LAST UPDATED – 9/12/26 – Deciding Where to Travel

Planning a big trip can feel overwhelming for many people — it’s often their least favorite part of travel. Call me strange, but it’s one of my favorites. Everything feels new and full of possibility, like a blank slate waiting to be filled with upcoming adventures.

Because of that (and because others don’t enjoy the task), I usually end up planning trips for family and friends. Over the years, I’ve picked up plenty of tips and tricks — mostly by making mistakes, learning from experience, and listening to other travelers. I’m not claiming to be an expert… unless booking a hotel halfway up a Swiss mountain with almost no winter access counts as expertise.

You can always use a travel agent or join a group tour, and sometimes those options make perfect sense. But in many cases, they cost more and offer less value — and I’m all about squeezing every bit of value out of my travel budget.

That’s why I wanted to write about my process. I’ve been fortunate to travel a lot in recent years and to learn from countless people online and on the road. It’s time to pay that forward.

You might think I go overboard with planning — and you wouldn’t be wrong — but if even one idea from these articles helps you on your next trip, I’ll consider it a win. Feel free to ask questions or share your own tips in the comments. This is an open space for travelers of all experience levels.

So, let’s get started.

The W’s and H’s

Most of us learned the Five W’s in grade school — who, what, where, when, and why. Trip planning has its own version: the 3W/3H approach. It boils down to what you want to see, where you need to go, how you’ll get there, how long you’ll stay, when you should travel, and how much it will cost.

Unlike the Five W’s, these steps work best in order. The what determines the where, which shapes the how, which affects how long, which leads to when, and ultimately reveals how much. Following this sequence helps you avoid common mistakes like booking flights for the wrong season or not budgeting enough time.

In Part 1, we’ll focus on the What and the Where — the foundation of any trip. If you don’t know what you want to see or where you need to go, the rest of the planning process becomes guesswork.

To make this clearer, I’ll use a trip I’m currently planning to Ireland, Scotland, and London (along with a few past experiences) as examples. It’s always easier to explain with real scenarios.

The What

Let’s start with the “what.” This simply means deciding what you want to see — not just which cities, but the specific sights and experiences within and around them. If you want to visit Ireland, what exactly do you want to see there? You need this list before you can decide where to go.

Create a detailed list, including nearby attractions outside the main cities. You can always remove items later, but having everything in front of you prevents the regret of realizing you had time to see something and didn’t.

If you’re traveling solo, this part is easy. In a group, it gets trickier — especially when people want to see different things in different parts of the country. To manage this, have everyone make their own list and then rank their top 10 items, with 10 being the highest priority. These rankings become essential when you don’t have time to see everything.

People can list more than 10 items, but only the top 10 should be ranked. If you’re planning a longer trip, ranking 15 or 20 is fine — just don’t feel obligated to rank the entire list.

When everyone is done, each person should have a list with their top priorities clearly ranked and the rest unranked. This gives you a solid foundation for deciding where to go next.

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

Once everyone has submitted their lists, compile them and average the rankings for each attraction. Any item someone listed but didn’t rank gets a zero. After sorting the combined list by average score, you’ll clearly see which sights matter most to the group. This weighted list makes the tough decisions—especially about where to travel when time is limited—much easier.

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

The “where” isn’t about what you want to see — it’s about deciding where you need to base yourself to see it. Sometimes that’s as simple as choosing the right part of a city; other times it means picking the best hub cities in a country to reach everything on your list. It all depends on what you want to see.

In my example trip to Ireland, Scotland, and London, I first need to understand how long it takes to travel between the places on our list. But before I can figure out travel time from Point A to Point B, I need to know exactly where those points are — that’s the “where.”

To map this out, I mark each location on a map. Since we’re visiting three countries and travel time between them is significant, I created three separate maps. The Ireland map below shows how plotting everything visually makes it much easier to decide what fits into the itinerary and what may need to be cut.

As you can see, mapping out all the Ireland locations from the list makes it easy to visualize which places are close together and which are farther apart. More importantly, it shows exactly where everything is, giving you a clear starting point when you move on to the next step — figuring out how to see it all.

Coming in Part II

Now that you’ve figured out where you’ll base yourself, you’re ready for the next phase of the 3W/3H approach. In Part II, we’ll cover the “How” — how to get from one point on your map to the next.

We’ll look at choosing the right transportation (which varies widely by destination), avoiding common booking mistakes, and using hub locations to simplify long trips. This strategy can save you a ton of time and frustration — unless you enjoy hauling luggage across Switzerland every day. I learned that one the hard way.

Most importantly, trip planning should be fun. If you’re still unsure about your “where,” don’t hesitate to run through the process again or take a short break for clarity. Just remember: travel is meant to be enjoyable.

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