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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.

Book your next holiday by 28th September 2023 and we’ll send you a £75 National Trust gift card for each adult on your booking

If you're looking for your next escape, search our late availability and you can find the perfect trip for you.

From gentle walking and cycling holidays soaking up the winter sun to unspoilt winter landscapes full of fun in the snow - Headwater has it all this winter!

Take a look at our latest offers, where you can save when you travel on selected dates

Our Headwater Product Development Manager, Emily Lockwood, recently visited the remarkable region of Northern Portugal. Read more about her experiences

Why choose Headwater?

100 NEW TRIPS FOR 2023