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

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.

My therapist used to explain it to me with children. There’s that age where little kids are toddlers, and they want to walk away from their mom. But, it’s very important to look back and still be able to see their mom. And they’re only able to go as far as they’re able to look back and see that they have that stability to go back to.

I also heard — not from my therapist but from a friend of mine who is a psychiatrist — about how I had gone through a breakup at the beginning of the year, and breakups are never fun. It was just a very bleak winter for me, I had also just moved over to New York. I had left L.A. And I was having a really rough time being alone. And one day, I just realized not only was I not going out every single night anymore, but I was completely at peace by myself, drawing cartoons, and reading books and watching movies, and going out whenever a nice opportunity presented itself.

I brought it up to her. I was like “I think I’m kind of able to be alone more now.” And it’s also why I like to travel. It’s always a good practice of leaving my comfort zone and learning about myself.

And you’re not just traveling, you’re traveling. You’re a world record holder, which isn’t something most people associate with travel. Explain what the world record is for, and then just tell me a little bit about that trip.

The world record was for the longest journey by car in one country, which really means longest road trip. It is not the longest; the longest road trip is still going on. I don’t know exactly, but it was started in the 70s I believe. It was a company, they’ve been to like a billion countries. The record that I hold is that me and my ex-girlfriend, Heather, hold the longest road trip in the confines of one country. The reason I wanted to do that — Heather certainly didn’t want to do that; I don’t believe — but the reason I had to do it was because I’d read every single book that Kerouac ever wrote. I was a huge fan when I was locked up as a kid. It was what I read; that’s how I busied myself. I follow a lot of travel bloggers. I read a lot of books about travel. And, I just I felt like I needed to be a part of the conversation. I also felt like I had done more traveling than many of the people that were talking about it. I really wanted to join the conversation a little bit. I also wanted to challenge myself in a way that I had never challenged myself. ‘Cause I had done a billion road trips by that time.

I took a 200-hour train ride. I’ve probably driven in the hundreds and hundreds and hundreds of thousands of miles on the road. And I didn’t feel like I had anything to show for it. I kind of wanted something material to represent it. It’s kind of like a tattoo for my travel experience. So, that’s what the world record is. That’s what it was; that’s what it still is. And I don’t know… does that answer part of your question at least?

Yeah, yeah. How many days were you gone?

We were gone for 122 days, it was 36,123 miles. And, we slept in the car; we never stopped. I mean we stopped a few times, but more or less, it was 122 days straight. Not only do the days start blending together, but like time just becomes this thing where sometimes it’s light and sometimes it’s dark. The hours don’t mean anything, the minutes don’t mean anything, the dates, nothing. The weekends, the months, nothing means anything. It’s just, “Okay we drive when it’s light, we sleep when it’s dark.” And everything else happens organically. I don’t know.

It was coming to peace with the mundane, all of a sudden realizing the mundane is all we have. And it’s living life to the fullest, but enjoying nothing. Like being able to enjoy nothing. I don’t know if this sounds crazy. But you know, after jumping off cliffs and doing this and doing that, eventually you just kind of reach … This was way before the road trip too, where my life had been so crazy and full of ups and downs that there really wasn’t anything that could bring me up. By the time I was probably about 26/27 (I’m 33 now), there was just absolutely nothing that got me off anymore, so to speak, in life.

I think people would be quite surprised about how I travel not for adventure. It gets boring writing from the same café. It’s interesting to remind myself we all want the same thing. It’s like no matter where you are, third world country, first world country, Europe, South America, Canada, Mexico, the people are all the same and everybody wants the same things. Like everything, what is important to us is important to them. Everyone values the same shit. I don’t want to put everybody in a nutshell, but more or less, it’s friendship and laughing. Those are the two things it seems like everybody wants, no matter where I go. It’s interesting to me to remind myself of that, and I don’t know. I’m kind of going off on a tangent here.

This relates to something I was curious about. About being present in these trips. You wrote about how to have car sex for Elle, and I was like “Wow, I wouldn’t have thought of that angle. That’s brilliant. Way to milk everything you can out of a trip.”

But do you actually get to remain present for these trips, or do you get wrapped up looking for angles or viewing things as a writer?

That’s a really good question. I do. I think looking for angles is my work, so I don’t think I necessarily get wrapped up in it. I think that what I do for a living appears to be nothing. And it appears as if I spend my whole day possibly writing about weird shit, taking weird photos, and coming up with odd ideas. And taking odd adventures. But I’m just doing what I’m best at, and what I’m best at is meeting people and telling stories about what it was like with those people. At least, that’s what I see myself as being best at. So yeah, I do find myself a little wrapped up in social media and taking pictures, and it is hard to stay in the moment sometimes when I know that I want to get to a certain landmark at a certain time in order to take a picture, in order to post it at the right time, in order to get the photos that I need for a particular article.

The time to stay present is obviously the whole day. But, I put my focus on the morning. I spend the first three or four hours of every single day meditating, journaling, doing breathing exercises, visualizations, reading. No matter where I am, that’s kind of where I touch base with myself. There are some days where I’m wrapped up in taking pictures and then writing stories like what the picture’s about, for sure. And there are other days where I do absolutely nothing but sit on a bench and drink mate with a friend and laugh. And usually, those are the best of days.

The answer is yeah. I do think of that often, and I think staying present is a huge part of where I put my focus. Just because it’s hard to experience anything, your head is either in the future, the past, or the present. If it’s in the future, it’s probably worried. If it’s in the past, it’s probably resentment or regret. There’s just simply no other way to live life. You can’t actually cope, not to steal any lines from Eckhart Tolle, but I think he nailed it when he said you cannot cope with the future and you cannot cope with the past ’cause it’s not currently happening.

I wouldn’t say that I get wrapped up in life and the distractions of life any more than other people. I think your question would be a good question for absolutely anybody; you know what I mean? ‘Cause if I had an office job, I would be equally as happy if I were able to stay equally as present.

You just started a new trip, and from what I’ve read, you are adamant that you don’t seem to have much of a plan. I guess you’ll be super present then ’cause you’ll have to figure stuff out every day.

That’s exactly what it is. Like, that’s exactly what it is. My work, half of my work, is organization. I don’t want to have too many plans. Plans are just kind of a trampoline to fall back on if everything falls apart.

I am structuring the trip, so I do spend a lot of time researching. Because I mean there have been many trips where I went there with absolutely no plans and literally nothing got done. I spent a couple months, something like that, in Argentina. And, I had so many friends there that I ended up doing nothing. I did have a great time. I did meet some awesome people. I did experience the culture of one particular place, Buenos Aires. Because I had absolutely no plans, I felt a bit more reliant on the plans of others. And that’s never fun for either party.

But you have intentions, right? Even if you don’t have plans? Plans feels very formal, but I get the impression there’s definitely things you intend to do.

Yeah, I intend to learn Spanish fluently. That’s probably number one. I intend to finish my second book. I would put them equal. I want to finish my second book as much as I want to learn Spanish. It’s funny, because I have friends all the time that send me maps, or ideas, adventures that they read about in some magazine, or whatever. And my friend Holly sent me this picture. I think. I’m pretty sure it was Holly. If not, I’m giving her credit. But I think she sent me a map of South America and was like “You should do this.”

I posted it as a joke and got inundated by emails and messages from people that were so excited. All these people that I had met in hostels and Airbnb just throughout my decades of travel were offering me places to stay. And those people that I didn’t know were there putting me in touch with people that I didn’t know and other places. It turned into this thing where I was like, “All right. I love telling a good story, and this is obviously a story that people want to hear. And why not? Let’s do it.”

My third intention is to actually finish what started out as a joke, just kind of to do it. You know, why not?

To follow along with Greg on his trip, read posts on his website and follow him on Instagram and Twitter.