Cycling In Southern Italy - 8 Days

Day 1: Arrive in Matera

The first stop on your tour of southeastern Italy is Matera, an ancient city where people have lived in houses carved into caves for thousands of years. Give yourself plenty of time to roam around the Sassi di Matera.

Many of the homes in these cave neighborhoods, known as sassi, have more recently been refurbished or transformed into boutique hotels, restaurants, bars, and more. Take time to wander through the narrow pathways and see the cave churches. Visit MUSMA, a sculpture museum set inside a 16th-century cave palace. Head to the edge of town to see uninhabited caves and get a sense of what it was like to live there years ago. 

Day 2: Matera — Alberobello

This morning you'll have a briefing and be outfitted with your bike. Then head out into the countryside with a ride over the Murgia plateau, where you'll see interesting caves and rock formations. Conclude your ride in Alberobello — a true hidden gem. Here you'll find trulli, or whitewashed little homes with conical roofs, built by its original inhabitants in the 14th century. 

Distance: 47 miles (76 km)
Elevation gain: 2,065 feet (629 m)

Day 3: Alberobello — Ostuni

Today you'll pedal through the Itria Valley past whitewashed villages, vineyards, and olive groves. Stop in some of the villages to explore. In Locorotondo, you'll see more trulli, but also an unusual circular town center and excellent local white wine. Break for lunch in the village of Cisternino, which is packed with piazzas offering spectacular views of the countryside. Head to a local butcher's shop for a fornello pronto lunch of freshly grilled meat.

Continue on to the coast, where you'll end your day in Ostuni. Explore the hilltop citadel known as the "White City" and visit its 15th-century cathedral, before sitting down for dinner. 

Distance: 30 miles (49 km)
Elevation gain: 2,115 feet (644 m)

Day 4: Ostuni — Lecce 

Today you'll board the train with your bike and head to the city of Lecce, where you'll have the day to explore on your own. Somewhat reminiscent of Florence or Rome, Lecce has its fair share of ancient Roman ruins, palaces, castles, theaters, and more. As you wander around, you'll find a half-buried Roman amphitheater, baroque cathedrals, wine bars, small museums, and excellent food.

Perhaps take a cooking class, or just enjoy the local cuisine. Lecce is known for its flavorful comfort food made from inexpensive seasonal ingredients.

Day 5: Lecce — Otranto

Don't forget your swimsuit today, because after a visit to the fortified village of Acaya, you'll ride out to the sparkling Adriatic coast. Beautiful limestone cliffs rise out of the crystal blue water as you approach the beaches of Torre dell'Orso. Continue cycling along the shores of the interconnected lakes known as Laghi Almini to Italy's easternmost town, Otranto. On a clear day, you can even spot Albania across the sea!

Take time to enjoy Otranto's intoxicating mix of interesting history, seafront restaurants, and white sandy beaches.

Distance: 32 miles (51 km)
Elevation gain: 1,355 feet (413 m)

Day 6: Otranto — Gallipoli

Today you'll bike across Salento, the southernmost region of Puglia. Along the way, you'll visit a unique collection of towns called Grecìa Salentina, which is home to an ethnic Greek minority. You'll hear the Griko dialect here and can find well-preserved musical traditions like the pizzica folk dance.

Roam around pretty towns like Melpignano and Corigliano D’Otranto on your way to Gallipoli on the west coast of Italy's heel. This old island town is reachable only by sea or via a 16th-century bridge. Wander around the narrow streets, explore its baroque churches, bask on the beach and indulge in fresh seafood before taking in a breathtaking sunset over the Ionian Sea.

Distance: 38 miles (61 km)
Elevation gain: 1,355 feet (413 m)

Day 7: Gallipoli — Lecce

Make your way back toward Lecce today. Although you'll have seen many churches on your trip so far, don't miss the ones along your route today. The Sanctuary of the Holy Crucifix in Galatone is well worth your while. In Galatina, head to the baroque Chiesa Madre and the vibrant frescoes of the Basilica of Santa Caterina d'Alessandria. Then ride north to Lecce and spend the rest of the afternoon at your own pace.

Distance: 35 miles (56 km)
Elevation gain: 1,200 feet (365 m)

Day 8: Departure 

Enjoy one last Italian breakfast before leaving Lecce. Head to the airport or train station to continue to your onward destination.