Puglia: The Heel of the Boot

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Bike Tours, Road cycling holidays, E-bike tours, Gravel bike tour


8 days





The beauty of this package is in the freedom it offers: without a guide, you are free to decide the timing, pace, and stops of your journey. Travel freely, travel your way!

3/5 Medium

Moderate, between 35 and 85 kilometers per day with an elevation gain between 300 and 1000 meters.



The starting point is different from the ending point, with overnight stays in different hotels and daily stages.


Day 1: Matera
Individual arrival in Matera, hotel check-in, and delivery of rented bicycles. Upon request: guided walking tour around the Sassi di Matera and the Park of the Rupestrian Churches. We recommend having dinner in the Sassi area, at one of the typical restaurants carved into the rocks.

Day 2: Matera – Alberobello (69 km)
In this first bike leg in Puglia, you will pass through the small villages of Gioia del Colle and Noci, before continuing toward Alberobello, the Capital of Trulli and a UNESCO site, World Heritage. Overnight stay in a Trullo, or a renovated farm house.

Day 3: Alberobello – Ostuni (45 km)
Today by bike you will cross the heart of Puglia: The Itria Valley. You will stop in characteristic villages of Locorotondo and Cisternino, and finally reach Ostuni, The White City, a jewel of architecture with its medieval center characterized by a tangle of streets that remind of an Arabian Casbah and its typical lime-white houses.

Day 4: Ostuni – Oria (55 km)
Pedaling towards the south, on quiet countryside roads, you will first reach the town of Francavilla Fontana and then Oria, Touring Club's Orange Flag, famous for its castle dating back to the XIII century and beautiful old town. At the end of the stage, you will arrive at a traditional Masseria (farmhouse), where you will stay for the night.

Day 5: Oria – Gallipoli and Ionian Coast (60 km)
Today's itinerary will take you through the nature park of Porto Selvaggio, one of the most beautiful and unspoiled places in Puglia. Continuing along the Ionian Coast, you will arrive at Gallipoli, whose name derives from the Greek word kalépolis (beautiful city). Organize a picnic on the beach and, if the weather permits, take a refreshing swim.

Day 6: Gallipoli – Otranto (71 km)
Pedaling towards Otranto, the itinerary will lead you through one of the wildest stretches of coast in southern Italy, up to its easternmost point. In this sunny land where Greeks and Turks once landed, the atmosphere is simply unique. Otranto also has a wonderful old town surrounded by walls and highlighted by the beautiful Aragonese Castle, as well as the Romanesque Cathedral of Santa Maria Assunta, which houses a work of immense value: a floor mosaic depicting the tree of life and some passages from the Old Testament.

Day 7: Otranto – Lecce (45 km)
This final bike leg of your marvelous Puglia tour will bring you to Lecce, the Capital of Baroque. Once in the city, don't forget to taste the Puccia, the typical local bread filled with vegetables and delicacies of local cuisine and take a coffee break with the unmissable Pasticciotto. Relax walking through the splendid streets of the center.

Day 8: Lecce
After breakfast, end of services and individual departure.

By choosing to travel by bike with us, you help us make the world a better place: we plant a tree for every trip sold

Why book online on Cyclando?

Because we guarantee you the lowest price and if your tour is not available or confirmed, you can always opt for the refund of the amount paid, or choose another tripfrom the over 800 on the platform.

Our cancellation insurance is the most advantageous you will find around!


Cancel for any reason

Trip cancellation for any documentable reason: pregnancy, illness, work and more, guaranteed.


Coverage of all costs

Full insurance covers all travel costs and penalties from companies, without worries.


Refund in 7 days

With Smart Claims, we guarantee fast refunds in just 7 days for complete peace of mind.

✅ What is included in the trip?

  • Travel/Medical Insurance 24/24
  • Overnight stay and breakfast
  • Luggage transfer
  • Local telephone assistance 7/7
  • Detailed description and maps of the itinerary
  • GPS or navigation APP

❌ What is not included?

  • Transfers not listed as "Included"
  • City tax
  • Tips
  • Journey to/from the starting point of the tour
  • Meals and drinks not listed as "Included"
  • Bike rental
  • Extras
  • Entrance fees, ferries and anything not listed as "Included"
  • Welcome briefing

💸 Cancellation fees

  • Time Range
  • Full refund
  • More 29 days of departure
  • 75%
  • From 13 to 29 days before departure
  • 50%
  • Up to 7 days before departure
  • Not refundable

Puglia: The Heel of the Boot

  • To immerse yourself among the olive trees, small whitewashed villages and of course the Trulli of the Valle d'Itria
  • For the long sandy beaches, dunes and Protected Nature Reserves you will encounter along the coast
  • To travel through history, cycling on the traces of the ancient Messapian civilizations between rock settlements and castles
  • For the unique charm of Salento, with its Masserie, the Baroque of Lecce, the pizzica dance and the gastronomic specialties
  • To pedal from the Stones of Matera right to the extreme point of the Heel of the Boot discovering the Puglia by bicycle

🙋 Frequently asked questions

  • Can I bring my own bike?

  • What kind of assistance will I have during the trip?

  • How do I know if a tour is within my capabilities?

  • What is the cost of renting bicycles?

  • Are rented bikes equipped with accessories like lights or bags?


Organized by


Ferula Viaggi (Slow Italy Srl)

Best Price Guaranteed!

Starting from 987per person

stariicon4.9/5on15 reviews

How many of you will there be?


Minimum participant number = 2




Single room surcharge




Do you want to rent bikes?


Chosen by 6 people

Do you have any doubts of any kind?

Cyclando srl

Tour operator with Europe Assistance RC Insurance 4249713 - Registered with the Guarantee Fund with A.I.A.V. Associazione Italiana Agenti di Viaggio trough IL SALVAGENTE s.c. a r.l.. All rights reserved.

VAT ID: 03880320365

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