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Headwater – Self-guided Walking and Cycling Holidays

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Journeys of discovery and wander - from place to place at your own pace

With the crocus already emerging and a subtle smell of spring in the air, it’s time to start thinking of booking some much deserved holidays. It’s never been  more important to make sure holidays offer meaningful experiences that allow for a true connection with the places visited and one’s travel companions.

Taking it the slow way with walking and cycling holidays, is the perfect way to create a memorable, meaningful getaway and Headwater Holidays offer the perfect solution.

Mobile concierge

With a team of dedicated travel experts, Headwater has become the leading provider of walking and cycling holidays, curating a range of tours and experiences that place the traveller at the centre of everything. Founded in 1985, Headwater has spent the last three decades discovering the best routes and designing unique itineraries that meet a variety of interests, not least wine tasting. These are anchored by stops at hand-picked, local-favourite hotels and restaurants and by the personalised service that has become Headwater’s signature.

Headwater supports travellers from the moment they start considering a walking or cycling holiday to the day of their return. The team provides advice, guidance and recommendations on which route to select, and goes on to take care of all details from the moment a tour is booked. These include luggage transfers, in-depth route plans, navigation apps and tailored add-ons, such as city and/or coastal breaks, e-bikes or visit to wine producers.

Think of Headwater as your mobile concierge.


Win a Headwater holiday for two

Enter your details here for a chance to win either a
Secrets of Sicily Walking Holiday or Contrasts of Catalunya Cycling Holiday.

The winner will be selected and contacted on April 5th

Tonnara di Scopello, Sicily


Not just a holiday

Headwater gives travellers the opportunity to engage in memorable experiences that will become much more than a simple holiday: they will be journeys of discovery and wander; active and purposeful getaways that will be equally stimulating for the body, the mind and the soul.

The tours place the travellers at the centre of everything, allowing them to savour every step of the way. They are an invitation for all those looking for a sophisticated adventure and a genuine connection with the people and places they visit. Each itinerary is designed to activate the senses and allow a full immersion in a region’s culture and landscape, with the confidence of itineraries built upon hard-earned insider’s knowledge. From places of historical interest to local restaurants by way of the best views and boutique accommodations, each route is a narrative with carefully written chapters. Headwater guides travellers, revealing the hidden gems, the path less trodden, the most authentic cuisine, the most talented craftsmen… It’s all about allowing discovery through the magic of wandering, pedalling and full engagement. A way to travel with purpose and meaning.

Pedal, walk, wander, become

Whether looking for a cycling or walking holiday the possibilities are endless – different paces for the same sense of wonder.

Exploring places on two wheels – which has long been a favourite among wine lovers wanting to truly discover a region’s landscape – allows for a wider breadth. These are itineraries to go further and faster, expanding the spectrum of possibilities within a specific time frame.

Particularly appealing when immersing oneself in a wine region, cycling routes make it possible to cover multiple sub-regions and visit a larger number of producers. The meticulous turn-by-turn directions provided by Headwater through audio navigation created for each itinerary, allow for a stress-free exploration, focused solely on the cinematic pleasure of the road.

Travelling on foot, on the other hand, is the best way to soak up the scenery, becoming one with the sounds, scents and textures of the world’s most wonderful places. It’s an experience of mindful connection with time and place, not just discovering but indeed breathing the soul of one’s destination. Winelovers will find this is a good way to understand the essence of terroir and to connect deeply with those working the land.

The call for a genuine, slower, more sustainable way of travel is answered by Headwater’s collection of self-guided and/or guided cycling and walking holidays, which can be browsed in Headwater’s free brochure.

Walking Tenerife

Among the most popular routes, whose success has granted Headwater five-star reviews on Feevo, are itineraries that will appeal particularly to wine lovers:

  • Walking in Tenerife and La Palma – amazing opportunity to discover two of the Canary islands home to sought after volcanic wines
  • Marvels of Madeira Walk – during which you can discover some of the world’s most iconic and ageworthy fortified wines
  • Cycling the Grand Crus of Bordeaux – a spirited discovery of the classic wine region
  • Classic Cotswolds Cycling – a great way to unveil the secrets of the award-winning English sparkles
  • Cycling along the Danube from Vienna to Budapest – unveiling the ancient traditions of renowned central European grapes and producers
  • Walking the Speyside Way – created in 1981, the Speyside Way takes in numerous whisky distilleries and places of incredible natural beauty.

Headwater is giving Decanter readers a £100 discount per person
on any self-guided trips booked until 31st March 2023.

Simply use code DECANTER100 to redeem the offer.

Visit this page for more information


The journey starts here and now.
Request your Headwater brochure

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