Scores of travelers submitted stories of their travels-turned-travails, vying for the top spot
HOUSTON, Jan. 6, 2026 /PRNewswire/ — Many travelers have had tales of trips-gone-horribly-awry, but only one could claim the mantle of “the all-time worst.” Continuing its annual travel promotion, Travel Guard solicited stories of travel nightmares from across the U.S. and Canada1. After weeks of voting, a winner has emerged.
As grand prize winner, Lloyd L. has received the title of “World’s Unluckiest Traveler” and won a cash prize of $10,000. In his story “From Holy Water to Holy Soaked,” Lloyd told of his once-in-a-lifetime trip to Rome to see the Pope, only to encounter an unholy storm that left him cold, water-logged and nearly unable to even see the object of his trip!
The runner-up entry “Flip Flop Fiasco” recounted Daniel B.’s travel to California to meet his goddaughter and then make an adventurous visit to the epic Vasquez Rocks, a sojourn marred by an unfortunate choice of footwear (and, perhaps, an unfortunate choice of friends). The runner-up winner won a cash prize of $5,000.
In third place, “The $28K Snowboarding Souvenir” tells of a snowboard trip to the Austrian Alps that only lasted two hours, followed by a shattered wrist and lengthy, expensive hospital stay. The third-place winner won a cash prize of $3,000. And in fourth place, “What Cancer Didn’t Take, Travel Tried To” tells of a nearly impossible trip to Copenhagen for a family event, challenged by obstacle after obstacle… and a plane catching fire. The fourth-place winner won a RIMOWA carry-on suitcase2.
“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 a twist, the 2025 World’s Unluckiest Traveler promotion also celebrated some “good luck”:
Paula B. was randomly selected – among the nearly 4,500 voters for the promotion – to win the sweepstakes prize of a GoPro® action camera and kit3.
The full stories from each of the winners can be viewed at www.worldsunluckiesttraveler.com.
For more information about Travel Guard, its products and services, visit www.travelguard.com or follow Travel Guard on Facebook, Instagram, TikTok, YouTube and LinkedIn.
1The Promotion was open to legal residents of the 50 United States and the District of Columbia who were 21 years of age or older at the time of entry, and residents of Canada (excluding Quebec) who were 19 years of age or older at the time of entry. The promotion is not available where prohibited by applicable law.
2RIMOWA and their respective logos are trademarks or registered trademarks of RIMOWA is not a participant in or sponsor of this promotion.
3GoPro, HERO and their respective logos are trademarks or registered trademarks of GoPro, Inc. GoPro is not a participant in or sponsor of this promotion.
About Travel Guard
Travel Guard, part of Zurich Cover-More, meets the diverse needs of travelers worldwide through its comprehensive portfolio of travel insurance plans and assistance services as well as a network of experienced providers. With global service centers placed strategically around the globe, our 24/7 multilingual team is always just a phone call away and ready to assist when our customers experience travel issues – from lost luggage or minor travel inconveniences to medical emergencies or life-threatening events. We help customers recover from travel disruptions and enjoy their journeys knowing Travel Guard has their back every step of the way. Learn more at www.travelguard.com and follow us on Facebook, Instagram, LinkedIn, YouTube and TikTok.
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SOURCE Travel Guard
