Ride Basilicata’s undulating landscape dotted with fields of swaying wheat • Ascend into Matera, where caves carved into limestone cliffs reveal one of the world’s oldest settlements • Wander narrow lanes and stairways for views of sassi cave homes • Gather for a lively welcome dinner, sharing regional dishes and stories that set the tone for the days ahead.

Pedal scenic backroads toward Alberobello, its iconic trulli rising like a fairy-tale village in the hills • See how mozzarella is made for a behind-the-scenes look at one of the region’s signature flavors • Ride through ancient olive groves toward Ostuni, the luminous White City perched across three hilltops • Climb into its maze of bright alleys and hidden courtyards crowned by a gothic cathedral • Cool off with a sweet espressino freddo before continuing along quiet scenic roads • Join a local cook for a pasta-making experience, then share a relaxed farmhouse dinner rooted in generations of tradition.

Bike inland through lesser-known villages and open farmland • Stop for a fresh, seasonal lunch at a working agriturismo • Opt into downtime at our stylish retreat or hop back on your bike for extra miles past coastal lakes and into Otranto • Get ready for the trip’s most spectacular ride along cliffside roads, seaside towns and hidden grottoes perfect for an unhurried swim break • Celebrate the journey with an evening of local music and dancing • End the trip in Lecce, known for its intricate baroque architecture carved from warm golden stone.