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“There’s a cooler with drinks and snacks in the back,” First Officer Mike Moraes tells us from the cockpit. “Help yourself. If you need anything, just tap us on the shoulder.” Soon the turn of the turboprop signals our ascent. As we fly over the New England coast, the small plane moves through fluffy cumulus clouds as if we were surfing a wave. Once we clear the cloud line, Mike leans in to punch his co-pilot, Captain Ed.
I’m one of eight passengers, including a couple of guys in suits and a local teenager who was dropped off by her mother, all traveling from White Plains, New York, to Martha’s Vineyard, Massachusetts, with trade wind aviationwhich ranks number 4 among the major domestic airlines in the United States, according to Condé Nast TravelerReaders’ Choice Awards. As part of a growing market known as semi-private aviation, the airline offers scheduled, per-seat flights aboard charter aircraft. In recent years, semi-private operators such as Tradewind, JSX (#6) and aero (#10) have expanded their scheduled service offerings with online reservations and real-time pricing and availability, making some of the benefits of private air travel more accessible than ever.
Instead of dragging myself to JFK, I arrive just before takeoff at Million Air, the private terminal at the appropriately named Westchester County Airport. There are no TSA security checkpoints or a crowded concourse. I am greeted by members of the concierge team, who take care of my luggage before handing me a red plastic card with the motto Flying Personal. It’s a surprisingly accurate slogan. But a trip on Tradewind should not be confused with a private flight: the seats on the Pilatus PC-12 aircraft are arguably worse than those in commercial economy class. The real luxury is being able to avoid the chaos of commercial airports. “Even if you fly first class, it’s a 20-minute walk just to get through the terminal,” says Jen Lozada, vice president of revenue at Tradewind. With Tradewind, passengers need to arrive just 30 minutes before takeoff.
It’s a convenience that travelers are often willing to pay more for. Tradewind reports an approximately 33% year-over-year increase in bookings for scheduled service on its routes in the US and Caribbean. As demand increases, semi-private operators are expanding their connectivity. In May of this year, Aero launched a bi-coastal flight from Los Angeles to New York with Erewhon meals and Starlink Wi-Fi. Last July, JSX launched two new routes from Southern California to Napa County Airport, one of 11 airports it flies to that are not eligible for commercial service. And in December, Tradewind will triple its flight capacity to the Bahamas, with new scheduled services to Nassau and additional routes from Fort Lauderdale to Marsh Harbor and North Eleuthera.
The result is a democratization of infrastructure; Westchester Airport’s private terminal, for example, had previously been off-limits to most travelers. “It’s all there,” says Alex Wilcox, CEO of JSX. “The runways are there, the air traffic control is there, but unless you have a private plane, you don’t have access to it. So we’re changing that.”
This article appeared in the November 2025 issue of Condé Nast Traveler. Subscribe to the magazine here.
