What counts as a challenging hiking tour?

A route with 6 to 9 hour days, steep climbs often over 3,000 ft and rough or exposed terrain. Some call for navigation skills, scrambling or a head for heights.

Which routes are Challenging?

The Walker's Haute Route (15 days), High Trail to the Matterhorn, the E5 Alpine Crossing, the Kerry Way and A Long Walk on the Isle of Skye. The Walker's Haute Route is also available as separate East and West sections. Certain shorter durations of the complete Coast to Coast Walk are challenging as well as you cover more mileage over less days.

Is luggage transfer included?

Where roads allow, yes. High-mountain and hut stages mean carrying an overnight pack, which your route information flags. Weight limits apply, such as one bag up to 44 lbs (20 kg) on A Long Walk on the Isle of Skye.

Do I need previous hiking experience?

Yes. Previous multi-day experience is essential, and for the Alpine routes, high-altitude or exposed-terrain experience helps. These aren't first-trek routes.

Can I hike a challenging route solo?

Most routes can be booked solo, with 24/7 support throughout. However, some tours are not available to solo travelers for safety reasons. Remote stages make preparation matter, so ask an Adventure Specialist about solo suitability for your chosen route.

Broken-in waterproof boots with ankle support, trekking poles, layers and waterproofs for fast-changing mountain weather. A full kit list comes with your booking.

Can I customize a challenging route?

Most follow set stages because of hut and guesthouse availability. Contact an Adventure Specialist about adding in rest days or extra nights at the start or end of your trip.

4.7(658)

Challenging Hiking Tours

Challenging hiking tours are our toughest self-guided routes - long days, big climbs and rough, exposed ground. They're built for experienced hikers who want a real test, and the sense of achievement that comes with finishing one.

Trek 120 miles from Chamonix to Zermatt on the Walker's Haute Route, cross the Alps from Germany to Italy on the E5, follow the high trail to the Matterhorn, or walk the length of the Isle of Skye. Expect 6 to 9 hours on your feet and climbs of 3,000 ft or more on many days.

Macs Adventure has graded routes from Easy to Extreme for 20+ years, so you know what you're signing up for before you book.

7 hand-picked routes

England
4.7 (454)
Coast to Coast Walk
Walking
9–18 days
Moderate to Challenging
from$2,795CAD pp
View Route
Scotland
4.4 (71)
A Long Walk on The Isle of Skye
Walking
8–9 days
Moderate - Challenging to Challenging
from$4,365CAD pp
View Route
Republic of Ireland
4.5 (67)
The Kerry Way
Walking
5–12 days
Easy - Moderate to Challenging
from$1,285CAD pp
View Route
France · Switzerland
4.8 (27)
Walker's Haute Route
Walking
8–15 days
Challenging
from$3,590CAD pp
View Route
Austria · Germany · Italy
4.6 (22)
The E5 Alpine Crossing
Walking
8–9 days
Moderate - Challenging to Strenuous
from$2,660CAD pp
View Route
Switzerland
4.4 (12)
High Trail to the Matterhorn
Walking
8 days
Challenging
from$4,235CAD pp
View Route
England
5.0 (5)
The Full South West Coast Path
Walking
57 days
Challenging
from$16,710CAD pp
View Route

Real photos, real stories, straight from the trail

Over 26,000 travelers strong, our community shares #MacsMoments, swaps tips and advice, and helps each other plan the perfect trip. Many connect long before they set off - and some even meet up on the trail!

I'm headed back to the states and have a mixture of emotions. So much to process. I feel like a different person!
October 2026
Camino de Santiago, Spain
Thank you Macs for the brilliant adventure! We loved all the accommodations provided
June 2026
West Highland Way, Scotland
October 2026
Hadrian's Wall Path, England
June 2026
Cotswolds to the Cornwall Coast, England
August 2026
Via Alpina, Switzerland
In fact, if you're looking for sensory magic, give this trip a try
October 2026
Walking the Dordogne in Style, France

Join our Macs Community

What does challenging mean in hiking
A Challenging route has steep, sustained climbs, long days and rough ground that keeps your heart rate up for hours. At Macs Adventure it means our hardest routes, with 6 to 9 hour days and often 3,280ft (1,000m) or more of ascent.
How does Challenging compare with our other grades
While Extreme denotes our most difficult trips, Challenging sits just below that on our scale. Moderate-Challenging trips have their own page, with shorter days and less exposure, and are a good stepping stone if you're building up.
Is hiking in the Scottish Highlands strenuous
It depends on the route. A Long Walk on the Isle of Skye is graded Strenuous, with rough ground and a head for heights needed. Our Highlands rail and hike trips are Easy to Moderate.
When to go
July to mid-September for the high Alpine routes, when passes are clear of snow and huts are open. Skye is walkable from April to October.
What fitness and experience do I need
Excellent hiking fitness, previous multi-day experience and comfort on exposed, rocky ground. Some routes also call for navigation skills, scrambling or river crossings. Build up with long hill days carrying a loaded pack before you go.
Where you stay
Guesthouses, small hotels and mountain huts. The E5 Alpine Crossing includes one hut night in a private room, and the Walker's Haute Route mixes hotels, auberges and mountain refuges.

Challenging Hiking Tours