A Record Setting Road Tripper Opens Up About His Next Great Adventure

Life & Culture Writer

Until Greg Cayea came into my life, I didn’t even know there were Guinness World record holders in the category of travel. Now that I do know, it seems logical because much of traveling is about reaching milestones. You gotta get those passport stamps. You gotta come correct with your Instagram. Why shouldn’t you be lauded for being the youngest person to visit every sovereign country? Or, in Cayea’s case, for taking the longest journey by car in a single country? It’s totally sensible (the acknowledgment of the record, not taking a car ride that lasts for months).

Now, Cayea is off to circumnavigate South America. Alone. Without a plan. Seems a little odd; sounds a lot awesome.

In person, Cayea doesn’t quite feel real — with his film star good looks, cool kid style, and vagabond lifestyle. He’s one part Kerouac, one part Holden Caulfield, and one part my favorite Portland barista. As if his charming personality and willingness for introspection weren’t enough to make him a blast to talk to, he comes with the wealth of unusual life experience. Dude has started a PR firm; promoted tons of concerts; produced a film starring Nelson Mandela, Sidney Poitier & Dennis Haysbert; written a book; started a rolling paper company; produced 143 one-act plays in NYC; launched a late-night theatre/ vaudeville/ burlesque festival; and been repped by William Morris. If you met him in a bar, you would buy him drinks, just to keep him near you, telling stories.

A week into his South America adventure, Cayea made time to talk to us from Uruguay about his wanderings, why he travels, and his world record. And, even though he’s adamant that this trip is without a firm plan or itinerary, he did identify some of his goals, which are surprisingly practical for a man who feels like wanderlust personified in a Puckish modern form.

Did you grow up traveling?

Kind of. I got into a lot of trouble as a kid, so I was shipped across many state borders to many different kinds of reform school/ bootcamp/ rehab type of places, from like 14 years old on. I suppose that was the beginning of when I started traveling. At some point, I ran away, I escaped from the last place I was, and I was hitchhiking around, squatting around the country until I was about 18. I never really stopped. I’ve settled down in places for multiple years, but I think the longest place I ever lived was in L.A. I lived in L.A. for five and a half years, but I would say I only spent about six or seven months of the year in the actual city, and the other months were spent on the road or in another country or whatever. Mostly on the road.

I don’t know if the answer to that is yes or no, but I guess I’ve always felt most at home traveling because I never really grew up with a clique of friends. I enjoy meeting new people, and I think that’s where my comfort zone is.

I completely understand. New relationships are fun.

You’re right; that’s a good way to put it. And I don’t want to go so far as to say I still flee the fear of intimacy because I don’t anymore, really. Now, it’s a different bit of motivation. I think I do feel at home meeting new people. I also have a very deep relationship with my family now.

I read this article (I don’t know if you’d consider it an article). It’s a study or a paper that was written in the 50s about the capacity to be alone. If you’ve read it, please stop me because I’m about to paraphrase this horribly. It’s basically all about how the power to be alone comes from the ability to know deep down inside that you’re not alone and to foster deep relationships with those around you. I think that’s kind of what’s given me the ability to continue to travel.

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