British Food and Travel

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There are few things I enjoy better than a good walk. So the idea of walking holiday is absolute bliss. In addition to being great exercise, it’s wonderfully meditative. Get up, walk, enjoy scenery, rest, repeat. But if you’ve never planned a walking holiday before, it might seem a little intimidating. I take a look at how to plan your perfect walking holiday so that once you reach your destination, all you need to do is lace up your hiking boots, grab your backpack, and go.

Step One: Where to Go?

Step one is deciding where to go. This can depend on a number of factors. What sort of walking holiday do you want? You might choose:

• Day-hikes. Stay in one location for several days or a week and use that as a base for shorter day hikes. This has the advantage of one hotel booking for the entire trip and no needing to move everything each day. It’s a great way to explore a new area. See my post about my trip last year to Ross-on-Wye.
• A circular walk. If you are driving somewhere, this can solve the problem of what to do when you reach the other end. Simply start and stop in the same place. There are a number of multi-day circular walks that you can do and the Cotswolds is a popular destination for this.
• A long-distance walk. This could be the Coast to Coast, a stretch of the Coastal Path, exploring the Scottish Highlands…. Plan an itinerary, with a certain number of miles each day, and different accommodation each night.

It can be tempting to dream of a lengthy multi-day walk and by all means do so. BUT if you are fairly inexperienced, you might want to try some shorter routes first to see if you really like being out there every day.

Other factors in deciding where to go include the time of year you want to go. (Midge season in Scotland might take all the fun out of your dream getaway). Also factor in your experience level.

And lastly, the most important factor: landscape. Do you imagine a coastal walk watching dolphins frolic in the waves and with the salt air blowing through your locks? Or do you want miles of open moorland? Do you want a relatively flat terrain? Or are you relishing the thought of steep climbs and rocky descents?

Step Two: Plan the Itinerary

You’ve picked your walking route. Now you need to plan the daily itinerary. If you are staying in one place and doing different day hikes, this isn’t as important. You can pick a walk each day based on your mood, the weather, etc. But if you are planning overnight stops, you need to route out each day. How far you can walk in a day can depend on your skill level, the terrain, and whether you are lugging a hefty backpack. But there’s more to it than that.

You are taking this holiday to enjoy the scenery so make sure you take time to do so. Occasionally I would meet a couple who were determined to power through as if they were on some sort of army march. Twenty plus miles a day and no time for dawdling. One of them would inevitably look miserable. They weren’t enjoying themselves and it showed. This is your trip so plan around what you enjoy. If you know that you will want to stop and explore a castle along the way, make sure to include it in the itinerary and walk fewer miles that day.

Also be sure to add some variety in the length of your days. After a day of walking 25 miles, I welcomed two shorter days of 10 miles of so where I could relax a little more and give my legs a chance to recover.

Key point: don’t overestimate your abilities. Overextending yourself will lead to injuries and a miserable holiday.

Step Three: Where to Stay?

You’ve got your destination. You’ve got your itinerary. Now you need to figure out where you are going to sleep each night. More than likely, this will be something to consider in step two. After all, it’s no use planning a fifteen-mile walking day if you end up nowhere near a town or campsite. And where are you going to get food?

Again, you have many options here. You might prefer camping in which case, you should be sure to have a list of available campsites and to see which ones require pre-booking. In some locations, you might be able to wild camp, although be sure to check local rules and respect people’s property, if choosing this option. Then there are hostels, B&Bs, and hotels to suit a variety of budgets. Be realistic about your needs. I stayed in youth hostels in the Lake District and enjoyed the simplicity, plus the opportunity to meet people. But on the Coast to Coast route, I welcomed the privacy of my own room and shower. Depending on the route you choose, you will need to make reservations in advance. Accommodation on popular walking routes can be booked solid for months.

Step Four: What to Pack?

You’ve spent all this time planning and now it’s time to pack. You don’t have to spend an absolute fortune on overpriced equipment. At the same time, now is not the time to skimp on certain items. I have previously written about some of my favourite walking gear and everyone has their own preferences. Be sure to check out our affiliate advertisers Rohan and Outdoor Gear – both carry an extensive range of clothing and equipment.

Let’s start with basics. A backpack. Are you going to be carrying all of your equipment with you each day? If so, you need a backpack that is sturdy enough to carry your gear, and comfortable enough that you can walk with it for miles at a time. Visit your local camping store. Try different ones for size. Then once you’re at home have a trial run of packing it up and testing it for comfort. If you are going to use a sherpa company to pick up your luggage each day and drop it off at your next B&B, then you will need a small daypack for essentials as you are walking. Whatever size pack you are carrying, don’t forget a waterproof cover.

Boots. If there is one item to consider carefully, it’s footwear. The wrong footwear will make this a trip you’ll never forget – for all the wrong reasons. On flatter ground, you might be fine with lighter footwear, but whatever the terrain and length of your walk, you need something that is well-cushioned and provides good support. And if there are some serious hills in your future, don’t forget ankle support. Whatever footwear you decide on, I suggest breaking them in before you leave home.

Those are obviously just two items on a lengthy list that could be an entire post in its own right. Other items include a map and a compass (don’t rely on your phone), walking poles (changed my life once I tried them), waterproofs, first aid kit, good quality socks and clothing (layers), camping equipment (depending on your accommodation choice), water bottle, toilet paper and plastic bags, camera, torch… this list will grow as you and I both remember other necessities.

Does Planning Sound Too Much?

If all of that planning sounds too much, there is another alternative. There are plenty of companies who can plan every detail of your walking holiday leaving you free to get up and go. This doesn’t mean a guided tour. While guided group walks are definitely available if that is your preference, most companies can also help you plan your self-guided walk.

When I did my half-Coast to Coast walk a few years ago, I planned my walking holiday in the Lake District by myself. Then, I took a train to Kirkby St Stephen to pick up Wainwright’s route through Yorkshire to Robin Hood’s Bay. For that part of my trip, I turned to the specialists at Absolute Escapes. They took care of everything except the actual walking and if there were any problems (there weren’t), their staff were just a phonecall away. In short, I had peace of mind knowing that everything was taken care of.

What a Walking Company Can Do for You.

Here are just a few of the benefits of using a company to plan:

• Can plan and book accommodation, and breakfast. And the accommodation is vetted. No damp fleabag hotel with lumpy beds.
• Can plan and book baggage transportation. Even if you make your own plans, baggage transportation is wonderful as it freed me up to enjoy my walks without (literally) the heavy baggage!
• Can provide maps, guidebooks, tips for eating, sights, etc. A handy packet arrived a few days before I started with maps, suggested equipment, recommended stops, and more.
• Schedule to suit you – start on the day that suits you.
• Emergency help if you need it just a phonecall away.

Advice from Hillwalk Tours

Another reputable company is Hillwalk Tours, which was established in 2008, and offers self-guided walking holidays through Ireland, the UK and along Spain’s Camino de Santiago. Within the UK, they offer tours along 10 trails: the Hadrian’s Wall Path, South West Coast Paths, Cotswold Way and South Downs Way in England, the Pembrokeshire Coast Path in Wales, the Antrim Glens & Coastline in Northern Ireland and the West Highland Way, Great Glen Way, Rob Roy Way and Speyside Way Whisky Trail in Scotland. The Fife Coastal Path will soon be added to the list.

Hillwalk’s Marketing Manager Richard Davis says that the West Highland Way is by far their most popular trail:

Its popularity has spread throughout the world and with good reason. It’s simply a stunning trail that should be experience by walkers at least once in their lifetime.

Davis and his colleagues recognise that planning a multi-day walking holiday can be difficult. Once you start planning, you realise you have more questions. What about last minute cancellations? How do you find alternative accommodation? That’s where they can help. Put simply, they remove the hassle. Davis says:

The customer doesn’t need to worry about the logistics of the tour such as where to stay each night, how to get their luggage transferred each day to the next location, where and when they need to be collected / dropped off for transfers and so on.

And believe me, after a long day of walking through the rain and the bogs of the Yorkshire Dales (I loved every minute), I appreciated nothing more than arriving at a lodge with a hot shower, a good meal, and a cosy bed.

If you decide to go with a tour company for planning your walk, be sure to choose one with experienced staff who are hikers themselves. The reputable companies will hire people who have walked the routes, often several times. They know which parts are particularly tricky. Or where there’s a great but little-known photo op. Or where to pause for the best ice-cream. Having hiked the routes themselves also means they know how to adapt the itinerary based on your needs and experience level.

Davis says:

I think walkers sometimes fall into the trap that if they pick up a guidebook, book a few accommodations here and there and carry a small backpack for the duration of their walk, they don’t need the assistance of a tour operator such as Hillwalk Tours. It’s not as easy as it looks! So I think if you want the hassle taken out of organising a walking holiday and want peace of mind of being able to rely on experts, then booking with a tour operator is a no-brainer.

So What Are You Waiting For?

Whether you do all the planning yourself, or choose a company, make no mistake that planning is essential for a walking holiday. You can’t hope to just show up and wing it, at least not without a lot of misery and regret. But with the right planning, you will have a wonderful holiday and, if you’re like me, you can’t wait to start planning the next one.

COVID-19 Note

With the pandemic still in full swing, a walking holiday within the UK may be just the break for you. At them same time, please be mindful of local restrictions that may mean businesses are closed. Walking tour companies, like many other businesses, are struggling at this time. Help to support them by buying gift vouchers which provide them with essential income at this difficult time while providing you peace of mind that you’ve already paid for a chunk of next year’s trip!