Every October, New York begins its annual negotiation with winter, and every October a certain portion of the city settles it the same way: with a nonstop flight to somewhere with a swim-up bar. This year, the map those New Yorkers are booking from has shifted in two directions at once. On Monday, a beloved island carrier leaves Kennedy for good. Twelve days later, a new nonstop opens out of Newark. And the terminal at the heart of the first story, it turns out, isn’t closing nearly as soon as anyone planned.
Farewell to Cayman Airways
On Monday, Oct. 19, Cayman Airways operates its final nonstop between Grand Cayman and John F. Kennedy International Airport, ending a route it launched in June 2007. The airline announced the decision in February, noting that the service had carried nearly 500,000 passengers over almost two decades, interrupted only by the pandemic.
The national carrier was gracious about it. “The New York route has been an important part of Cayman Airways’ history, and we are proud of the role we have played in connecting the Cayman Islands with one of its most significant international markets,” said Fabian Whorms, its president and chief executive. The airline’s four Boeing 737-8s will be redeployed to newer routes; it has added seasonal service to Austin, Texas. Rosa Harris, the Cayman Islands’ director of tourism, emphasized that “New York remains one of our top tourism source markets.”
Travelers bound for Seven Mile Beach will not be stranded. The airline notes the New York–Cayman route is served by multiple carriers. But for a certain sort of New Yorker, flying the islands’ own flag carrier, nearly 20 years on the route, was part of the point.
The terminal that wouldn’t close
Here is the curious part. Cayman Airways said it timed its exit to coincide with a seasonal schedule change and “the planned closure of the existing Terminal One facility at JFK,” from which it has flown since 2007. The plan was that the old Terminal 1, a 1998 building that frequent fliers tend to describe in unprintable terms, would soon give way to its gleaming successor.
That successor is running late. In September, officials at the New Terminal One told The Points Guy that the facility, once hoped to open in the summer of 2026, is now slated to open in the first quarter of 2027. “We want to ensure that all systems and processes are well-tested and prepared to deliver on our commitment to set a new standard in customer experience, from day one,” a spokesperson said.
When it does open, the first phase will include 13 gates plus a temporary one, according to TPG; the old Terminal 1 is to be demolished afterward, making way for a nine-gate second phase. The Port Authority‘s project page lists 2027 for the first phase and 2030 for completion of the whole. Eventually the terminal will span 2.6 million square feet and serve more than 30 airlines, with a half-dozen lounges, including a large new Air France club the carrier announced in September.
So Cayman Airways is leaving a building that will keep running without it for another winter, at least. The rest of us will keep using it.
Newark’s new island
Meanwhile, across the Hudson, United Airlines is adding an island. On Saturday, Oct. 31, it begins nonstop service between Newark and St. Croix in the U.S. Virgin Islands, the airline and the territory’s tourism department announced in June. The flight operates on Saturdays on a Boeing 737-700 with 126 seats, 12 of them in business class, leaving Newark at 9:03 a.m. and arriving at 1:20 p.m.; the return departs St. Croix at 2:25 p.m. and lands at 6:58 p.m.
United says it will be the only airline flying St. Croix to the New York area, and that the route brings its Caribbean list from Newark to 23 destinations, more than any other carrier from the region. “United is proud to connect more customers to more Caribbean destinations than any other airline in the New York City region,” said Tom Kozlowski, a senior manager of network planning.
For St. Croix, the route is a coup. “As someone born and raised on St. Croix, I know firsthand how transformative direct connectivity to the New York market can be for our community, our businesses and our tourism economy,” said Jennifer Matarangas-King, commissioner of the U.S. Virgin Islands Department of Tourism. For New Yorkers, it is a useful option: no passport required, U.S. dollars, and an island that has always been the quieter sibling of St. Thomas, which United also serves from Newark.
What it means for your winter
The practical lessons are three. If Grand Cayman is your habit, book on one of the remaining carriers and expect Monday to be the last Cayman Airways departure from Kennedy. If you have been curious about St. Croix but deterred by connections, the Saturday nonstop removes the excuse. And if you are flying out of JFK’s Terminal 1 this winter, adjust your expectations accordingly: the new building is next door, visible through the windows, and still not open.
New York’s relationship with the Caribbean has always been one of the city’s great quiet romances, carried on through Brooklyn’s neighborhoods, through Labor Day on Eastern Parkway, through a million winter weekends. The routes change. The romance, judging by United’s count of 23 destinations, does not.
The City Politic has reached out to Cayman Airways, United Airlines, the New Terminal One and the Port Authority of New York and New Jersey for comment and will update this story with any response.
Photo: JFK’s existing Terminal 1. Quintin Soloviev / Wikimedia Commons, CC BY 4.0.
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