From Sassi of Matera to Salento (8 days)

Day 1 – Arrival in Matera

Welcome to Matera, one of Italy’s most extraordinary destinations, famous worldwide for its ancient Sassi cave dwellings and breathtaking scenery. Located between Basilicata and Puglia, Matera boasts over 30,000 years of history and is a UNESCO World Heritage Site.
Spend your time exploring rock-hewn churches, visiting a traditional cave home, and enjoying the unique experience of dining or sleeping in a beautifully restored cave hotel.
Arriving late? Consider adding an extra night to fully immerse yourself in this unforgettable city.
Overnight stay in Matera.

Day 2 – Matera to Alberobello

78 km | +650 m

After your bike delivery and personalized fitting, your cycling adventure begins through the stunning landscapes of the southern Murgia region. Today’s destination is Alberobello, one of the most iconic towns in Puglia.

Known as the capital of the Trulli, Alberobello features more than 1,500 unique cone-shaped stone houses clustered in the historic districts of Monti and Aia Piccola, both UNESCO-listed since 1996.
Enjoy peaceful country roads, olive groves, and timeless rural scenery along the way.
Overnight stay in Alberobello.

Day 3 – Alberobello to Ostuni

52 km | +600 m

Today you’ll ride through the rolling hills of the breathtaking Itria Valley, one of southern Italy’s most picturesque areas. Expect postcard-perfect landscapes of ancient olive trees, vineyards, red soil, and traditional white trulli houses.

Along the route, stop in:

• Locorotondo, for a refreshing aperitivo and local white wine

• Martina Franca, known for its elegant baroque old town

• Cisternino, the perfect place for a rustic lunch in a traditional butcher’s grill

Your ride ends in Ostuni, the famous “White City,” perched on three hills and crowned by its impressive cathedral.
Overnight stay in Ostuni.

Day 4 – Train Transfer: Ostuni to Lecce

This morning you’ll take a direct regional train from Ostuni to Lecce (approx. 55 minutes, ticket €5.50 not included). Bikes are carried free of charge on regional trains.

Spend the day discovering Lecce, the baroque jewel of southern Italy. Wander through charming streets and lively piazzas, and admire masterpieces of 17th-century architecture.

Highlights include:

• Piazza Duomo

• Piazza Sant’Oronzo and the Roman amphitheatre

• Basilica di Santa Croce

Overnight stay in Lecce.

Day 5 – Lecce to Gallipoli

62 km | +220 m

Today’s cycling route crosses the peaceful countryside of Salento, surrounded by olive groves, dry-stone walls, and authentic rural charm.

Your first stop is Galatina, home to the magnificent Basilica of Santa Caterina d’Alessandria, famous for its stunning 15th-century frescoes.

After lunch—don’t miss a typical Rustico Leccese—continue toward the seaside town of Gallipoli. In the evening, explore its atmospheric old town set on an island connected by a bridge.
Overnight stay in Gallipoli.

Day 6 – Gallipoli to Otranto

68 km | +390 m

Today you’ll cycle from the Ionian coast to the Adriatic Sea, crossing the heart of Grecia Salentina, where traces of the ancient Griko culture still survive.

Pass through charming villages such as:

• Corigliano d’Otranto

• Melpignano, famous for hosting the spectacular “Night of the Taranta” festival in August

Arrive in Otranto, a coastal gem with a fascinating historic center. Enjoy a seafood dinner, stroll through the old town, and browse local artisan shops.
Overnight stay in Otranto.

Day 7 – Otranto to Lecce

56 km | +285 m

In the morning, take time to explore Otranto’s extraordinary cathedral, home to the relics of 813 martyrs and one of Italy’s most impressive medieval mosaic floors.

Cycling onward, you’ll ride past the beautiful Alimini Lakes and reach the seaside village of Torre dell’Orso. Don’t miss a swim in the magical Grotta della Poesia, one of the most stunning natural pools in Italy.

Before returning to Lecce, stop in Acaya, perfect for an espresso or a sunset drink overlooking the castle.
Overnight stay in Lecce.

Day 8 – Departure Day

Breakfast and end of services. Time to say goodbye to beautiful Puglia!
Before leaving, make sure to stock up on pasticciotti, Lecce’s famous shortcrust pastry dessert.