Planned Travel Vs. Unlplanned Travel Vs. Whatever The Hell We Are Doing

Travel planning is one of my favorite things in the world. There’s receiving extra Chipotle meat without getting charged, there’s winning the Hamilton ticket lottery, there’s barrel aged imperial stouts with vanilla beans, and there’s planning a trip.

And for most of my travel career, I’ve been a believer in planning excursions to an upper case, bold-faced T (with shadow effects and a glitter background). The thinking being that because we were going so far (see also: spending so much money, taking so many days off work, ignoring the impending march of time) we had to make it worthwhile by seeing everything we possibly could. This doesn’t mean I’m the kind of traveler that has an itemized itinerary, 8 must-see attractions per day and a motorcade to get us from point A to points B through F. But it does mean that when I traditionally planned trips I would minimize “relax” days, push to keep transportation time to a minimum, and try not to miss anything in a reasonable radius of the place we’d worked so hard to get to. If you were to give me 3 extra days on a trip, I’m the kind of planner that would use those to fit in another whole city as opposed to another few days on the beach.

But Megatrip is different.

In fact, the rapid-fire nature of all of our previous adventures was, consciously or not, a big part of our desire for something more drawn out, more extemporaneous, and more unpredictable. Just traveling for the sake of traveling, without a stress aneurism if a flight gets delayed, or a line is too long, or (GASP!) you love a place so much you want to stay there a few extra days. We’ve experienced all kinds of travel, but time was always the limiting reagent. This trip, among a million other things, is an attempt to experience places without time being as big a part of the equation.

So then is this just a blank canvas of a trip? Absolutely not. We do have a rough outline, both in general trajectory and in countries/cities to hit within that trajectory. Not only that, but there are several things we knew we wanted to do that may have been difficult to book a just few days prior to arrival. Things like a private tour of Jordan or an overwater bungalow in the Maldives. These book up weeks/months in advance because people generally travel like responsible adults. But without that luxury or maturity, we had to find a solid middle ground.

So in the end, the most apt planning metaphor for Megatrip (megaphor?), is an ocean with several prominent, jagged islands in it. For the most part, the trip is fluid and dynamic. We book as we go and follow the current where it takes us. But, as we make our way across this megaphorical sea, there are certain solid points where we have to be at certain times. It’s less “Complete the maze on the Denny’s placemat”, less “Draw a portrait of your 3rd grade teacher from scratch” , and more “Connect the dots on your reckless life decision.”

And of course the beauty of this design is that a few months from now, this post will be woefully dated. Either pedestrianized or desperately yearned for in the wake of whatever this trip ends up becoming.