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


Rethink discovery, think Headwater. 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.

Think Headwater. The very best self-guided walking and cycling holidays, tailored to you.

Uncover the world on two wheels; relaxed cycling holidays that’ll make you revaluate how you see the world.

Get up close and personal with the world; walking holidays immerse you in the very best of a region.

Delicious meals, fine wines and the warmest of welcomes: this is what defines the gastronomic experience of a Headwater guest.

Enjoy the best of both worlds: an active break with family and friends, no matter what the mix.

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

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