Walking Holidays

Walking Holidays

Headwater's Europe walking holidays offer unforgettable experiences from which you’ll make lasting memories. You have the choice between independent exploring on a self-guided trip or and following the lead of an experienced guide with a small group on a guided walking holiday.

Whether over a long weekend, an eight-day holiday or more, our tailor-made itineraries explore hidden off-the-tourist-trail gems, so you’re 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.

Types of walking holidays

Whatever your experience with walking holidays, we aim to provide options that are suitable for all. We offer guided walks, for those who are just starting out and wanting to learn about an area's history and culture, or our self-guided walks free you up to take the reins.

Alternatively, if you fancy taking the weight off, our hotel-to-hotel walks mean you can enjoy the beautiful landscapes and scenery of your surroundings - whilst we take care of transporting your luggage. We also offer UK walking holidays for those wanting a staycation.

Popular walking destinations

There's no better way to explore Europe than to choose from one of our popular walking holiday destinations. No whistle-stop tourist tours here - just you and your companions walking through beautiful scenery, taking in the flora and fauna of the natural surroundings. We have various walking holidays that are perfectly situated so you can enjoy the hills, mountains, coastlines and unrivalled history that this glorious continent has to offer.

Experience rolling hills, fantastic forests, and delicious cuisine when walking through the coastal trails of Italy. Walk at your own pace whilst taking in the beautiful landscapes and exceptional views of France. Or, immerse yourself into a Swiss Alps adventure with dramatic backdrops of glacial valleys and mountains.

We understand not everyone is a world-class map reader, especially when visiting a new country for the first time. That's why we provide step-by-step instructions that point out various landmarks, distances, and confusing turnings. But, if you prefer something more hi-tech, we can offer GPS route navigation for that extra peace of mind.

How are walking holidays graded?

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. When searching for your ideal walking holiday, look out for the activity level in the search panel and on each individual holiday page.

Each tour is marked with a rating from 1 to 4 using the Headwater activity grading system. Alternatively, you can choose your required activity level when searching for your next walking holiday on our website.

For some of our walking holidays, there will be a choice of route with two difficulty ratings. Depending on how you're feeling that day, you'll be free to choose between the routes at your leisure.

Learn about our walking ratings

Our walking ratings »

Why choose Headwater?

At Headwater, we have over 35 years' experience taking people on off-the-beaten-track adventures. We offer a selection of idyllic destinations to our customers, allowing them to experience them at their own pace.

We can provide you with flexibility and financial security should your plans change.

If you have any queries and would like to get in touch with us, contact our friendly team today who will be more than happy to assist.

Frequently asked questions

Will I be walking in a group or on my own?

It's up to you! We offer both independent and group walking holidays.
Our self-guided walks offer you the flexibility to explore at your own pace and discover the heart of your chosen region. Our guided walking holidays mean you'll be walking with a group (typically 4-16 people) along with an expert guide. These walks will be tailored to suit the ability and interests of the group.

What do I wear on a walking holiday?

When planning what to wear on each day of your walking holiday, consider the weather and the walking conditions of your chosen route.
Choose appropriate footwear to suit the terrain and ensure these are comfortable, as you'll be spending a lot of time on your feet! If it's raining, you'll need a waterproof jacket and trousers that can be folded away for when the sun comes out. Or, if it's a hot, sunny day, wear lightweight clothing to keep you at a suitable temperature. A sun hat is also essential.
Don't worry about bringing a large rucksack with you, as you should only require a small day pack. If you've chosen one of our hotel-to-hotel holidays, we will transport all your luggage for you, so you're not having to carry it around. All you'll need to carry on your walk are your route notes, maps, and any food and drink you'll need during the day.

Is there a different walk each day?

Yes. If you've booked a hotel-to-hotel holiday, your route will take you from one hotel to the next. Our detailed route notes and maps (all included in the price) will ensure you don't end up lost, whilst still giving you the opportunity for additional exploring.
On our self-guided holidays, we provide maps and walking suggestions - then it's up to you how often you walk, and where you explore. Guided walking holidays offer a different trip each day - tailored to suit the ability and interests of the group, and the local weather conditions.

How are the routes planned?

All Headwater independent walks are researched by our staff, in collaboration with the local authorities. Our routes are selected to give you a real insight into your chosen destination, whether it's quaint villages, spectacular panoramas, or must-see hotspots.
All this information is included in the detailed route notes that you'll receive in your pre-holiday documents. You can request one of our free brochures to find out more information.

How difficult are the walks?

All our holidays are graded so you can choose one that best suits your abilities.
Level 1 walks are fine for even the most occasional walkers, as there is no scrambling or dizzy heights and the longest day is around 4-6 hours.
Level 2 walks are better suited to those who are used to walking all day - although you don't need to be especially fit or have a head for heights (unless specified on the holiday page). The longest day is typically 5-7 hours, with ascents up to 700m and some occasional scrambling.
Level 3 walks are suitable for the fairly regular walker. The longest day is 6-8 hours and may include ascents up to 1000m, so you'll need a reasonably good head for heights. Some scrambling (but not rock-climbing) may be involved. These holidays are not suitable for children under 12.
Level 4Daily walks of between 6-8 hours and ascents up to 1,200m mean your fitness is important. Trekking experience is useful but not essential as long as you're confident of your physical condition - as high altitudes, changes in climate, and remote locations can all play a part in your experience. Again, not for under-12s.

What do I pack for a walking holiday?

You should always pack appropriately for your destination, whether that means lots of warm layers, or some suncream and a hat! It is also essential that you have comfortable walking boots. We always recommend walking boots over shoes, as they offer your ankles much more support and are long-lasting.
Some people like to walk with pedometers, a compass or GPS but these are not essential as our route notes (which are sent out approximately one month before your departure) are detailed enough for beginners who are just starting out.

Are the holidays suitable for families?

Many people take younger children on Level 1 independent walking holidays and, of course, very young children can be carried in papooses. We can also carry passengers in our bag-moving vehicle, if necessary. If you have teenage children who enjoy an active lifestyle then check our suggested family walking holidays.