Walking Holidays

Our most popular walking holiday destinations include Italy, Spain, Portugal, France and Switzerland, each offering outstanding scenery and well‑maintained walking trails. Italy, it feels, is everyone’s favourite destination with walking holidays available in Puglia, Piedmont, Amalfi Coast, Dolomites, Sicily and of course Tuscany and Umbria. Spain offers both the winter sun Canary Islands as well as the white washed villages of Andalucia. Whilst Portugal’s Madeira is a perennial favourite promising year round good weather, and the golden islands of the French Riviera is also proving popular for a spring walking holiday. You cannot fail to be in awe of the Alpine peaks on show in glorious Switzerland.

Many of these trips are ideal for first‑time walking holidays as well as experienced walkers.

To help you choose the right trip, all our walking holidays are graded by difficulty, based on distance, ascent and terrain, using our in‑house activity grading system developed from decades of experience.

When searching for your ideal walking holiday, look out for the activity level in the search panel and on each individual holiday page. Each walking holiday 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. To learn more about our activity grading please click here

Trusted by walkers for over 40 years, Headwater has been creating award‑winning walking holidays since 1985.

Our holidays are designed by experienced walkers and destination specialists, and reviewed continuously using verified customer feedback. We are ABTA and ATOL bonded, a certified B Corp, and proud recipients of the Feefo Platinum Trusted Service Award. And finally, we love what we do and love hearing your amazing feedback, which is why we now offer over 300 trips to 45 countries.

No, you will not have to carry your bags. Our hotel‑to‑hotel walking holidays with luggage transfer mean you only carry a light day pack. You simply leave your clearly labelled luggage in reception in the morning, and hey presto, it will be waiting for you at your next hotel. You will only need to carry the bare minimum for the days walk, leaving you free to enjoy the journey. Your holiday made simple by Headwater.

It depends on what type of walking holiday you choose. On a self-guided walking holiday and our pilgrimages it will be just you and your party walking together, following simple navigation. Private guided walking holidays will be just you and your party plus a local expert guide who will lead the navigation. Group Guided walking holidays will have a local expert guide as well as up to 16 like-minded individuals.

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! Do not use a walking holiday to break in your new boots! 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 walking 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 is what you will need during the day, including your navigation and any food and drink.

Yes. If you've booked a hotel-to-hotel holiday, your route will take you from one hotel to the next. Our detailed you simple to use route navigation (all included in the price) will ensure you don't end up lost, whilst still giving you the opportunity for additional exploring. Any rest days will be detailed in the itinerary. If you are on a single centre walking holiday then the choice is yours. We will provide you with lots of walking options and you can choose which one you want to walk or simply enjoy a well-deserved rest day.

On our self-guided holidays, we provide 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.

All Headwater independent walks are researched by our expert staff, in collaboration with the local destination management companies and local authorities. Our routes are carefully 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 your pre-holiday documents and held in our navigation app keeping you well informed on your walk - it is like having a guide in your pocket.

What’s challenging for one person can be leisurely for someone else, but while it’s not possible to be precise about how easy or difficult an activity will be, our activity ratings can offer a practical guide as to what to expect. When assigning an activity level to a holiday, we consider factors such as gradient and length of walk, as well as the terrain, route conditions, and location.

All our holidays are graded from 1-4 so you can choose one that best suits your abilities:

Level 1 – Leisurely Suitable for anyone who is reasonably fit and healthy, enjoys the occasional weekend walk. Holidays may involve short, steeper sections or gentler, but longer ascents/descents - be prepared for altitude changes of up to 400m. A head for heights is not necessary.
Level 2 – Moderate For anyone looking for longer walks and is confident with daily ascents/descents of up to 700m. You need to be able to navigate via the app or map. Some sections may be on uneven terrain where scrambling is required. A head for heights may be required on some routes.
Level 3 – Demanding Fitness is important as you can expect full day walks, including up to 1,000m ascents/descents and an ability to navigate by map and app. Where applicable, experience of walking in mountains is important as is a head for heights. Some scrambling likely. Recommend age 12+.
Level 4 – Challenging Full day walks, factoring ascents/descents up to 1200m, high altitudes, longer distances, climate and remoteness. Trekking experience desirable, but not vital if confident of physical condition and navigating by app or map. Scrambling or challenging elements are likely. Recommended age 12+.
+ Trips Plus trips have small sections of the route that are more challenging than the overall grading.
Dual LevelsDual levels signify a choice of routes at either level. You can choose which level route to walk on a daily basis.

To learn more about our activity grading please click here

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 walking poles, but this is a personal preference.

It depends. If you are an active family who enjoys the outdoors and are confident in walking the distances and terrain on the trip, then a walking holiday is a great option for a family and the perfect distraction from screen time! We have put together a short-list of trips we would recommend for younger families; if you are interested, please just ask one of our friendly and knowledgeable sales consultants for advice.

To view our short-list of family friendly walking holidays click here

Yes – many of our trips are ideal for solo walking holidays, with clear guidance on suitability and support. However, there are a few trips we deem unsuitable, for example where the routes take you to more remote locations.

To view our short-list of recommended walking trips for solo’s click here

Good question. Group guided holidays are where a local guide is with you throughout your holiday and leads the walks, tailoring them to the groups capabilities. The positives are that you do not have to navigate and there is support immediately on hand, however, you are behest to the group and the guide will tailor the walks to suit everyone meaning there maybe some compromises. Alternatively, self-guided is where you walk independently in your holiday party. You choose the start time, you set the pace, you decide when to pause and drink in that view (or glass of wine, why not both!). You are in charge, and you are armed with simple, clear navigation which is easy to use even if it is your first time on a walking holiday. The navigation also comes with lots of local points of interest, so it is like having a guide in your pocket, meaning you will not miss out on those local insights. Which will you choose?

Lots of people love the idea of a walking holiday in some incredible destinations like the Italian Dolomites or Swiss Alps, but do not know how the holiday will work in practice. Plus, the term self-guided can be confusing if you have not done this type of holiday before. Let’s see if we can help clear things up…

To be self-guided, means that you do the navigation. But don’t worry, we’re here to help every step of the way. Our easy to follow navigation means that you will not get lost, even if it is your first time on this type of holiday. Rest assured, you don’t need to read OS maps or use a compass to navigate. The majority of the time the route is on our Headwater App which gently talks to you at each junction, explaining the next turn and even points out places of interest along the way. Being self-guided also means that there is no group and no guide, so you can walk at your own pace and pause whenever you want – this is your holiday, so why follow the crowd?

We offer a range of hotel-to-hotel, twin centre or single centre holiday’s. You can filter by Accommodation type on our website, so let’s take each one in turn:
A hotel-to-hotel walking holiday, means that in the morning you leave from one hotel and your ultimate destination that day is your next hotel You will be walking in your own group and setting your own pace, expertly guided by our simple to use navigation. Meanwhile, the luggage you left clearly labelled at your hotel that morning is magically collected and whisked to your next hotel. This means you only carry what you need for that day. Walking hotel-to-hotel allows you to explore more of a destination as you are covering more distance, whilst allowing you to stop in authentic, off-the beaten track locations along the way.
A twin centre walking holiday means less unpacking as your holiday is between only two hotels. The first half of your holiday can enjoy a range of walks centred around your first location. Then on the change-over day, either by public transport or private transfer, you will head to your new hotel and from here you can enjoy a new collection of walks in this new location.
A single centre walking holiday is where you are based at the one hotel for the full duration of your holiday. You can unpack, relax and really get to know the area through a collection of walks that you can choose from at your leisure. And if you fancy a day off from walking, no problems, it is a holiday after all. Often our single centres have a lot more walks than days and at differing activity levels, so you will be spoilt for choice.

Private guided walking holidays offer the support and reassurance of a guide, without the complications of a group. The guide, your guide, is there purely for your party and will expertly lead you on the walks bestowing local insights along the way and able to tailor the day’s walk to suit you perfectly.

Yes, absolutely. In addition to being provided with all the local emergency numbers, on a self-guided walking holiday you are provided with an emergency telephone number which is available 24/7, meaning support is just a phone call away.

This can vary depending on the trip, but we make it clear on each individual trip page with a transparent 'What’s Included' section.

Beauty is in the eye of the beholder? But simply put, this is your holiday and we are passionate about you enjoying it and we know the accommodation is really important to you and therefore we go to great lengths to pick just the right ones. However, in some remote locations choices may be limited, and so we may have had to rate hospitality above facilities.

On the individual trip webpage expand the day’s itinerary to find out more about your accommodation. If the holiday is a single centre the hotel information will be shown only in Day 1. We clearly mark each accommodation with our own star rating for guidance purposes.

All our accommodation has been inspected and classified by the authorities of the relevant countries. As there is no direct British equivalent of many classifications, the broad expression ‘hotels’ refers to all the different types of accommodation we use, from friendly family-run B&B and country inns to luxury ***** hotels (where * is the country’s official hotel rating).

Headwater’s accommodation star ratings are provided to give you guidance on the relative standard of the accommodation you will be staying in. In most occasions this will match the official star rating of the accommodation, however, if we feel it necessary Headwater will adapt a rating to what we believe is fair. This is based on a variety of checks which can include property visits, customer feedback, facilities and location, or if the accommodation does not hold an official rating of its own. These ratings are reviewed regularly to ensure their accuracy and relevance for guidance purposes.

Yes, absolutely. Adequate and valid travel insurance for your chosen itinerary is compulsory for all travellers and it is a condition of accepting your booking that you agree you will have obtained adequate and valid travel insurance. We recommend you take out insurance as soon as your booking is confirmed. You are strongly advised to insure yourself against any possible risk that may occur and in particular to ensure that you have sufficient insurance in respect of dependent relatives and force majeure events. You are required to carry proof of insurance with you during your holiday.

We can easily arrange extra nights at the start or end of your holiday, and often highly recommend it so you get to enjoy more of the destination you have reached. As for customising the walk itself, it depends. It is your holiday and we want it to be perfect for you, so where we can help we will. Just ask and we will be happy to advise you.

It is really easy to navigate Headwater’s self-guided walking holidays. We give you all the information you need and our state-of-the-art, easy to use navigation app ensures you will never get lost. And don’t worry, it doesn’t use mobile roaming data.

To learn more about our Navigation App click here

We love our canine friends and as such have put together a short-list of holidays which are dog friendly.

To view our short-list of recommended dog friendly walking trips click here