Hiking Puglia and Calabria

Heel to Toe across Italy’s Southern Realm


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 “boot” of Italy, a world apart from the north and a magical place for a WT's style of adventure. With Trip Leader Gianluca Canalicchio, our captivating guide to all things Italian, we’ll make a heel-to-toe arc from Puglia to Calabria, 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 with Gianluca, 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, visit an artistan cheesemaker or two, taste the bounty of the sea (fresh-caught octopus, swordfish, anchovies, sardines, and more), and sample southern cheeses including delicious pecorino calabrese and 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 olive orchards stretch as far as the eye can see here, dotted with trulli, the whitewashed, conical-roofed houses Puglia is famous for.  In Alberobello, we’ll visit the 17th century Trullo Sovrano, the largest of the famous 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 4-8
Otranto / Santa Maria di Leuca / Manduria Wine Tasting / Matera

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. Heading to the wine town of Manduria, we taste Primitivo di Manduria wines at a local cellar. At fascinating Matera, Benedictine monks carved elaborate churches and monasteries into the canyon walls. We set out for a canyon walk, exploring the picturesque alleys and warren of “sassi” dwellings.

Hotel Corte di Nettuno
Otranto, Italy
Days 3 to 4 (2 nights)
Hotel Terminal
Castrignano del Capo, Italy
Days 5 to 6 (2 nights)
Le Grotte Della Civita
Matera, Italy
Days 7 to 8 (2 nights)
Palazzo Viceconte
Matera, Italy
Days 7 to 8 (2 nights)
Days 9-12
Corigliano / Sila Massif / Reggio Calabria

In still-undiscovered Calabria, we visit the 11th century fortified castle at Corigliano Calabro, head up to the Sila Massif for mountain hikes in pine and beechwood forests, and hike the Tracciolino Trail on the Costa Viola. Our final overnight is in Reggio Calabria, with its beautiful seafront. Depart on Day 12.

Torre Camigliati
Camigliatello Silano, Italy
Days 9 to 10 (2 nights)
Grand Hotel Excelsior
Reggio Calabria, Italy
Day 11 (1 night)



Hike shepherds’ paths and spectacular coastal trails across the beautiful landscapes of Puglia and Calabria
Visit two World Heritage Sites: the trulli houses of Alberobello and the picturesque cave dwellings of Matera
Explore Lecce’s Baroque palazzi and the striking “white city” of Ostuni
Savor the best regional delicacies of Puglia and Calabria


Length: 12 days
Cost From: $5995  
Arrive: Bari, Italy
Depart: Reggio Calabria, Italy
Lodging: 11 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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