Technology

7 Unforgettable Group Trips That Went Horribly Wrong

2025-07-14

Author: Charlotte

Planning a group trip can often lead to disaster. From personality clashes to unexpected illnesses, these shared adventures can turn into unforgettable tales of chaos. Here are seven horror stories from travelers who faced the ultimate trip from hell, proving that sometimes, it’s not the destination that matters, but the journey—especially when things go wildly off course.

Keely's Bachelorette Nightmare

Keely Bennett Morgan, 28, from New Jersey, embarked on a bachelorette getaway in Fort Lauderdale with 14 friends but ended up experiencing pure pandemonium. Everything went smoothly until the final night when she suddenly felt ill and discovered she had contracted norovirus. As the night unfolded, girl after girl began to get sick, turning their vibrant celebration into a scene reminiscent of a horror movie. They scrambled for bathroom space at their Airbnb, and in a frantic attempt to survive, had to order toilet paper and Pedialyte via DoorDash. Some faced the unfortunate fate of getting sick on the plane ride home.

Shelby's Awkward Gala Experience

For Shelby Filangi, 30, from Colorado, a trip to New York City for an awards ceremony quickly soured due to romantic tension between her friends. What began as a trip meant for celebration turned into an uncomfortable spectacle of jealousy and drunken debauchery. First, her friends faintly denied any romantic entanglement but soon acted like lovesick teenagers, leaving Shelby to wander museums alone. The night of the gala, they got excessively drunk, leading to spills and fights, ultimately resulting in a blow-up that saw Shelby cutting ties with them after the trip.

Carolyn's Airbnb Horror

In 2016, Carolyn and her friends thought they hit the jackpot with an Airbnb for the HARD Summer music festival in L.A., only to walk into a squatter's nightmare. The family living there restricted them to certain areas and made their stay a chaotic mess without the essential comforts. Following a frustrating experience with the police and no reimbursement, the group could only laugh at their misfortune—at least it brought them closer together.

Ben's European Trip That Shook Friendships

At 25, Ben joined a tight-knit group on a European adventure that turned sour when personal issues arose. A romantic entanglement caused dramatic fallout, particularly when one of the friends, suddenly the moral police, intervened during a night at the club. The incident left the group fractured, with hurt feelings that ultimately meant the end of some friendships.

Jenna's Disastrous Bachelorette Dinner

Jenna Apel, 29, faced her own disaster during her best friend's bachelorette trip to the Hamptons when their highly anticipated private chef canceled last minute. After a frantic search for alternatives that led to an extravagant and costly restaurant meal, the girls left feeling frustrated and much poorer than expected, marking it as a weekend defined by financial blunders.

Yasamin's Birthday from Hell

For Yasamin, 32, in Washington, D.C., her birthday trip to Mexico City spiraled into chaos. While she tried to enjoy her day, disaster struck with a flooded apartment back home and a stomach bug that kept her from fully celebrating. Watching friends indulge in the food and experiences she longed for only added to her frustration, wrapping up her trip with lost memories and a ruined apartment.

Megan's Awkward Beach Weekend

Finally, Megan, 29, from New York City, thought she would be spending a fun-filled Fourth of July weekend, but instead found herself in a rundown Airbnb. The place was filthy and sketchy, leading to a quick realization that the vacation was a disaster. The situation worsened when her friend seemed overly reliant on Xanax, rendering the entire trip painfully awkward. Despite their friendship taking a hit, they couldn't laugh off the bizarre week.

These stories serve as a reminder that group trips can often morph into unforgettable tales of mishaps that teach us about patience, friendship, and just how chaotic life can get when traveling in groups.