Walking holidays
let's enjoy a walking holiday together
At Boots On Adventures, we run unforgettable walking holidays that are so much more…
You wake up to the gentle sound of birdsong, lace up your boots, and set off on a journey where every step unveils breathtaking views, hidden trails, and moments of pure serenity. No rushing, no stress – just the simple joy of exploring at your own pace.
Whether you’re after a peaceful countryside escape, an epic coastal adventure, or a journey through history-steeped landscapes, our expertly designed routes ensure an experience that’s as refreshing as it is rewarding.
Are you ready to experience the perfect blend of adventure, relaxation, and discovery? Book your Walking Holiday today and let the journey begin!
Find further details and book your next holiday at Boots On Adventures.
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What our walking holidays are like?
Adventures awaitwith our walking holidays
Step into nature and explore breathtaking trails with our walking holidays. Follow in the footsteps of explorers, pilgrims, and settlers as you journey through ancient landscapes where history and legend intertwine.
Wander along scenic routes that lead you through rolling countryside, past hidden ruins, and along rugged coastlines – each step revealing a new story.
We specialize in creating walking holidays that are so much more than just the trail, offering the thrill of discovery without the stress of planning. Wake up to stunning views, spend your days exploring, and unwind under vast, starlit skies.
- Tailored experiences for all levels
- Make great memories and lasting friendships
- Connect with nature and step back in time
We do the planningso you can enjoy the experience
Our expert team meticulously plans every detail of your walking holiday, allowing you to fully immerse yourself in the experience without the stress of logistics. Whether we’re walking through ancient woodlands, trekking across rolling hills, or tracing the footsteps of history along scenic trails, we ensure a seamless journey so you get the most from your time with us.
With carefully crafted itineraries, hand-picked accommodations, and in-depth local knowledge, we create unforgettable walking experiences tailored for all abilities. Our commitment to quality, comfort, and authenticity transforms every step into a meaningful connection with nature, history, and the landscapes around you.
No stress, no hassle – just enjoy the walk and we’ll do the rest.
- Supported by qualified, professional guides
- Carefully selected itineraries (routes)
- Seamless, stress-free experience
Get readyhow to be well prepared for your walking holiday
What you need to knowbefore joining a walking holiday
At Boots on Adventures, we make outdoor exploration effortless. Here’s everything you need to know before joining our walking holidays:
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Expertly Guided Adventures
Explore breathtaking trails with knowledgeable guides who bring the landscape to life, ensuring a stress-free and immersive experience.
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Tailored for All Abilities
Whether you prefer a gentle countryside stroll or a more challenging hike, our trips provide clear details on daily distances, elevation, and terrain to help you find the perfect adventure.
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Comfort & Convenience
Enjoy carefully planned itineraries, comfortable accommodations, and, where applicable, luggage transfers and delicious meals. Some trips include the unique experience of camping under the stars, fully supported for your comfort.
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Transparent Booking & Costs
With no hidden fees and a clear cancellation policy, you can book with confidence, knowing exactly what to expect every step of the way.
Read the checklist of what you should bring on a walking holiday
Being prepared is the key to a successful holiday, so we’ve put together this checklist to help you gear up, ready for the big adventure.
The suggestions are born of our own experiences of walking, the terrain and weather you will likely encounter whilst on a walking holiday.
Just a few of our walking holidays
West Highland Way Adventure
The route spans a total of 96 miles and we have completed this iconic trail in 7 days. We averaged around 13 miles a day. Began in Milngavie, near Glasgow, the route culminates in the picturesque Fort William, the scenic Loch Lomond and the Highland valleys of Glen Coe. While not overly challenging, the West Highland Way did test endurance due to factors like blisters and variable weather.
Notable featured include Conic Hill at 351 meters, the demanding day 2 along Loch Lomond, and the longest stretch on day 5 covering approximately 19 miles. The expedition unfolded against breathtaking backdrops, from the majestic Loch Lomond to the mountainous valleys of Glen Nevis, the desolate Rannoch Moor, and camping in the captivating Glen Coe.
The Neolithic Trail Kent
This unique 2-day experience took us on a pilgrimage through the historic area of Medway passing pagan and Christian sites, all swimming with myths and mystery.
We started our journey from West Malling Station and over the next two days followed the trail along ancient footpaths and trails such as the Medway Valley Trail, North Downs way, and Pilgrim’s way. Parts of these trails are thousands of years old and walked by our Neolithic ancestors, as well as pilgrims making their way from London to Canterbury (and on to Rome) throughout the centuries.
In the evening we camped nestled on the top of the North Downs way relaxing in a local pub, where we enjoyed a well-deserved evening meal. At sunset we made our way to the top of the North Downs way and to watch the sun set over the valley with amazing views.
The Neolithic Trail Stonehenge
In April, we took on the Neolithic Trail, immersing ourselves in the rich history and stunning landscapes of this ancient region.
We camped under the stars, cooking delicious meals over the fire, and spent the evenings sharing songs and stories around the campfire. Friday night was filled with fun as we kicked off the weekend with a friendly quiz.
On Saturday, we walked 11 miles with Ben, our passionate historian guide, who brought the ancient Neolithic past to life. We explored fascinating sites and learned about the area’s rich history. The views were breathtaking, and the experience was both educational and invigorating. On Sunday, we visited the iconic Stonehenge, marvelling at the prehistoric monument and reflecting on the weekend’s journey before heading home.
It was a weekend full of adventure, history, and great company.
Hadrian's Wall Adventure
The route spans a total of approximately 84 miles and our group completed this historic trail in 6 days, averaging around 14 miles per day. We began in Bowness-on-Solway, near the western coast, and the route culminates at Segedunum (Wallsend) on the eastern coast, tracing the length of Hadrian’s Wall through the heart of northern England. While not technically extreme, the trail tested endurance due to uneven terrain, long stretches of walking, and variable weather.
Notable features include Housesteads Roman Fort, the scenic Sycamore Gap, and the rugged high sections near Steel Rigg. The expedition unfolded against historic and dramatic backdrops, from rolling Northumberland countryside to the crumbling remnants of Roman forts, the iconic wall snaking over hills, and peaceful river valleys. Camping and group accommodations along the route provided an opportunity to share stories, recover, and experience the camaraderie of walking this iconic trail together.
Awesome reviews for our walking holidays
- West Highland Way - I would definitely recommend a walking holiday with Boots On Adventures - Rob 2024
- Neolithic Trail Stonehenge – A fabulous walking weekend in Stonehenge – Nicky 2025
- Hadrian's Wall - Such a great bunch of people, both the leaders and other walkers – Julie 2025
- Sup, Hike and Camp – Great experience - lots of fun, well organised and excellent hosts – Katie 2025
