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.

Guide: Included for the day

Meals: Breakfast

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.

Guide: Included for the day

Meals: Breakfast, Snacks

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.

Guide: Included for the day

Meals: Breakfast

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.

Guide: Included for the day

Meals: Breakfast