Home > Jewels of Southern Italy: Matera to Lecce

Jewels of Southern Italy: Matera to Lecce

Ride through peacefull country roads in Apulia 6
Alborobello: see the iconic trulli, a UNESCO world heritage site Visit rustic villages with ancient architecture Ride through peacefull country roads in Apulia Ostuni, the white town on the hill Riding through typical and paved village streets Spend some time along the Adriatic coast
Ride through peacefull country roads in Apulia

Jewels of Southern Italy: Matera to Lecce

  • Level
  • PriceFrom 690 euros
  • DAY7 nights / 8 days

More info: Receive detailed hotel list, bike specs, and route description

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If Mediterranean sunshine and flavorful cuisine are what you crave, Italy is the obvious destination choice. Not so visible are the cities of the southeastern peninsula, in Apulia (Puglia in Italian) —Sassi di Matera, Alberobello, Lecce, Otranto and Gallipoli — that are off the beaten tourist track (for now!) One of Italy’s best-kept secrets, Apulia is home to an incredible mix of natural beauty and historic relics, plus two UNESCO World Heritage Sites

Cyclists in Apulia enjoy virtually traffic-free country roads over mostly flat terrain, some of which follow the coastline while others cover the lush inland plateaus. Whether you want to stop for a swim, enjoy a coffee in the piazza, or visit every castle, church, and museum is up to you!

If your time constraints don't allow you to spend a whole week visiting the Apulia region, keep in mind that we also offer a 3 night/4 day trip from Bari to Brindisi.


For travel and cycling tips to Apulia, visit our "Travel and cycling tips" section.


D1Arrival in Matera


Arrive in Matera at the time of your choosing. We recommend an early arrival to give yourself plenty of time to explore the ancient cave dwellings of Sassi di Matera, a UNESCO World Heritage Site.

D2Matera — Alberobello 76 km/47 miles, 629 meters/2,064 ft of climbing


After your briefing and bike outfitting this morning, set out on a ride over the Murgia plateau, a region littered with interesting caves and rock formations.
You’ll conclude your ride through nature in Alberobello, one of Italy’s best-kept secrets. Its trulli — huts with conical roofs — are what earns the city its UNESCO World Heritage Site designation.

D3Alberobello — Ostuni 49 km/30 miles, 644 meters/2,113 ft of climbing


White villagesvineyards, and olive groves will be a recurring theme as you wheel through the Itria ValleyLocorotondo, one of Italy’s ‘most beautiful villages’ is home to more trulli — but it’s best known for its unusual circular city center and the local white wineCisternino, another village, is covered with various piazzas offering unsurpassed views of the countryside. While you’re in town, stop at a local butcher shop for a fresh fornello pronto lunch!

Wheel on to coastal Ostuni, where the hilltop citadel lends more drama to the beautiful white town.

D4Ostuni — Lecce by train


Bring your bike aboard the train for free today and head straight to Lecce, where you can enjoy the rustic local cuisine and explore the city’s incredible jewels at your leisure. Reminiscent of Rome or Florence, Lecce is home to Roman ruins (like a half-buried amphitheater), palaces and castles, theatres and opera houses, and monuments to heroes and their heroic deeds.

D5Lecce — Otranto 51 km/32 miles, 413 meters/1,355 ft of climbing


Pack your swimsuit today, because, after a stop at the fortified village of Acaya, you’re headed to the Adriatic coast! Gorgeous limestone cliffs rise out of crystal-clear blue water in Torre dell’Orso. Ride along the shores of the linked Laghi Alimini to Italy’s easternmost town, Otranto.
On a clear day, you may be able to spot Albania across the water.

D6Otranto — Gallipoli 61 km/38 miles, 413 meters/1,355 ft of climbing


Crossing the Salento — the region that makes up the “heel” of Italy’s boot shape — you’ll encounter a unique subregion called Grecìa Salentina, which is home to an ethnic Greek population. It’s here that people speak Griko and carry on traditions like the taranta and pizzica dances.

You’ll encounter beautiful towns like Melpignano and Corigliano D’Otranto on your way to Gallipoli, all the way along the west coast of the “heel”. From the island-based old town, you may enjoy a breathtaking sunset over the Ionian Sea.

D7Gallipoli — Lecce 56 km/35 miles, 365 meters/1,198 ft of climbing


Even if you’ve seen many churches along your ride, don’t miss the ones on your route today! In Galatone, the Sanctuary of the Crucifix is worth your while. In Galatina, don’t miss the baroque Chiesa Madre and the frescoes of the Basilica of Santa Caterina d'Alessandria.

The ride north brings you back to Lecce with plenty of free time to do as you please.

D8Departure from Lecce


After breakfast, depart Lecce at the time of your choice.

Booking & Pricing

  • Option A
  • 7 nights in guesthouses "of character"

  • 690 euros per person in January through April and October through December. Single supplement is 240 euros
  • 840 euros per person in May, June and September. Single supplement is 280 euros
  • 1,040 euros per person in July and August. Single supplement is 335 euros
  • Option A+
  • 3 nights in 5-star hotels, 3 nights in 4-star hotels and 1 night in a luxury guesthouse

  • 1,020 euros per person in January through April and October through December. Single supplement is 335 euros
  • 1,330 euros per person in May, June and September. Single supplement is 435 euros
  • 1,660 euros per person in July and August. Single supplement is 525 euros

These prices include:

  • 7 nights’ accommodation as described above
  • Daily breakfast
  • Meeting with our local representative
  • Luggage transfers
  • Marked maps and/or cue sheets and route notes
  • Tourist information
  • Pre-loaded GPS unit
  • Assistance if necessary (you will be provided with our local rep’s mobile number)
  • Service charges and most taxes

These prices do not include:

  • Nominal city taxes, to be paid in cash directly at each hotel
  • Expenses of a personal nature
  • Travel insurance
  • Train ticket from Ostuni to Lecce (5.70 euros per person) – Bikes are free of charge in regional trains
  • Bicycle rentals. Hybrid bikes are available at the rate of 115 euros per bike.
    Electric bikes are available at the rate of 245 euros per bike (these prices include the drop-off fee).

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