Who Owns Tradewind Aviation?

Eric and David Zipkin grew up around aviation and entrepreneurship. Eric learned the charter business working for another operator, and in 2001 the brothers founded Tradewind at Waterbury-Oxford Airport in Connecticut to serve regional travel in the Northeast.

The breakthrough came quickly: clients chartering whole aircraft began asking to share flights and buy individual seats. In 2002 Tradewind launched one of the industry's first shared charter concepts, scheduled shuttle service by the seat between private terminals at Westchester County Airport and Teterboro and Nantucket Memorial Airport. In 2004 it added its first Pilatus PC-12, the single-engine turboprop that became its fleet backbone.

The Nantucket and Martha's Vineyard shuttles grew into roughly 80 percent of that market by the company's estimate, with Tradewind flying 30 to 40 Nantucket flights on peak summer days. It also created the first jet-card program built around the PC-12.

Caribbean expansion followed: scheduled service from San Juan, Puerto Rico to St. Barths, Anguilla, Virgin Gorda, Tortola, and Antigua, plus Southeast routes from Stuart and Fort Lauderdale to Marsh Harbour, North Eleuthera, and Nassau in the Bahamas. Operating bases now span Oxford, Westchester (White Plains), Stuart, and San Juan.

As of 2026 the fleet numbers around 40 aircraft, more than 35 PC-12s plus Citation CJ3 jets, with roughly 350 employees including more than 140 pilots. The company reports over 20 years of spotless safety record and about 5,500 passengers flown monthly alongside 400-plus charters.