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Walking Holidays

Walking Holidays

Headwater's walking holidays

With a Headwater holiday, you’ll get an unforgettable experience from which you’ll make lasting memories. Follow our detailed route notes on a self-guided walk (while we transport your luggage) or join a small group of like-minded people for a guided tour.

With our tailor-made itineraries exploring hidden, off-the-tourist-trail gems, we want you to have "moments" – those times when you feel invigorated, refreshed and immersed in the culture of the region you’re visiting.

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

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

Explore at your own pace

If you prefer to explore at your own pace our self guided walking holidays give you the flexibility to set off when you're ready, stop when and where you like, and visit the places that most interest you.

We provide free and comprehensive route notes, proper maps, and on hotel-to-hotel walking holidays our local representatives transport your bags so you've no heavy backpacks to carry. Our easier independent walking holidays can be suitable for children too.

Find out about self guided walking holidays

Self guided walking holidays »

Small groups with a local guide

On guided walking holidays our expert guides will introduce you to the hidden delights of your destination whether it's the amazing creatures on the Galapagos Islands or the intriguing wildlife of Costa Rica - you'll discover more than you ever could on an ordinary holiday.

And closer to home our walking holidays in Montenegro and Croatia take you through stunning natural beauty and ever-changing landscapes. But wherever you chose to go, you'll come back with something to remember.

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 from 1 to 3 using our "boot rating system". Simply look for the activity level in the search results and on the individual holiday pages.

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!

Learn about our maps and notes

Our maps and notes»