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Headwater - Est 1985

Moments that matter
On foot and by bike

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

Handcrafted holidays for moments that matter

Headwater has a huge choice of walking and cycling holidays. Travel across France, Italy and Spain, discover central Europe, explore the Med, and visit Bermuda too.

It's not about getting from A to B; it's about what you discover along the way: spellbinding locations, vibrant local cultures, jaw-dropping scenery and world-class food and wine. We've been handcrafting holidays for over 32 years and we believe the best way to experience a destination is to slow right down to walking or cycling pace so you can find your very own moments that matter.

On foot

Headwater has a greater choice of walking holidays than ever before, offering options throughout Europe, the Mediterranean, and Bermuda too.

From woodland rambles along leafy lanes to mountain, gorge and ridge hikes, all our walks offer interest-packed insights into some of the most beautiful and unspoilt corners of the world.

Find out more about walking holidays »

Choose a walking holiday »

By bike

Cycling holidays give the most scope for independent exploring, as you follow any route you choose using our maps and notes.

Our suggested routes use quiet country lanes, and go by the places we think are most interesting - from pretty chateaux to delightful hidden coves to quaint village squares - and our e-bikes make exploring even more relaxing!

Find out more about cycling holidays »

Choose a cycling holiday »


Our winter snow holidays offer a great choice of activities from cross-country skiing and snowshoeing to dog sledding, snow mobiling and sleigh rides.

If you'd rather enjoy snow in the city, our Christmas market holidays allow you to discover some of Europe’s shopping hotspots and well and truly get in the festive spirit.

Find out about winter snow holidays »

Choose a winter snow holiday »


Self-catering villas and cottages, ideal for multi-generational families and groups of mixed abilities who have the complete flexibility to do as much or as little as they wish on holiday.

You’ll have access to a range of itineraries, for walking and/or cycling, giving you a choice of activities, and you’re free to choose how much or how little you do each day.

Find out more about villas and cottages »

Choose a villa or cottage »


Headwater's activity holidays give you the opportunity to discover your chosen destination through a mix of outdoor activities. They're perfect for families looking for a bit of variety.

Choose from walking, cycling, water sports, boat trips and more in Austria; walking and cycling around the tranquil island of Gozo; or maybe canoeing along the Dordogne.

Find out about family activity holidays »

Choose a family activity holiday »


Travel through Europe, the Mediterranean, and beyond, on foot, by bike or on water, creating your very own moments that matter along the way.

Whether you prefer the fairytale chateaux of the Loire, the gastronomic wonders of Piedmont or the stunning scenery of Croatias Istrian Coast, our destinations will awaken your senses and you’ll be surrounded by fine food and first-class accommodation.

Explore our destinations »