Simon is a TV writer turned travel journalist and photographer who specialises in walking and hiking holidays in the United Kingdom, Europe and beyond. He writes on walking holidays in England for the Wall Street Journal, The Guardian, The Daily Mail, among others.
The Pennine Way

- Distance: 268 miles (431km)
- Duration: Three to four weeks, or shorter segments
- Start point: Edale, Derbyshire
- End point: Kirk Yetholm, Scottish Borders
- Difficulty: Moderate/strenuous – hilly, often remote upland, long stretches between accommodation
- Suitable for: Experienced walkers
This iconic trail follows the rugged ridge forming the backbone of northern England. Don’t be deceived by crowds of day walkers at popular spots, the full route is a tough, varied but memorable undertaking.
At a glance
Destinations
Yorkshire Dales National Park
Activity
Adventure, Hiking & Trekking, Active, Walking, Nature & WildlifePhysical Level
Strenuous
Duration
30 days
Related Guides

The best walking holidays in the UK

The United Kingdom is a walking holiday paradise: Hundreds of thousands of miles of well-mapped public footpaths, beautifully varied landscapes, excellent hospitality, and easily accessible. It’s no wonder this is a nation of walkers.

Walking holidays in England

There are two broad categories of walking holidays in England: single location (‘centre based’) or long distance (‘inn-to-inn’) walks. When I've been walking with a big group or with kids in tow, it can work better being based in one location and heading out on day hikes as the group (and weather) sees fit.

The best walking holidays in Europe

Europe is a famously popular and, in places, crowded travel destination. Escaping the bustle on a walking holiday in Europe's more-remote corners is a good way to escape the day trippers, tour buses and cruise ships that plague the continent’s busier hotspots.

Simon Heptinstall
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The Pennine Way
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