Europe Travel Basics

Why Over-Planning Travel is a Good Thing

April 30, 2016

In September, I kicked off this blog by telling you about my fantasy of visiting Europe for the first time. In January, I told you that fantasy was becoming a reality, and that I’d bought my plane tickets. But despite all that, I haven’t really talked much about my actual plans!

Honestly, I’ve just been so swept up in the millions of details, I haven’t even known where to begin in telling you everything. There’s always a lot to consider for any vacation, but that list grows exponentially longer when you’re on a budget…and have a limited number of vacation days…and are a solo female traveler…and, oh, yeah, when you’re so insanely prone to structure that one of the common nicknames for your Myers-Briggs personality type is “The Architect.”

Suddenly, you’re not just looking for any great hotel room. You’re looking for a great hotel room that’s also crazy inexpensive but also super safe and well-lit and in a great neighborhood that also happens to be really central to all the sights and is an easy journey from/to the airport so as to spend minimal time commuting. And you want to be able to book that perfect place months and months in advance so you can begin mapping out your routes around the city.

Nearly one year ago, when my Europe vacation was just a dream, I went through a giant stack of old Travel + Leisure issues to get ideas for a trip. And I cut out clips for an actual travel binder, because I am nothing if not obsessively organized.

Nearly one year ago, when my Europe vacation was still just a dream, I went through a giant stack of Travel + Leisure issues to get ideas. I cut out tons of clips and put them into a three-ring binder just for travel planning, and organized by destination, because I am nothing if not obsessively organized.

Phew. That’s quite a challenge. And despite beginning to think about this trip almost a year ago, I’m already thinking, “Holy cow, I fly in four months! I’m never going to have everything ready in time!”

(I actually only just realized my trip is just four months away by counting on my fingers, and now I’m honestly kind of terrified.)

Lots of people I know would scoff at this. But most people I know also don’t, say, optimize their shopping lists for maximum efficiency by listing all their items so they perfectly align with the counter-clockwise way they shop their local grocery store’s aisles. And that’s fine! But I do. I need to.

The thing is, though, there are thousands of articles and blogs out there pitting “over-planning” against “spontaneity,” dissecting the pros and cons of both, and all too often stating that over-planning travel kills the magic of trips and spontaneity is essential to avoiding disappointment.

I don’t buy that at all, and I think many of those writers are missing two key points:

  • There is a huge difference between planning every minute of your trip and planning too much for every minute of your trip. Don’t throw us Type A(ish), “over-planners” under the (tour) bus just because so many people are horrible with time management! These are two completely separate issues.
  • Your joy of spontaneity is not a universal truth. I know myself well enough to know that if I don’t have specific plans and goals for my day, I won’t get anything done. This is why I keep very obsessively detailed to-do lists, both at work and at home. (Seriously, without my lists I would just stay in bed all day with the great companion and love of my life, Netflix.)

And I think what’s key to any trip—and to life in general—is to be true to yourself. If you are a fly-by-the-seat-of-your-pants person and thrive on being unencumbered by a clock or plans, then that’s wonderful! Wonderful for you, that is.

For me? I do two very important things to make sure I have a great time:

I Plan to the Minute—But I’m Realistic

If it takes one hour to see the main sights at a museum, do you plan to spend one hour there?

I hope your answer isn’t “yes.”

What about the time it takes to get from the subway stop/parking garage/taxi stand to the front door of the museum? Waiting in line for your ticket? Dropping off your bag at the check-room? Grabbing a map and orienting yourself inside the museum? Bathroom breaks?

If you only planned an hour, you’re either going to end up rushing through everything you wanted to see in the paltry 20 minutes you have left, or you’re going to be late to the next stop on your itinerary (or miss it altogether!). Either way, you’ll end up disappointed.

That is where planning goes wrong.

So, really, when people criticize “over-planners,” they’re actually criticizing “under-planners.”

Because I may create packed itineraries with detailed time stamps for when I want to be somewhere, but I also take into account all those boring but necessary bits of the day that eat up a traveler’s time.

And, just as important, I remember to add an extra five minutes to each estimate—because you never know when you’ll miss a train and have to wait for the next one, or find the queue for tickets unusually long.

I Structure My Spontaneity

I do agree, however, that some of the best moments in life are those you never really planned for.

But because I have to plan for everything, I work to create spaces for these extra moments of fun. And I swear, it doesn’t suck the joy out of things! In fact, for someone as structured as I am, it actually helps me to let loose and be spontaneous by knowing I’ve giving myself the permission and the time.

For example, when I go to Spain in the fall, I plan to spend one of my evenings on a group tapas crawl. This is my bit of structured-yet-unstructured time for that leg of my trip. I obviously want to eat lots of amazing food as I travel, and this way I can check that off my to-do list for Spain. But I can also indulge in the unexpected, because I don’t really know what’s going to happen in those four or five hours. I don’t know where we’re going; I haven’t read the reviews on TripAdvisor. And I don’t know the people. Maybe I’ll go back to my hotel promptly after the tour and get a good night’s rest. Or maybe I’ll make new best friends and stay out all night.

Again, for someone like me, this is the perfect degree of spontaneity. Too much unknown, and I am paralyzed by indecision and wind up staying in, ordering room service, and lounging around in my hotel bathrobe for hours. (Which, by the way, is an amazing way to spend a day…but probably counter to the point of traveling across the world.) On the other hand, if there’s too little unknown, then I miss out on a major opportunity to challenge myself, and to experience something new.

It all circles back to knowing yourself, and being true to that. I know what kind of traveler—and person—I am. What about you?


Thousands of people will tell you over-planning travel kills the magic of trips and that spontaneity is essential to avoiding disappointment. They're wrong.

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