The Type A Guide to Spontaneous Travel

Winging it has advantages, even if you love planning your trips down to the minute

Photo by Jakob Owens on Unsplash

There’s something undeniably alluring about the idea of traveling without an itinerary: showing up at the airport with little more than a ticket in hand and a thirst for adventure, leaving the door open for whatever may come your way. Maybe you’ll have a whirlwind romance! Join a ragtag band of roaming street performers! Become a confident wearer of scarves! The world is your oyster, ready to be sucked from its shell and swallowed whole, probably at that adorable seaside café you just chanced upon while parading around with the street performers.

Or at least it sounds romantic and exciting. But for many of us, moving from idea to reality — that is, actually winging an entire trip — is the stuff that anxiety attacks are made of, particularly if you’re the type of person who usually plans a full schedule for even a casual weekend getaway, down to the route you’ll take to the dinner you reserved months in advance.

“Some people might think, ‘Oh, you’re so crazy. You’re not researching or planning.’ But you are — it’s just doing it on the fly.”

Is it even possible for a Type A traveler to enjoy a vacation when faced with the daunting prospect of a million unknowns? Can anyone who loves planning, logistics, and control really have a good time without a set agenda? The short answer is “yes and no.” The longer answer — based on a few more questions — can be found below.

Shouldn’t I Plan at Least a Little Bit? Please?

Yes. Rest easy, Type A traveler, because at least some planning is essential. First thing’s first: If you’re traveling internationally, you must check the visa and vaccination requirements of the country you’re visiting.

Next up: What’s the weather like? It’s a question that goes beyond packing: If you were hoping for an exotic beach vacation on a little-known Thai island, say, you should check to see if your trip falls within monsoon season. And always look to see whether your destination is having a major holiday or festival. I once visited Bolivia…