A Canadian influencer found herself begging strangers for a ride home from a luxury Caribbean island after a sudden wave of flight cancellations — sparked by a dramatic U.S. military operation — left hundreds of travelers stranded just days before her wedding.
The chaos followed news that President Donald Trump authorized a large-scale operation in Venezuela that resulted in the capture of longtime strongman Nicolás Maduro and his wife, Cilia Flores. The move effectively shut down Venezuelan airspace and rippled across the region, forcing major airlines to cancel nearly 900 flights throughout the eastern Caribbean.
Among those caught in the fallout was Syd Wingold, a Toronto-based influencer with more than one million followers, who was vacationing in St. Barts when her flight home was abruptly canceled.
With her wedding approaching and no commercial flights available for nearly a week, Wingold took to Instagram with a series of desperate — and at times tongue-in-cheek — pleas aimed at anyone with access to a plane.
“Is anyone currently in St Barts or St Martin with a plane flying back to North America who would be open to letting me come along?” she wrote in one post. “I can come in a costume and will be extremely respectful.”
In another story, she added: “If you have a plane, please hit me up. Very happy to dress as your captain.”
Wingold later shared a photo of herself and a friend lounging outdoors, revealing that the next available commercial flight wouldn’t depart until Friday — nearly a full week away. She joked that the situation felt eerily similar to getting stranded in Las Vegas during her bachelorette party, another mishap she previously documented online.
Hours later, the influencer posted again, posing in front of two massive construction cranes in a remote field.
“I am considering alternative modes of transportation at this time,” she wrote. “These cranes seem reliable based on size and structural integrity. There is a chance they could lift me to Toronto.”
As travel confusion mounted, U.S. Transportation Secretary Sean Duffy said the FAA had restricted airspace across parts of the Caribbean and Venezuela to ensure passenger safety. He later announced the restrictions would lift at midnight Saturday, though officials warned it could take days for airline schedules to fully normalize.
Whether Wingold ultimately secured a flight remains unclear. Her final Instagram update showed a cocktail menu, with a grapefruit drink option circled.
“While my flight options remain unclear,” she wrote, “my drink order has never been more certain.”
She wasn’t the only high-profile traveler affected. Actor Leonardo DiCaprio was also unable to travel due to the airspace shutdown, forcing him to miss the Palm Springs International Film Festival, where he was scheduled to receive the Desert Palm Achievement Award.
DiCaprio, who was spotted ringing in New Year’s Eve aboard Jeff Bezos’ yacht near St. Barts, accepted the honor via video after organizers announced his absence was due to restricted airspace.
Festival officials later confirmed his travel disruption, praising his work and noting that his co-stars accepted the award on his behalf.
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I can only hope they enjoyed their extra time on honeymoon!! Tell them to take dramatic pictures of this mess. Have them published when they get home. Some nespaper will pay them for the photos.