Q&A: To the End of the World and Back with Steve Hely

The writer (and all around funny guy) talks about his newest book, his big adventure, and why he won’t tell you where he ate along the way.

You’re never more aware of the absurdities of a place than when you’re witnessing them for the first time. That could be why travel and humor pair so well, as Mark Twain proved with books like Roughing It and The Innocents Abroad. This month, veteran jokesmith Steve Hely (The Office, Late Night with David Letterman) submits his entry to the “bumbling American comedy writers overseas” genre with The Wonder Trail, a hilarious account of his solo journey from Los Angeles to Punta Arenas, at the tip of Patagonia. Though the book is littered with wisecracks—he can’t help himself—it’s just as full of practical tips, fascinating historical trivia, and the kinds of sublimely ridiculous moments that are the reward of true adventure. I chatted with Hely about his trip, his yearning for Colombian arepas right about now, and his suspicion of any travel book with a poignant emotional climax.

About 10 years ago, you wrote a book called The Ridiculous Race with your fellow comedy writer/curious person Vali Chandrasekaran. How has your approach to travel and travel writing changed in the intervening decade? (Aside from doing it on your own now.) Even in that short span of time, the world's become so much more connected. It's easier to get WiFi anywhere, for instance. That's made it a lot easier to tune out your surroundings, but also easier to find fast and relevant information as you travel. On that trip I tended to rely on written guides and maps; this time I could log on to a travel forum in El Salvador and find places to eat or what street I was on.

This time around, did you miss the human element of the guides, and the imposed spontaneity of relying on paper maps? It can take the adventure out of things to know you can connect to WiFi and find your way out of a maze, but on the other hand, travel in Central and South America still has plenty of adventure, surprise, and spontaneity to it.

What was the thing you did on this latest trip that surprised you the most, that you could never have planned for in a million years? In Popayan, Colombia, I ended up at a birthday party for a stranger. I'd met some university students who were looking for tourists to interview for a school project. One thing led to another and I was at a birthday barbecue in the outskirts of town. The mother of the birthday kid, a young man, was really impressed that his friends were so international.

Your book weaves in so much fascinating tangential information—jumping from topic to topic in a narrative that runs parallel to your trip. Was it all from books you were reading while traveling? Were you constantly on Wikipedia while on the move? How did you do your research? Some of it I picked up along the way, from talking to people, visiting historic sites, or just trying to sort out how a place got to be the way it was. A lot of it I learned from reading after I got back.

The book has a diary-like feel. Did you keep a literal diary? One thing I did was write down everything I ate, every day. I don't know where I picked up this idea, but I found it's a great memory aide when you're trying to reconstruct days past. I scribbled a lot in tiny little notebooks. It just helps you remember where you were, what you were doing. Something about the vivid sensory connection maybe.

Speaking of that, in Mexico City you mentioned that you ate mostly street food. What is the most memorable meal you had on the whole trip? And is that the same thing as the best? Some fried arepas from a street cart in Cartagena come to mind as something I'd really like to have in front of me right now. The food in Peru is tremendous, there's so many different influences and unique vegetables. A Chinese restaurant I went to in Lima was also fantastic. 

As an editor at a travel magazine, my instinct is always to ask for specifics, but you deliberately didn't take that approach, saying you avoid doing travel journalism. Do you even remember the names of any of these places? Writing a book of recommendations wasn't what I was out to do—I wanted to just put together a collection of interesting, surprising, funny, bizarre, thought-provoking stories and experiences. But hang on I can find the name of the Chinese place… [long pause] Xin Xing in Miraflores.

What, from your initial checklist of things to see, lived up to your expectations? The Panama Canal completely lived up to the hype. I was picturing kind of just a dug canal, but the engineering ingenuity, the use of the natural landscape and the absolute maximization of ship size, so that enormous ships are BARELY scraping through, was mesmerizing to see. The vastness of the Amazon is also not a disappointment. I would love to take down Machu Picchu a few pegs, but the fact is it lives up to its dramatic reputation. Just a jaw-dropping location.

Do you regret not going through the Darien pass, disrupting the continuity of your journey? (Is that a spoiler?) No, no spoiler. I'm kind of curious about it, but sailing around it through the San Blas islands seemed a lot more pleasant than hacking through dangerous and lawless jungle. But the geography nerd inside me will always feel a little cheated that I can't draw a straight line of travel through that part of the map.  

What kind of travel writing do you find yourself drawn to? Well, I love reading true badasses who are slogging through war zones and camping out with guerrillas. But for myself, the activity and the experience of travel, and the nature of the world's absurdities make it seem unnatural to not be at least a little funny about it.

Where does this wanderlust come from? Were you naturally adventurous as a kid, or did it come in adulthood? From curiosity. I've always been curious about maps, about geography, about how places came to be the way they are. Whenever we were on a family road trip I would find some weird corner of the map and become obsessed with it. I remember begging my dad to drive us to Sydney, Nova Scotia.

If someone were making a Cheryl Strayed–type film of your trip, what would the emotional climax be, the bit where you just had this glorious sense of oneness with the world (if indeed that happened)? Well I get very suspicious of travel books that find a moment like that. I think a more real moment might be staring at the freezing Strait of Magellan after three months of traveling and realizing, hey this has been terrific but I'm lonely here and it's time to go home.

Out now from Dutton books; $27; penguinrandomhouse.com.


Photos: Courtesy Steve Hely / Penguin Random House