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How I Learned to Stop Overplanning My Travels and Go With the Flow

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At some point over the past few years, I realized I’d forgotten how to travel—and as a travel writer, that was a bit of a problem. The pandemic changed almost every aspect of my job, my lifestyle, and indeed, my very identity. While a more mature writer might have spent lockdown reflecting on the meaning of life and how to be a better human—or you know, writing—I spent it mostly just… feeling sorry for myself. 

So when I started traveling internationally again in 2021, I did so with an insatiable, voracious energy that probably made me a fairly tedious travel companion. I made traveling—even on personal vacations—feel like work. I ignored my own interests and desires in order to see and do as much as possible. I felt like I had to make up for lost time, that I had to squeeze every last drop from every day that I was traveling, because I didn’t know when the next COVID wave—or world war—would strike, shutting down borders. 

Before each trip I’d scour “best of” lists, painstakingly creating custom Google Maps with hundreds of places I wanted to see. I’d make a point to visit crowded museums and mediocre cafés solely with the intention of becoming a better traveler and a better travel writer—I never wanted to have a conversation with somebody where they said “you went to insert city here and didn’t go to insert activity/museum/restaurant here?!”

I’d return home from trips exhausted—and exhausted with myself. Seeing the things I was supposed to see and eating at the places where I was supposed to eat had become the sole impetus for my vacation. Somewhere among that, I forgot to leave room in the itinerary for, well, having fun.

That changed when I got an invitation I couldn’t refuse. A week in Patagonia, leaving in six days. I didn’t have time to research and plan and make a map of all the places I want to visit. In truth, I wasn’t even 100 percent sure where I was actually going until we got there. I was familiar with the broader sweeps of what a Patagonia trip might look like, of course, having seen photos of El Chalten and having heard about epic hiking trips in Torres del Paine. But when I looked on the map, I couldn’t even find the new lodge where we’d be staying. I tried to figure out what the weather would be like when I arrived, but I had no idea where the nearest town was. So I gave up trying and decided to sit back and just let the trip happen. After all, I was traveling with Extraordinary Journeys—a luxury safari operator I’d traveled with before—and I knew I’d be in safe hands.


At some point over the past few years, I realized I’d forgotten how to travel—and as a travel writer, that was a bit of a problem. The pandemic changed almost every aspect of my job, my lifestyle, and indeed, my very identity. While a more mature writer might have spent lockdown reflecting on the meaning of life and how to be a better human—or you know, writing—I spent it mostly just… feeling sorry for myself. 

So when I started traveling internationally again in 2021, I did so with an insatiable, voracious energy that probably made me a fairly tedious travel companion. I made traveling—even on personal vacations—feel like work. I ignored my own interests and desires in order to see and do as much as possible. I felt like I had to make up for lost time, that I had to squeeze every last drop from every day that I was traveling, because I didn’t know when the next COVID wave—or world war—would strike, shutting down borders. 

Before each trip I’d scour “best of” lists, painstakingly creating custom Google Maps with hundreds of places I wanted to see. I’d make a point to visit crowded museums and mediocre cafés solely with the intention of becoming a better traveler and a better travel writer—I never wanted to have a conversation with somebody where they said “you went to insert city here and didn’t go to insert activity/museum/restaurant here?!”

I’d return home from trips exhausted—and exhausted with myself. Seeing the things I was supposed to see and eating at the places where I was supposed to eat had become the sole impetus for my vacation. Somewhere among that, I forgot to leave room in the itinerary for, well, having fun.

That changed when I got an invitation I couldn’t refuse. A week in Patagonia, leaving in six days. I didn’t have time to research and plan and make a map of all the places I want to visit. In truth, I wasn’t even 100 percent sure where I was actually going until we got there. I was familiar with the broader sweeps of what a Patagonia trip might look like, of course, having seen photos of El Chalten and having heard about epic hiking trips in Torres del Paine. But when I looked on the map, I couldn’t even find the new lodge where we’d be staying. I tried to figure out what the weather would be like when I arrived, but I had no idea where the nearest town was. So I gave up trying and decided to sit back and just let the trip happen. After all, I was traveling with Extraordinary Journeys—a luxury safari operator I’d traveled with before—and I knew I’d be in safe hands.

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