









Italy: Puglia
Average customer rating 4.7 / 5(55 verified reviews)
In the heart of the Mediterranean lies Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas. We explore the very best of this captivating region from our start point in Alberobello, known for its UNESCO-listed Trulli houses, to the end point in Lecce, known as the ‘Florence of the South’.
Cube, Nature Trekking or equivalent. Your bike hire is included in the price of your holiday and comes equipped with the relevant essentials, plus rear pannier and phone holder.
Our travel specialists can arrange flights, rail and transfers to this holiday from wherever you are. Call us to plan your journey. +44 1606 720099


Make your way to Alberobello, famous for its Trulli houses.
You stay at Trullidea

Alberobello
A unique and authentic experience staying in a trullo, a traditional 15th century Apulian stone building with conical roof.
Each trullo house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.
The trulli are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.

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.
Elevation

You stay at Relais Sant’Eligio

Ostuni
Situated a stone’s throw from Ostuni’s Old Town, the Relais Sant’Eligio dates back to the first half of the 1500s when Queen Bona Sforza d’Aragona imposed all coastal cities from Naples to Otranto to have a resting station. The Resting Station of Camposada – as it was then – has welcomed many couriers and royal officials from yesteryear, whilst today, each of the 22 elegant and individually decorated rooms offer every comfort for the 21st century guest.

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.
Elevation

You stay at Masseria Strazzati

Avetrana
Masseria Strazzati is an old farm estate and is set within 100 hectares of olive groves. Your evening meal is taken at the Masseria Bosco where the pool can also be used.

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.
Elevation

You stay at Hotel Joly Park

Gallipoli
Located in the centre of Gallipoli and only a short walk from Corso Roma, Hotel Joli Park is modern and comfortable.
The rooms are well equipped and contemporary. The hotels offers guests a private shuttle service to take you to and from the private beach “Lido delle Sirene”.

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.
Elevation

You stay at Hotel Terminal

Leuca
Hotel Terminal is nestled among the eclectic villas on the central 19th century seafront dedicated to Cristoforo Colombo in the heart of town, with a beautiful view on Punta Ristola and Punta Melis. Rooms here are comfortable and well equipped and the hotel also benefits from its own private beach.

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.
Elevation

You stay at Hotel Albania

Otranto
Located in the centre of Otranto, Hotel Albania owes its name to the majestic Albanian mountains which on a clear day offers guests breathtaking views and are visible from the hotel terrace.
Rooms are comfortable and modern.

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.
Elevation

You stay at Eos Hotel

Lecce
Situated just outside of the historic town of Lecce, Hotel Eos is a modern hotel with modern facilities.
Rooms are contemporary and fully furnished.


Bari
The Hotel Excelsior has large and bright rooms. There is also a bar and restaurant offering Mediterranean dishes.
15.0
Kg CO₂e
per person, per night
Relative to other Headwater trips
We measure emissions from the parts of the holiday we organise — including accommodation, in-trip transport, meals and activities — and express them as CO₂e per person, per night. Our label doesn’t include your travel to and from the start of the trip. As a Certified B Corp, Headwater is committed to reducing this figure and to positively impacting local communities, the local environment and our staff. Learn more
Graded Level 4, it offers gently varied terrain that suits fair-weather cyclists and more active riders looking for a relaxed trip. No special skills are needed, just reasonable fitness and good health. You ride quiet roads past Puglia’s archetypal olive groves and trulli, with the Headwater Navigation App guiding every turn and your luggage moved between hotels.
You begin among the extraordinary conical trulli houses of Alberobello, a UNESCO World Heritage site, ride through the whitewashed towns and olive groves of the Itria Valley, and finish in Baroque Lecce with its honey-coloured stone. It is a wonderful blend of quiet cycling and rich Puglian culture, with all breakfasts plus one dinner included.
Yes, quality hire bikes are included with a bike fitting and briefing at the start, and e-bikes are available for a supplement if you would like assistance on the climbs. You are also welcome to bring your own bike. Panniers and a phone holder for the navigation app come as standard.