Arrive in Matera at the time of your choosing. We recommend an early arrival to give yourself plenty of time to explore the ancient cave dwellings of Sassi di Matera, a UNESCO World Heritage Site.

After your briefing and bike outfitting this morning, set out on a ride over the Murgia plateau, a region littered with interesting caves and rock formations.
You’ll conclude your ride through nature in Alberobello, one of Italy’s best-kept secrets. Its trulli — huts with conical roofs — are what earns the city its UNESCO World Heritage Site designation.

White villages, vineyards, and olive groves will be a recurring theme as you wheel through the Itria Valley. Locorotondo, one of Italy’s ‘most beautiful villages’ is home to more trulli — but it’s best known for its unusual circular city center and the local white wine. Cisternino, another village, is covered with various piazzas offering unsurpassed views of the countryside. While you’re in town, stop at a local butcher shop for a fresh fornello pronto lunch!

Wheel on to coastal Ostuni, where the hilltop citadel lends more drama to the beautiful white town.

Bring your bike aboard the train for free today and head straight to Lecce, where you can enjoy the rustic local cuisine and explore the city’s incredible jewels at your leisure. Reminiscent of Rome or Florence, Lecce is home to Roman ruins (like a half-buried amphitheater), palaces and castles, theatres and opera houses, and monuments to heroes and their heroic deeds.

Even if you’ve seen many churches along your ride, don’t miss the ones on your route today! In Galatina, don’t miss the baroque Chiesa Madre and the frescoes of the Basilica of Santa Caterina d'Alessandria. In Galatone, the
Sanctuary of the Crucifix is worth your while. 
From the island-based old town, you may enjoy a breathtaking sunset over the Ionian Sea.

Crossing the Salento — the region that makes up the “heel” of Italy’s boot shape — you’ll encounter a unique subregion called Grecìa Salentina, which is home to an ethnic Greek population. It’s here that people speak Griko and carry on traditions like the taranta and pizzica dances.

You’ll encounter beautiful towns like Corigliano D’Otranto and Melpignano on your way to Otranto, all the way along the west coast of the “heel”. From the island-based old town, you may enjoy a breathtaking sunset over the Ionian Sea.

Pack your swimsuit today! Leave Italy’s easternmost town, Otranto, and ride to the Adriatic coast! Gorgeous limestone cliffs rise out of crystal-clear blue water in Torre dell’Orso. Ride along the shores of the beautiful linked Laghi Alimini to Italy's easternmost point. On a clear day, you may be able to spot Albania across the water. Then, take a break at the fortified village of Acaya

The ride brings you back to Lecce with plenty of free time to do as you please.

After breakfast, depart Lecce at the time of your choice.