The air charter company is best known for its Westchester to Nantucket summer ticket books, and its Puerto Rico to St. Barths scheduled service.

Brothers Eric and David Zipkin, both pilots and aviation enthusiasts, recognized a gap in service on shorter flights, initially on the Cape and Islands, and began operations in 2002.

[3] In March 2022, Tradewind marked a major fleet renewal and expansion program with the purchase of 20 new Pilatus PC-12 NGX aircraft in a deal valued at over $100 million, with deliveries proceeding at 3-4 per year through 2027.

In October 2022, Tradewind opened a new base at Hudson Valley Regional Airport near Poughkeepsie, New York for in-house and open-market hangar space.

In June 2024, Tradewind announced plans to offer scheduled service from Palm Beach to Marsh Harbour and North Eleuthera in the Abacos, Bahamas, beginning in December 2024.