Kick off your ride with a steady climb through open countryside and quiet back roads • Tackle a challenging ascent into Matera, where stone stairways and cave dwellings reveal 9,000 years of human history • Explore this UNESCO World Heritage Site on foot, from ancient frescoes to cliffside views • Wrap up the day with a welcome toast and dinner featuring bold local flavors.

Bike rolling country roads to the trulli-filled town of Alberobello, where 1,500 conical stone dwellings hint at a cross-cultural past • Ride or shuttle to a peaceful countryside retreat, then wind down with a mozzarella-making demo • Climb through olive groves and past coastal views en route to Ostuni, the striking whitewashed hill town crowned with a Gothic cathedral • Cool off with an espressino freddo (a sweet local coffee), explore maze-like alleyways, and cap the day with hands-on pasta making and a home-cooked dinner at a traditional farmhouse.

Spin through quiet farmland and lesser-known inland villages, with a farm-fresh lunch at a working agriturismo • Enjoy downtime at our chic Mediterranean hotel or opt for extra miles past coastal lakes and into Otranto • Tackle the trip’s most spectacular ride along cliffside roads, hidden grottoes and seaside towns—one of the best biking days in the region • Cap off the adventure with a festive night of local music, dancing and a celebratory dinner • End your journey in Lecce, where ornate Baroque architecture sets the stage for a final stroll or espresso before heading home.