Cycling Puglia – The Heel of Italy

Overview

Discover Southern Italy’s charm on a bike tour through Puglia, the sun-soaked heel of Italy’s boot. Ride past olive groves, vineyards, and whitewashed villages as you explore UNESCO-listed Alberobello, coastal Monopoli, the “White City” of Ostuni, and Baroque Lecce. Along the way, experience authentic Apulian life through local wines, olive oils, and farm-fresh cuisine. For those wishing to begin their journey earlier, an optional pre-tour in Matera offers the chance to visit its ancient Sassi cave dwellings, one of the world’s most fascinating UNESCO sites. Today’s ride takes you deep into the Itria Valley, a landscape dotted with trulli, the cone-shaped stone houses that make this region famous. Follow the Apulian Aqueduct cycling route (Ciclovia dell’Acquedotto) toward Alberobello, a UNESCO World Heritage Site. As you pedal along country paths framed by ancient olive trees and dry-stone walls, you’ll reach this magical town where more than 1,500 trulli create a fairytale skyline. Today, cycle from the rolling hills of Putignano toward the Adriatic coast. Your first stop is Polignano a Mare, a town perched dramatically above limestone cliffs. The birthplace of singer Domenico Modugno (“Volare”), Polignano offers panoramic terraces and sea-view trattorias where you can sample fresh seafood and handmade pasta. Depart Monopoli through a landscape filled with centuries-old olive trees, some dating back over a thousand years. As you move inland, the horizon reveals Ostuni, known as “La Città Bianca” (The White City) for its dazzling whitewashed buildings. Once in Ostuni, explore its cobblestone streets on a guided Ape Calessino tour, an iconic Italian three-wheeled vehicle that winds through narrow lanes. Your longest ride leads through Salento’s red earth landscapes and endless olive groves. Stop in Oria, a medieval gem crowned by a Swabian Castle built by Frederick II and a cathedral topped with a colorful tiled dome. Continue along the Primitivo Wine Route to Manduria, considered the birthplace of the Primitivo di Manduria DOC wine. Today’s loop ride leads to the Taranto province, where golden beaches meet the waters of the Ionian Sea. These shores remain one of Puglia’s best-kept secrets, perfect for a swim or a picnic by the water. In the afternoon, visit a local olive farm for an in-depth olive oil experience. Learn about cultivation, harvesting, and cold-pressing techniques, then enjoy a guided tasting of six distinct olive oils. The final ride brings you inland through serene Salento countryside, passing by vineyards and dry-stone walls that define the region’s agricultural heritage. Your destination is Lecce, often called the “Florence of the South” for its elaborate Baroque architecture. Explore landmarks like the Basilica di Santa Croce, Piazza del Duomo, and Roman Amphitheater, and watch the limestone façades glow golden at sunset. This is the perfect finale to your cycling adventure through Puglia. Enhance your trip with a pre-tour stay in Matera, one of the oldest continuously inhabited cities in the world. Discover its remarkable Sassi cave dwellings, carved into limestone cliffs and recognized as a UNESCO World Heritage Site. The city of Matera, a UNESCO World Heritage Site, is world-renowned for its ancient “Sassi” cave dwellings carved directly into limestone cliffs. These remarkable homes, some dating back to the Paleolithic era, were continuously inhabited until the 1950s. Today, many have been beautifully restored and repurposed into boutique hotels, restaurants, and museums, offering a glimpse into a lifestyle that once defined southern Italy’s earliest communities. The surrounding gravine (canyons) create a striking natural backdrop, making Matera one of Italy’s most beautiful destinations. Departing Matera, today’s route follows quiet country roads through the Parco Naturale Regionale delle Gravine, or Ravines Regional Park, known for its dramatic cliffs and archaeological sites. You’ll cycle past golden wheat fields and olive groves, with occasional glimpses of shepherd huts and stone farmhouses typical of rural southern Italy. After breakfast, your ride continues through the Ravines Regional Park, crossing an impressive stone bridge spanning one of the deep canyons that characterize this region. As you leave the rugged landscape behind, the terrain softens into the classic scenery of Puglia’s heartland: dry-stone walls, olive trees, vineyards, and trulli, the cone-roofed limestone huts unique to this area. Throughout this tour, you’ll stay in a thoughtfully curated selection of lodgings that reflect the authentic charm and heritage of southern Italy. Accommodations range from historic townhouses and boutique hotels in medieval centers to converted farm estates (masserie) surrounded by olive groves. In some locations, you may experience alberghi diffusi, where rooms are spread among restored village homes.

Daily Ride Schedule

Accommodation & Services

Accommodation

Hotel

What's Included