A wonderful trip right on the end of Italy’s boot, enjoying what the Southeast of Italy and the Ionian and Adriatic Sea have to offer. This area is home to multiple olive groves, grain fields and vineyards. Your route begins in Alberobello, this unique area is a UNESCO World Heritage Site due to its “trulli”. Your tour will end in Lecce, aka the “Florence of the South” due to its amazing baroque architecture. Enjoy incredible landscapes which are testaments to ancient culture and remain untainted by tourism.

Calender 8 days

Difficulty: Moderate

From £1165.00 P/P

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After making your own way to Alberobello, get to know this truly unique city, which is the only urban settlement of the so-called “trulli” (cone buildings), meaning it has had UNESCO World Heritage Site status since 1996.

It’s time to kick off your cycling and the first route takes you through the countryside and to Ostuni. Often named “the White Town”, this is an architectural marvel for its sea of white buildings.

It’s time to say goodbye to Ostuni and the Murge hills and begin cycling on the Salento Plain, characteristic for its green and red colours that come from its olive trees and red soil. A point of interest on the route is Oria, this town has an interesting historical centre and a castle which was built by emperor Federico II. Your stop for the night will be the Manduria area, this is the capital of famous Primitivo grapes.

The journey for the day will head for the coast, characterised by ancient maritime towers and fine sand. Your first stop for the day will be Porto Cesareo, an ideal stop to have a fish or seafood lunch. As you continue south your destination is Gallipoli, this is the Greek Kale Polis, which is today home to a beautiful historical centre. Enjoy a gorgeous walk around its streets and gorgeous views of the surrounding sea.

As you continue on the coast you will reach Santa Maria di Leuca, whose name was given by the ancient Greek sailors who’d come from the East; seeing this place lit up by the sun, they called it “leukos” which means white. Today’s Santa Maria di Leuca is a popular coastal resort.

Heading north along the Adriatic coast you will get to Otranto, the most eastern point of Italy. Here there is a stunning cathedral and the great Aragonese Castle.

As you head to Lecce you will pass the Alimini Lakes with the characteristic Mediterranean bush. Lecce is famous for its Baroque style and has thus been nicknamed the Florence of the south.

Either end your trip here or choose to extend it.

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Route overview

Start point: Alberobello

End point: Lecce

Total distance: approx. 340km

Much of the route is on lowlands with the occasional hills. There is very low traffic in this area and much of it will be alongside beautiful coastline.

What’s included

  • 7 nights hotel accommodation
  • Standard Bike Hire
  • Breakfast
  • App including maps
  • roadbook
  • points of interest and GPS tracks Digital tour information
  • Luggage transportation
  • Hotline service

Not included

  • Local taxes (approx 10-15 €)
Whats included

Check Availability

We have put a calendar of events together that will provide you with some inspiration of what you can expect on your holiday, and when the best time to jet off is. Now’s your chance to travel further than you can by foot and be part of a memorable and exciting two-wheel journey with us.


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We are excited to announce that we are offering a 20% discount on all European Cycling Tours!


Terms and Conditions: The discount is valid for bookings made before July 31, 2023. The discount must be used for travel before November 30, 2023. The discount cannot be combined with any other offers or discounts.