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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.

Take a look at our late availability and you might find the perfect trip for you

Soak up the scenery as you explore on two wheels, follow expertly crafted routes whilst we take care of everything else

We have a selection of Headwater trips under £1000 that are perfect for a spontaneous getaway

All our UK walking holidays are carefully designed to take you through unique regional landscapes, histories and cultures

We offer GPS route navigation on most of our walking and cycling holidays. Find out more about the app here

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

NEW FOR 2022



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.