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Headwater - Est 1985

Moments that matter
On foot and by bike

"Headwater are an excellent and efficient organisation with well planned holidays."
Mrs V Merrill, London

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.

The finest self-guided walking and cycling the world has to offer, all in one place: Headwater’s 2019/2020 brochure available now.

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The finest self-guided cycling as chosen by you. Our most popular cycling holidays, known to please, charm and delight in equal measures.

Bestselling Cycling Holidays »

Our most popular self-guided and guided walking holidays, full of stunning viewpoints and vistas to discover on foot.

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Why choose Headwater?

Our exclusive Headwater Reps (available in 16 regions) 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.

NEW FOR 2019