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Writer's pictureZak Goldstein

How Do I Walk? A Guide to Walking Holidays.

Updated: Dec 15, 2023

When the D.I.N.Ks plan a walking holiday, they are looking have new experiences, get a little exercise but still treat themselves well. Walking holidays require a plan whether it be do-it-yourself or hiring a tour group . This guide will cover popular options, our preferences, and how to make the most out of your walking holiday.


A woman walking into a Nakasendo post town on a golden pebble road

DINK Details

To make planning easier, we use our D.I.N.K. Planning Template

Deets:

- These are our tips that work for us

- They may not work for you¹

First Aid:

- Address issues immediately

- Know your limits

​Packing:

- We try to fit everything into one bag

- No one likes to wait for checked bags

- Airlines lose luggage

​Plan Ahead:

- Creams and (sometimes) hiking poles must be checked.

- If you can, buy it at the destination.

1. Be smart and double check our tips work for you


If you feel anything, Compeed!


 

What is a Walking Holiday?

It's just like a normal holiday except you wake up in a new place every day. Instead of taking a train or driving everywhere, you walk and get to experience the places in-between. A great way to experience the road less traveled.


Which Walking Holiday Do I Take?

There are many multi-day trails in many countries. With these usually comes companies that offer services to make the walking holiday a lot easier. One of the most well known trails is the Camino de Santiago network. It spans across 3 countries and has many fans.


D.I.N.K. Walked

  1. Camino de Portuguese: Camino De Santiago (Portugal / Spain)

  2. Nakasendo Way ( Japan)

  3. Camino del Norte: Camino De Santiago (Spain)

  4. Giant's Causeway & Glens of Antrim (Northern Ireland)

  5. Via Francigena (Italy)


D.I.Y. vs. Company Tours

A tour will book all your hotels, coordinate meals and transport your luggage so you do not have to carry it. Incase of trouble, they offer services to assist you. This makes the planning and walking much easier, a great choice for first timers.


If you are interested in planning the holiday yourself (our preferred choice), there are many factors to consider but the advantage is you get more opportunities pick what you want. The sections below will review what to consider.



Self-guided Planning

Once you've chosen the trail for your self-guided walking holiday, food and sleep come next.


Hotels & Airbnb

Most of our stays have been hotels using booking.com due to their reliable check-in processes and realistic cancelation options. As of 2023, we are finding Airbnb is becoming usable again. Usually due to regulation outside the U.S.



In larger cities, getting a place is not a problem but in rural areas, you may not have many options. The ideal town may not be on a major booking service. In some cases, we've had to call or fill out an online form. It's old school but it works.


Here is what we keep in mind when picking a place.

  1. You have been walking all day, you will want something close to the trails

  2. Try to find a places that are equidistant from each other. You don't want have a 3 hour walk one day and an 8 hour on another.

  3. If it's a fair sized town, we use booking.com for finding a places with a few amenities (like the spa outside of San Sebastian)

  4. Know the season. Tourist season can lead booked hotels while off-season will have closed restaurants.

  5. Holidays too. New Year's usually ends up with us eating dinner from a grocery store we hit up before 4pm


Meals

Similar to finding places to stay, the more remote the location, the more limited your meal options. Many classic B&Bs offer a dinner service so make sure to reserve a meal ahead of time especially if you are traveling out of season.


Walking holidays take you through so many places and options. We've had the most amazing 7 course Kaiseki of lives and other times, a romantic dinner alone at our hostel table with ham, cheese and wine from the local market.



Tickets To and From the Trail

How and when you are getting to the beginning of the end of your walking holiday? We like to leave at least one full day as a buffer when arriving in-case of any flight issue. Plan on delays!


Some places, have multiple transportation options. When traveling from Madrid to San Sebastian we had the option of train or plane. We chose to take the train because there were multiple times we could leave if our flight was delayed.


I'm Here, What Do I Do?

Local Transit


Walking injury or need to leave early? Familiarize yourself with the areas local busses, trains, cabs, how to pay for them, and where they are. Make sure to have local currency on hand just in-case.


D.I.N.K Tip: Download local apps for transportation for trains and busses ahead of time.


The Language

English speakers are everywhere but not everyone knows it. Learn a few words and phrases to help move the conversation along. If you like food, learn some basic words to help the flow of ordering. *Points to salad* | "Con cerdo por favor"!


D.I.N.K Tip: Download relevant languages on Google Translate.


The Area

Know the names of the towns you are coming from / heading to, they will come up in conversation. If you can, try to find out how the are pronounced ahead of time. YouTube can be helpful with this.


D.I.N.K Tip: Download the area in Google Maps / other map apps on your devices so you have access to them offline.


What's on The Trail?

Trail Specs

Distance and elevation. These two numbers can make or break your day. We learned this is Basque very quickly. When planning self-guided walks, try to keep it easy enough to enjoy. For company guided walks, wake up early, leaving enough time for breaks.




D.I.N.K Tip: Rule of 24k (15 miles). We try to keep our days around that MAX length. This allows us to explore the local towns at the end of our daily trek and wake up without crying. It also gives us a buffer in case we get turned around. If you want a more leisurely pace and your route allows it, bring it down to 16k (10 miles).


Trail Markings

Know how to read the signs of the trail and know the names of places. A lot of walking holiday routes are made up of other existing routes. For example, in Japan, we would see signs for unrelated trails that would take us in the wrong direction. We would have to look for 中山道 (Nakasendo) or learn the next city's name and find those signs.


Camino (Western Europe)

Nakasendo (Japan)


What to Pack?

Medical

We are human. We wear and tear. Even if you want to be a tough gal/guy/person, I still recommend being comfy. We have a first aid bag which we always bring with us and its used every time.


A layout of important medical supplies to bring on a walking holiday.
  1. Compeeds!

  2. Band-Aids for various wounds

  3. Tweezers for a ticks

  4. Small packs of bacitracin (antibiotic ointment)

  5. Asprin

  6. Anti-inflamitor spray (used it for an ankle issue)




Clothes / Shoes

Hot, cold, sun, rain... all of this can happen and you don't want an avoidable situation ruining an exciting day.


1) Important! Good Hiking Socks

A thick woolen, hiking sock will take care of you. This can make or break a walking holiday. Take care of those feet!

2) Waterproof Coat or Poncho

Of course, this depends on the season and if walking makes you hot. We often have fold up/disposable ones. Either pack one or keep an eye on local transit.


3) Good boots - Hiking and Waterproof

The better these are, the more walking you can do and the less Compeeds you'll use. You will learn this after your first day with elevation gains. Monserrat taught me this because I had something happen to my foot I prefer not to explain.


An example layout of clothing and supplies to pack in a backpack on a walking holiday

4) Layers

Again, you will get hot while walking no mater how cold it is. Leave space in your bag for your top layer, you will 100% take off after 15 minutes.



Gear

Example of packing for one bag
All fits in one bag
  1. Head Lamps - Some walking days may take longer than expected and it's good to have this just in case it starts getting dark (especially in fall/winter)

  2. Sunscreen

  3. Backup Battery for phones, lights

  4. Converters for outlets

  5. Walking Sticks

  6. Lip balm (Burt's Bees) - This is a life saver, can't explain it.


Luggage

We are a big fan of no checked bags . If you are planning your own trip, you have to carry everything with you. We use bags around 30L. This allows enough room for everything but isn't too big to schlep.


Who are You?

This is the most important part of walking. Know what you can do, can't do, and what you want to do. This is something you'll definitely learn during your first trip.


Fitness

We aren't close to competive athletes but we move around enough to prepare for walking holidays. Get an idea for what you are capable of. Walking gets exponentially harder the more you add onto it: distance, backpack weight, number of consecutive days walking, etc.


A brave dink couple ontop of a waterfall in Iceland

Final Thoughts

That all being said, every holiday we take, we end up choosing do some walking. You truly get so see the world this way. Every top ten list for a location will tell you the same places to go and they rarly change. But when you're walking, it's what catches your eye that makes the list, something unique to you. Nothing will ever compare to casually walking past a bodega mid-day with a hand written sign saying "Lunch Special". You will have no idea what the special will be, you do know it will be the best damn meal you will have.

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