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Tailwind Air, an air carrier and charter airline based in Westchester Airport, New York, and Sikorsky Memorial Airport, Connecticut, operated a fleet of 16 aircraft until its closure in 2024. The airline, founded in 2014, specialized in using seaplanes like the Cessna 208 Caravan to provide travel to destinations otherwise difficult to access. Despite its innovative approach, the company was unable to sustain operations due to profitability challenges.
"Tailwind Air was founded in 2014 to offer a convenient, fast, and luxurious travel experience," indicating a focus on business and leisure travelers who prioritized time efficiency. Despite a niche market targeting affluent, efficiency-minded travelers, Tailwind Air ceased operations after losing its commuter license in late 2024. High maintenance costs, fluctuating demand, and other operational challenges compounded the airline's difficulties.
The fleet of Tailwind included amphibious seaplanes that connected urban areas to coastal destinations. Expanding its route network, Tailwind launched operations at the Boston Harbor Seaplane Base in 2021 and expanded further in 2022 and 2023. The Cessna Grand Caravan EX’s amphibious capabilities allowed Tailwind to offer a unique travel option, attracting passengers to its services from Boston Logan Airport to Nantucket Airport.
