Tradewind Aviation

The Insider’s Way There

Tradewind Aviation has quietly changed the way to reach places like St. Barths, Nantucket and Martha’s Vineyard, combining private-aircraft convenience with scheduled service across the Northeast, Bahamas and Caribbean.

Fly Tradewind

Celebrating Twenty Years of Service

Fly Tradewind

Private, Without the Private Jet

By Ken Panton

My first Tradewind flight was in 2010, from San Juan to St. Barths, just after landing on a Delta flight. Within minutes, I was through the private terminal and boarding a sleek Pilatus PC-12. No long airport ritual, no waiting around—just a remarkably easy transition from commercial flight to island life.

That feeling remains the point.

Tradewind operates scheduled and private flights throughout the Northeast, the Bahamas and the Caribbean, connecting places that can otherwise feel unnecessarily complicated to reach. In the Northeast, that means Nantucket and Martha’s Vineyard from the New York area, with new seasonal service from Boston’s Hanscom Field. In the Bahamas, new scheduled routes connect Florida with destinations including Marsh Harbour, North Eleuthera and Nassau.

But it is the Caribbean where Tradewind really makes its case.

San Juan remains a central hub, with scheduled service to St. Barths, Anguilla, Virgin Gorda, Tortola and Antigua, while private charter extends the network considerably further. Tradewind’s 2026–2027 St. Barths service is available from both San Juan and Antigua, with multiple daily departures during peak periods.

The aircraft is a big part of the experience. Tradewind operates a fleet of Swiss-built Pilatus PC-12s—pressurized, air-conditioned, and flown by two pilots. There is room for the luggage that actually accompanies a weekend away, rather than the luggage that fits neatly into an airline overhead bin. And, of course, the PC-12 is perfectly suited to smaller airports and short regional routes.

Because St. Barths Is Calling

The Better Way There

Then there is St. Barths.

The approach is still one of the great arrivals in travel. As the aircraft drops toward Gustaf III Airport, the island opens beneath you—hills, harbor, brilliant water—and then suddenly you are on the ground, close to everything that brought you there in the first place.

Tradewind has expanded since my first flight, but the appeal is remarkably unchanged. Scheduled service gives you the convenience of buying a single seat, while private charter lets you travel on your own terms. In San Juan, there is even a VIP transfer service that can meet arriving airline passengers at the gate, handle luggage and move them into Tradewind’s private lounge before the connecting flight.

It is a different idea of regional air travel: less airport, more journey.

From New York to Nantucket. Boston to Martha’s Vineyard. San Juan to St. Barths. Florida to the Bahamas. Tradewind has quietly built a network around the places people actually want to go—and made getting there feel like part of the trip. Tradewind Aviation.

Photography: David Lewis Taylor.