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 / Cisternino / Ostuni / Lecce

We head across the orchards and vineyards of the Valle d’Itria and visit Alberobello for a walk through its maze of trulli-lined lanes. After exploring the fairytale setting of Cisternino and the “white city” of Ostuni, with its tumble of alabaster buildings, we’ll taste olive oils at rural farmsteads and enjoy the opulent Baroque architecture of Lecce, which offers architectural surprises around every corner.

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Days 4-6
Otranto / Santa Maria di Leuca

Like much of Puglia, Otranto has a layered past. First a Greek port, then a Roman one, it was later ruled by the Byzantines, Normans, and Aragonese. We explore the town and hike a spectacular coastal trail past the Punta Palascia lighthouse to lovely Santa Maria di Leuca, where the Adriatic and Ionian seas meet. We’ll hike to caverns and cliffsides alongside the coast and take a cruise to visit grottos and caves that were once ancient sanctuaries.

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Days 7-8
Manduria Wine Tasting / Matera

We taste Puglia’s own Primitivo di Manduria wines at a local cellar, then walk through the canyon of Matera, exploring its labyrinth of traditional dwellings. Matera dates to the early Middle Ages, when Benedictine monks carved churches and monasteries into the walls of the ravine.

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Days 9-12
Sila / Reggio Calabria

We visit a Ship Musuem, take mountain hikes in pine and beechwood forests around the Sila Lakes, and hike along the Tracciolino Trail, a fern-carpeted path of aromatic Mediterranean shrublands on the Costa Viola. Our final overnight is in Reggio Calabria, with its beautiful seafront and views across to Sicily. Depart on Day 12.

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Hike shepherds’ paths and spectacular coastal trails across the most 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 opulent Baroque palazzi and the striking “white city” of Ostuni
Savor the best regional delicacies in Puglia and Calabria


Length: 12 days
Cost From: $6295  
Arrive: Bari, Italy
Depart: Reggio Calabria, Italy
Lodging: 11 nights hotels and inns
Meals: All meals included except 3 dinners (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, van support (for luggage or if you wish to skip a day’s hike)

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