Start cycling from Matera to Gioia del Colle, known for one of Emperor Frederick II’s castles. From there, ride through a landscape of olive groves and vineyards en route to the Valle d’Itria – the heart of Puglia’s “trulli” region. These iconic and charming conical stone dwellings, once used as farm shelters, are unique to this area and guaranteed to capture your imagination! Join us for a wine tasting (included) to sample some of what is growing in the vineyards you have been cycling past. Have dinner and spend the next two nights in Alberobello at Hotel Silva (or similar).

Cycle to lunch immersed in more picturesque vineyards and olive groves. We encourage you to spend time getting lost in the vibrant little town of Locorotondo, wandering around and taking in the maze of whitewashed lanes. Afterward, we return to Alberobello to join a guided walking tour to learn more about the history and charm of the trullis before dinner.

Today’s ride winds through vineyards and olive groves en route to Ostuni, the stunning “White City” perched across three hilltops. Originally destroyed by Hannibal during the Punic Wars, Ostuni was rebuilt by the Greeks—who named it Astu Néon, or “new town”—and later restored by the Normans in the 10th century. It thrived during the Renaissance under Duchess Isabella of Bari. Whether viewed from a distance or explored up close, Ostuni is both striking and full of character. Nearby Cisternino we’ll stop at a local dairy producer where we’ll learn more about and sample the fresh mozzarella, burrata and stracciatella for which Puglia is renowned. Enjoy a olive oil mill visit and tasting before dinner and stay tonight at Masseria Valente, a typical farmhouse estate of the region (or similar property).

Starting in the whitewashed hill town of Ostuni, the route descends through olive groves and quiet country roads toward San Vito dei Normanni, rich in Norman history. From there, the ride continues to Mesagne, a charming town with a well-preserved historic center and impressive castle. The landscape flattens out as you pedal through sun-drenched fields and vineyards typical of the Salento region. The tour ends in the elegant baroque city of Lecce, known as the “Florence of the South” for its stunning architecture and vibrant atmosphere. Spend the next two nights at Hotel delle Palme, Le Club Lecce (or similar hotel).

Spend the full day discovering the wonders of Lecce. We start with a two-hour guided walking tour together to get you oriented before turning you loose to explore more of the city at your own pace and according to your individual interests. Lecce captivates visitors with its stunning baroque architecture, especially in Piazza Duomo and the ornate Basilica di Santa Croce. Strolling through the historic center reveals elegant palaces, hidden courtyards, and lively cafés. The Roman amphitheater in Piazza Sant’Oronzo offers a glimpse into the city’s ancient past. Local crafts, particularly papier-mâché art, and traditional Salento cuisine complete the cultural experience. Join us again in the evening for a celebratory dinner!

After breakfast it’s time to say goodbye. We hope you’ve enjoyed cycling with us through some of the highlights of southern Italy. Whether you are bound for home or planning to explore more, we wish you buon viaggio!