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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.

Indulge in Michelin Star dining experiences, intimate wine tastings and local cooking classes on our gastro-led trips

Explore our range of planet friendly trips that lower your impact, whether that's accessible destinations by train or single accommodation holidays

Discover Europe’s most serene lakeside walks, quaint towns and river trails

Take the scenic, more sustainable route with accessible train returns across Europe

Enjoy beautiful landscapes, charming villages and historical sites on a Great British break

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

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.

NEW FOR 2021