Home > Jewels of Southern Italy: Matera to Lecce
A minimum of 2 riders is required for this tour
If Mediterranean sunshine and flavorful cuisine are what you crave, Italy is the obvious destination choice. Not so visible are the cities of the southeastern peninsula, in Apulia (Puglia in Italian) —Sassi di Matera, Alberobello, Lecce, Otranto and Gallipoli — that are off the beaten tourist track (for now!) One of Italy’s best-kept secrets, Apulia is home to an incredible mix of natural beauty and historic relics, plus two UNESCO World Heritage Sites.
Cyclists in Apulia enjoy virtually traffic-free country roads over mostly flat terrain, some of which follow the coastline while others cover the lush inland plateaus. Whether you want to stop for a swim, enjoy a coffee in the piazza, or visit every castle, church, and museum is up to you!
If your time constraints don't allow you to spend a whole week visiting the Apulia region, keep in mind that we also offer a 3 night/4 day trip from .
For travel and cycling tips to Apulia, visit our "Travel and cycling tips" section.
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.
Pack your swimsuit today, because, after a stop at the fortified village of Acaya, you’re headed to the Adriatic coast! Gorgeous limestone cliffs rise out of crystal-clear blue water in Torre dell’Orso. Ride along the shores of the linked Laghi Alimini to Italy’s easternmost town, Otranto.
On a clear day, you may be able to spot Albania across the water.
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 Melpignano and Corigliano D’Otranto on your way to Gallipoli, 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.
Even if you’ve seen many churches along your ride, don’t miss the ones on your route today! In Galatone, the Sanctuary of the Crucifix is worth your while. In Galatina, don’t miss the baroque Chiesa Madre and the frescoes of the Basilica of Santa Caterina d'Alessandria.
The ride north 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.
7 nights in guesthouses "of character"
3 nights in 5-star hotels, 3 nights in 4-star hotels and 1 night in a luxury guesthouse