Cycling the Heel of Italy - Matera to Lecce

0044 1606 720199

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  • Holiday code
    C11PI
  • Holiday type
    Self-guided cycling
  • Duration
    11 nights
  • Accommodation
    hotel-to-hotel
    , and
  • Activity level
  • From $3185per person, tour only
  • Departure months
    JFMAMJJASOND
  • What your holiday price includes
  • 11 nights hotel-to-hotel accommodation in a mix of , and hotels
  • All breakfasts and 2 evening meals
  • Bike fitting and briefing at the start of your holiday
  • Headwater navigation app
  • Bike hire included
  • Luggage transfers between hotels
  • Optional Upgrades
  • Electric bikes available
  • Suitable for
  • Solo travellers
  • Couples
  • Excellent choice for
  • Food lovers, wine lovers, art & history, swimming opportunities, vegetarian meals, coastal routes
      from 5 reviews

David Carlyle says...
Was a good trip. Valued the free day in Matera and the shorter cycling day to Alberello so had time to visit the limestone caves. The app was easy to ...
Read reviews »

Italy: The Bay of Naples

Cycling the Heel of Italy - Matera to Lecce

  • Matera - UNESCO World Heritage Site; visit the cave houses
  • Alberobello's fairy-tale trulli houses
  • Olive groves, towering limestone cliffs and Roman amphitheatres
  • The white city of Ostuni, the majestic castle of Otranto and Baroque Lecce
  • Based on our popular 7 night, Cycling the Heel of Italy - Alberobello to Lecce

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.



We're here to help

If you have any questions about this holiday call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com

Cycling information

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.




We're here to help

If you've any questions about this holiday call our sales team on 0044 1606 720199 , or email sales@headwater.com

Day 1: Arrive in Matera

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

Day 2: Free day in Matera

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

Day 3: Matera to Castellaneta (60km/37.3mi)

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.
Breakfast and evening meal included

Day 4: Castellaneta to Putignano (55km/34.2mi)

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.
Breakfast included

Day 5: Putignano to Alberobello (35km/21.7mi)

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.
Breakfast included

Day 6: Alberobello to Ostuni (49km/30.4mi)

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.
Breakfast included

Day 7: Ostuni to Avetrana (55km/34.2mi)

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.
Breakfast and evening meal included

Day 8: Avetrana to Gallipoli (60km/37.3mi)

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.

Day 9: Gallipoli to Santa Maria di Leuca (50km/31.1mi)

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.
Breakfast included

Day 10: Santa Maria di Leuca to Otranto (53km/32.9mi)

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.
Breakfast included

Day 11: Otranto to Lecce (54km/33.6mi)

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.
Breakfast included

Day 12: Leave Lecce


Where you stay

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.

To find out more call our sales team on 0044 1606 720199, use our live webchat or email sales@headwater.com


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Belvedere, Matera

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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.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Trullidea, Alberobello

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A unique and authentic experience staying in a trulli, a traditional 15th century Apulian stone building with conical roof.

Each trulli house is made up of a double bedroom, small bathroom with shower and living area with sofa and small kitchenette.

The trullis are located in the centre of historic Alberobello, a UNESCO world heritage site, within walking distance of cafes, restaurants and shops.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Relais Sant'Eligio, Ostuni

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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.


Find out more on the hotel website.

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.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Joly Park, Gallipoli

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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”.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Terminal, Leuca

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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 it's own private beach that can be reached by a picturesque underpass. Rooms are comfortable and well equipped.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Hotel Albania, Otranto

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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.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

Eos Hotel, Lecce

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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.

Extending your stay

If you'd like to extend your trip with extra nights at the start or end, or if you'd like to arrange a stop off point en-route, then we recommend the following hotels.


Find out more on the hotel website.
Read customer reviews on Tripadvisor.

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.

Travel

Transfers can be arranged at a supplement from Bari Airport at 14:20.

Call now to speak to our specialist team at 0044 1606 720199 or email us at sales@headwater.com for enquiries or to book your trip.

Reviews

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.


David Carlyle, 23/09/2023

Was a good trip. Valued the free day in Matera and the shorter cycling day to Alberello so had time to visit the limestone caves. The app was easy to follow. Welcomed opportunity to upgrade the hotels.


Alexander Whiteside, 14/09/2023

All in all we had a great time. We would recommend Headwater to other people.


Mark Stead, 10/09/2023

Another great holiday from Headwater, thoroughly enjoyed the cycling and loved the location and the Puglian people, very friendly indeed. The contrasting accommodation was extremely interesting from a cave once inhabited by the Sassi in Matera, to a B&B where we had breakfast in the owners dining room in Putignano, a Trulli in Alberabello and a 4 star hotel in Otranto. The itinerary was full on and definitely showed us all that Puglia has to offer. Fantastic!


OATES, 22/05/2023

A lovely itinerary with something different every day. Good accommodation and food.


Mrs Unwin, 11/04/2023

We had a wonderful holiday in Puglia cycling from Matera to Lecce over 9 days. It is a stunning part of the world and on a bike you have the advantage of seeing things and meeting people that you wouldn't if traveling by car. Overall, we would highly recommend this holiday. As we were cycling in April we did find a lot of the coastal areas were just getting ready for holiday season, so they were quiet and cafes were not always open. However, this was also a positive in that the roads were extremely quiet (apart from towns), so on balance this was good for us. The introduction and bike hike through Puglia Cycle Tours was excellent and our choice of electric bikes definitely the best decision for us as it was hilly in places. The electric bikes meant that we didn't walk up any hills! My only regret bikewise was that I didn't take my gel saddle with me but otherwise all worked well and we would love to return to this part of the world to explore further.



Dates and prices

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.

This 11 night self-guided cycling holiday includes:

Hotel-to-hotel accommodation in a mix of , and hotels

All breakfasts and 2 evening meals

Bike fitting and briefing at the start of your holiday

Headwater navigation app for your smartphone

Bike hire

Luggage transfers between hotels


How to book:

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' or 'check availability' button below.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'check availability' button below.

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25th Apr 2024 US$3275 US$480 Tour only: US$3275
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1st Sep 2024 US$3800 US$480 Tour only: US$3800
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1st May 2025 US$3875 US$576 Tour only: US$3875
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3rd May 2025 US$3875 US$480 Tour only: US$3875
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8th May 2025 US$3875 US$480 Tour only: US$3875
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10th May 2025 US$3875 US$480 Tour only: US$3875
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15th May 2025 US$3875 US$576 Tour only: US$3875
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17th May 2025 US$3875 US$576 Tour only: US$3875
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19th May 2025 US$3875 US$576 Tour only: US$3875
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24th May 2025 US$3875 US$480 Tour only: US$3875
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26th May 2025 US$3875 US$480 Tour only: US$3875
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29th May 2025 US$3875 US$480 Tour only: US$3875
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31st May 2025 US$3875 US$480 Tour only: US$3875
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2nd Jun 2025 US$3875 US$576 Tour only: US$3875
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5th Jun 2025 US$3875 US$576 Tour only: US$3875
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Single supp: US$576
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Check availability
23rd Jun 2025 US$3875 US$576 Tour only: US$3875
Single supp: US$576
Check availability
Check availability
26th Jun 2025 US$3875 US$576 Tour only: US$3875
Single supp: US$576
Check availability
Check availability
28th Jun 2025 US$3875 US$576 Tour only: US$3875
Single supp: US$576
Check availability
Check availability
30th Jun 2025 US$3875 US$576 Tour only: US$3875
Single supp: US$576
Check availability
Check availability
DepartingTour only Prices   Single supplement
3rd Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
5th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
7th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
10th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
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Check availability
12th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
14th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
17th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
19th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
21st Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
24th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
26th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
28th Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
31st Jul 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
DepartingTour only Prices   Single supplement
2nd Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
4th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
7th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
9th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
11th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
14th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
16th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
18th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
21st Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
23rd Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
25th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
28th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
30th Aug 2025 US$4220 US$576 Tour only: US$4220
Single supp: US$576
Check availability
Check availability
DepartingTour only Prices   Single supplement
1st Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
4th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
6th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
8th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
11th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
13th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
15th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
18th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
20th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
22nd Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
25th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
27th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
29th Sep 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
DepartingTour only Prices   Single supplement
2nd Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
4th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
6th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
9th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
11th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
13th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
16th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
18th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
20th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
23rd Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
25th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
27th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
30th Oct 2025 US$4055 US$576 Tour only: US$4055
Single supp: US$576
Check availability
Check availability
DepartingTour only Prices   Single supplement
1st Nov 2025 US$3185 US$576 Tour only: US$3185
Single supp: US$576
Check availability
Check availability
3rd Nov 2025 US$3185 US$576 Tour only: US$3185
Single supp: US$576
Check availability
Check availability
6th Nov 2025 US$3185 US$576 Tour only: US$3185
Single supp: US$576
Check availability
Check availability
8th Nov 2025 US$3185 US$576 Tour only: US$3185
Single supp: US$576
Check availability
Check availability
10th Nov 2025 US$3185 US$576 Tour only: US$3185
Single supp: US$576
Check availability
Check availability

The prices quoted for each individual departure supercede those published in our current brochures. Air prices are subject to change and we advise early booking to obtain the best prices. Please see our Planning your holiday and What's included in the price? pages for additional information.

Holiday details

Solo travellers
Please call for details and prices

Children
This holiday is unsuitable for children.

Holiday type
Self-guided cycling Managed by Headwater rep.

Departures
Tuesday, Thursday & Sunday departures from 25th Apr 2024 to 10th Nov 2025, for 11 nights. All dates are subject to availability, please contact us to check.

Meals
All breakfasts and 2 evening meals

Electric bikes
It is possible to hire electric bikes for this holiday at a supplement of £364 per person. As these are available on a first come first served basis, we recommend early booking to avoid disappointment.

Other details
This holiday is also available with mainly 4 Star accommodation.

Tailor-made travel

This holiday does not include any flights or rail.

How to book

To book this holidays speak to our sales team on 0044 1606 720199 or click on the appropriate 'book now' button above.

If you need further information before you book simply complete our Holiday Enquiry Form and a member of our sales team will get back to you.

To book this holiday call our sales team on 0044 1606 720199 or click on the appropriate 'Book now' or 'Check availability' button below.

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