Canadian influencer Syd Wingold pleads for a ride home from St Barts as US strike on Venezuela shuts down Caribbean airspace

What started as a dreamy Caribbean getaway quickly turned chaotic after a sudden U.S. military operation brought air travel across the region to a standstill.

Late Friday, former President Donald Trump announced what he called a “large-scale” strike in Venezuela, claiming President Nicolás Maduro and his wife, Cilia Flores, had been captured.

By Saturday morning, the ripple effects were unmistakable: Venezuelan airspace was empty, and airlines had pulled the plug on hundreds of flights throughout the eastern Caribbean.

Nearly 900 flights were scrapped as safety restrictions rolled out, leaving tourists, celebrities, and locals alike stuck far from home—with no clear timeline for relief.

An Influencer’s Unusual SOS From St. Barts

Among the stranded was Canadian influencer Syd Wingold, who boasts more than a million followers and an upcoming wedding back in Toronto.

Trapped in St. Barts, Wingold took to Instagram with a creative plea: if any pilot was heading back to North America, could she tag along?

Her stories struck a mix of desperation and humor.

She promised to be “extremely respectful,” even joking that she’d happily dress up as the captain if that sweetened the deal.

One post showed her lounging with a friend as she explained their flight had been canceled, with the next available seat not departing for another week.

Humor as a Coping Strategy

Wingold leaned into comedy as the hours dragged on.

She compared the situation to a previous travel nightmare—being stranded in Las Vegas during her bachelorette trip, another misadventure her followers remembered well.

Later, she posted a tongue-in-cheek update from a remote field, posing in front of two massive cranes.

No pilot had answered her call, so she joked about “alternative transportation,” assessing the cranes’ size and “structural integrity” as if they might hoist her all the way to Toronto.

Officials Promise Relief, Eventually

As frustration mounted, U.S. Transportation Secretary Sean Duffy addressed the growing backlash online.

He explained that the FAA had restricted airspace over parts of the Caribbean and Venezuela purely for safety reasons.

While he later said those limits would lift at midnight Saturday, industry experts warned it could still take days for airline schedules to fully recover.

Whether Wingold managed to snag a flight once restrictions eased remains unclear.

Her final update of the day showed a cocktail menu instead, with one drink—“Pimp My Pamp,” a grapefruit-based option—circled in red.

Her caption summed it up: flight plans uncertain, drink order locked in.

A Bigger Question About Travel Privilege

Wingold’s viral posts sparked debate online.

Should influencers or celebrities receive special consideration during travel emergencies, or does a crisis level the playing field for everyone?

The comments section quickly filled with strong opinions on both sides.

Even Hollywood Felt the Fallout

The disruption didn’t stop with influencers. Leonardo DiCaprio also found himself grounded.

The actor was unable to attend the Palm Springs International Film Festival, where he was set to receive the Desert Palm Achievement Award for his role in Paul Thomas Anderson’s One Battle After Another.

Ironically, DiCaprio had been spotted just days earlier ringing in the New Year aboard Jeff Bezos’ yacht near St. Barts.

But restricted airspace kept him from reaching California in time for the ceremony.

An Award Accepted From Afar

Festival organizers announced DiCaprio’s absence during the event, citing unexpected travel restrictions.

Still, the moment didn’t lose its impact. According to a source, the room was filled with warmth as a tribute reel played and his co-stars spoke on his behalf.

DiCaprio accepted the honor via video, delivering a speech that drew applause despite his physical absence.

The festival later confirmed the situation in a statement, emphasizing their pride in recognizing his work even under unusual circumstances.

What Happens Next?

As airlines work through backlogs and travelers wait for normalcy to return, one thing is clear: the Venezuela strike sent shockwaves far beyond politics.

From influencers improvising their escape plans to Oscar winners missing major career moments, the sudden shutdown reminded everyone how fragile global travel can be—even in paradise.