Turn your next getaway into an inspiring journey through southern Italy, where every moment invites discovery, connection, and wonder. Between the sparkling Adriatic Sea and storybook whitewashed villages, Puglia and the Salento unfold as a landscape rich in culture, beauty, and timeless charm. No prior cycling experience is required—just a sense of curiosity and a desire to explore.
Travel from the ancient wonders of Matera to the vibrant streets of Lecce, uncovering the soul of the region along the way. Wander through the fairytale trulli of Alberobello, soak in the coastal beauty of Monopoli, and discover the dramatic shores of Otranto and Gallipoli. With gentle routes, authentic flavours, and time to truly immerse yourself in each destination, this journey offers the perfect blend of exploration and ease. It’s more than a trip—it’s an invitation to experience Italy in a way that stays with you long after you return
Rates starting from:
- Trekking Bike - $3365 per person
- e-Bike - $3580 per person
Departures: June 20, September 5, October 10, and December 12, 2026.
Inclusions:
- 7-night accommodation in 3 and 4-star B&Bs or farmhouses
- 7 breakfasts, 7 lunches or dinners
- Bike rental and accessories
- Wine and cheese tasting as well as other typical local products
- Cooking class
- Boat tour in Santa Maria Di Leuca
- 24-hour English-speaking guide
- Luggage transportation from hotel to hotel
DAY 1 WELCOME TO OTRANTO!
Arrival at Brindisi airport. Transfer on your own to your hotel in Otranto, and check in. With the group, you will receive an initial briefing of your trip. The rest of the day is at leisure.
Accommodation: Otranto for 2 nights
DAY 2 OTRANTO REGION (29 KM)
Today, your first bicycle excursion will be in the surrounding area of Otranto. Riding along the small river “Idro” (“water”), you will visit an ancient Byzantine crypt from the 13th century before continuing to Casamassela. Here, at the “Le Costantine” foundation, traditional looms are still in use today. In Giurdignano, we pass through a fascinating Bronze Age megalithic garden, where dolmens and menhirs can be observed up close. Surrounded by imposing rocks and ancient olive trees, we’ll also carry out an initial assessment to divide the group by levels. For lunch, we stop at one of the region’s most characteristic bakeries, run by a farming family dedicated to transforming ancient grains into traditionally crafted baked goods full of authentic flavor. Afterwards, return to Otranto with a free afternoon to visit the city.
DAY 3 OTRANTO – CASTRO (30 KM)
This day is devoted to one of the most captivating stretches of the Italian coastline. Highlights include the stunning Palascía lighthouse—the easternmost point of Italy—and a striking lake that has formed within a disused bauxite quarry, creating a landscape of remarkable beauty. Arrive at your hotel in Castro and check in. In the afternoon, you will have Italian classes on the roof of the hotel.
Accommodation: Castro for 1 night
DAY 4 CASTRO – SANTA MARIA DI LEUCA (27 KM)
Today, continue along the stunning Otranto - Leuca coastline, where 16th-century fortified watchtowers rise dramatically above the sea. Upon arrival in Marina Serra, you take part in an Italian lesson set in a fragrant coastal pine forest, followed by time to chat with members of ‘Coppula Tisa’, an association dedicated to active citizenship. In the early afternoon, relax by a picturesque bay (perfect for a refreshing swim). Later in the day, reach Santa Maria di Leuca just in time to admire the sunset over the Ionian Sea.
Accommodation: Santa Maria di Leuca for 2 nights
DAY 5 SANTA MARIA DI LEUCA AT LEISURE
Today is a well-deserved day of relaxation, without cycling. After breakfast, attend an Italian lesson in the elegant early-20th-century villa that hosts the group. Late in the morning, the group will set out on a boat excursion to enjoy the coastline from the sea. The rest of the day is at leisure.
DAY 6 SANTA MARIA DI LEUCA – GALLIPOLI (61 KM)
Today is rich in discoveries as you cycle through the villages surrounding the remarkable Capo di Leuca region, while being engaged in Italian lessons with your teachers. Along the way, you will visit ancient coastal towers, underground olive-oil mills, the ruins of a pre-Roman city, a mausoleum adorned with traces of Byzantine frescoes, a semi-abandoned castle, and an ancient pilgrims’ station with vast underground spaces once used as resting quarters. In the afternoon, return to the Ionian coast, reaching Punta Pizzo Natural Park and St. Andrew’s Island. The day ends in Gallipoli, a charming fishing town set on an island, where you can enjoy an aperitif on a seaside terrace or wander through its narrow alleys in the golden light. Accommodation: Gallipoli for 2 nights
DAY 7 GALLIPOLI – COOKING CLASS (39 KM)
Today marks the final “exam” of your Italian course, with a hands-on cooking class and family-style lunch at a local farmhouse. Depart Gallipoli in the morning, cycling first to Alezio, an ancient Messapian city with a fascinating museum dedicated to pre-Roman civilizations, and then on to Sannicola. Your destination is ‘Tenuta Mamma Anna’, a family-run agriturismo where the cooking lesson takes place. Using ingredients harvested directly from the family garden, you will prepare traditional local dishes under the guidance of your hosts (in Italian, of course!). Recipes may include “pitta di patate, pittule”, handmade “orecchiette” pasta, and the beloved “pasticciotto” filled with custard cream. After a convivial family lunch, you cycle back to Gallipoli. The rest of the day is at leisure.
DAY 8 DEPARTURE FROM GALLIPOLI
On your final day, you say arrivederci to Puglia, carrying back with you new Italian skills, unforgettable cycling memories, and meaningful connections made along the way. This journey was as much about language and people as it was about the ride itself. Transfer to Brindisi airport on your own for your return flight home.
