Guided walking Holidays

Guided walking tours & holidays

Our guided walking holidays are perfect for people who want to experience an escorted tour in a small group of like-minded people. On our tours, share cheerful moments with new friends, stroll together through beautiful countryside admiring the landscape, and cap off days enjoying a glass of luscious local wine over dinner.

Whether travelling alone, as a couple or with friends, everyone is welcome on our walking tours. There are plenty of opportunities to socialise with group members, as well as your expert guide. All are based locally and are either Headwater employees or local partners  and all are passionate about their homelands and committed to sharing their experiences with you. That way, you experience a refined, hand-picked and high-quality walking holiday with every detail expertly taken care of.

And importantly, we keep our group sizes small  typically four to 16 people. This gives our guided walking tours a good mix of travellers while giving everyone the opportunity to benefit first-hand from our guides' local knowledge. This also lets us use smaller, hand-picked guest houses, which is not possible with larger groups.

View our guided walking holidays in the UK and beyond below. If you have any questions, don't hesitate to get in touch, and be sure to check out our blog.

Types of guided walking holidays

We offer a variety of guided tours and holidays that let you experience the best walking destinations around the UK and globe.

Hotel-to-hotel guided walking holidays

Often, the best guided walking is located further afield than your hotel - and, to experience everything that's great about your chosen destination, you need to move between hotels.

On these escorted walking holidays, resident Headwater guides and local partners look after every detail of your tour. They provide comfortable transport and move your bags between hotels for you - each is hand-picked to give you an authentic flavour of the region in which you're staying, from the sweeping mountains of Montenegro or intoxicating Annapurna foothills in Nepal to the ancient Kumano Kodo Trail in Japan.

View our hotel-to-hotel guided walking holidays

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Single and twin-centre guided walking holidays

If you would prefer to stay and explore one or two certain regions during your trip, our single and twin-centre guided walks are perfect. They offer the same features as our hotel-to-hotel holidays but are situated in one or two locations where a varied and interesting week's walking is within easy reach by minibus.

That way, whether you're exploring the stark Norwegian wilderness, the dizzying Amalfi Coast in Italy or the stunning Gower Peninsula in Wales, you can truly get to know a unique part of the world the best way: up close, on foot.

View our single/twin centre guided walking holidays

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Why choose Headwater's guided walking holidays?

For over 35 years, we've helped intrepid travellers to access amazing walking holidays around the world. Exploring on foot in small groups, our approach to travel is personal - from the lasting relationships forged between walkers to the great level of choice and flexibility that we offer with our itineraries. It's just one of the many reasons why you should let us show you the world:

  • We're award-winning - We've been the proud recipients of awards from the likes of the British Travel Awards, including the Best Travel Company for Central & Western Europe, UK Short Breaks, and Culinary & Wine Holidays.
  • We're sustainable - Our sustainable People, Places, and Planet Plan is part of our commitment to becoming Nature Net Positive. This means that each of our trips doesn't just offset the impact of travel on the environment; they make a positive impact, too.
  • We're flexible - Our trips allow you to select not just the date of travel but the form of travel, too, so, if you want to travel first class, hire electric bikes or get a regional connection to your local airport, we can help.
  • Quality accommodation - Every hotel featured in our itineraries is carefully checked before we add it to our tours. That means that you get to stay in interesting, comfortable and charming hotels, with a focus on family-owned businesses that benefit their communities.
  • Exquisite food - Travel with Headwater and explore the best of your destination's cuisine, from bustling street-food markets to delightful local restaurants and everything in between. Hearty breakfasts, light lunches and rich suppers - with us, taste the best during your guided walking tour.
  • Travel safely - Now more than ever, it's important that you feel safe and sound when travelling, whether that's booking your trip, staying at a hotel, walking a route or heading home. That's why we promise to ensure that every aspect of your trip is safe, so that you can enjoy your trip to the fullest.

Frequently asked questions

How difficult are guided walks?

Our guided walks come in a range of difficulties designed for walkers of all skill levels. Each tour comes with one or several Activity Levels, rated between one and four and shown in the tour's information panel.

  • Level-one guided walking holidays are the gentlest offered - perfect for less mobile people, young children and people who want to relax and take it easy.
  • Level-two and three tours are more physically demanding, requiring greater levels of fitness and experience, but designed for most fit and healthy people.
  • Level-four tours are recommended for fit and experienced walkers who aren't afraid of challenging routes and have been doing plenty of training in the run up to their trip.

If you're not sure which grade to choose, get in touch and our team will be able to provide insight on each holiday.

How do guided walks work?

Guided walking holidays see you and a small group of other travellers explore a range of areas on foot.

You will be staying in hotels and guest houses by night, before heading off along a range of well- and lesser-known walking routes to explore the landscape and other places of interest. Each day's itinerary will typically feature breakfast, though may well include lunch and dinner, and there will typically be opportunities to explore towns and villages at our own pace after the day's walking has finished.

If you choose a single-centre guided walking holiday, you'll spend most of your trip in a specific location, walking routes in the local area. Hotel-to-hotel tours, on the other hand, will include transport between different areas and regions throughout the trip, letting you explore a wider area.

Are guided tours worth it? What are the benefits?

Walking tours are an excellent choice for anyone who wants to holiday off the beaten track with like-minded people. They give you the chance to see the best that a location has to offer up close and personal, with in-depth knowledge from local guides who take you beyond the guidebook. Throughout your journey, you'll have plenty of opportunities to get to know your fellow travellers, too.

If you want an active holiday, a guided walking tour makes sense as plenty of time will be spent strolling and hiking between locations - but culture lovers will be at home, too, as many of our tours are designed to show you brilliant towns and villages.

How do you plan your walking tours?

Headwater's local experts design our tours to bring you the best of a particular location. Every aspect is thoroughly hand-picked, planned through, then checked and tested to make sure that it delivers a brilliant experience, so that you will get the best from your holiday.

To learn more about what's planned for your chosen guided walking holiday, view the itinerary tab on its webpage or request a brochure to browse away from a screen.