2025 World’s Unluckiest Travelers Revealed

Image: Travel Guard World's Unluckiest Traveler Contest (Photo Credit: Travel Guard)
Image: Travel Guard World's Unluckiest Traveler Contest (Photo Credit: Travel Guard)
Noreen Kompanik
by Noreen Kompanik
Last updated: 1:20 PM ET, Wed January 7, 2026

Who would have guessed that a story of a trip-gone-horribly-awry could actually win a contest prize?

Many travelers have shared tales of trips gone wrong.

As a result, travel insurance provider Travel Guard solicited stories of travel nightmares from across the U.S. and Canada. After scores of visitors submitted stories of their travels-turned-travail, four winners emerged after weeks of voting.

The grand prize winner received $10,000 USD for his submission “From Holy Water to Holy Soaked” a story of his once-in-a-lifetime trip to Rome to see the Pope, only to encounter an unholy storm that left his cold, water-logged and nearly unable to see the object of his trip.

Second place story “Flip Flop Fiasco” recounted the writer’s travel to California to meet his goddaughter, then make an adventurous visit to the epic Vazquez Rocks, a sojourn marred by an unfortunate choice of footwear (and perhaps an unfortunate choice of friends). However, the runner-up’s tale did pay out $5,000.

“The $28K Snowboarding Souvenir” garnishing third place, told the story about snowboard trip to the Australian Alps that only lasted two hours due to a shattered wrist and lengthy, expensive hospital stay, but won a $3000 cash prize.

In fourth place “What Cancer Didn’t Take, Travel Tried” shared the experience of an almost impossible trip to Copenhagen for a family event, met with numerous obstacles, including a plane catching fire. The winner received a RIMOWA carry-on suitcase.

And as luck would have it, one randomly selected voter in the 2025 World’s Unluckiest Travel sweepstakes won a GoPro action camera and kit.

“The stories of our winners are not typical, but travel mishaps can befall anyone, so we encourage travelers to prepare for the unexpected and protect their trips,” said Rhonda Sloan, Senior Vice President of Marketing at Travel Guard in a statement.

She added, “We launched the World’s Unluckiest Traveler to recognize those who have endured hardships in pursuit of their love of travel and to highlight those sorts of misfortunes – particularly medical issues – that might make a travel insurance plan worth considering.”


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