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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, the Mediterranean and Bermuda. Our tailor-made tours combine winning routes, idyllic destinations and hand-picked accommodation (with delicious local cuisine) for all levels of walker or cyclist.



Join us on a journey to wander, pedal, absorb and discover our incredible world

Walk through the world and discover amazing places on foot

Book and travel with confidence. Read more about our enhanced flexibility

Our most popular holidays together in a single collection

A selection of trips in open destinations and everything you need to know about travelling internationally

Our brochures contain a great range of relaxed activity holidays

Why choose Headwater?

Our overseas team ensure everything runs like clockwork and are on-hand whilst you’re away for any advice or recommendations.

We seek out the exceptional in the locations that we offer. Every interest-packed route is checked annually by our activity experts.

Our itineraries can be customised to your exact requirements, whether that's flying from a local airport, adding extra nights or upgrading hotels.

We hand-pick small, family-owned hotels, with delicious regional cuisine, and owners who take a genuine interest in their guests.

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