Refine search

Your itinerary

Cycling the Heel of Italy – Matera to Lecce route map

Make your way to Matera, one of the oldest inhabited human settlements in the world.

Meals: Breakfast

Explore the UNESCO-listed Sassi of Matera; a complex of houses built into the natural caves of the Murgia.

Meals: Breakfast

Your first cycling day takes you through a landscape of wheat fields and wide panoramas. Visit the town of Laterza, famous for its tasty bakery products and majolica pottery. Continue to Castellaneta, a small city perched on the edge of a ravine.

Meals: Breakfast,Dinner

Today you will cycle in the Terra delle Gravine Natural Park, amongst deep canyons, carved by rivers over millions of years. Leaving the ravines you will soon discover the iconic Puglia scenery: dry stone walls, old masserie (fortified stansteads) and trulli, rural houses with a conic roof typical to the area, built without any cement or mortar. Reach Putignano, known for its ancient carnival.

Meals: Breakfast

Leaving the medieval centre of Putignano, cycle in the lush countryside to reach Castellana Caves. It is the main karst site in the South of Italy and a visit is recommended.After the caves, continue along the rolling lanes of the countryside where olive, almond, apricot and cherry trees grow. Continue to the UNESCO heritage site of Alberobello, the world capital of Trulli.

Meals: Breakfast

Cycle through the lush Valle d’Itria, passing more white-tipped trulli houses on the way. Boasting beautiful coastal views, the route takes you through the famous wine town of Locorotondo, regarded as one of Italy’s most stunning villages. After sampling some of the local sparkling white wine, continue to the white city of Ostuni – so called for the dazzling effect of its whitewashed houses.

Meals: Breakfast

Cycle through the colourful Salentinian countryside, characterized by olive groves and red soil towards the medieval towns of Oria and Manduria with their authentic historic centres.

Meals: Breakfast,Dinner

Head to Torre Colimena on the Ionian Sea, then follow the coast alongside a series of beaches and the old coastal towers of Salento. Reach Gallipoli, known as the ‘Ionian Pearl’ with its Old Town situated on a rocky island. Take time to wander the narrow lanes of the historic centre to discover its baroque cathedral, elegant palazzi and enticing restaurants.

Meals: Breakfast

Cycle towards the most southerly point of Salento at Santa Maria di Leuca, where the crystal waters of the Ionian and Adriatic Sea meet. This village is home to one of the most important lighthouses in Italy, as well as numerous villas built at the turn of the century.

Meals: Breakfast

Pedal along the south coast of the Adriatic Sea, stopping off at the famous Grotta Zinzulusa and the thermal baths of Santa Cesarea Terme. Your final destination is Otranto, the most eastern point of Italy with a stunning cathedral and Aragonese castle.

Meals: Breakfast

Follow the shoreline through olive groves to the Baroque metropolis of Lecce. Known as the ‘Florence of the South’, Lecce is home to over 30 churches, an amphitheatre and a Roman theatre dating back to Emperor Augustus.

Meals: Breakfast

Make your own way back to the airport for your flight home.

Meals: Breakfast

What’s included

All breakfasts and 2 evening meals
Management by your local Headwater-appointed agent, plus the Headwater navigation app
High-quality bikes
Luggage transfers between hotels
11 nights in a mix of HHH, 3 and 4-star hotels

What’s not included

Request a single room or e-bike if required, purchase travel insurance and arrange any visas and vaccinations. On this trip, you may also need to pay a solo traveller supplement (where only one person is travelling on a departure date)

Additional information

Breakfasts are included and consist of a continental-style buffet. However, please note that the typical Italian breakfast are generally light; usually a cup of coffee and a cream-filled or jam-filled croissant.

In Puglia you will find genuine regional cooking that has strong links to the land and the sea. To give you just a small list of the types of food on offer in Puglia: Bread from the Murge, durum wheat pasta, olives, the pasta delicacy Orecchiette served with a sauce of turnip-tops or fresh tomato and sheep’s ricotta-cheese, Cavatelli with pulses, aubergine and parmesan bake, grilled fish and seafood, burrata (soft mozzarella and cream cheese), plus excellent wines. This region is a food lovers paradise and the abundance of delicious vegetables makes it a perfect destination for vegetarians! On this trip there will be many opportunities to taste the best local specialities.

Suggestions of what to do for lunch and dinner are given in the cycling route notes.

Sample local sparkling white wine in the renowned hilltop town of Locorotondo during the Alberobello–Ostuni stage; tastings are at your own expense.

Stop to visit the famous coastal cave between Santa Maria di Leuca and Otranto; entrance/tour fees are payable locally.

Relax in the historic thermal baths along the Adriatic coast en route to Otranto; spa entry and treatments are additional.

Explore the fortress overlooking Otranto’s harbour, a highlight of the Salento; museum/castle entry tickets are not included.

Explore the UNESCO-listed Sassi and visit cave houses on your free day in Matera; entrance to specific cave dwellings or museums is at additional cost.

A recommended visit to the Castellana karst cave system near Alberobello; join a guided underground route and admire spectacular formations. Entrance fees apply.

Included daily cycling across the Murgia and Salento: ride through Terra delle Gravine canyons, the trulli-dotted Valle d’Itria, and the Adriatic coast to baroque Lecce; luggage is transferred for you while you follow detailed route notes or app maps.

Price & availability

October 2026 November 2026 March 2027 April 2027 May 2027 June 2027 August 2027 September 2027 October 2027 November 2027
Be first to hear about our latest news and special offers.

Be first to hear about our latest news and special offers.

Newsletter