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Tradewind Aviation

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Adapted from the English Wikipedia article Tradewind Aviation, available under CC BY-SA 4.0Updated 25 July 2025
Tradewind Aviation, LLC
Company typePrivate
IndustryAirline
Founded2001
FounderEric Zipkin, David Zipkin
Headquarters
Oxford, Connecticut
,
United States
Area served
Northeast United States, Southeast United States, Caribbean
ProductsPrivate and scheduled flight services, aircraft management

Tradewind Aviation, LLC, doing business as Tradewind Aviation and Tradewind Shuttle, is a U.S.-based airline with its headquarters located at Waterbury-Oxford Airport in Oxford, Connecticut. The company specializes in private and scheduled flight services throughout the Northeast, Southeast, and Caribbean regions, in addition to offering aircraft management solutions. Tradewind is particularly recognized for its seasonal ticket packages from Westchester to Nantucket and its scheduled routes connecting Puerto Rico to St. Barths.

History

Established in 2001 by entrepreneurial brothers Eric and David Zipkin, both licensed pilots, Tradewind commenced operations with a single Cessna Caravan aircraft, focusing on underutilized short-distance routes such as those serving Cape and Islands. The company expanded its charter services across the U.S. and Caribbean territories, obtaining authorization for scheduled flights in 2005 and eventually serving 11 destinations. Domestic departures are exclusively conducted through fixed-base operators (FBOs), whereas Caribbean flights operate from conventional airport terminals. At Luis Muñoz Marín International Airport in San Juan, Tradewind provides upscale amenities including a semi-private lounge catering to passengers traveling to high-end Caribbean locales.

Since 2006, Tradewind has maintained the sole year-round nonstop scheduled connection between the United States and Gustaf III Airport in St. Barthelemy, establishing a unique offering within the luxury travel sector.

In June 2019, Tradewind introduced "Goodspeed," a jet card program presenting fixed one-way pricing on its Pilatus PC-12 fleet within three designated regions: Westchester County (NY), Palm Beach (FL), and San Juan (Caribbean). These jet cards are available in increments of 10, 25, or 40 hours.

A significant fleet enhancement initiative began in March 2022 with a $100 million commitment to acquire 20 new Pilatus PC-12 NGX aircraft. This move solidifies Tradewind's status as the largest global operator of PC-12s available for charter. Delivery of these aircraft is planned at a rate of three to four units annually through 2027.

In October 2022, Tradewind inaugurated a new operational base at Hudson Valley Regional Airport near Poughkeepsie, NY, expanding hangar space to support both internal activities and open-market charters. Following this, September 2023 saw the launch of another hub at Witham Field in Stuart, Florida, aimed at capturing growth opportunities within the Southeastern market.

Looking forward, Tradewind has announced plans for December 2024 to commence scheduled flights from Palm Beach, Florida to Marsh Harbour and North Eleuthera in the Bahamas' Abaco Islands region, further extending its presence in the Caribbean.

Since 2021, Tradewind has consistently ranked among the top American airlines in the Condé Nast Traveler Readers' Choice Awards, advancing from fifth place to third by 2023 before settling at fourth place in 2024.

Currently, Tradewind stands as the second-largest operator of Pilatus PC-12 aircraft within the United States, holds the distinction as the largest global scheduled airline operator of PC-12s, and ranks among the leading worldwide charter providers for this aircraft type.

Destinations

Tradewind Aviation Scheduled Destinations
Country State/Territory Destination
Antigua and Barbuda Antigua
Bahamas Marsh Harbour
North Eleuthera
France Saint Barthélemy Saint-Jean
United States Massachusetts Martha's Vineyard
Nantucket
New Jersey Teterboro
New York White Plains
Florida Palm Beach
Puerto Rico San Juan
U.S. Virgin Islands St. Thomas
United Kingdom Anguilla Anguilla
British Virgin Islands Virgin Gorda
Tortola


Fleet

Tradewind Aviation operates a fleet consisting of 34 aircraft, predominantly Pilatus PC-12 models. The company has placed orders for 11 additional PC-12 NGX planes to enhance its regional and charter flight offerings.

Tradewind Aviation fleet
Aircraft Current Fleet Pending Orders
Pilatus PC-12/45 6 0
Pilatus PC-12/47 1 0
Pilatus PC-12 NG 13 0
Pilatus PC-12 NGX 14 11
Tradewind Aviation historic fleet
Aircraft Year Introduced Year Retired
Cessna 208B Grand Caravan 2001 2013
Cessna Citation CJ3 2007 2024