Visiting: Italy

Hotel & Bike

7 nights from £543 to £965pp
Guiding Self-Guided i
Level Easy to Moderate i
Standard Superior i
Code IT046
Good For Coasts and Islands, Foodies
Distance 199mi/320km !
Runs Mar, Apr, May, Jun, Aug, Sep, Oct
Departs Saturday
Fly to Bari
Return from Bari


What to expect

Discover the ancient silver olive groves, hilltop towns and unique coastal villages of south east Italy, a region that extends into the Ionian and Adriatic Seas. Tour the countryside on quiet roads, stopping off at historic towns to try the famous local fare or taking a break on long sandy beaches backed by limestone cliffs.

A region rich in culture, the Romans, Byzantines, Normans and Bourbons all left their mark in Puglia but it's the Greek and quirky local influences that are strongest – expect white washed towns and hobbit-style huts, called 'Trulli'. Cycling through rich vine growing regions, you’ll have plenty of opportunity to try some of Italy’s best wines. Towards the end of the tour, soothe your muscles in the thermal spa near Otranto and look forward to the intricate and breathtaking architecture of Lecce.

Read about Head of Freedom Treks, Catherine's time cycling this tour in her blog post.

  • Greek villages, Roman roads and dry-stone huts
  • Glistening grottos, sparkling seas, sandy beaches & limestone cliffs
  • Intricate architecture in Lecce and Otranto’s Romanesque cathedral
  • Cycling through sun-drenched olive groves

The Trip



  • Day 1: Arrive in Matera

    Discover the amazing and beautiful cave town of Matera with its fascinating and beautiful maze of caves known as 'Sassi' carved into the rock, where amazingly people still lived into the 1950s.

  • Day 2: Matera - Alberobello 43 miles (70 km)

    Cycle through rural countryside covered with ancient olive trees and scattered with pretty white washed 'trulli', traditional dry stone huts with a conical roof. Stay in your own 'trullo' in the small town of Alberobello which dates back to the 16th century and is famous for its cluster of UNESCO listed 'trulli' huts.

  • Day 3: Alberobello - Ostuni 28 miles (45 km)

    Cycle through the undulating countryside stopping off at pretty towns or at the famous Locorotondo vineyards to try the local wine before reaching the white buildings of Ostuni for breathtaking sea views.

    There is the possibility to shorten the itinerary by taking the train today.

  • Day 4: Ostuni - Lecce - Gallipoli Train + 28 miles (50 km)

    Take the train to the beautiful Baroque town of Lecce before riding through the countryside to the beautiful Greek town of Gallipoli which sits on a rocky outcrop jutting into the sea – look back for fantastic views along the Italian coast.

  • Day 5: Gallipoli - Santa Maria di Leuca 31 miles (50 km)

    Reach the most southerly point of Italy's heel, where the Ionian meets the Adriatic Sea at Santa Maria di Leuca, a town well known for its church, pilgrimages and lighthouse.

  • Day 6: Santa Maria di Leuca - Otranto 31 miles (50 km)

    Ride along the south coast, with views of the Adriatic Sea, stopping off at the famous Grotta Zinzulusa to reach the Messapian town of Otranto. The old part of the town is surrounded by a mighty wall and contains the impressive Habsburger Castle and its beautiful cathedral. 

  • Day 7: Otranto - Lecce 34 miles (55 km)

    Continue along the coast, passing olive groves and stopping for a break on Torre dell’Orso beach which is backed by limestone cliffs. Arrive in Lecce, capital of Salento, a town with beautiful Baroque buildings and churches – visit the amphitheatre and the Roman theatre, both built under Caesar Augustus.

  • Day 8: Depart from Lecce

    Making your way home from Lecce, the airports at Bari and Brindisi are easily reached by train - or extend your stay and explore and cafe hop further.


3 & 4* Hotels

We use a pool of 3 and 4 star hotels to maximise our availability for this tour, so regardless of the time of year we do our best to secure your dates of choice. The accommodation often has a lovely local flair, with a chance to experience local life with an authentic flavour of your destination.

  • A mix of 3 and 4-star hotels and sometimes in Alberobello a "trullo" hotel
  • Breakfast included
  • Secure bike storage
  • Luggage transferred each day

Dates & Prices

Please click on a departure date for price options at a glance 

Price includes

  • 7 nights accommodation in 3 and 4 star hotels and sometimes in Alberbello in a "trullo" hotel
  • Board Basis: Bed and breakfast
  • Luggage transportation
  • Maps and route information (GPS tracks available on request)
  • Bike handover (if renting bikes) 
  • Local contact number for assistance
  • Train from Ostuni - Lecce 

Price excludes

  • Flights and transfers
  • Bike hire
  • Cycle helmets
  • Tourist taxes (approx €10-15)

Which hotel?

Month Selector

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  • Fully Booked

Bike Hire & Extras

Bike hire

Pannier, handlebar bag or map holder and lock all included at no extra cost when you hire a bike. The bikes are also equipped with puncture-resistant Schwalbe tyres. One repair kit per room is provided and includes a spare inner tube, glue, patch, pump, allen keys and tyre levers. 

Mens Hybrid Bike
Bike hire

Hybrid bike with 27 gears

E bike
E-Bike hire
Example Helmet
Helmet hire


You can add these when you price your trip

Extra nights

Matera: Double room (B&B)
Matera: Single room (B&B)
Lecce: Double room (B&B)
Lecce: Single room (B&B)

How to Get There

Getting there

Fly to Bari

Take the train from Bari airport to Bari Centrale (14 minutes) then change trains to go to Matera (90 minutes).

You will need to change stations in Bari, however the FAL train station (Ferrovie Appulo Lucane) in Bari is located next door (immediately to the left). 

Getting back

Take the train (Trenitalia) from Lecce to your return airport.

Fly from Bari or Brindisi

News, Reviews & FAQs


Simply click on a question to reveal the answers

Why are the hotels not listed in the itinerary?

We use a pool of hotels to maximise availability for you.


Lake Garda

The Best Cycling Tours In Europe For 2019

5th October 2018 As we pedal towards the new year, we’ve put together a selection of tours that we've tried out and can highly recommend for 2019. Whether it’s beautiful scenery in Italy, peaceful cycling in Germany and Austria or luxurious cruising around Croatia, these tours demonstrate the best that Europe has to offer in 2019. READ POST
Tuscany landscape Italy

Ten Reasons To Love Cycling In Italy

9th March 2018 A jewel of the Mediterranean, Italy is home to some of the world's best food, art and architecture. We think it ticks almost every box as a fantastic destination for a cycling trip. READ POST

Customer reviews

What other customers have said

Been on this tour? Add your review!

Leave your review below

Date *
out of 5

Caring company, great organisation, fab bikes and beautiful routes in wonderful destinations.

Elaine Heeler, UK, November 2018
out of 5

Such a beautiful tour seeing loads of Puglia! So much fun to swim in the sea and eat lots of tasty seafood. Just a tip to anyone booking for October to be prepared that quite a few restaurants and attractions are closed or have different opening times! Still plenty of places to eat and visit though!

Ruth Taylor, UK, November 2018

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