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Are You Planning a First Walking Holiday? Here’s What You Need to Know

By Jackie Parsons September 22, 2025 Travel

So, you’re this side of 60 and toying with the idea of embarking on your first walking holiday. It’s not as mad as it sounds. And it’s not just you – walking holidays are becoming increasingly popular as we seek out more immersive experiences and embrace the benefits of slow travel.

Whether you’re planning a series of gentle strolls or heart-busting alpine hikes, a walking holiday will get you out in the fresh air, surrounded by natural beauty, and hopefully, leave you at the end of each day weary but inspired.

However, the key to a successful trip is most definitely in the preparation. If this is your first hiking holiday, you need to decide from the outset how independent you want to be. After that, it’s all about getting as hiking ready as you can to ensure your trip runs smoothly.

Planning Your Holiday

Checking into a rural hotel and enjoying some pleasant local walks may feel like the simplest option, particularly if you have concerns about the hiking. But if you’re new to hiking, planning and navigating routes can be tricky. Bear in mind also that trail signposting varies enormously from one country to another.

If you like the idea of point-to-point hiking and want to hand over the research to someone else, some companies offer the independence of self-guided hiking, allowing you to follow planned routes with the aid of maps and GPS directions. They’ll also transfer your luggage, so you get to stay in several locations and experience different environments.

Alpine hiking in Italy.

Alternatively, a popular option for a first walking holiday is to join a guided group hiking holiday where literally everything is done for you. No need to worry about routes or directions, or fret over where to stop for lunch – just put one foot in front of the other and enjoy the view and company!

Choosing the Right Level Holiday

Whichever option you select, it’s vital that you know the right level holiday for you. Look carefully at both the average and maximum length of the hikes, as well as any ascents and descents involved. Check also if you can cut short your walks if you’re feeling weary or if you have to complete the whole route. The secret really is to feel moderately challenged without feeling out of your depth or so tired that you can’t face walking the next day.

Spectacular scenery hiking in Italy.

How to Prepare for Your First Walking Holiday

It’s never too early to start training! The better prepared you are, the more you’ll enjoy it, so start some sort of training programme as soon as you’ve booked your holiday. Apart from anything else, it’ll make you feel great!

Jogging, running, cycling, swimming and Pilates are all excellent ways of building your leg muscles and core strength but putting in the walking hours will also stand you in good stead. Intersperse long training walks with shorter brisk 30-minute walks, perhaps with a few hills, to raise your heart rate.

This is also the time to break in new boots if you want to avoid blisters and other common feet-related ailments on your holiday.

Gentle walks through Piedmont’s vineyards.

What to Take

If you’re travelling with a tour operator, you should receive a comprehensive kit list. In addition to your boots and socks, take lightweight quick-drying clothes to keep your luggage light. Little extras such as a waterproof cover for your rucksack, a sustainable water bottle and a small portable charger can come in very useful, and a basic first aid kit is always a good idea. I’m a staunch supporter of walking poles but do recommend trying them out before your holiday.

Hiking poles reduce the strain on your joints and provide stability.

Local Culture

But it’s not just about the walking. Part of the beauty of a walking holiday is the joy of walking through the landscape and getting to see things you might not see if you were travelling by car or train. Get the most from your trip by reading up on the local culture, wildlife and history before you go and consider choosing a book that’s set in the region you’re visiting for your holiday reading material.

Eat Healthily

We all know the benefits of eating healthily but sometimes need that extra little push to put it into practice. Eating well during the run-up to your holiday will definitely stand you in good stead so fuel up on complex carbohydrates such as brown rice and wholewheat bread, lean proteins and healthy fats to build energy reserves.

Enjoy gastronomic picnics with Hedonistic Hiking.

What to Expect from Your Holiday

Managing your expectations will make quite a difference to how much you enjoy your holiday. Read through the itinerary carefully so you have a good idea about the terrain you’re going to cover, as well as the accommodation and restaurants on the schedule, so there are no nasty surprises.

If you’re joining a group, inevitably there will be a mix of people. Of course, you may not want to be best friends with everyone, but the more open-minded you are, the more you’ll get out of meeting your fellow hikers.

Stunning coastal hiking.

As for the walking, you’ll quickly find out that there’s nothing quite like the thrill of reaching a mountain peak or the end of a lengthy trail and discovering that you can become a hiker at any age!

Let’s Have a Conversation:

Have you ever been on a hiking holiday and if so, where to? Did you hike independently or join a guided group? Is there anywhere you’d particularly like to explore on foot?

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Carol Chidsey

Has your company looked at either Via Francigena or the Magna Francigena? What a way to see the back roads of Italy & find the “locali” restaurants. Plus the amazing fellow trekkers!

lauren

I went on a hiking holiday in Georgia, saw a lot of waterfalls and wildflowers. It was an organized guided group of just women. It was GREAT! Looking forward to going on another such group trip. Vacations I plan myself are all actually “walking holidays” as I try to see as much as I can on foot – being that my hobby is landscape photography!

Jackie Parsons

Hello Lauren. I would love to go to Georgia, which company did you travel with. It looks like a stunning country, definitely on my wish list

Janel

Over the years, I did a lot of hiking. Much was done on the Appalachian Trail hiking different segments of it. So glad I did it 25 years ago because walking has become a challenge now at 77.

Jackie Parsons

Well done! I hope you are still able to get out walking, even if the distances are shorter. It is one of the best ways to keep moving and has many health benefits

Livy Javier

where can you buy the stick? what do you call the stick – is it available in Amazon?

Jackie Parsons

Hello Livy
Hiking poles/sticks are readily available either from a hiking equipment store or online (Amazon or elsewhere). The basic versions are very inexpensive, if you pay a bit more you can buy ones which are very compact and more lightweight which is an important consideration. Please be aware that if you travel overseas with hand luggage only you are not able to pack hiking poles (they are considered a weapon). On our tours we have several pairs to loan to guests if they don’t have their own.

The Author

Jackie Parsons is the co-owner of Hedonistic Hiking. She has been a tour guide since 1992 and has lead walking tours since 2000. She creates and guides Hedonistic Hiking’s all-inclusive gastronomic hiking tours throughout Italy. Alongside the hikes, all tours provide an unforgettable insight into the local history, art, culture, food, and wine, and are graded for ability. Find out more at https://www.hedonistichiking.com

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