The Joy of Planning Trips I’ll Never Take

The weather is perfect. You get to do everything on your list. No one gets food poisoning or giardia or blisters.

It’s well-documented that we actually enjoy the anticipation and planning of vacations more than we enjoy actually going on our vacations. (Photo: Brendan Leonard)
It’s well-documented that we actually enjoy the anticipation and planning of vacations more than we enjoy actually going on our vacations.

Throughout the pandemic, we'll keep publishing news to help you navigate the state of travel today (like whether travel insurance covers the coronavirus), as well as stories about places for you to put on your bucket list once it's safe to start going more far-flung.

I was opening a fifth browser tab when I caught myself. Researching a 600-plus-mile bikepacking route had nothing to do with what I needed to get done. I was just procrastinating, and my inner disciplinarian caught me and wagged his finger disapprovingly. I closed the tabs and went back to battling my unread emails. I mean, I’m never going to do that bike trip anyway. Why waste the time on it?

But wait—is that really that bad?

On a shelf at home, we have a stack of 59 maps, which, if spread out, I believe would wallpaper every interior wall in the house. We have dozens of guidebooks, from Lonely Planet guides covering entire countries to books detailing rock climbing routes in a single national park. Have we been to all these places or used even 5 percent of the information in each of these guidebooks? No, we have not.

You could argue that the purpose of these tools—maps, guidebooks, the websites and online mapping resources—is to plan things. That is the obvious purpose. As you’re buying a guidebook at a bookstore, the sales associate ringing you up might ask, “Planning a trip?” and you might say yes because the trip is on your calendar, you have the flights, but you want some information on where to go and what to do.

Or you might say yes because you are loosely “planning” something that your ideal self might get to do someday when things line up correctly, or maybe not, but what’s the harm in learning more about that country or destination or national park and imagining yourself being there sometime?

It’s well documented that we actually enjoy the anticipation and planning of vacations more than we enjoy actually going on our vacations. In your daydreams before the trip, no one camps too close to you. Your flights are never late. The weather is perfect the entire time. You get to do 100 percent of the things on your list. No one gets food poisoning or giardia or blisters or altitude sickness. You imagine it being amazing. And then it happens, and some things go wrong, maybe the whole thing goes wrong, and it’s not quite perfect, or far from perfect, but it’s an experience. And as the months and years stack up afterward, the trip becomes just as rosy in your memories as it was when you were planning it.

Or you just dream about the trip, clicking around the internet, looking at photos and maps, and you never actually go. And it stays perfect in your head, with no disappointment, exactly like all the romantic relationships you had with celebrities from the ages of 14 to 18 that ended up existing only in your head.

Have you ever read articles like “The 10 Best Hikes to Waterfalls,” “The 7 Best Weeklong Backpacking Trips in the U.S.,” or “The 7 Best Ridge Routes”? I have written many of those articles over the years, and for me, the research is the best part. Because no one’s paying a writer to do all eight or ten of those trips before you write the piece. But holy shit, the dreaming you get to do, imagining yourself leading the pitch-four hand crack, getting that view from the top of peak X or alpine lake Y on day three, or watching a sunset from somewhere without windows—that’s what makes it fun.

No matter who you are, I would guess you won’t get to do every single thing you want in life. Doors close on certain experiences as time passes and we get older: OK, I guess I’m not going to play in the NBA. OK, I guess I’m not going to live in New York in my twenties, now that my twenties are over. OK, according to my doctor, I will not be able to eat pizza every single day of my life. But why focus on the stuff we can’t do anymore?

I am not as good at practicing gratitude as several of my friends are, but I have to remind myself every once in a while that I’ve gotten to do plenty of amazing things I never imagined I’d get to do. Especially during a pandemic, when travel, even a couple hours away from home, often feels like a risk, and I spent more time at my desk than in any 12-month period of my adult life. Like many people, I planned almost nothing, and any suggestion of A Thing We Could Do When This Is Over seemed like too big of an emotional risk, so let’s just sit tight and be patient for now, for now, for now, for a few more months, OK, a year, OK, who knows.

But as hope for normalcy starts to seep back in, slowly and gradually, I find myself starting to look at maps again, and websites, and calculate logistics I may never need: Could it be done in six days? When’s the busy season? Is it doable without a mountain bike? How much does the map cost? And I think that’s a sizable chunk of the fun.

Brendan Leonard’s new book, I Hate Running and You Can Too, is out now.

Filed To: Travel EssaysBooksClimbing
Lead Photo: Brendan Leonard