to 6 (2 nights)
Days 7-10
Manduria / Matera

Heading to the wine town of Manduria, we taste Primitivo di Manduria wines at a local cellar. Our grand finale brings us to fascinating Matera, one of the most spectacular ancient cities in all Europe, where Benedictine monks carved elaborate churches and monasteries deep into the sheer canyon walls. We set out for a canyon walk, exploring the picturesque alleys and warren of “sassi” dwellings. Depart on Day 10.

Palazzo Viceconte
Matera, Italy
Days 7 to 9 (3 nights)
Aquatio Cave Luxury Hotel and Spa
Matera, Italy
Days 7 to 9 (3 nights)



Hike through ancient olive orchards and across shepherds’ paths
Visit the World Heritage trulli houses of Alberobello and the breathtaking ancient world of Matera
Explore Lecce’s Baroque palazzi and the striking “white city” of Ostuni
Enjoy Puglia’s unique local dishes and the best Primitivo wines


Length: 10 days
Cost From: $5795  
Arrive: Bari, Italy
Depart: Bari, Italy
Lodging: 9 nights hotels and inns
Meals: All meals included except 3 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Cultural Adventures, Hiking / Trekking
Trip Level:

Moderate hikes of 2-4 hours over rolling countryside, rocky coastal trails, and steep canyons

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