11 of the Most Disastrous Vacations in Literature

Murder, mayhem, drunken fights and long walks on the beach. 11 vacations that went horribly wrong but made for timeless fiction

We pour our hopes, dreams, and ludicrously high expectations into vacations, in part because we get to enjoy them so rarely (thanks, America) and in part because when a longed-for holiday is good, it’s sublime. By the same token, when vacations go bad — in one of the countless, cruel ways from tropical storms to familial implosions— they’re terrible.

The only people who get any kind of pleasure out of seeing people suffer through bad vacations must be liquor store owners and writers. For writers, sending characters on vacations is a neat trick, a way to ramp of the stakes. Why see a marriage erode under the weight of infidelity in some house in the burbs when you can have it play out in a villa in Mallorca? How better to show a murderer’s chilling lack of regret then by having him off his friend in a row-boat in the Ligurian Sea, his bloodied hands clean in time for appertivo hour?

So in time for Memorial Day and the kick-off to the vacation season, here are 11 of the most disastrous vacations in literature.

1. Death in Venice by Thomas Mann

Plague. Inappropriate fascination with a young boy. Sudden death. Mann’s claustrophobic novella about a writer named Gustav von Aschenbach who takes a holiday on the Lido island in Venice and becomes creepily obsessed with a boy before succumbing to cholera is a nightmare from its beginning to the untimely end.

2. Fear and Loathing in Las Vegas by Hunter S. Thompson

Going on vacation with Raoul Duke and his attorney, Dr. Gonzo, is not for the faint of heart. Though they theoretically head to Vegas to cover a motorcycle race for an unnamed magazine, the duo spend most of their time on a combination of LSD, cocaine, cannabis, alcohol, ether, and mescaline. Their drug-fueled trip is a hallucinatory, violent, psychotic roller-coaster and it’s enough to keep you away from drugs forever.

3. Giovanni’s Room by James Baldwin

Baldwin’s breathtaking novel opens with the protagonist, David, drunk and alone in a rental house in the South of France, a vacation he was supposed to be enjoying with his fiancé. David recounts the devastating story which brought him to this point, of falling in love with a man named Giovanni, his own refusal to accept his sexuality, and now Giovanni’s imminent execution.

4. The Talented Mr. Ripley by Patricia Highsmith

Tom Ripley is a con man who sweet talks himself into the prime job of traveling to Italy to convince the rich playboy Dickie Greenleaf to come home to his family business. Tom becomes obsessed with Dickie and his jet-set lifestyle, and just as Dickie begins to tire of him, they take a vacation within their extended vacation to the beach town of Sanremo. Against the beautiful blue of the Ligurian sea, Tom bludgeons Dickie in a rowboat, dumps his body overboard, and assumes his identity.

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5. The Past by Tessa Hadley

If your family didn’t like each other back in the day, it’s never a good idea to gather together for a forced vacation as adults — the same gripes, manipulations, and subtle yet searing psychological tortures are bound to be brought out alongside the old Scrabble set. Tessa Hadley mines all the awkwardness and pent-up emotions of this scenario by bringing together the adult Crane siblings for three fraught weeks as they decide what to do with their crumbling family property.

6. The Woman in the Dunes by Kobo Abe

In this existential novel, a schoolteacher named Jumpei Niki visits a fishing village for a little vacation to pursue his hobby: collecting insects. Things quickly go off the rails when he misses his bus home and the villagers offer him a house in the dunes to stay the night. Niki wakes up to find that the villagers have taken away the house’s rope ladder, trapping him alongside a young woman with whom he’s forced to shovel out the encroaching sand dunes that threaten to bury them.

7. The Story of a New Name by Elena Ferrante

In the second novel in the Neapolitan trilogy, Elena and Lila are only teenagers, yet Lila is already in an unhappy marriage and carrying a child. When her abusive husband Stefano sends Lila to the island of Ischia for the summer to rest while she’s expecting, Elena joins her, but the supposedly recuperative beach vacation takes turns that mark both girls forever. Lila starts an affair with Nino, the boy that Elena has always loved, and in her despair Elena loses her virginity to Nino’s creepy old father. The trip ends as it began, with the girls’ unhappiness and Stefano’s violent fists.

8. The Sun Also Rises by Ernest Hemingway

Hemingway captures that feeling, familiar to many Spring Breakers, when a fun drunken vacation tips into a grossly intoxicated mess. A group of American and British expatriates, led by Hemingway stand-in Jake Barnes, take a trip to see the bullfights at Festival of San Fermín in Pamplona. Many, many jugs of wine later, and hearts and noses are broken, and one lucky woman got to bed a matador.

9. The Vacationers by Emma Straub

Straub chose one of the most beautiful settings in the world, the Spanish island of Mallorca, to stage her disastrous vacation. A New York family comes to the island to celebrate the head couple’s 35th wedding anniversary, but things get awkward as it turns out that everyone (literally, everyone) there is dealing with some kind of infidelity.

10. Tender is the Night by F. Scott Fitzgerald

Fitzgerald also chose a glamorous Mediterranean beach town to set his tale of infidelity, though he adds murder to the mix. Rosemary Hoyt is a young American actress who gets swept up in the dysfunctional, hard-partying circle of Dick and Nicole Diver. Her vacation takes a particularly bad turn after one of the Diver’s parties, when a man is murdered and ends up in her bed.

11. The Beach by Alex Garland

Even vacations can go on too long, as Garland shows in his 1996 novel about Richard, a British backpacker who discovers a secret community on an idyllic island in Thailand. On the surface, the community is a dream hippie commune living an extended vacation away from society, but after a few weeks Richard realizes that the scene is actually closer to Lord of the Flies than Utopia, and things turn just as violent.

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