by Natasha Lair
Last updated: 9:55 AM ET, Wed January 7, 2026
Travel Guard has announced the winners of its 2025 World’s Unluckiest Traveler promotion, recognizing travellers from the U.S. and Canada whose trips were derailed by a series of extraordinary mishaps.
The grand prize went to Lloyd L., who was named the “World’s Unluckiest Traveler” and awarded $10,000. His winning entry, From Holy Water to Holy Soaked, described a long-planned trip to Rome to see the Pope that was disrupted by severe weather, leaving him cold, soaked, and barely able to see the event he had traveled for.
Second place was awarded to Daniel B. for Flip Flop Fiasco, a story detailing a trip to California to meet his goddaughter followed by a visit to Vasquez Rocks that went wrong due to unsuitable footwear. The runner-up prize was $5,000.
Third place went to The $28K Snowboarding Souvenir, recounting a snowboarding trip to the Austrian Alps that ended after two hours with a shattered wrist and an extended hospital stay. The third-place winner received $3,000.
In fourth place, What Cancer Didn’t Take, Travel Tried To told the story of a challenging journey to Copenhagen for a family event, compounded by multiple disruptions, including a plane catching fire. The fourth-place prize was a RIMOWA carry-on suitcase.
“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.
“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.”
In addition to the main prizes, the promotion also included a voter sweepstakes. Paula B. was randomly selected from nearly 4,500 voters to receive a GoPro action camera and kit.
The promotion was open to eligible residents of Canada and the U.S., excluding Quebec.
Full stories from the winning entries are available on the contest website.
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