Why We Can’t Quit the Cruise Essay

In March of 1995, David Foster Wallace went on a cruise. More importantly, he wrote about it.

The piece, originally titled “Shipping Out,” filled 24 pages of Harper’s with Wallace’s alienation from the “structured fun” and “nearly insanity-producing pampering” of a massive Celebrity Cruises vessel. All that fun drove the self-proclaimed “semi-agoraphobe” to frequent retreats to his cabin, meditations on mortality, and solitary gazes at the sea. His dry descriptions of conga lines, conch fritters, and the “sheer and surreal scale” of the ship struck a chord with readers mystified or repulsed by the ubiquitous cruise ship marketing of the 1990s. 

It was a terrific fit for the audience at Harper’s—an outlet portrayed by The Onion as the natural reading material of the “Area Man Constantly Mentioning He Doesn’t Own A Television” in a humor piece from 2000. It also helped bring a new generation of readers to the magazine, including Harper’s future editor-in-chief Christopher Beha, as he wrote in 2021.

“I think his brutal honesty about cruise ships was really appealing to a lot of people,” Chuck Thompson, author of the travel writing memoir Smile When You’re Lying, told me. “A lot of people who probably harbored misgivings about cruises, and even the people who enjoy cruises, because, you know, people like to laugh at themselves as well.” 

The piece would later be retitled and anthologized in Wallace’s essay collection of the same name, A Supposedly Fun Thing I Will Never Do Again, a now-classic title referenced everywhere from The Simpsons to a chapter of Tina Fey’s memoir Bossypants about her honeymoon. It also paved the way for dozens of first-person stories from cruise ships over the past three decades, including dispatches from successive holders of the record for largest ship, accounts of concerts and music festivals at sea, and reports from special interest voyages for conspiracy theorists, Gone Girl superfans, and self-care enthusiasts. The “cruise ship story” has become a genre in itself, persisting even as budgets for travel reporting, and really any journalism requiring resources beyond an internet connection, dry up.

“To journalists, a ‘cruise piece’—in addition to being a free vacation you’re paid to express all your darkest thoughts about—is a career achievement; it carries associations with the great cruise piece of 1996… indeed also published in this swanky East Coast magazine,” wrote Lauren Oyler last year in her own well-received Harper’s piece about Gwyneth Paltrow’s Goop cruise, a voyage which she wrote hosted enough journalists to populate their own WhatsApp group and a tour of the vessel just for press.

But Wallace’s essay wasn’t the first sardonic report from a pleasure cruise. One clear forerunner is Mark Twain’s The Innocents Abroad, an 1869 account of his newspaper-sponsored journey on a guided sea tour of Europe and the Middle East. It was praised at the time for Twain’s “dry, self-contained, unobtrusive and pervading fun.” But as writers like Oyler (who didn’t respond to inquiries for this article) have written, and others told me in interviews, “Supposedly Fun” is the clear standard-bearer of modern cruise reporting. 

“The ground zero piece for cruise ship journalism is the one David Foster Wallace wrote,” said Drew Magary, author of a 2013 GQ story covering a Kid Rock cruise. “That’s the one from which everything sort of stems out.”

It defined the tone for the genre. Because of Wallace, writers tend to approach the subject not with the gonzo excesses of a Hunter S. Thompson but a bemused, self-deprecating detachment, where the author’s thoughts and observations are more memorable than their personal exploits. Even when writers are enjoying the food, booze, activities, or music on a cruise, we’re more likely to hear their dry observations about capitalism or their childhoods, than colorful anecdotes about how hard they partied or snorkeling to a tranquil cove.

“Cruise ships are meant for well-adjusted people who want to relax and have a good time,” said Sam Apple, a writer who teaches a course on “guinea-pig journalism” at the University of Pennsylvania, in an email. “Writers aren’t particularly good at relaxing and having a good time, so it makes for good fish-out-of-water comedy.” 

Even when writers aren’t aiming chiefly for humor, themed cruises in particular naturally attract obsessives willing to devote their funds and vacation days to some fandom or enthusiasm, which generally makes for some good interviews. “Everyone’s so giddy and buoyant and on vacation, there’s kind of a bonding that happens in those environments,” said Luke Winkie, who recently covered a Creed-headlined concert cruise for Slate. “So people are just ready to talk.”

That candor, and the time to observe passengers as they let loose, can help reporters understand what a particular group is really thinking about. Laurie Penny’s 2018 story on a cryptocurrency cruise documented bitcoin bros entertained by investment pitches and Eastern European “hostesses.” Reports in 2007 and 2012 captured right-wing concerns and preoccupations aboard the conservative magazine National Review‘s cruise.

“If any of the conservative cruisers asked who I was, I answered honestly, telling them I was a journalist,” wrote Johann Hari in 2007 for The New Republic. “But, mostly, I just tried to blend in—and find out what conservatives say when they think the rest of us aren’t listening.”

Cruises also provide guaranteed, non-stop spectacle journalists to cover, from the time the boat leaves the harbor to the minute it returns, with plenty of time to observe the atmosphere, identify characters, and gather quotes (and drinks) in between. The defined time frame and largely fixed costs also make cruises an easier sell to editors, Magary suggested, than open-ended stories and investigations with unpredictable timelines and budgets. The confined setting doesn’t have to be a hindrance to storytelling, as fans of fiction from Death on the Nile to Titanic well know.

“I think that cruise ship stories are popular for the same reason that locked room mysteries are, where it presents a smaller stage and somewhat sort of limited cast of characters,” said Anna Merlan, who covered Conspira Sea—a conspiracy theory cruise—for Jezebel in 2016. “Something about that is really appealing for folks.”

And many readers and writers just find the very notion of cruises entertaining. Like “On Ice” or “The Musical,” adding “Cruise” to any concept—Weezer, a 24-hour dance party, Paula Deen, Disney, or climate change, to name a few—is objectively funny.

Besides the knowledge there’s basically no escape from the boat, the sheer corporateness of a big time music cruise, not to mention the association of cruising with seniors, can make a current act playing at sea seem inherently surreal. And to hear about a band from your youth headlining a cruise ship is like spotting a gray hair in the mirror—shouldn’t cruise shippers be listening to Sinatra or something?

“It feels goofy to take a Caribbean cruise with REO Speedwagon,” music critic Chuck Klosterman wrote in a report from a 2005 classic rock cruise, where he genially describes middle-aged music fans lamenting the bygone era of Journey and Styx. “At risk of sounding reductionist, the whole idea just seems… insane.”

Since then, concert cruises have become commonplace, and not just for nostalgia acts—though many cruises (and reporters) do highlight bands “just around the corner from middle age,” as writer Torie Bosch described the Backstreet Boys for a Buzzfeed story back in 2014. Part of the appeal of reading about a concert cruise can be learning who’s still so into an old musical favorite that they’d devote thousands of dollars and a week’s worth of vacation time to seeing them—and, perhaps, reflecting on how your own priorities have evolved.

In 2012, Hadley Freeman opened a piece for The Observer on a Coachella cruise, headlined by Pulp and featuring “nail art with Alexis from the Sleigh Bells,” with a quote from the David Foster Wallace story, calling cruises “unbearably sad.” Generally confused by the experience, she wondered “what on earth” Pulp frontman Jarvis Cocker had done to entertain himself on the ship when not on stage. And wasn’t there something strange, she asked, about singing “Common People”—Pulp’s song about rich people slumming—”to a roomful of people rocking out less than a stone’s throw from various duty-free Estée Lauder and Bulgari concession stands?”

Maybe. The social dynamics around who cruises are complicated, and a reminder that even in the United States, class and wealth aren’t synonymous. Almost every cruise story going back to Twain at some point comments on how the excursions aren’t cheap. Wallace referred to customers spending “more than $3,000” in ’90s money, around $6,000 today. Novelist Gary Shteyngart, who in April published an article in The Atlantic about a stay on the current record-holder for largest cruise ship, wrote that the magazine paid nearly $19,000 for his onboard suite. In other words, cruises aren’t for the poor, which can let writers pull apart stereotypically American excesses and blandness without being immediately pilloried for snobbery as they would for making similar observations about a visit to Walmart or the local county fair. “I teach a class at Columbia… about humor, and punching up and punching down are terms that we certainly use,” said Shteyngart, who didn’t respond to inquiries for this article, in a public radio interview. “And here, I would say that the people on this ship are probably in the same economic class as I am, and possibly the same social class, given that almost everyone went to college.”

Wallace, back in the ’90s, described the cruise he took as “mass-market luxury,” a not-quite contradiction that seems to still apply today. 

“I think what makes Wallace so interesting when he writes about these things is he was skeptical in a good way of his own assumption, or the assumption of a lot of writers, that there was this sort of muddled, consumerist mass and then there was the sophisticated, sensitive writer who was alienated from it,” said Jon Baskin, a former editor at Harper’s and author of the book Ordinary Unhappiness, about David Foster Wallace. “I think he definitely felt that to some extent, but he was also suspicious of it.”

And subsequent writers are aware of the need to advance the genre, which some argue is growing stale. Shteyngart’s Atlantic piece contains support from other big-name writers for the idea, presented not quite tongue-in-cheek, that the cruise story might be due for retirement. (After, of course, Shteyngart’s own excursion, byline, and paycheck). 

“It is also unseemly to write about the kind of people who go on cruises,” he wrote. “Our country does not provide the education and upbringing that allow its citizens an interior life. For the creative class to point fingers at the large, breasty gentlemen adrift in tortilla-chip-laden pools of water is to gather a sour harvest of low-hanging fruit.”

In an ideal world, less cruise coverage might mean more publications taking a chance on other kinds of in-depth reporting, and introducing readers to something more novel and engaging than snarky descriptions of vacationers enjoying a swim. But the familiarity of the genre will likely keep it sailing on, even as much other journalism flounders.

“If you’re willing to pay 20 grand to send Gary Shteyngart on a boat, then maybe you should be willing to spend a few thousand bucks to send journalists traveling to report on conflict zones, or a weird nightclub, or a niche museum in the middle of Appalachia,” said Merlan, whose own cruise reporting helped lead to a book on U.S. conspiracy theorists. “If I were a venture capital person or a billionaire who owned a media outlet, I would look at the success of these stories and say, wow, I should really be putting money towards paying for journalists to do things and paying them well.”