Tradewind Aviation, LLC, doing business as Tradewind Aviation and Tradewind Shuttle, is an American airline headquartered at the Waterbury-Oxford Airport in Oxford, Connecticut,^[2] United States. Tradewind Aviation provides private and scheduled service in the Northeast, Southeast, and the Caribbean, as well as aircraft management services. The air charter company is best known for its Westchester to Nantucket summer ticket books, and its Puerto Rico to St. Barths scheduled service.

Founded in 2001, Tradewind Aviation commenced operations utilizing a single Cessna Caravan. 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. Charter service expanded throughout America and the Caribbean, with authorization for scheduled flights coming in 2005 and eventually expanding to 11 destinations. Each domestic Tradewind scheduled service flight within the United States departs and arrives at an FBO.

Caribbean network flights operate from normal terminals. Tradewind offers premium service at Luis Muñoz Marín International Airport in San Juan with a semi-private lounge area while customers await their trips to the high-end Caribbean destinations served by Tradewind. Tradewind operates year-round service to Gustaf III Airport in St. Barthelemy, providing the only year-round, nonstop scheduled service between this ultra-luxe French territory and the United States, which it has operated since 2006.

In June 2019, Tradewind launched a jet card, called "Goodspeed." The program offers fixed, one-way rates on its PC-12 fleet in three service areas, 300 nautical miles from Westchester County Airport in New York, Palm Beach International Airport in Florida, and San Juan Luis Muñoz Marín Airport in the Caribbean. Jet cards are offered in 10, 25 and 40-hour denominations.^[3]

In 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. The program cements Tradewind's status as the operator of one of the world's largest fleets of Pilatus PC-12s, and the largest available for charter.

In September 2023, Tradewind opened a new hub in Stuart, Florida at Witham Field, serving the burgeoning Southeast market. Today, Tradewind is the second-largest operator of the Pilatus PC-12 in the U.S., and the world's largest operator of PC-12s for charter.

In 2021, 2022, and 2023, Tradewind was nominated for the Condé Nast Traveler Readers' Choice Awards as one of America's best airlines, and was voted 5th, 4th, and 3rd best, respectively.

Tradewind Aviation operates scheduled flights to the following destinations:

As of January 2024^[update], Tradewind's fleet consists of the following aircraft:

On March 1, 2022, Tradewind Aviation, in partnership with Pilatus Aircraft, announced that it would take delivery of 20 Pilatus PC-12 NGX aircraft between the third quarter of 2022 and 2027, at a rate of four aircraft per year. The order marks a doubling of Tradewind's fleet and cements the relationship that Tradewind has had with Pilatus since beginning to operate the PC-12 in 2003. Between 2001 and 2013, Tradewind also operated a fleet of Cessna 208B Grand Caravans, and has also managed a variety of other aircraft for clients.

• List of airlines of the United States