You arrive individually in Matera and check in at your hotel. This first day allows you plenty of time to get settled and begin exploring the city’s unique atmosphere. Matera, known for its ancient Sassi neighborhoods filled with rock churches and cave houses, offers a fascinating introduction to the region’s history. You can choose to independently visit cultural sites or simply enjoy a walk along the main street. There are many cafes and bistros where you can relax, and if you are interested in local crafts, you will find small workshops and ateliers specializing in stonework and handmade Italian goods.

Matera’s Sassi districts are among the oldest continually inhabited settlements in the world, recognized as a UNESCO World Heritage Site.

You begin the day in Matera with a welcome briefing led by your tour guide. This session includes an introduction to the tour, checking and adjusting your bikes and accessories to ensure everything is ready for the journey ahead. After the briefing, you set out on a guided three-hour trek through Matera. The walk takes you to some of the city’s most evocative corners, highlighting its status as a UNESCO World Heritage Site and former European Capital of Culture. The route also leads into the Murgia Materana Natural Park, where you cross the Gravina stream canyon and follow scenic paths up to a panoramic viewpoint overlooking the landscape.

In the evening, you have the option to join your guide and fellow travelers for dinner at a typical local restaurant.

The Murgia Materana Natural Park protects a unique environment of limestone ravines and prehistoric cave dwellings surrounding Matera.

You leave Matera and begin cycling through the Lucanian countryside, passing wide valleys, rolling hills, and wheat fields with straw-colored clay. The route continues into the Land of the Gravines, a regional scenic park, and brings you to the small village of Ginosa, set in the ancient bed of the Bradano River. From Ginosa, you ride on to Laterza, a town known for its baked goods, beautiful majolica tiles, and the deepest canyon in Europe. After passing through a forest, the landscape opens to reveal a view of the Gulf of Taranto. Upon arrival at your accommodation, you join a guided visit of an archaeological excavation site featuring remains from the protohistoric and Roman periods, set in a rural area of notable beauty. In the evening, you enjoy a substantial dinner at your lodging to celebrate your first day of cycling.

• Distance: approximately 56 kilometers
• Elevation gain: 730 meters
• Elevation loss: 990 meters

The Laterza canyon, part of the Gravina system, is considered one of the largest and most dramatic canyons in Europe.

You begin the day cycling through the Land of the Gravines, experiencing one of the area’s most scenic stretches. As you climb the hills, you enter the Murgia of Trulli countryside, where the landscape is defined by dry stone walls, ancient farms, and trulli—traditional rural houses with conical roofs built without cement or mortar. The route takes you along winding paths through oak forests, pastures, and masserias before reaching Locorotondo. This village is recognized as one of Italy’s most beautiful, featuring a historic center with a labyrinth of alleys and distinctive houses. Upon arrival, you participate in a wine tasting to sample local white and rosé wines, a specialty of this region.

• Distance: approximately 56 kilometers
• Elevation gain: 800 meters
• Elevation loss: 440 meters

Trulli are unique to the Itria Valley in Puglia and have been used as rural dwellings for centuries due to their efficient construction and distinctive style.

You cycle along well-maintained rural lanes, quickly reaching Alberobello, a UNESCO World Heritage Site famous for its concentration of trulli with conical stone roofs. After a stop and some free time to explore, you continue through the rolling countryside of Castellana Grotte, the last extension of the karst Murgia landscape. The route then descends toward the Adriatic Sea, leading you to Polignano a Mare, a town perched dramatically on cliffs above the water. Polignano is known for its stunning coastline, its connection to singer-songwriter Domenico Modugno, and its reputation for excellent ice cream. The final segment takes you along the coast for ten kilometers to Monopoli, a town blending seafaring traditions and history. Your accommodation is in the historic center, close to the old port and the castle.

• Distance: approximately 55 kilometers
• Elevation gain: 370 meters
• Elevation loss: 800 meters

Alberobello’s trulli are recognized by UNESCO for their unique construction and cultural significance in southern Italy.

You start your day cycling through the courtyards and arches of Monopoli’s historic center, then follow the coastline with alternating views of rocky coves and long sandy beaches. After about ten kilometers, you reach the area near the Archaeological Park of Egnatia, showcasing the remains of a Messapic-Roman city. You pause for photos before heading south to Savelletri and Torre Canne, small fishing villages and holiday destinations, ideal for a coffee break. The route then leaves the coast, winding along rural paths through a landscape filled with centuries-old olive trees. Here, you visit an ancient fortified masseria and learn about extra virgin olive oil production, finishing with a tasting. The final stretch takes you gradually uphill, revealing the outline of Ostuni, known as the “white city” for its lime-plastered houses and walls. A short, steep climb brings you into town, where you can explore narrow alleys and white stairways, enjoying a drink or glass of wine at sunset.

• Distance: approximately 52 kilometers
• Elevation gain: 400 meters
• Elevation loss: 200 meters

Ostuni’s striking whitewashed architecture has earned it the nickname “La Città Bianca,” and it is a prominent landmark visible from miles away across the Puglian landscape.

You begin with a relaxed ride among monumental olive trees, cycling to the village of Carovigno. Here, the Dentice-Frasso castle stands on a hill, offering a scenic spot for early morning photos. Continuing through rural roads, you reach San Vito dei Normanni before heading south through varied landscapes. The final kilometers bring you into Brindisi, a port city with historical significance as the “Gateway to the East” since Roman times. You ride two more kilometers through the city center to reach the train station. From Brindisi, you board a train to Lecce, a city celebrated for its Baroque architecture. Upon arrival, you check in at your accommodation in the heart of Lecce’s old town, return your bike, and mark the end of your cycling journey with a toast.

• Distance: approximately 50 kilometers
• Elevation gain: 160 meters
• Elevation loss: 360 meters

Lecce is often called the “Florence of the South” due to its rich Baroque architectural heritage and artistic history.

After breakfast, your cycling adventure concludes. You have time to prepare for your onward travel as all scheduled services end today. There are no further group activities, allowing you to depart Lecce at your own pace.

Lecce’s historic center is known for its ornate Baroque buildings, crafted from the region’s distinctive golden limestone.