How to plan the perfect walking holiday (beginner-friendly guide)

There’s something magical about setting out on foot and leaving the everyday behind. And here’s the best part – you don’t have to be a seasoned hiker to enjoy it! 

If you’re dreaming of coastal paths, rolling hills, or forest trails, planning your first walking holiday is easier – and more rewarding than you might think. We’ll walk you through the essentials, so you can plan your first walking holiday with confidence.

Why plan a walking holiday?

A walking holiday isn’t just good for your body – it’s brilliant for the mind and soul too. It’s the perfect way to slow down and savour the world around you, while experiencing travel in a more meaningful way.

• Reconnect with nature - Leave the screens behind and breathe in the fresh air.
• Explore at your own pace - Walk as much (or as little) as you like.
• Make unforgettable memories - Whether you’re travelling solo, with friends, or family, there’s something special about discovering new places on foot.‍
• Affordable adventures - From budget-friendly hostels to charming country inns, there’s a walking holiday for every budget.

And nothing beats that first moment when you reach the top of a hill and see miles of natural beauty stretched out before you.

How to choose the right route for you

If you’re new to walking holidays, the key is to start small and build confidence. Picking the right trail can make all the difference between a wonderful adventure and a struggle – so it’s worth spending the time to get it right.

Choose the right distance for your comfort

Look for shorter routes – around 5 to 10 miles (8 to 16 km) a day is a comfortable starting point for most beginners. If you’re planning a multi-day trip, choose trails where the daily distances are manageable and where you can easily find overnight accommodation to break up the journey. It’s much more enjoyable to finish each day with energy to spare than to push yourself too hard early on.

Pick easy, well-marked paths to start with

Stick to well-marked, maintained paths with gentle slopes when you’re starting out. Save steep climbs, rocky trails, or remote stretches for later, once you’ve built up your confidence and stamina. Easy paths mean you can focus on enjoying the scenery – not worrying about your footing.

Choose routes with villages, cafés and places to stay

Choose routes that pass through villages or towns with cafés, shops, and accommodation nearby. Knowing there’s a cosy tea room or welcoming B&B waiting for you at the end of a day's walk can make a real difference – especially when you’re ready to put your feet up and relax!

Time your trip for the best weather

Some trails are at their best in spring or early autumn, when the weather is mild and the paths are quieter. Always check local advice before you set off, and pack for all conditions – even the sunniest morning can turn into a damp afternoon! A lightweight waterproof jacket and layered clothing are essential.

Match the route to your fitness level

Be honest with yourself about how active you are right now. It’s much more enjoyable to complete a manageable walk and still have energy for a relaxed evening than to overdo it and feel worn out. Start with gentler distances and work your way up – walking holidays are about enjoying the journey, not racing to the finish.

Our top tip: Always check local guidebooks and walking forums for up-to-date advice – and double-check the elevation profile of your chosen trail. A walk might sound short on paper, but a few steep climbs can make it much more challenging than it seems!

What do you pack for a walking holiday?

You don’t need the latest high-tech gear to enjoy a brilliant walking holiday. But a few essentials will make all the difference to your comfort and your confidence.

• Sturdy walking boots - Your feet will do the hard work, so treat them well. Pick supportive, waterproof boots and break them in with a few local walks before your trip.
• Lightweight, breathable clothing - Layers are your best friend. They’ll keep you comfortable whether the weather is chilly in the morning or sunny by lunchtime.
• Waterproof jacket - Eleven if the forecast looks good, pack a lightweight, packable waterproof. A sudden shower is all part of the adventure – as long as you’re dry underneath!
• A small backpack - Choose one that’s comfortable and adjustable, with enough room for your essentials without weighing you down.
• Water bottle and snacks - Staying hydrated and fuelling your walk is vital. Easy-to-carry snacks like trail mix, bananas, or cereal bars are perfect.
• A basic first-aid kit - Prevention is key! Keep a few plasters, antiseptic wipes, and pain relief handy.
• Hat, sunglasses and sunscreen - Even on cloudy days, sun protection is a must. A wide-brimmed hat can also help keep you cool on warmer trails.‍
• Your route map - Even if you’re planning to use your phone for navigation, always carry a backup. A paper map or a downloaded offline version can be a real lifesaver if your signal disappears – and it often does when you least expect it!

The lighter you pack, the easier and more enjoyable your walk will be. Think practical, not heavy – and leave a little room in your backpack for the unexpected (like a scenic picnic stop you just can’t resist!).

How to prepare for your walking holiday

A bit of planning before you set off can make all the difference between a smooth, stress-free trip and unexpected hiccups along the way. Here's what you should think about:

• Plan your accommodation in advance - Even if you're only walking short distances, knowing exactly where you're staying each night gives you one less thing to worry about – and helps avoid last-minute stress, especially on popular trails.
• Book transport where needed - Check if you’ll need taxis, trains, or luggage transfers between stops. Having the details booked ahead gives you more time to enjoy the journey.
• Check travel requirements and local advice - If you’re travelling abroad for your walking holiday, double-check passport requirements, local health guidelines, and whether you’ll need extra documents like visas or health forms.
• Prepare for unexpected changes - Sometimes plans change, whether it’s a missed connection, a change in weather, or needing to cut a walk short. That’s why having travel insurance (even in the UK) that covers trip interruptions, cancellations, and medical emergencies is essential.

Protecting your walking adventure with travel insurance

Even with the best planning, unexpected things can happen – and that's where Travel Insurance gives you real peace of mind. From missed connections to medical help, our specialist cover means you can focus on the moments that matter – not the ‘what ifs’.

‍Get a quote today and walk your way to an unforgettable adventure.