They are tales of trips-gone-horribly-awry that will make your getaway gripes pale into insignificance.
The ‘world’s unluckiest travelers of 2025’ have been unveiled in an annual contest run by a travel insurance provider that solicits vacation nightmares from across the U.S. and Canada.
After weeks of voting, the winners have been declared, with Travel Guard giving the grand prize of $10,000 to Lloyd L, whose once-in-a-lifetime trip to Rome to see the Pope became a soggy, soul-destroying saga.
Here, we reveal the whole, sorry tale of his waterlogged adventure, along with the calamities honored with the $5,000 runner-up and $3,000 third-place prizes.
A hellish soaking — the grand prize winner
Lloyd L flew to Rome for “a once-in-a-lifetime general audience with the Pope in St. Peter’s Square” — a trip he’d been looking forward to for months.
Before setting off, he told Travel Guard that he “imagined sunshine, reverent silence, maybe a few tears of joy.” But nonstop rain drenched him in misery.
He explained: “From the moment we stepped out, it poured like the heavens were testing our devotion.”
Recounting the ordeal, he remarked: “We left the hotel before sunrise, with a bagged breakfast of fruits and pastries to eat once we arrived at St. Peter’s Square. By the time we reached our destination, the bag was soaked and split open like a piñata, spilling all the food onto the cobblestone pavement.”
Then the situation worsened.
Lloyd continued: “We huddled shoulder-to-shoulder with thousands of other hopeful pilgrims; all soaked in their ponchos and holding umbrellas, waiting patiently for the Pope to parade around the square in his popemobile.”
“With all the rain and umbrellas, it was hard to see him as he drove among the crowds of people. At this point, I was drenched, cold and hungry and couldn’t wait for it to end and get out of there,” he added.
Lloyd admitted that Rome had baptized him, just not in the way he expected.
He added: “While I couldn’t wait for it to be over, I’ll admit it’s the kind of miserable memory that makes for a great story.”
Flip-flop fiasco — the runner-up
Daniel B admitted that his sorry tale is “less about bad luck and more a testament to my ignorance, arrogance, and a generous dash of stubbornness.”
He recalled how, during a high-school reunion in California, two of his longtime buddies had the “bright idea” of exploring Vasquez Rocks, an area in the Sierra Pelona Mountains of northern Los Angeles County known for its awe-inspiring rock formations and beloved by Hollywood directors.
He explained: “My friends pitched it as a cool Star Trek filming location. I vaguely remembered seeing it in a travel guide, but didn’t give it much thought. I pictured a few modest rocks in the desert. No big deal. I just wanted to chill with my friends.”
He showed up in a T-shirt, shorts and flip-flops, which were ideal for the heat but, as he soon found out, “terrible for what came next.” And that was a competition to see who could climb the highest.
Daniel realized that he’d “misjudged the situation,” with his friends sporting “proper shoes.”
But he joined the ascent regardless, with “pride being a powerful motivator.”
He recalled: “At first, I held my own. But as the rocks got steeper, my fear of heights kicked in hard. I froze. My friends, perched above me like smug mountain goats, sneered down in triumph. I waved the white flag. Then came the real challenge: getting down.”
“My anxiety went into overdrive. I panicked. Vultures — actual vultures —started circling overhead. My friends couldn’t stop cackling. I was furious at them, and even more furious at myself,” his continued.
He added: “After 20 agonizing minutes of inching down on my backside, I finally made it to solid ground. My flip-flops survived. My dignity? Not so much.”
The $28,000 snowboarding souvenir — third-place winner
Canadian Ryan P revealed he had the “snowboarding trip of a lifetime” in Austria, just not the way he’d imagined.
He recalled: “Two hours into our first day on the slopes, I made a wrong move and suddenly found myself sliding on my back towards a blind drop. Even though I had years of experience, I was a foreigner on this slope. “
“As I approached the edge, I stuck my palms into the snow. I slammed into the icy bank and braced myself for the fall beyond. Next thing I know, I am lying on my back in deep powder. I giggled at my apparent luck and continued down the hill,” he added.
But things soon took a turn for the worse: “At first, I was in total denial… I rode down the slope to the next hut and unstrapped my board as if nothing had happened. But when I took off my gloves, everything changed. My wrist was deformed. It looked like it had been assembled by Picasso.”
The ski patrol arrived and insisted that Ryan had to be flown by helicopter to a hospital, as a snowmobile ride might have aggravated a wrist that was badly fractured.
Ryan continued: “At the hospital, X-rays confirmed the bad news: my wrist had exploded. Surgery was immediate, expensive, and unavoidable. The next few days were a blur of more pain meds and awkwardly trying to cut steak with one working hand. On top, it was my birthday the day after I left the hospital; not the kind of celebration I had in mind.”
“By the time I was released, I had enough metal in my arm to set off every airport detector, and a collection of receipts that could wallpaper a room.”