Tailwind Air LLC was an American commuter scheduled air carrier and charter airline based in Westchester Airport and Sikorsky Memorial Airport. Its main seaplane base was New York Skyports Seaplane Base (NYS) and it also owned its own Boston Harbor seaplane base (MA17), near Logan International Airport in Boston. The airline had a sister company named Tailwind Air, LLC, which charters and manages a fleet of land planes.
History Tailwind operated scheduled and charter seaplane services out of the 23rd Street Seaplane base in Manhattan (NYS). Tailwind serviced Boston Logan Airport, Boston Harbor Seaplane Base, Shelter Island, Bridgeport, and the East Hampton Airport and Nantucket Airport with multiple shuttle flights. Initial competitors on these routes included Amtrak, American Airlines, and Delta's hourly shuttle services. Tailwind intended to move its routes to all water airports after regulatory approval. The routes were not serviced by any existing seaplane operator. In-flight service included complimentary snacks and beverages.
Tailwind Air ceased scheduled services in early 2024 and was currently charter-only. The airline had reported that scheduled operations had not reached profitability, and they failed to get a large enough investment to continue slow growth in ticketing.
On January 15, 2026, Tailwind Air filed for Chapter 11 bankruptcy protection, marking the end of Tailwind's 4 year service.
Destinations Tailwind operated flights to the following destinations: +List of destinations City Country (subdivision) Code Airport Notes New York City United States (New York) NYS New York Skyports Seaplane Base Shelter Island United States (New York) SH1Sunset BeachBridgeportUnited States (Connecticut)BDRSikorsky Memorial AirportBostonUnited States (Massachusetts)BNHBoston Harbor Seaplane BaseService began on August 3, 2021NantucketUnited States (Massachusetts)ACKNantucket Memorial AirportService began on May 17, 2023PlymouthUnited States (Massachusetts)PYMPlymouth Municipal AirportProvincetownUnited States (Massachusetts)PVCProvincetown Municipal AirportService began on May 25, 2022NewportUnited States (Rhode Island)NPTNewport State AirportDullesUnited States (Virginia)IADDulles International AirportService began on October 14, 2022.
Fleet
The Tailwind Air fleet consisted of the following aircraft:
3 Cessna 208EX Caravan 1 Dassault Falcon 50 2 Dassault Falcon 900EX 3 SOCATA TBM-700 3 SOCATA TBM-900 1 Beechcraft King Air 250 1 Cessna Citation CJ3 1 Dassault Falcon 100 1 Pilatus PC-12
Former fleet 1 × Embraer Phenom 300
References .
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