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Introducing a selection of new cycling holidays for 2024, all based around our tried-and-tested formula of carefully researched cycle routes

Our brochures contain our great range of relaxed activity holidays. Order your copy now!

From the pink sand beaches of Bermuda to exploring the beauty of the Canary Islands, our selection of cycling and walking holidays are all guaranteed to keep you in the heat

Our activity holidays in the Algarve are the perfect way to explore striking natural beauty, taste delicious local dishes and immerse yourself in the cheerful Portuguese culture

Join our Sales Consultant, Megan Wyatt, as she shares what she loved most about her recent trip to Bermuda with Headwater

Why choose 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.

100 NEW TRIPS FOR 2024