Spend a week cycling through Italy's Apulia region in the Mediterranean southeast. Start in ancient Matera to see 9,000-year-old cave dwellings, then continue to the laid-back Ionian coast. Cycle through endless olive groves, white-walled coastal resort towns, and quiet country roads.

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

Matera by night
Matera by night

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

Trulli in Alberobello
Trulli in 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

Group photo with a view on Ostuni
Group photo with a view on 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

Mediterranean Coast
Mediterranean Coast

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

Approaching the village of Leuca
Approaching the village of 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

Otranto on the Adriatic Coast
Otranto on the Adriatic Coast

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

Dawn in the medieval Lecce alleys
Dawn in the medieval Lecce alleys

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

Paintings inside Church of Santa Irene in Lecce
Paintings inside Church of Santa Irene in Lecce

After breakfast head to the airport, or head on to your next adventure. Safe travels! 

Map

Map of Cycling Tour of Southeast Italy - 8 Days
Map of Cycling Tour of Southeast Italy - 8 Days