Susannah Ray, a teacher at a Manhattan high school, was supposed to be in class on Monday morning, welcoming her photography students back on the first day of the winter quarter. Her daughter, Bettina, 14, should have been at her own high school to start the second semester of her freshman year.
Instead, they waited in Barbados, taking turns on a single laptop to teach and attend their classes after the U.S. military operation on Saturday to capture Venezuela’s president, Nicolás Maduro, caused widespread flight cancellations in the Caribbean. JetBlue rebooked them, along with Ms. Ray’s husband, on a flight that departs on Jan. 11, eight days after they were originally scheduled to return to New York.
Ms. Ray, 53, and her family are among the estimated thousands of travelers stuck in the Caribbean for a third straight day since the military operation, during which the Federal Aviation Administration closed parts of Caribbean airspace to U.S. civilian aircraft.
On Sunday and Monday, major airlines were operating extra flights and, in some cases, using larger airplanes to bring back stranded passengers. But the scale of the disruption, which grounded hundreds of flights at the end of the holiday travel season, meant some passengers had to wait days for available seats. Travel insurance was unlikely to reimburse the extra expenses, since most plans exclude coverage for disruptions related to military activity.
“Everyone’s like, ‘Great, you get another week in Barbados,’” Ms. Ray said in a phone interview on Sunday. “But we feel like, Wow, we are stranded here. We have things we need to do and people depending on us.”
Ms. Ray said the disruption had forced the family to spend at least an additional $2,500, and had sent them into overdrive trying to plan and budget for the extra time abroad. One immediate concern: Ms. Ray and her daughter did not have another week’s supply of a medication that they take daily. They planned to visit a local clinic on Monday, hoping to get a new prescription.
Charlie Ballard, 44, and his husband were visiting Tortola, in the British Virgin Islands, to celebrate the holidays and their 10th wedding anniversary. After hearing from Delta Air Lines that their connecting flight home to Atlanta had not been canceled, the couple headed to the airport on Saturday to catch their first flight, on an island hopper to San Juan, P.R.
“We arrived at the airport, and they had a sign hanging on the door that literally just says all flights are canceled, no flights leaving whatsoever,” Mr. Ballard said. They rebooked on American Airlines, but they can’t fly until Jan. 9.
“In the span of 30 or 45 minutes, our travel budget had to double,” Mr. Ballard said. “What else are we going to do? We have no choice.”
Still, Mr. Ballard said he felt lucky to find a hotel room. “There’s very limited availability anywhere, and what availability there is, it’s not cheap,” he said.
Alex Marquardt, 26, who was celebrating the New Year in Aruba with his girlfriend’s family, planned to fly home to Chicago on Saturday morning. As the group prepared to leave for the airport, they learned that Frontier Airlines had canceled their flight. They rebooked for Jan. 10, a week later.
Now, Mr. Marquardt said, at least one of them was searching for earlier flights “pretty much around the clock.” He said his girlfriend’s father, a doctor who had procedures scheduled this week, managed to get a flight out on Sunday.
“We’ve been figuring out an order of operations of, if we can get one flight, who’s going to be the next person to go,” he said. “But it sounds like every one of us is going to be on a different flight.”
By Monday morning, Mr. Marquardt had secured a flight that leaves on Thursday. But some members of the family remain stuck until the weekend.
In the meantime, they were also searching for a place to sleep. Mr. Marquardt said he and the family stayed an extra night at their condo rental because the next guests’ inbound flight had been canceled, too. After that, they expected to move somewhere new each night. They found a place for Sunday, he said, “but the people at that condo didn’t check out on time because their flight was also canceled.”
“So yeah,” he said, “it’s kind of a mess.”
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Gabe Castro-Root is a travel reporter and a member of the 2025-26 Times Fellowship class, a program for journalists early in their careers.
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