Cycling Puglia & Matera traces an arc across Italy’s heel, starting amid the cave dwellings of Matera and rolling toward Lecce. Days unfold on quiet rural roads through the Valle d’Itria and its trulli-dotted countryside, past whitewashed hill towns such as Ostuni, and through long belts of olive groves. The rhythm is relaxed but active: undulating rides with time to pause in small piazzas or swim from the Ionian shoreline near Porto Cesareo, before turning across the peninsula to the Adriatic and the medieval lanes of Otranto. Overnight stays reflect the region, from traditional trulli to a working masseria where home-grown produce shapes the local dishes. The finale in Lecce brings baroque streets and a last coastal stop at Torre dell’Orso, rounding off a journey that balances inland heritage with easy seaside miles.
Adventure begins in Matera
Ride past the historic Sassi houses of Matera before heading to Alberobello
Cycle through the lush Valle d'Itria, past the fairytale trulli houses to the hilltop town of Ostuni
Ride through quaint villages and country lanes to a typical masseria (renovated farmhouse) where we spend the night
Cycle to the coast and swim in the crystal-clear sea before continuing towards Gallipoli with its old town on a rocky island
Head towards the Adriatic Sea and the ancient town of Otranto
Continue along the shoreline to the beautiful baroque city of Lecce
Adventure ends in Lecce
Hotel