LAST UPDATED – 7/27/23 – Deciding Where to Travel

Planning a big trip?  For some people, this can be a daunting task.  For many people, this is their least favorite part of taking a trip.  Call me strange, and I probably am, but this is one of my favorite parts.  Everything is new and exciting, like a blank slate waiting to be filled in with all of your upcoming adventures.

Perhaps it is for these reasons (other’s disdain for the task and my enjoyment of it) that I am typically tasked with planning trips with family and friends.  And it is likely a result of this that I have picked up on so many tips and tricks along the way.

Now, before I get too far into outlining my process, let me be the first to say that I am in no way claiming to be an expert.  Unless of course, you call someone who has booked a hotel up a mountain in Switzerland with little access in or out in good weather, let alone a snowstorm, an expert.

Nope, I am just a guy who has made a lot of mistakes, and learned a lot from experience and talking to others, who might have a few insights to point out.

You always have the option to use a travel agent to book your trip or take a group tour, as both options can make a lot of sense in some circumstances.  However, in many cases the prices you get from a travel agent or for a group tour will give you much less bang for your buck.  And I am all about squeezing in as much value for my travel dollar as I possibly can.

That is why I decided to write on this topic.  I have been extremely fortunate to have been able to travel as much as I have the past several years, and extremely fortunate to have learned as much as I have from people on both the Internet and while traveling.  It’s time to pay that forward.

You might read this article and think I am crazy about how overboard I go in planning my travel, and you probably wouldn’t be crazy for thinking that.  But if you take just one thing from these articles and put it to use in your travel adventures, then I will have done my part.  By the way, don’t be afraid to ask questions or leave your own travel tips in the comments section.  This is an open forum for travel enthusiasts of all levels.  All are welcome, and no feedback is unwelcome.

So, let’s get started!

The W’s and H’s

I’m sure most of you are probably familiar with the Five W’s from grade school.  When writing a story, it is always important to come up with the Five W’s: The Who, the What, the Where, the When, and the Why.

Well, when it comes to planning a trip, it’s the three W’s and three H’s. For simplicity’s sake, let’s call this the 3W/3H approach.  They can be most easily described as the What, the Where, the How, the How Long, the When, and the How Much.  Figure these out, and you will be well on your way to planning a successful trip.

The big difference between the Five W’s of story writing and the 3W/3H approach to trip planning is that the Five W’s can be determined in any particular order.  You can determine the who before the what, the what before the who, and so on.

However, with the 3W/3H approach to trip planning, it is always best to go in sequential order.  The what determines the “where”, which leads to the question of how, which determines the “how long”, which leads to the “when”, which all adds up to the how much.

Instead of diving headfirst into your trip planning, booking your flights, then realize that you either booked your trip for the wrong time of year, or for not long enough, it is always good to let your trip planning progress from the most basic of principles, what you want to see, all the way to the end result of how much is it going to cost you.  Then you can always go back and make adjustments should the “how much” be too much.

In Part 1 of this article, I am going to talk about the What and the Where.  These are essential first steps in planning any trip.  After all, if you don’t know what you want to see and where you need to go, how are you going to make any of the other travel decisions that probably have your head spinning?

To help illustrate this process, I am going to use a trip I am currently planning to Ireland, Scotland, and London (as well as some past experiences from other trips I have taken) to illustrate.  It’s always easier to explain with examples.

The What

So, let’s begin with the “what”.  Simply put, this is a matter of what you want to see.  And I don’t mean just which cities you want to see, but what you want to see in those cities.  You want to go to Ireland?  What is it in Ireland that you want to see? You must determine this before you start deciding where to travel in Ireland.

Create a list.  And don’t just limit it to things you want to see in the city, but things you want to see in the surrounding area.  You’ll be surprised at how much you can fit in and at what cost with some proper planning.  One of the biggest disappointments for me when traveling is getting back from a trip and regretting not stopping to see something when I had time I didn’t think I would have.  Anyways, you can always cross things off later if it doesn’t work out.

If you are traveling by yourself, this will be easy.  Just create a list of what you would like to see.  However, if you are traveling with others, it can be more difficult.  This is especially true if you are traveling in a large group.  There may be some things you all want to see, but I am guessing there is going to be some disagreement on other things.  In some cases, this can be solved by simply splitting up.  However, what happens if people want to see different things on different sides of the country?  That can be more difficult when it comes time for deciding where to travel.

Here’s what you can do.  When you have everyone put together their list of what they would like to see (remember, be specific), have them rank the Top 10 things they would like to see in order (“10” being the Top 10 thing they are most anxious to see and “1” being the Top 10 thing they are least anxious to see).  Ultimately, you are going to use these rankings when it comes time for deciding where to travel if you don’t have enough time to see everything that everyone wants to see.

Now, people can list more than 10 things, but only have them rank 10 items. Everything else is unranked.  If you want to rank the Top 15 or 20 places because you’re planning to take a long trip, that is fine to.  Just don’t feel obligated to rank everything on the list.

When you are done, you should each end up with something like the list below.  Notice how the top 10 items on the list are ranked from 10 to 1 in decreasing order, and the other items on the list have no ranking.  This is what you want from everyone.

Attraction	Rank
Cliffs of Moher	10
Giant’s Causeway	9
Edinburgh Castle	8
Blarney Castle	7
Dark Hedges	6
Loch Ness	5
Tower of London	4
Edinburgh Castle	3
Ring of Kerry	2
Old Head Golf Links	1
Sherlock Holmes Tour
The Highlands
Rosslyn Chapel
Dromoland Castle
Big Ben

When everyone has gotten their lists back to you, the next step is to compile the lists and then average out the rankings for each attraction.  For the items that people listed, but did not rank, they will get a zero for the ranking.  That should leave you with something like this (notice I sorted the compiled list by average ranking). This is going to add some weight to the things that the majority of people feel the strongest about seeing, so it will really help make those difficult decisions a little easier when deciding where to travel on your trip.

Attraction	Josh	Nick	Mitch	Brad	Pat	Avg
Ring of Kerry	6	10	6	8	9	7.8
Cliffs of Moher	10	5	5	9	8	7.4
Edinburgh Castle	7		8	10	10	7
Old Head Golf	8	8	10	7		6.6
St. Andrews Golf	5	7	9	6		5.4
Giant’s Causeway	9	9				3.6
Cahir Castle		2		2	7	2.2
Tower of London		4		3	3	2
Tower Bridge		3	3		4	2
Blarney Castle					6	1.2
Big Ben	2			4		1.2
Sherlock Holmes Tour		6				1.2
Dromoland Castle Hotel					5	1
Loch Ness				5		1
Aran Islands			2		2	0.8
Carrick-a-Rede Bridge			4			0.8
Rosslyn Chapel	3					0.6
Dark Hedges	1	1			1	0.6
The Highlands				1		0.2
Dublin						0
Galway Cathedral						0
Tantallon Castle						0
Westminster Abby						0
Trafalgar Square						0
London Eye						0
Churchill War Rooms						0
Slieve League Cliffs						0

This gives us a great starting point from which to plan the trip.  Now that we know “what” everyone wants to see (with the added bonus of how badly they want to see it), we can start to figure out the “where”.

The Where

If you haven’t figured it out already, the “where” isn’t so much about what you want to see as it is about deciding where to travel, or more importantly stay, to see it.  The “where” can be as simple as what side of the city you plan to stay in to get you the closest to the majority of the attractions you want to see, or as complex as which cities in a country you should use as hubs to allow you to explore as much of the country as possible.  It all depends on what you want to see.

In my example, we are planning on visiting Ireland, Scotland, and London.  Before I can figure out how much of the things on our list we can see, I need to know how long it would take to get from one place to the next.  From Point A to Point B, if you will.  But before I can figure that out, I need to know where Point A and Point B are.  That is the “where” in the equation.

To do this, I take a map and then put a marker (or pin) on that map for each place on the list.  Since we are hoping to visit three places:  Ireland, Scotland, and London, and I know it will take considerable travel time to get between these places, I chose to create three separate maps.  The map I created for Ireland is below. This map is going to really simplify the process of determining how much you can fit into a trip and what to leave on your itinerary and what to take off when deciding where to travel.

As you can see above, I have all of the places on my compiled list that are in Ireland laid out on this map.   This allows me to conceptualize how close some of these places are to one another, and how far apart from one another others are.  More importantly, it lets me know exactly where each of these places is, so when it comes time to figure out the “how”, as in how to see each of these places, I’ll have a place to start.

Coming in Part II

Now that you have completed the process of deciding where to travel, you are ready for the next phase of my travel planning process. In Part II of this article, I will be discussing the “How” in the 3W/3H approach.  We will begin to look at how exactly you plan to get from one place on your map to the next place on your map, to the next.

I will talk about how to choose the right transportation to use on your trip (this can differ greatly depending on where you are traveling), and how to avoid some of the common mistakes people make in choosing and booking transportation.

We’ll also start to look at my favorite logistical tip in trip planning, which is to use hub locations for long trips.  Believe me, this can save you a TON of time and headache when taking long trips abroad.  Unless of course you absolutely love lugging your suite cases around Switzerland every day.  Yup, I made that mistake too.

Most importantly, planning your travel is supposed to be fun. If you complete the first phase of this process and still unsure when deciding where to travel, don’t be afraid to run thru the process a few times. Sometimes, even taking a little break from planning can give you some clarity. Just remember to have fun as travel is supposed to be fun!

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