Highlights
- Visit the ancient cave dwellings of Matera, a UNESCO world heritage site
- See magnificent baroque architecture in Lecce, the "Florence of the South"
- Cycle alongside the sparkling blue Mediterranean Coast
- Enjoy quiet country roads, endless olive groves, and vineyards
Brief Itinerary
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | Matera | Matera |
| Day 2 | Matera – Alberobello | Alberobello |
| Day 3 | Alberobello – Ostuni | Ostuni |
| Day 4 | Ostuni – Lecce – Gallipoli | Gallipoli |
| Day 5 | Gallipoli – Santa Maria di Leuca | Santa Maria di Leuca |
| Day 6 | Santa Maria di Leuca – Otranto | Otranto |
| Day 7 | Otranto – Lecce | Lecce |
| Day 8 | Lecce |
Detailed Itinerary
Day 1: Matera
Welcome to Italy! Arrive in Matera, an ancient city that has been occupied for nearly 10,000 years. Over the years inhabitants have carved dwellings directly into the soft honey-colored tuff stone of the ravines and gullies, creating homes called "Sassi". These homes are a World Heritage Site, and a must-see for visitors to the region.
Day 2: Matera – Alberobello
Cycle to see the famous trulli, conical dwellings used as homes and storehouses, in the Alberobello region. The homes are separated into two districts: the Monti and Aia Piccola, both World Heritage Sites.
Cycling distance: 43 miles (70 km)
Day 3: Alberobello – Ostuni
Cycle through the peaceful countryside to reach the architecturally renowned town of Ostuni. This coastal city is commonly referred to as "The White Town" for its iconic white walls and airy Mediterranean vibe.
Cycling distance: 34 miles (55 km)
Day 4: Ostuni – Lecce – Gallipoli
Chat with a local specialist who can help organize your trip.
Start your day with a short train journey to the town of Lecce, where you get back on the bike and head deep into the Salentinian countryside. Reach the Ionian coast and your destination for the day, Gallipoli, with enough time to relax before dinner in the medieval downtown center.
Cycling distance: 31 miles (50 km)
Day 5: Gallipoli – Santa Maria di Leuca
Cycle along the coast to reach Santa Maria di Leuca, which was named by Greek sailors for the way the sun illuminated the hills. Today the town is a famous seaside resort.
Cycling distance: 31 miles (50 km)
Day 6: Santa Maria di Leuca – Otranto
Cycle north along the Adriatic Coast towards Otranto, the easternmost point of Italy, to see the medieval cathedral and the impressive Aragonese Castle.
Cycling distance: 31 miles (50 km)
Day 7: Otranto – Lecce
Ride along the Alimini Lakes to reach the medieval town of Lecce. Its Baroque style and ornate architecture have earned it the nickname "Florence of the South".
Cycling distance: 34 miles (55 km)
Day 8: Lecce
After breakfast head to the airport, or head on to your next adventure. Safe travels!
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