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Best Trails for the Scottish Highlands from £549

Would you like to experience what makes Scotland so special? Try these routes through the Highlands.

The Scottish Highlands offer a landscape of incomparable scale and raw, natural structure, where the geographical boundary fault separates the rolling lowlands from a world of rugged peaks and legendary lochs. This vast and sparsely populated region remains deeply tied to the land, where the weather and light dictate the rhythm of daily life and the scenery provides a profound sense of peace and freedom. From the dramatic summits of Ben Nevis to the haunting beauty of Glencoe’s steep valleys, every corner of the Highlands reveals a terrain shaped by powerful geological forces and a constant, powerful presence of nature.

Woven into this majestic backdrop is a tapestry of social and cultural legacies that reach back through centuries of human history. Ancient standing stones and strategic medieval castles like Eilean Donan and Urquhart illustrate a long history of settlement and defense, while the echoes of the 18th-century Jacobite rebellions still resonate through the glens. This inherited culture remains vibrant in the local communities, where Gaelic influences and a storied past are as integral to the experience as the trails themselves, transforming a simple hike into a walk through time.

The uniqueness of the region is further defined by its world-renowned hospitality and a sensory experience that celebrates the finest local produce. Whether sampling a “wee dram” at a legendary distillery along the Speyside Way or enjoying fresh seafood in a quiet coastal village, the flavors of the Highlands are deeply rooted in the surrounding environment. This combination of breathtaking wilderness, immersive history, and warm, welcoming spirit creates a destination where hikers can truly reconnect with the great outdoors and become part of a story that continues to shape this incredible land.

The Best Hiking Trails in the Scottish Highlands

Speyside Way & Cairngorms
5 Star Hiking Holidays
5 Star Hiking Holidays
9.0/10 - 108 reviews

The Speyside Way & Cairngorms trail is a gentle trail which uses old railway tracks, military roads and forest tracks. These gentle trails are perfect for groups offering a delightful journey through Scotland’s malt whisky heartland. Spanning 116km from Buckie on the Moray Firth coast to Aviemore and Kincraig near the Cairngorm Mountains, this area has the largest concentration of whisky distilleries in Scotland. The whiskies produced in the more than 30 distilleries here include some of the most famous in the world, such as Glenfiddich, The Glenlivet and The Macallan. There is more than just scotch whisky to attract you to the Speyside Way, you can also visit the magnificent Ballindaloch Castle or enjoy two of Scotland’s Heritage railways at Dufftown, Boat of Garten and Aviemore. A little bit of something for every member of your group tour.

from £699 per person View Details
Rob Roy Way
5 Star Hiking Holidays
5 Star Hiking Holidays
9.3/10 - 584 reviews

The Rob Roy Way spans 127km (79 miles) from Drymen to Pitlochry, offering some of Scotland’s greatest scenery along ancient cattle drovers’ trails used by Rob Roy MacGregor, Scotland’s legendary outlaw and folk hero. Ideal for group hikes, family outings, and adventures with friends, this trail winds through glens, alongside lochs, rivers, and burns. There’s also breathtaking views of lochs, falls at Abefeldy and Dochar as well as majestic mountains. Historical landmarks abound, including Roman forts, crannogs, and standing stones, enriching the journey with tales of clan feuds and  derring do from the gallic Robin Hood. Each day ends in picturesque towns like Callander, Killin, Aberfeldy, and Pitlochry, where evenings can be spent enjoying local ales, highland dishes or even a dram of whisky at Dewar’s world famous distillery in Aberfeldy.

from £569 per person View Details
West Highland Way
5 Star Hiking Holidays
5 Star Hiking Holidays
9.3/10 - 1560 reviews

The West Highland Way, starting in Milngavie near Glasgow, offers some of Scotland’s best mountain hikes and challenging routes through picturesque landscapes. This iconic 154km trail ascends Conic Hill, follows Loch Lomond’s rugged eastern shores, traverses remote Glen Orchy and Rannoch Moor before descending into Glencoe. You will remember climbing the Devil’s Staircase, the highest peak on the trail, you will also and skirt along Ben Nevis’s foothills. This is the highest mountain in the uk and for avid hikers looking for an extra challenge you could take an experience day to climb it. The hike concludes in Fort William which is a climbing and hillwalking mecca for people who want to explore other Munros in the region. 

from £599 per person View Details
West Highland Line: Train & Hike
5 Star Hiking Holidays
5 Star Hiking Holidays
9.1/10 - 44 reviews

Experience the wild magic of the western Highlands by combining one of the world’s most scenic railway lines with globally renowned hiking trails. This unique adventure allows you to travel deep into Scotland’s heart, sampling the best stages of the West Highland Way and Great Glen Way while enjoying a front-row seat to breathtaking landscapes from the comfort of a train. From the iconic Glenfinnan Viaduct, famous for its role in the Harry Potter films, to the remote wilderness of Rannoch Moor, this tour offers a perfect balance of exploration and relaxation. Discover legendary towns like Fort William and Oban on a journey where the romance of rail meets the trail.

from £789 per person View Details
Great Glen Way & Loch Ness
5 Star Hiking Holidays
5 Star Hiking Holidays
9.4/10 - 562 reviews

The Great Glen Way & Loch Ness is another top hiking trail in Scotland for beginners, offering easy hikes through the Scottish Highlands along famous Lochs. This 127km route stretches from Fort William on the Atlantic coast to Inverness on the North Sea. This tour is a great introduction to walking in the Highlands. Enjoy spectacular surroundings minus the climbing as most of this relatively gentle hike keeps to lower levels of the Great Glen. In addition to its accessibility, hikers are treated to the stunning views of Loch Linne, Loch Oich and the legendary Loch Ness. Key highlights include Neptune’s Staircase, the longest staircase lock in Britain, the historic Urquhart Castle and the chance to spot the Nessie, the mysterious Loch Ness Monster. Like most Scottish trails, this beginner-friendly route beautifully combines nature, history and adventure.

from £549 per person View Details

Want to learn more about our hiking trails?

Match the type of hiking adventure you are looking for by reading through our ‘Best For’ guides below.

Why book with Hillwalk Tours?

We book your tour direct, always!

We don’t book third-party companies to organise tours for our customers or resell tours from other third-party companies. We always directly book and operate all of our tours ourselves giving you a seamless experience from start to finish.

Creating memorable self-guided hiking tours is all we focus on, nothing else!

We just focus on creating and organising self-guided hiking tours, and nothing else! And we’ve been doing it for quite some time (since 2008), with over 20,000 hiking tours taken with us so far, and growing…

The biggest choice of itineraries for the trails we offer, guaranteed!

We want you to explore these areas of outstanding natural beauty at your own pace, with nearly 400 itineraries to choose from across 21 different trails (and we’re always looking to add more).

You can access your tour information easily!

You will receive a designated Hillwalk Tours account where you can login to access all your tour documents, trail GPS file, and other important details. Access your tour information anytime, anywhere, and on any device.

We’re here to support you 24/7!

You can reach us by phone 24/7 if you ever need additional support while on the trail.

What People Say about Hillwalk Tours

5 Star Hiking Holidays
5 Star Hiking Holidays
My wife and I have now been on three different Hillwalk Tours. Each one has been a tremendous experience. The walks themselves are special, but Hillwalk nails all the details and logistics. I mean, in three trips, there hasn't been even a single small error in their planning. That goes a long way toward letting you just enjoy your hike instead of worrying about details. I can't recommend them more. Dave Blazek - US Google Reviews
5 Star Hiking Holidays
5 Star Hiking Holidays
We had a fantastic experience with Hillwalk Tours last week! So thankful for the before-the-trip organization and communication - it helped to know that everything was all in place for us before we got there. The accommodations were amazing, the views were spectacular, and the experience was once-in-a-lifetime! Thank you to the Hillwalk crew for all of your time and support! Cathy T - US TripAdvisor
5 Star Hiking Holidays
5 Star Hiking Holidays
Great walk in Wales along the Pembrokeshire Coast Path from Amroth to Pembroke. Great weather (a little bit to warm 😉 for the walk), so we could take a bath in the Atlantic Sea even in September! Everything was fine organized, and with 2 additional days we had the luck to stay for 2 nights in every location! Christian Schlegel - AU Google Reviews
5 Star Hiking Holidays
5 Star Hiking Holidays
My wife & I just completed a self guided hiking trip along the Western Way/Connemara in September.I was somewhat hesitant about booking online & doing a self guided hike but Hillwalk Tours website was great. Staff responded to all questions promptly & helped modify to hike to account for extra days including hikes on Aran Island. The detailed information on the hike including maps was easy to follow. Accommodations & recommendations were excellent. This is a great way to see the country side without the crowds associated with typical bus tours. Most days we didn’t see anyone else on the trail and could just absorb the natural surroundings. Exactly what we were looking for in this vacation. Although we experienced above average rainfall during our hike we dressed accordingly & made an adventure out of some days. Would highly recommend this vacation to anyone that enjoys visiting less populated destinations, enjoys nature & solitude. Will definitely be doing another hiking trip in the future. Hillwalk tours has a great staff with remarkable customer service. Michael T - CA TripAdvisor
5 Star Hiking Holidays
5 Star Hiking Holidays
We had such a wonderful time hiking along the absolutely stunning coastline and through wonderful Ireland and Hillwalk Tours made our trip just so easy. The transport of our luggage went really smoothly and we were grateful that everything was taking care of so we only had to hike and enjoy those amazing views. I would always book a tour with Hillwalk Tours again. Carsten Reetz - DE Google Reviews

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