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Walking Holidays

Walking Holidays

A Headwater walking holiday is an unforgettable experience from which you’ll make lasting memories. You have the choice between independent exploring, on a self-guided trip, and following the lead of an experienced guide with a small group on a guided walking holiday.

Our tailor-made itineraries explore hidden, off-the-tourist-trail gems, so you are guaranteed to experience special moments – those times when you feel invigorated, refreshed and immersed in the culture of the region you’re visiting.

Travel across the UK, Europe, the Mediterranean and Bermuda – from woodland rambles along leafy lanes to challenging mountain, gorge and ridge hikes, each of our walking holidays offer interest-packed insights into some of the most beautiful and unspoilt corners of the world.

Explore at your own pace

On a self-guided walking holiday you have the flexibility to set off when you're ready, stop when and where you like, and visit the places that interest you the most.

We provide comprehensive route directions and detailed maps, and on your “stay put” days we suggest pretty day walks and suggest details of local attractions so you can make the most of your trip. On hotel-to-hotel walking holidays our local representatives transport your bags for you from one hotel to the next.

Find out about self guided walking holidays

Self guided walking holidays »

Small groups with a local guide

On a guided walking holiday you have the opportunity to mingle with other walkers – perfect if you’re travelling alone or as a couple – and the trips are full of camaraderie. Your experienced local guide will lead the way and share their knowledge with you en route, introducing you to the hidden delights of your destination.

Each group is typically made up of 4 to 16 people, allowing for a more personalised and better quality of service from your guide.

Find out about guided walking holidays

Guided walking holidays »

Walking routes for all abilities

To help you choose a holiday that best suits your level of fitness all our walking holidays are graded, focusing primarily on distance and ascent. Look out for the activity level in the search panel and on the individual holiday pages. On some holidays there are a choice of routes and, for these, two ratings will be shown (you’re free to choose between routes on a day-by-day basis).

Learn about our walking ratings

Our walking ratings »

You won't get lost with Headwater

We understand that not everyone is a world-class map reader so, on all our walking holidays, our routes provide step-by-step instructions – pointing out landmarks, distances and even highlighting any confusing turnings – so you can be sure of a relaxed journey. We also include detours to places of interest, shortcuts to avoid hills, and places to stop off for lunch too!

On some of our walking holidays we offer GPS route navigation devices too, for that extra peace of mind.

Learn about our maps and notes

Our maps and notes»