Self-guided cycling
11 nights,
hotel-to-hotel
Level: 2
Moderate
Flights
available
14.0Kg CO2e
Headwater
Navigation App
Optional
e-bike hire
Starting in Matera, the city of 'Sassi' and a UNESCO world heritage site, and through the local canyons, the 'gravine', you will enter Puglia, a unique landscape sandwiched between the Adriatic and Ionian seas. We explore the very best of this captivating region from Murgia to Salento.
Your daily cycle routes allow you to explore a series of architectural and natural wonders, sites of immense historical and cultural interest, and of course, to be tempted by local culinary specialties! Cycle through the Murghe plateau, the Salento plain and along the coast through a landscape of ancient olive groves and vineyards and past traditional masserie, coastal watchtowers and splendid Baroque towns.
This holiday is offered with a choice of mainly 3 Star, or mainly 4 Star accommodation. The 3 Star accommodation is listed on the hotels page. Stays are in the UNESCO listed towns of Matera and Alberobello; Putignano, known for its ancient carnival; white-washed Ostuni; Galipolli, where the historic centre is on an island; Santa Maria de Leuca, where the Ionian and Adriatic seas meet; Otranto, known as the gateway to the Orient and Lecce, known as the 'Florence of the South'. Stay also in Castellaneta and Avetrana where evening meals are included.
95% of the cycling is on asphalt roads, with 5% on strada bianca. The routes generally keep to quieter, secondary roads although you should expect more traffic in the towns.
Make your way to Matera, one of the oldest inhabited human settlements in the world.
You stay at Hotel Belvedere.
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Located in the Sasso Caveoso, and just a few steps from the Sassi di Matera UNESCO site. Il Belvedere Hotel is a unique location for a perfect view of the Sassi and is close to the typical cave churches, on the main access street to the town. Hotel Il Belvedere is an elegant and typical Hotel in Matera, the rooms are elegant and unique, most of them are built within the cave and each one presents original tufa wall.
Explore the UNESCO-listed Sassi of Matera; a complex of houses built into the natural caves of the Murgia.
You stay at Hotel Belvedere.
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Located in the Sasso Caveoso, and just a few steps from the Sassi di Matera UNESCO site. Il Belvedere Hotel is a unique location for a perfect view of the Sassi and is close to the typical cave churches, on the main access street to the town. Hotel Il Belvedere is an elegant and typical Hotel in Matera, the rooms are elegant and unique, most of them are built within the cave and each one presents original tufa wall.
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.
You stay at Le Grotte di Sileno.
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Le Grotte di Sileno is an agriturismo, set on a farm that produces olive oil and wine. The agriturismo has only recently been completed and rooms are spacious.
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.
You stay at B&B Santo Stefano.
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Located in the centre of Putignano, B&B Santo Stefano rooms have a balcony, fan and are decorated with stone vaulted ceilings.
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.
You stay at Trullidea.
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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.
You stay at Relais Sant'Eligio.
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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.
You stay at Masseria Strazzati.
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.
You stay at Hotel Joly Park.
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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.
You stay at Hotel Terminal.
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Hotel Terminal is nestled among the eclectic villas, on the central nineteenth-century seafront dedicated to Cristoforo Colombo, the heart of the town, with a beautiful view on Punta Ristola and Punta Melis.
The hotel has its own private beach that can be reached by a picturesque underpass. Rooms are comfortable and well equipped.
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.
You stay at Hotel Albania.
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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.
You stay at Eos Hotel.
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Situated just outside of the historic town of Lecce, Hotel Eos is a modern hotel with modern facilities.
Rooms are contemporary and fully furnished.
If you'd like to extend your trip with extra hotel nights we recommend: Hotel Excelsior, Bari.
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The Hotel Excelsior has large and bright rooms. There is also a bar and restaurant offering Mediterranean dishes.
These tour prices are based on two people sharing. Single supplement from £296.
We can book your flights, protected by ATOL and ABTA. Please ask at time of enquiry.
This holiday is also available with mainly 4 Star accommodation.
If you choose a flight inclusive package with us, you will fly into Bari airport. We can provide transfers from the airport, please contact us for details and prices.
We hold an ATOL License and are fully ABTA bonded, so you can book your flights with us in confidence. We can book most airlines and will advise you of your most convenient airport and flight options.
Flight prices vary massively and change quickly. At Headwater we will sell you your flights at the same price you can buy them yourself. We simply add £35 per person to cover your flight protection, to learn more please click here.
Subject to availability and dependent on service provider, please ask at time of enquiry and book early to avoid disappointment.
Self-guided cycling
11 nights,
hotel-to-hotel
Level: 2
Moderate
Flights
available
14.0Kg CO2e
Headwater
Navigation App
Optional
e-bike hire
