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 and begin by cycling through two towns that both possess UNESCO world heritage sites. The region is mainly flat, which lends itself perfectly to the self-guided cycle ahead; filled with spectacular views; beautiful coastline and mouth-watering cuisine.
Make your way to Matera, 2019's European Capital of Culture, and one of the oldest inhabited human settlements in the world.
On leaving Matera, ride past its beautiful UNSECO recognised honey-coloured stone houses. Called 'Sassi', these dwellings have been housing residnets for the past 9,000 years. From one famous world heritage site to another, head towards Alberobello, where you can admire its distinctive trulli houses made from local limestone.
Cycle through the lush Valle d'Istria, 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.
Take a train to the fascinating Baroque town of Lecce. From here cycle deep into the Salentinian countryside before appraoching the Ionian coast. here you will reach Gallipolli, known as the 'Ionian Pearl' with its Old Town situated on a rocky island.
Cycle towards the most southerly point of Salento at Santa maria di Leuce, where the crystal watersof 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.
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.
We follow the shoreline through olive groves to the Baroque metropolis of Lecce. Known as the 'Florence of the South', Lecce is home to over30 churches, an amphitheatre and a Roman theatre dating back to Emperor Augustus.
During your holiday you stay at the following hotels. If you'd like to extend your time at any of these or, if you'd like to enhance your stay with an upgraded room, just let us know at the time of booking.
You will spend 7 nights in comfortable en suite hotels, when available we use traditional accommodation in Alberobello. Most of the towns are close to the seaside.
Extra nights: Please contact us for details.
Everyone who goes on a Headwater holiday will be emailed a link to our post-holiday questionnaire where they can give us an honest assessment of all aspects of their holiday - everything from how quickly we answer the phone to how clean the hotels were - plus an overall rating and comments about their holiday.
Any feedback collected is posted to our website, so that people can make an informed decision based on past experiences before heading off on holiday. We don’t edit the reviews, the only thing we do is proofread them and alter any typos, where necessary, to ensure they are easy to read for everyone. All reviews will be published (except in certain extreme circumstances), and a member of the Headwater team will respond to any constructive criticisms/comments under the reviews, at their discretion. So, for the real tales, twists and turns of our holidays, look no further than the reviews from our previous travellers.
Excellent holiday with good hotels, great scenery and realistic riding days for the described activity level. The bikes were excellent and comfortable.
This was our first cycling holiday (we are in our seventies) We had the most enjoyable time, meeting up with fellow cyclist from other countries on route
The towns we stayed in and the hotel were all very good. The cycling was almost all on quiet roads. We would certainly like to book another trip. Mary and Tim
You can be confident that our pricing includes all the standard requirements of your holiday and many additional extras. Always ensure that you are comparing like for like when booking your holiday.
Find out about The Headwater Price Promise to ensure you're getting the very best value for money.
This 7 night self-guided cycling holiday includes:
Hotel-to-hotel accommodation in a mix of hotels
Management by your local Headwater-appointed agent
Route directions and maps
High quality bikes
Luggage transfers between hotels
How to book:
|21st Mar||US$1799||Check availability|
|28th Mar||US$1799||Check availability|
|4th Apr||US$1979||Check availability|
|11th Apr||US$1979||Check availability|
|18th Apr||US$1979||Check availability|
|24th Apr||US$1979||Check availability|
|25th Apr||US$1979||Check availability|
|1st May||US$2079||Check availability|
|2nd May||US$2079||Check availability|
|8th May||US$2079||Check availability|
|9th May||US$2079||Check availability|
|15th May||US$2079||Check availability|
|16th May||US$2079||Check availability|
|22nd May||US$2079||Check availability|
|23rd May||US$2079||Check availability|
|29th May||US$2079||Check availability|
|30th May||US$2079||Check availability|
|5th Jun||US$2079||Check availability|
|6th Jun||US$2079||Check availability|
|12th Jun||US$2079||Check availability|
|13th Jun||US$2079||Check availability|
|19th Jun||US$2079||Check availability|
|20th Jun||US$2079||Check availability|
|26th Jun||US$2079||Check availability|
|27th Jun||US$2079||Check availability|
|21st Aug||US$2099||Check availability|
|22nd Aug||US$2079||Check availability|
|28th Aug||US$2079||Check availability|
|29th Aug||US$2079||Check availability|
|4th Sep||US$2079||Check availability|
|5th Sep||US$2079||Check availability|
|11th Sep||US$2079||Check availability|
|12th Sep||US$2079||Check availability|
|18th Sep||US$2079||Check availability|
|19th Sep||US$2079||Check availability|
|25th Sep||US$1979||Check availability|
|26th Sep||US$1979||Check availability|
|2nd Oct||US$1979||Check availability|
|3rd Oct||US$1979||Check availability|
|10th Oct||US$1979||Check availability|
|17th Oct||US$1799||Check availability|
|24th Oct||US$1799||Check availability|
|31st Oct||US$1799||Check availability|
This holiday is unsuitable for children.
Self-guided cycling Managed locally by Headwater appointed agent.
Selected from 21st Mar 2020 to 31st Oct 2020, for 7 nights. All dates are subject to availability, please contact us to check.
It is possible to hire electric bikes for this holiday at a supplement of £100 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.
Transfers can be arranged at a supplement from Bari Airport at 14:20.
Due to the tailor-made nature of our holidays, we need a little more information in order for us to check availability for Puglia - Cycling the Heel of Italy. Simply complete the form below (fields marked * are mandatory) and a member of our sales team will contact you (when it's most convenient for you) to provide availability information, travel options and an accurate price. Of course there's no obligation, but if you do wish to proceed with a booking they will be on-hand to assist you throughout the process.
Alternatively, you can call our sales team on 1-800-267-3347 to discuss your requirements in more detail.