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How to Choose Your Holiday


by Catherine Sempill

The UK’s unique variety of accessible long distance walking trails and extensive network of public footpaths make it an amazing place for walking enthusiasts. The only downside is deciding which one to tackle next. With so many options, how do you decide on your next Contours walking holiday? 

Here are some questions to ask yourself to get clarity on what you want, which will help you narrow down your options.

What Are Your Personal Interests?

When you envisage your holiday, think about what you want to do and see.

Are you drawn to wild terrain with wildlife and interesting geological features to discover, or are you after postcard-pretty English countryside and a wealth of historical sites?

At the top of Devil's Staircase, a challenging climb in remote Scotland, a walker stands with poles raised in a victory pose.
A walker looks across a field to a town in the Cotswolds.

Our inspiration pages sort our favourite holidays by interest.

How Fit Are You and Your Walking Companions?

Your fitness level affects your speed, which in turn determines how long and far you can enjoyably walk each day. Think about your usual walking rhythms and consider how you might feel walking for multiple consecutive days.

If you’re unsure or know you’re not very fit, err on the side of caution and opt for shorter, less demanding routes and walks with shorter daily mileages. Always plan with the least fit member of your party in mind.

How Mobile Are You and Your Holiday Crew?

Your physical ability to handle different challenges and obstacles on the trail affects your safety in the countryside, as well as how much fun you have. For example, trails like the West Highland Way involve steep uphills and uneven ground, while The Ridgeway is mostly a wide, flat gravel track.

The flat chalky path of the Ridgeway stretches into the distance, crossing a field of grass and poppies.
A walker poses halfway up a rocky scramble on the Bob Graham Round.

If you’re undecided, the Contours team will gladly provide you some options for accessible walks, and you may enjoy our stile-free routes

When Are You Planning to Take Your Walking Holiday?

If you have a trail in mind, consider how the trail conditions may differ by season. For example, a lovely track in summer can turn into a muddy quagmire in winter (here is some trail inspiration by season). 

Sunset over the trail. The sun sinks beneath the hills, with trees silhouetted and the view mirrored in a still lake at the bottom of the photo.

Differing daylight hours are also worth remembering, as factors like fitness and mobility become more relevant in winter, when limited daylight forces you to tackle tricky terrain at a quicker pace to beat the sunset.

How Far Do You Want to Travel to the Starting Line?

Are you up for the added adventure of taking public transport to the start of your walk? Are you willing to drive a long distance to the start? Or would you prefer to keep the “getting there” simple and save the “adventure” for the trail?

Once you answer these questions, check out our list of trails that are easily accessible from major cities or ask about Contours’ circular, single-centre or twin-centre tours for easy onward travel or minimal packing and transfers.

What’s Your Walking “Style”?

Be honest with yourself about what you actually enjoy. Do you like a casual amble with lots of stops at coffee shops and pub lunches along the way, or do you genuinely love the feeling of exerting yourself for seven hours a day?

Bath Abbey surrounded by walkers and tourists exploring Bath town.
Two walkers, armed with waterproofs and walking sticks, cross a burn flowing across the path.

Find Your Ideal Walk

Contours Holidays has something to suit anyone, including stile-free walks and short daily mileage walks. The team is always happy to chat with you to decide the perfect route for you, but considering the factors listed here is a great start for your conversation.

Catherine Sempill

Independent Copywriter

Catherine is a freelance copywriter and content marketer who loves to travel and spend time outdoors. Born and raised in Cape Town, South Africa, she grew up stomping up and down mountains. Now she splits her time between strolling in the UK countryside and exploring mountains further afield.

Read more blogs by Catherine Sempill



Originally published 18/09/25


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