Bad Trips: Wonderful Essays about Awful Travel Experiences

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Vacations are sacred, especially in America, where we work longer hours than our counterparts in Europe and still aren’t legally entitled to a single paid day off. But what we often forget — that is, until we’re getting stung by a jellyfish or stranded at an airport — is that they’re also rarely the ideal escapes we build them up to be. In an essay about Disney World for last weekend’s New York Times magazine, John Jeremiah Sullivan reminds us. Since others’ holidays of misery make us feel better about our own failure to plan a summer vacation, we’ve rounded up some of our favorite tales of awful travel experiences, by authors including David Sedaris, Sloane Crosley, David Foster Wallace, and more.

John Jeremiah Sullivan on Disney World

Blood, ungodly heat, and a whole lot of marijuana turn up in Sullivan’s cleverly titled “You Blow My Mind. Hey Mickey!” The essay follows the author, his wife, their daughter, and another family on a roadtrip to Disney World. Complicated by bad weather, the other father’s pack-of-joints-a-day weed habit, and Sullivan’s ambivalence about the “Happiest Place on Earth,” the trip becomes a way of talking about the mega-theme park’s unsettling history. Did you know, for instance, that “Disney World is a giant mound, one of the greatest ever constructed in North America”? The park tourists know is actually about 15 feet off the ground, built on top of an intricate system of tunnels built to conceal off-duty characters and other not-so-magical sites. Then there’s the dark, weird origins of Epcot. Sullivan’s essay isn’t a straight-up condemnation of Disney, but it will definitely make you think twice before making plans to get back on that tram.

Sullivan photo by Harry Taylor

David Sedaris on Amtrak’s bar cars

David Sedaris has made a career on dramatizing his most embarrassing moments, in stories so conducive to uncontrollable laughter that we’ve had to stop reading them in public. But “Guy Walks into a Bar Car,” a piece Sedaris wrote for The New Yorker a few years ago, is more sad than funny. The essays follows our author on a train trip home from Chicago to New York, as he mourns the end of a six-year relationship and strikes up a brief friendship with a drunk who he’s drawn to because he finds “ruined-looking men” attractive. We meet the characters on the bar car — the guy who won’t stop telling terrible jokes, the woman in the “decorative sweatshirt” — and watch Sedaris hole up in a women’s restroom, high on pills and pot and alcohol. Not only is it a terrible moment in the writer’s life (pre-fame), but the piece also evolves into a meditation on aging, relationships, and diminishing opportunities for happiness.

Sloane Crosley on Lisbon

There are two great travel essays in Sloane Crosley’s wonderful second book, How Did You Get This Number . In “Le Paris!,” she explains why she and Paris have never gotten along. We’re partial to “Show Me on the Doll” (excerpted here), though, which finds Crosley alone in Lisbon. The solo trip is supposed to be an empowering celebration of her 30th birthday, but she spends much of it hiding in her hotel room, getting lost, and wanting to go home. She finally does meet some locals on her final night in town — and it turns out they’re hipster carnies!

David Foster Wallace on cruises

In the world of neurotic travel writing, no essay is as widely cited or celebrated as David Foster Wallace’s “A Supposedly Fun Thing I’ll Never Do Again,” originally titled “Shipping Out: On the (nearly) lethal comforts of a luxury cruise” when it appeared in Harpers in 1996. We fear that going into too much detail will ruin it for those of you who haven’t yet read the piece, so let’s leave it at this: Wallace, in all his hyper-footnoted glory, simply cannot submit to the totalitarian regime of pleasure that rules the American cruise industry.

Umberto Eco on America

Years before anyone had ever heard of Second Life, the postmodernist Italian philosopher Umberto Eco wrote a long essay called “Travels in Hyperreality,” chronicling America’s bizarre fascination with simulated reality. Eco takes on everything from holograms to wax museums to William Randolph Hearst’s California castle, with its loud and cartoonish mix of genuine art and gaudy reproduction. Our favorite part will always be his exploration of the Madonna Inn, a hotel in San Luis Obispo whose themed guest rooms represent everything from a caveman’s quarters to a Hawaiian tiki-themed chamber. “The Madonna Inn is the poor man’s Hearst Castle,” Eco writes, “it has no artistic or philosophical pretensions, it appeals to the savage taste for the amazing, the overstuffed, and the absolutely sumptuous at low price.” You can read the essay, which appears in a collection of the same name, at Google Books.

Gary Indiana on Branson

Writer/filmmaker/photographer Gary Hoisington may have adopted as his pseudonym the name of a Midwestern city, but rest assured he has little love for Middle America. The title of “Town of the Living Dead,” a Village Voice piece that appears in his collection, Let It Bleed: Essays 1985-1995 , pretty much sums up Indian’s thoughts on Missouri’s own country-music mecca. From theme parks to the Osmond Brothers, Indiana points out that Branson represents the ultimate in reactionary nostalgia, whose visitors are “profoundly out of whack with the trajectory of American popular culture, which, for all its inanity, is generally libertarian, multicultural, and secular.” Or, to put it less gently, he describes the city as “the tightest little cultural sphincter you are likely to find in the United States.”

Rachel Shukert on Europe

A freshly graduated (and flat broke) Rachel Shukert uses an unstamped passport and a trip overseas as a bit player in a theater production to wander around Europe in search of, well… she isn’t quite sure. There’s love, intoxication, and other forms of embarrassment in Everything Is Going to Be Great , but (luckily for those who aren’t big on 20-something navel-gazing) Shukert makes it all funny. Bonus: The book doubles as an irreverent travel guide, featuring everything from “Foreskin FAQs” to a brief guide to the Dutch obsession with Phil Collins.

Ian Frazier on getting sick while traveling

In a piece for Outside magazine, New Yorker writer Ian Frazier tackles the ultimate vacation bummer: getting sick while we’re traveling — and why it seems to happen so often. “A Kielbasa Too Far” combines anecdotes from Frazier’s own life with a substantial history of diarrhea (which the author has the delicacy not to name) in travel literature of the past, some tips (“Alcohol, in strengths you drink, does not purify anything”), and a conversation with a doctor who notes the prevalence of travel-related psychosis. It’s enough to make you want to stay home. Almost.

Illustration by David Hughes at Outside