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


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.

Make your money travel further with our discounted Cycling & Walking trips!

Take a look at our late availability and find your perfect last minute trip.

Free 8 Bottle Luxury Mixed Wine Selection when you book a trip from the new Cycling brochure by 8th November 2019.

Unspoilt wild coastlines take you on a trail back to a land that time has forgotten, where pretty white villages intermingle with rich valleys.

New 2020 Walking Brochure coming soon with a great range of relaxed walking holidays. Pre-order now!

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 2020