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The Art of Packing for Walking Holidays

Whether you’re a seasoned hiker or taking your first steps into the great outdoors, one thing’s for sure: packing smart is the key to unlocking a fantastic walking holiday. Years of international travel have taught us how to pack the essentials while still fitting everything into a carryon. We’ve also picked up good tips for choosing hiking clothes and gear (without breaking the budget). So, let’s dive into the ultimate packing guide and make sure your journey is all about the stunning views and exciting memories – not the stress of what to put in your luggage.

clothes, shoes and necessities packed in a carryon for walking holiday in Faroe Islands
everything fit in a carryon for 2-week walking holiday in Faroe Islands

Table of Contents

Essential Clothing and Footwear

When we first began hiking, Eric and I wasted so much money on fancy clothes that REI convinced us we needed. Don’t get me wrong, good quality clothes and shoes are important, but keep it simple. When packing for a walking holiday or any trip, remember that less is more.

Comfortable Walking Shoes

This is the most important choice you will make. When deciding between hiking boots or shoes, consider the terrain you’ll be navigating and any specific foot concerns you might have. Focus on shoes that fit well, offer good cushion from hard surfaces and proper support. If they’re a good neutral color and waterproof, even better!

Hiking Boots

Hiking boots are the heavyweights of the footwear world, designed to provide exceptional support and protection on rugged trails. If you’re planning to explore rocky, uneven, or steep terrain, hiking boots are your go-to companions. High-cut designs offer ankle stability, reducing the risk of sprains or injuries. The sturdy construction and thick soles provide protection against sharp rocks and debris, making them essential for more challenging trails.

Hiking Shoes

Built for hiking but with lower-cuts around the ankles, hiking shoes are a popular choice with most day-hikers. They can handle most trails and last a long time but they don’t offer the same level of ankle support. Choose these if you don’t like having something around your ankles.

We purchased our boots from REI and they were very helpful in helping us choose, but any local outdoor specialty store will work. Make sure they measure your foot and have you practice walking on an incline – this is to see if your feet move in the boot (movement equals blisters).

muddy boots means it was a good day
Hiking Sandals

If your walking holiday is in a hot climate or you know you’ll be getting your feet wet, hiking sandals may be a good option. But be wary, any friction (wet feet, sand, dust) can cause blisters and there’s nothing to protect your toes from rocks, poisonous plants, etc. I hiked in Greece with Teva sandals and it was worth the risk because my feet would have gotten too hot, but I was nervous about injuring my toes the entire time.

Trail Runners

Lighter and more flexible than hiking boots or shoes, trail runners are perfect for well-maintained paths, smoother terrains, and hard surface walking (pavement, stone). If your walking holiday involves more urban walking and you value agility, trail runners are a good choice. They offer a comfortable fit and breathability, allowing you to maintain a brisk pace without compromising on comfort. Keep in mind that trail runners don’t provide the same ankle support or long-lasting quality as hiking boots.

In a nutshell, it’s a balancing act between protection and agility. If your journey involves a mix of terrains, consider packing two types of shoes, using hiking boots for challenging sections and trail runners or sandals for lighter days. The best shoes are the ones that feel like an extension of your feet and suit your adventure’s demands. Before your trip, take some practice hikes in your new shoes and try walking on hard surfaced pavement and rocky terrain.

WHAT WE PACK

We always pack 2 pairs of shoes, usually wearing our hiking boots on the airplane and packing the lighter shoes in our luggage. Eric wears Keen Targhee Mid Waterproof Hiking Boots and a sneaker of choice. Clare wears Ahnu Montara Waterproof Hiking Boots and Frye Ivy Low Lace Leather Sneakers.

Hiking Socks that Prevent Blisters

The key with proper hiking socks is to get good quality merino wool, make sure they fit snugly around your foot, and choose appropriate thickness (midweight for warm weather, thicker for cold weather). You don’t want bulky socks that will bunch up and you don’t want slippery socks that cause your foot to move around. If you are prone to toe blisters (like I am), consider toe sock liners underneath your hiking socks. I haven’t suffered any blisters since I started hiking with my Injinji toe socks.

feet showing off gray toe sock liners used for hiking and walking holidays
hiking with toe socks, best decision I ever made!

Moisture-Wicking Clothing

When you’re packing light for a walking holiday, you’ll want breathable shirts, moisture-wicking socks, and quick-drying pants in your gear. These items are not only lightweight and space-saving but also incredibly comfortable. With moisture-wicking fabrics, you can easily wash your clothes in a sink, hang them up, and wake up to dry garments ready for another day of exploration.

Do I need to spend a fortune on merino wool clothing?

The short answer is “no” but if you can purchase at least one shirt that is 100% merino wool and is in a color and fit that goes with just about anything, then you will never regret that purchase. I prefer merino wool for winter hiking because it keeps me warm without sweating and smelling nasty, but for general hiking temperatures Eric and I are happiest with our cheap synthetic blend activewear shirts that can be found anywhere these days. Look for labels that say “odor resistant” or “antimicrobial treatment.”

Should I hike with leggings?

I hike with leggings all the time and love that they offer a little circulation support. However, they get stinky fast so I alternate them with my hiking pants. They’re also not a good choice for hot weather hiking, even though I see women wearing them in the summer all the time. It’s really a personal preference. Whatever you choose, make sure it has deep pockets to fit your phone so you can quickly grab it for photos.

Do I need waterproof hiking pants?

Yes and no. If you anticipate hiking in a downpour then you need some type of waterproof pants but it doesn’t have to be your hiking pants. We prefer water-resistant pants that dry quickly because they’re more comfortable and work for light to medium rain. For heavy rain, we usually find cover or pull out our waterproof pants that fit over our regular pants. Once the rain stops, we can quickly pull them off and let everything breathe again.

WHAT WE PACK

The best choice depends on the climate and your personal preferences. Prioritize comfort, breathability, and the ability to keep you dry throughout your adventure. For packing purposes, choose colors and styles that you can mix and match with everything on your trip. For example, our hiking pants are a neutral color that go with every shirt we pack and we’ve never regretted splurging on these. Eric wears Sherpa Bara Pant and Clare wears Kuhl Trekr Pant.

Layering

Your layering strategy is the key to packing light and staying comfortable on a walking holiday, regardless of weather. For hiking in warm weather, you’ll want a fitted (but not tight) moisture-wicking undershirt (sleeveless or short sleeves) and a mid-weight long-sleeve top or jacket if there’s a chance of cooler temps (which often happens when changing elevations or hiking in windy conditions). For colder weather, you’ll still want that undershirt but add warmer layers (insulating mid-layer or a vest) plus an insulated coat that’s easily packable. You’ll be surprised how hot you’ll get walking, even in very cold weather, so make sure you can strip down or bulk up easily.

I pack some version of this for every walking holiday

Rain Gear

Whether your walking holiday is in rainy Ireland or dry Greece, chances are you will encounter rain at some point during your travels. A good rain jacket is a must, as are water-resistant pants. A hat is also helpful, even if you have a hooded rain jacket, as it will give you better face coverage so you can see better.

What is the best rain jacket for hiking?

The best rain jacket is one that is fully waterproof (make sure it says waterproof on the label), in a color that goes with everything (hiking and town clothes), has covers over the zippers to prevent water intrusion, air vents underneath armpits, is easy to pack, and is loose enough to fit over several layers of clothing. Brand is really not important, quality and flexibility with different outfits is, so purchase wisely because this is a piece you will bring on every trip.

What is the best packable coat?

This is where I say spend the money to get exactly what you want and to ensure high quality. A coat that keeps you warm, packs down to practically nothing and looks good with everything is an important investment, just like your boots. If you want a coat that doubles as a rain jacket, choose something like what Eric uses and just add warm layers underneath. If you prefer a puffer coat, get one like mine that keeps me warm but packs as thin as underwear.

WHAT WE PACK

We always pack a rain jacket and usually a coat since we prefer cold weather hiking. Eric wears  North Face Apex Flex Rain Jacket when he wants a waterproof coat. Clare wears Patagonia Nano Puff Hoodie for her coat. We both wear Marmot PreCip Rain Jackets.

Backpack or Daypack

You’ll need one if not both, depending on the type of walking holiday. We recommend trying several on, making sure it’s comfortable on your shoulders and neck and that it falls comfortably on the hips. Look for packs designed to let air flow between your back and the pack. Think about what you’ll be putting in the pack before choosing so you know what size and compartments work best for you. If your pack doesn’t come with a rain cover, purchase a generic one.

Daypack

For inn to inn or center-based hiking, all you need is a daypack. These range in size from 15 to 30 liters and the size will depend on what you think you’ll need for a full day of walking. Prioritize features like adjustable straps for comfort, multiple compartments for organization, and hip belt pockets for quick access to essentials. Make sure it has room for a good-sized water bottle or fits your water bladder of choice. We prefer using a water bladder because we can drink without stopping, which means we hydrate more often.

Backpack

You’ll only need a larger backpack if you are sleeping on the trail or doing a trekking holiday where you have to carry your own luggage each day. Eric and I never hike with a backpack but we travel with one. We’ve learned the hard way that places are not as luggage-friendly as we are accustomed to in the United States. Inns don’t always have elevators, roads can be rough cobblestone, public transit rarely has room for large suitcases, and so forth. Which brings me to the next tip…

Pack Light

Pack only what you need, not what you think you’ll need. Considering how often airlines misplace luggage and the points we made in the previous paragraph, you can see why it’s wise to pack what you can easily carry. We understand how difficult this is for most people. It took us years of traveling to reach the point where we’ve figured out exactly what we can and can’t live without, so just try and do your best. Eventually maybe you’ll end up like us, able to pack enough for 50 days into one backpack and a daypack.

WHAT WE PACK INTO

Whether it’s a week or 2 months, we now travel with one daypack and one luggage backpack. We trialed several backpacks before finding the perfect one that fits each of us comfortably and is accepted as carryon by most international airlines. Eric packs with an Osprey Daylite and Aer Travel 35L Pack. Clare packs with a Thule Vital Hydration Pack and Tortuga 40L pack.

shoes, hiking boots, clothes and necessities for walking holiday in Canada
everything fit in carryon and a small bag for 50-day roadtrip to Canada

Navigation and Communication Tools

Maps

If you book with any of the walking tours on our website, you won’t need to worry about this at all. They will provide you with maps and walking directions. Just make sure you have data on your phone if you’ll be using it for GPS (which we always recommend).

Phone Calls and Data

If you’ve never traveled internationally, contact your phone service provider for international data plans or purchase a local SIM card when you arrive at your destination. It’s also a good idea to download WhatsApp and create an account before your trip. It allows you to make calls using WiFi, which we’ve had to use several times when cell service wasn’t available. We travel so often that we’ve permanently switched our phone service to Google Fi which offers long term international calling and data.

International chargers

If traveling internationally, pack an international charger adapter appropriate to your destination. We use a cheap adapter that works for Canada, UK and Europe. If you just want a smaller adapter that’s good for that one region, they have those too.

Packing the Necessities

Most of this should be common sense, but we mention it because packing for a walking holiday can be overwhelming and we don’t want you to forget the important necessities.

Sun Protection

When choosing sunscreen for hiking, opt for a broad-spectrum formula with a high SPF rating that doesn’t contain oxybenzone or octinoxate. These chemicals have been linked to disruption of marine ecosystems so several countries, particularly those with coral reefs, have restrictions on certain types of sunscreens.

Insect Repellent

Know the insects for the region you’ll be visiting and bring appropriate bug repellant. This is especially important if you’re hiking in regions prone to ticks or malaria-carrying mosquitoes. We prefer walking in cooler weather to avoid them entirely, but we always bring small packs of bug repellant wipes. If hiking in areas with heavy insect populations, consider treating your clothes with permethrin (just make sure to read the warnings before handling this insecticide).

Water and Snacks

Again, common sense, drink plenty of water! Bring a reusable water bottle or water bladder and pack a LifeStraw or water cleaning tablets if you’re unsure of water quality where you’re visiting. For most walking holidays you’ll have plenty of food available but it never hurts to pack a few of your favorite energy bars or can’t-live-without snacks.

some walking holiday companies give you snacks & water bottles

First Aid and Emergency Gear

Regardless of what kind of walking you anticipate, always pack a basic hiking first aid kit. For us this includes adhesive bandages, antiseptic wipes and moleskin. We also pack small packages of hand sanitizer, a small quick-drying towel, an extra pair of socks (in case your feet get wet), portable phone charger, and a small flashlight. If hiking in more extreme conditions, your tour company should provide a detailed list of gear.

Personal Care

When traveling outside the United States, pack a small washcloth. While larger towels are standard in most places, personal washcloths are not. We like compressed towel tablets because they’re lightweight but don’t fall apart after one use. Pack shampoo and soap as well, it’s not always guaranteed at smaller guest houses or cottages. If you’ll be washing clothes, pack some travel-size detergent.

Medications

In general, you can bring prescription medications with you when you travel to other countries, but there are important considerations to keep in mind:

Check Local Regulations

Different countries have varying regulations regarding the importation of prescription medications. Some medications (even over-the-counter) that are legal and readily available in one country might be controlled substances or banned in another. It’s crucial to research the specific regulations of the country you’re visiting before you travel.

Carry Documentation

Carry a copy of your prescription and a letter from your doctor explaining your medical condition and the need for the medication. This can be helpful if you encounter any questions from customs or security personnel.

Follow Quantity Limits

Some countries have limits on the amount of medication you can bring with you. Make sure you’re aware of these limits and comply with them.

Use Original Packaging

Keep your medication in its original packaging with the prescription label on it. This helps customs officials verify the authenticity of the medication.

Declare Medications

When going through customs, it’s a good practice to declare your prescription medications if required by the country’s regulations. This can help avoid misunderstandings and ensure a smooth entry.

couple hiking in yorkshire dales national park
my bootlaces broke on walking holiday in England, now I pack extra laces

Embarking on a walking holiday is a wonderful adventure that deserves thoughtful packing and strategic gear choices. By focusing on simplicity, comfort and versatility, you can streamline your packing process and ensure a seamless experience throughout your trip. Your choice of footwear will depend on the terrain and your personal preferences. Equally important are your clothing selections, which should prioritize moisture-wicking fabrics, proper layering, and protective rain gear. Remembering the necessary accessories ensures your safety and comfort. Ultimately, mastering the art of packing for a walking holiday allows you to embrace the natural beauty around you, savoring each step with confidence and ease. So lace up your shoes (or boots), pack your essentials, and get ready to create some unforgettable memories.

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