Every traveller has a story of a trip gone wrong, but the winners of the annual 'World's Unluckiest Traveler' contest have tales that eclipse ordinary holiday gripes. Organised by travel insurance provider Travel Guard, the 2025 competition solicited vacation nightmares from across the United States and Canada, with voters selecting the most catastrophically unfortunate journeys.
The Soggy Papal Audience: A Grand Prize Calamity
The grand prize of $10,000 was awarded to Lloyd L, whose long-awaited pilgrimage to Rome dissolved into a waterlogged ordeal. He had flown to Italy for a once-in-a-lifetime general audience with the Pope in St. Peter's Square, a moment he had envisioned for months. "I imagined sunshine, reverent silence, maybe a few tears of joy," he recounted. Reality, however, delivered a relentless baptism by downpour.
"From the moment we stepped out, it poured like the heavens were testing our devotion," Lloyd explained. His pre-dawn departure with a bagged breakfast ended with the soaked bag splitting open on the cobblestones, scattering its contents. He then joined thousands of other drenched pilgrims, their view of the papal procession obscured by a forest of umbrellas. "I was drenched, cold and hungry and couldn't wait for it to end," he said, though he later admitted the miserable experience had transformed into a great story.
A Flip-Flop Fiasco on the Rocks
Securing the $5,000 runner-up prize was Daniel B, whose tale was a self-confessed blend of ignorance and stubbornness. During a high-school reunion in California, friends suggested exploring the dramatic Vasquez Rocks in the Sierra Pelona Mountains. Daniel, picturing modest desert stones, arrived in a T-shirt, shorts, and flip-flops.
The casual outing turned into an impromptu climbing competition. As the rocks grew steeper, Daniel's fear of heights kicked in. He froze, stranded while his better-shod friends watched from above. The descent was worse, involving a 20-minute, panic-stricken shuffle on his backside as vultures circled overhead. "My flip-flops survived," he noted. "My dignity? Not so much."
The $28,000 Snowboarding Souvenir
Canadian Ryan P claimed third place and $3,000 with a painful snowboarding story from Austria. Merely two hours into his 'trip of a lifetime', a wrong move sent him sliding towards a blind drop. In a fateful instinct, he braced with his palms, resulting in a catastrophic wrist injury.
Initially in denial, the truth became apparent when he removed his glove to see a wrist deformed "like it had been assembled by Picasso." Ski patrol insisted on a helicopter evacuation to hospital, where immediate surgery was required. The aftermath involved a birthday celebrated in pain, a wrist full of metal, and medical bills totalling a staggering $28,000 – an extraordinarily expensive souvenir.
These three stories, crowned the worst of 2025, serve as stark, and sometimes darkly humorous, reminders of how quickly dream holidays can unravel, highlighting the unpredictable nature of travel and the value of being prepared.
