Itinerary
- Day 1
Matera
You'll arrive in Matera and check into your hotel near the historic centre. The afternoon is yours to walk through the narrow alleys of the Sassi cave-dwelling district at your own pace. Later there's a welcome briefing where you'll meet the group and your tour leader.
- Meals
- Breakfast
Included Activities
- Welcome briefing and group meeting
Optional Activities
- Explore Sassi UNESCO-listed cave-dwelling district
Landmarks/POIs Sassi di Matera - Day 2
Matera to Alberobello
Starting out on your bike, you'll cycle through the Apulian countryside on mostly hilly terrain with some gentle climbs. The route passes through Noci and Gioia del Colle where you'll see the cone-shaped trulli houses dotting the landscape. By evening you reach Alberobello.
- Meals
- Breakfast
Included Activities
- Cycling tour through Apulian countryside to Alberobello
Optional Activities
- Explore historic centre of Alberobello with trulli houses
Landmarks/POIs Alberobello Historic Centre Noci Gioia del Colle - Day 3
Alberobello to Ostuni
Today's a shorter, more relaxed ride through the Valle d'Itria on rolling terrain. You'll pass through Locorotondo and Cisternino, both with whitewashed houses and historic centres worth a look. After that it's on to Ostuni, known as the White City because of its bright appearance.
- Meals
- Breakfast
Included Activities
- Cycling tour through Valle d'Itria to Ostuni
Optional Activities
- Explore Locorotondo
- Explore Cisternino
- Explore Ostuni's historic centre
Landmarks/POIs Valle d'Itria Locorotondo Cisternino Ostuni - Day 4
Ostuni to Avetrana
You'll cycle through quiet country lanes heading toward Francavilla Fontana and Oria, which has a 13th-century castle you can see from a distance. Your destination is Masseria Bosco, a working farm where you're staying the night. Before dinner, there's an olive oil tasting featuring organic oil made right on the property.
- Meals
- Breakfast
Included Activities
- Cycling tour to Oria
- Organic olive oil tasting at Masseria Bosco
Optional Activities
- Explore Oria's historic centre with cobbled streets and historic castle
Landmarks/POIs Oria Castle Oria Masseria Bosco - Day 5
Avetrana to Gallipoli
Pedalling toward the Ionian Coast, you arrive in Gallipoli, also called the Ionian Pearl. The old town sits on a rocky island with great views of the water. Depending on weather, you'll have chances to swim in the Ionian Sea near Porto Cesareo during the afternoon.
- Meals
- Breakfast
Included Activities
- Cycling tour to Gallipoli
Optional Activities
- Swimming in the Ionian Sea near Porto Cesareo
- Explore Gallipoli's old town, churches and narrow alleys
Landmarks/POIs Gallipoli Porto Cesareo - Day 6
Gallipoli to Otranto
Today's ride crosses the peninsula from the Ionian Sea over to the Adriatic Sea, finishing in Otranto at Italy's easternmost point. This ancient Messapian town has medieval architecture worth exploring, restaurants along the seafront, and white sandy beaches. You'll have free time before dinner to walk around.
- Meals
- Breakfast
Included Activities
- Cycling tour to Otranto
Optional Activities
- Explore medieval town centre of Otranto
- Visit white sandy beaches
Landmarks/POIs Otranto - Day 7
Otranto to Lecce
Your bike ride follows the shoreline through olive groves heading to Lecce, a baroque masterpiece people call the Florence of the South. It's a relatively short and easy ride, leaving time for a final seasonal swim at Torre dell'Orso, a bay with limestone cliffs. After arriving, you have free time to check out Lecce's historic centre, with an optional farewell dinner available.
- Meals
- Breakfast
Included Activities
- Cycling tour to Lecce
Optional Activities
- Swimming at Torre dell'Orso
- Explore Lecce's historic centre with palazzi and churches
- Optional farewell dinner
Landmarks/POIs Torre dell'Orso Lecce - Day 8
Lecce
You'll have your final breakfast and the tour ends this morning. If you want to stay longer in Lecce, arrangements can be made for extra accommodation.
- Meals
- Breakfast
Optional Activities
- Explore Lecce further
- Post-tour accommodation in Lecce (contact sales representative)


















