Walking Holidays

We pride ourselves in creating wonderful self-guided walking holidays, that allow you to discover incredible scenery, diverse walking trails and delicious local fare across the UK, Europe and further afield. Sometimes the best way to uncover a new destination is on foot, which why our hand-crafted itineraries are designed so you can travel from place to place at your own pace, giving you time to stop for a picnic, linger in places of historical interest, or go off the beaten track - the choice is yours.

Make 2024 the year you wander along the flower-lined levadas in tropical Madeira, follow in the footsteps of ancient pilgrims while Walking the Camino de Santiago in Spain or head to Italy and trek towards the world-famous Tre Cime in the Dolomites.


Why choose Headwater?

New walking holidays for 2024


Types of walking holidays

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.