We are the self-guided specialists, with an incredible range of relaxed walking and cycling holidays to tempt you to change the way you think about your next escape. Uncover the perfect balance between relaxation and discovery with an unforgettable walking or cycling holiday.

Since 1985 we have been creating relaxed walking and cycling holidays across the UK, Europe, and beyond. Our tailor-made tours combine winning routes, idyllic destinations and hand-picked accommodation (with delicious local cuisine) for all levels of walker or cyclist.

Our expertly curated itineraries are designed to activate the senses, immersing you deeper into your region's local culture, where you can visit places of historical interest, sample food that epitomizes the local cuisine and enjoy enchanting stays in characterful accommodations. Rest assured, we'll help you find the hidden treasures, the lesser-known path, and the best regional cuisine. You'll soon find there's an incredible world to wander, pedal and absorb in 2023.

£100 off Headwater trips  
We’re offering you the chance to save £100 off any Headwater holiday. Simply use code WH100 when booking with one of our expert team. See full terms and conditions at the bottom of this page.

Win a Headwater Holiday  
Can't wait to get out and experience a self-guided holiday this summer? Enter our competition to be in with the chance of winning a Headwater holiday for two, from a choice of Secrets of Sicily Walking Holiday or Contrasts of Catalunya Cycling Holiday . To enter, simply enter your details below – the winner will be selected on the 5th April – good luck! See full terms and conditions at the bottom of this page.

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Why choose Headwater?

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