The most spectacular holiday disasters of the past year have been crowned, with a waterlogged pilgrimage to see the Pope in Rome taking the dubious honour of the grand prize. The annual contest, run by travel insurance provider Travel Guard, solicits tales of vacations gone horribly wrong from across the United States and Canada.
The Soggy Papal Audience: A Grand Prize Calamity
After weeks of public voting, the title of 'World's Unluckiest Traveler of 2025' and a $10,000 prize was awarded to Lloyd L. He had embarked on a long-awaited trip to Rome for a general audience with the Pope in St. Peter's Square, dreaming of sunshine and reverent silence. Instead, he was met with relentless, torrential rain that defined his entire experience.
"From the moment we stepped out, it poured like the heavens were testing our devotion," Lloyd recounted. His pre-dawn departure with a bagged breakfast ended in disaster when the soaked bag split open on the cobblestones, scattering his food. He then joined thousands of other drenched pilgrims, their view of the papal procession obscured by a sea of umbrellas.
"I was drenched, cold and hungry and couldn't wait for it to end," he admitted. While the trip was a miserable ordeal, Lloyd philosophically noted it was "the kind of miserable memory that makes for a great story."
A Flip-Flop Climbing Catastrophe
The runner-up prize of $5,000 went to Daniel B, for a tale he described as a testament to his "ignorance, arrogance, and a generous dash of stubbornness." During a high-school reunion in California, friends convinced him to explore the dramatic Vasquez Rocks, a popular Hollywood filming location.
Daniel arrived dressed for the heat in a T-shirt, shorts, and flip-flops, wholly unprepared for an impromptu rock-climbing competition. Despite his unsuitable footwear and a growing fear of heights, pride drove him upwards until he froze, stranded on the steep rock face.
"My friends, perched above me like smug mountain goats, sneered down in triumph," he said. The descent was a 20-minute ordeal of panic, accompanied by circling vultures and the laughter of his companions. "My flip-flops survived. My dignity? Not so much," he concluded.
The Snowboarding Souvenir Worth $28,000
Canadian Ryan P secured third place and $3,000 with a painful story from a snowboarding holiday in Austria. Merely two hours into his first day on the slopes, a wrong move sent him sliding towards a blind drop. In a moment of denial, he even giggled after the fall and continued riding.
The reality hit when he removed his glove at a mountain hut. "My wrist was deformed. It looked like it had been assembled by Picasso," Ryan said. The ski patrol insisted on a helicopter evacuation to hospital, where X-rays confirmed a badly fractured wrist requiring immediate surgery.
The incident, which occurred just before his birthday, left him with enough metal in his arm to "set off every airport detector" and a stack of medical bills. His snowboarding trip of a lifetime became an unforgettable and expensive lesson.
These three cautionary tales, selected from numerous public submissions, highlight how even the most anticipated getaways can spiral into unforgettable disasters, underscoring the value of being prepared—and perhaps having good travel insurance.
