Top Tips for Your First Walking Holiday

During lockdown, many people took to walking for the first time; the 2020 National Travel Survey concluded that 7 out of 10 adults walk once a week. A CBI report published in September 2021 found that, post-pandemic, society is motivated to spend more time in nature. With travel back on the cards, walking holidays look set to trend. Specialist operator, Inntravel, have been providing self-guided walking holidays in the UK and Europe since 1984 and are the only Which? Recommended Provider 2022 for self-guided tours. Comprising ‘easy’ to ‘moderate’ walking, and suitable for new and inexperienced hikers, 80% of their holidays are Grade 1, 1-2 or 2. Andy Montgomery, experienced route-finder has worked with Inntravel for over a decade and has helped to create walking holidays across Europe. Here, she shares her tops tips for your first walking holiday.

Table of Contents


Choosing your first walking holiday

Finding the right walking holiday is the crucial first step. Attempt something that takes you too far out of your comfort zone and, as well as possibly ruining your holiday, it could be hazardous. Get it right and you will never look back; every holiday from now on may be a walking holiday.

Deciding on the location

Walking holidays are not just about the walking, they are also holidays. Approach it like any other in terms of deciding if has the elements that are important to you. Think about good food, historic sites, coastal views, as well as good walking routes. Do you want to stay in one location, or explore an area, staying in two or three different places? If travelling with a specialised walking company, your luggage is transported between hotels for you; otherwise think about how to get your luggage from one accommodation to the next.

Your first walking holiday abroad

In terms of tips for your first walking holiday abroad, think about how hot it will be, and avoid the peak summer months. Consider booking the so-called ‘shoulder seasons’ of spring and autumn. The weather will often be perfect for walking at those times; flights are cheaper, and places tend to be less crowded. It’s also important to check hours of daylight; southern European destinations have shorter daylight hours during summer, and longer during winter. If some routes are long, you’ll need to set off early to ensure you don’t get caught out when daylight fails, like the couple in Tenerife who set out from Vilaflor at 3pm to walk to Paisajes Lunar. They found themselves, four hours later, lost in the pine forest in pitch dark.

Tips for judging how difficult the walking will be

Understanding the difficulty level of routes is paramount.

What is the difficulty grading for the holiday?

Walking holidays are usually given a grading of some kind. Unfortunately, there isn’t a universal system, and lots of guides, leaflets, and even tour operators have their own version of how they classify the difficulty level of their holidays. But they are all usually based on length, ascent/descent, and type of terrain so the points covered here will help you to make sense of them. There may be routes within a holiday that fall outside the overall grade for the trip and if so, ensure you have the option to choose not to do those, or to shorten them to an easier option.

Unless you’re an experienced hiker, one of my tips for your first walking holiday is to opt for the easiest graded holidays. Once you’ve completed your first walking holiday, you’ll have a better idea of what grade will suit you best. Bear in mind too, that you’re likely to get stronger as the holiday goes on. Don’t be afraid of holidays where routes towards the end of the week are a little longer or have a slightly higher ascent and descent.

How long are the routes?

Inexperienced walkers need to carefully consider what distance they are comfortable walking each day. It’s one thing to go for ‘a long walk’ once a week, and something else entirely to go walking day after day. It’s best to err on the cautious side and book a walking holiday that has routes which are around the length you’re used to, probably under 10km. Look to see if routes can be shortened if you get tired or risk running out of daylight. The option to have rest days, when you can choose to do something else, is also a good one.

Ascent and descent

There’s a big difference between walking long distances on the relative flat and hiking in the mountains. When choosing a walking holiday, look at the cumulative ascent and descent for the routes. An ascent will be less difficult if it’s over a long distance, for example an ascent of 100m if spread over 5kms will barely be noticeable but over 1km, you’ll know you’re ascending. Route guidance with profile graphs is particularly helpful as you can see just how steep a route is. Sometimes even the fittest and most experienced hikers can get it wrong, like the one who, while walking with a guide on mountainous Gran Canaria, insisted that he wanted routes longer than the planned 14km. He ran out of energy a couple of kilometres short of the end point.


What sort of ground is the walking holiday covering? This is important for ensuring you have the right footwear. Are there places which might make you nervous if you don’t have a head for heights, such as exposed ridges or steep descents down cliffs?


If you’re not part of an organised holiday or self-driving, can you easily get to the start of routes by public transport? Are planned routes circular or linear? If they’re linear, how do you get back to your car or your accommodation?

Should I consider self-guided, or a group walking holiday?

There are pros and cons to each:

Group walking holidays mean the work is done for you in terms of choosing which routes to follow, and then navigating them. You’ll have company while on the trail; someone who will give you (hopefully) insider information as you go along, and who will provide help if you struggle at any point.  It’s also a great way to meet like-minded people, particularly if you’re a solo traveller.

On the other hand, being in a group means you’re tied to the given start times and itineraries included in the trip, leaving no scope for ad hoc exploration. The whole group has to walk at the pace of its slowest members which is fine if that’s you but can be frustrating if it’s not. You may also struggle to hear what the group leader is sharing if you’re not up at the front.

Self-guided walking gives you the flexibility to choose what time you set off in the morning, walk at your own pace, and linger at a waterfall or gardens. You can also decide for yourself when and where you want to stop for lunch. Additionally, it gives you scope to stay additional nights anywhere you would like to spend more time or enjoy an extra rest day. Experienced specialist walking companies usually provide detailed route directions for self-guided walking, supplemented by information on culture, flora, local gastronomy and so on. That means you don’t have to invest time doing research yourself.

What equipment do you need?

Walking holidays do not have to mean paying out a lot of money on specialist clothing or equipment, but you do need to consider essential items. Here are some tips for your first walking holiday.


Even if you’re following detailed route directions, a good map which shows walking paths will help to ensure you don’t get lost. A specialist walking company may provide relevant maps for your holiday. If they don’t, get advice on the best map to use for the region/area. If you’ve never used maps before, you need to learn the basics of map reading before you go.

Hiking shoes/boots

Choosing the right hiking shoes or boots will largely depend on the type of terrain you will be walking on. Experienced mountain walking requires quality, sturdy hiking boots with good grip and ankle support. For lower-level walking, hiking shoes should be all you need. Shoes and boots should fit comfortably, allowing for the thicker socks you’ll be wearing. As a rule of thumb, with your boot/shoe fastened and your toes at the top, you should be able to slide a couple of fingers between your heel and the boot. But don’t have them so loose that your foot slides in and out – that will cause blisters.

NB Ensure that, when your hiking boots/shoes are fastened, you hook the loops of the bow around the hooks on your shoes to hold them in place. Otherwise, they could catch on the other foot and bind your feet together – something that has happened to me on more than one occasion.


Choose lightweight, breathable materials that will dry easily if you get caught in rain. Layers are always the best way to dress for walking. Start with a base layer or tee shirt, then add a fleece and, depending on the season and location, a warm windproof or waterproof jacket. Choose comfortable, breathable (not cotton or denim) trousers with pockets in which to carry your compass/map/GPS device/phone etc. Even if you’re walking somewhere that’s usually arid, it’s sensible to have a light, waterproof jacket that you can carry with you too.

If you’re planning on walking on consecutive days or over long distances, it’s worth investing in bespoke walking socks. They are fitted around heels and toes, so snugly that they have a L & R to denote which foot they go on, ensuring they don’t slip and cause blisters. You may be out in the sun for lengthy periods, particularly in southern Europe; having a hat with a brim wide enough to cover or cast shadow over the back of your neck, is critical.


Having hands free while walking is essential so you will need a comfortable, lightweight rucksack/backpack with removable waterproof covering. It needs to be large enough to take your daily supplies (sandwiches, map, compass, waterproofs, first aid items etc.). Deep side pockets ensure you have somewhere to keep your water flask.

Knee supports

Some people may find long descents hard on the knees. Invest in basic knee supports and your knees will thank you.

Walking poles

Unless the terrain can be tricky, or there are some steep ascents/descents involved, it’s not essential to have walking poles. Having said that, lots of people do like to use them, regardless of distance or terrain.

Tips for your first walking holiday preparation

•   If you usually only go walking once or twice a week or are planning to walk longer routes than normal, practice will help get you fitter before you go. Try walking on two consecutive days, and gradually increase the length of routes, or find ones with some ascents and descents. You can expect to feel a bit stiff for a couple of days afterwards but that’s normal and your muscles will soon recover.

•   If you’ve invested in a new pair of hiking shoes/boots, make sure you break them in before you go, and give your feet, and the shoes, a chance to get used to each other.

•   One of the best tips for your first walking holiday is to make sure to trim your toenails right down to the tops of your toes before you go. Otherwise, you’ll pay the price in bruised and sore cuticles. I should know – I’ve lost a few toenails to long distance hikes in my time!

What should I pack for a walking holiday?

In addition to the tips given here, North Yorkshire stylist, Laura Downey, has shared her top tips for embracing your personal style without exceeding the luggage allowance, in the How to pack for a walking holiday article that she wrote for the Inntravel blog.

•   The essentials listed above

•   Sunscreen. Lengthy exposure to the sun is dangerous if skin is not properly protected, particularly on exposed hiking routes. Always apply high-factor sunscreen before setting off and reapply at intervals.

•   A GPS device if you’re using one. Even if you’re not yet comfortable in following a GPS track, a device will mean you can measure distances between points which is extremely helpful for navigating and for following route guidance.

•   A compass is always useful for navigating. If you have a GPS device or a smartphone, they will have a compass inbuilt.

•   Walking holidays are often located in rural areas, so a torch is essential, particularly in winter when daylight hours are at a premium.

•   Spare batteries for your GPS device and your torch. A power pack is also useful to have, although they are heavy.

•   Basic first aid items (plasters, sterile wipes, bandages).

•   A water flask helps keep water cool and is more environmentally friendly than plastic bottles. It’s recommended that you carry 1 litre of water per person for every 2hrs of walking.

•   Tissues and plastic food bags for ensuring nothing is left behind when ‘nature calls’ on the trail. A small bottle of antiseptic hand gel helps with hygiene.

•   Sunglasses

•   Vaseline helps to prevent lips from cracking and if applied to heels and toes before putting socks on, will help prevent blisters.


Although it might seem like a lot of information to take in, the most important tips for your first walking holiday are about preparation and planning. Once you’re out on the trail, everything falls into place. There’s a reason why walking is the most popular holiday activity (AITO Insight Report 2021); it’s an unforgettable way to experience a destination.

James Keane, Inntravel’s Portugal expert and a keen walker, has this advice for your first walking holiday: “Make sure you’ve got a comfortable pair of walking shoes or boots that you’ve broken in, and good walking socks; take care of your feet and the path ahead will be easier.”

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