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.
At a glance
- 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
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.
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.
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.
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.
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.
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 Aragonese Castle and its beautiful cathedral.
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.
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
- 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
- Flights and transfers
- Bike hire
- Cycle helmets
- Tourist taxes (approx €10-15)
Bike Hire & Extras
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.
Hybrid bike with 27 gears
You can add these when you price your trip
How to Get 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).
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.
What other customers have said
Been on this tour? Add your review!
This was an amazing tour, and because we had never visited this region before, we found it to be full of surprises. Matera is absolutely stunning, and the accommodation was excellent. My husband, who trusted me to choose the holiday, was blown away by every single city we saw, as well as the cycling. We met some lovely people along the way, and even though we were all on the same itinerary, we all went at our own pace, often meeting up in the morning or evening only. Each hotel was different, and the local meals and wine were amazing. Our bikes were in top condition, and we enjoyed the kick-off meeting with the host from the local partner. Our only regret was not spending an extra day on both ends of the trip. We enjoyed ourselves so much, we'd do exactly the same tour again!Laura Jenkins, Kendal, UK, January 2019
Caring company, great organisation, fab bikes and beautiful routes in wonderful destinations.Elaine Heeler, UK, November 2018