Tailwind Air


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 and it also owned its own Boston Harbor seaplane base, 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. 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.

Destinations

Tailwind operated flights to the following destinations:
CityCountry CodeAirportNotes
New York CityUnited States NYSNew York Skyports Seaplane Base
Shelter IslandUnited States SH1Sunset Beach
BridgeportUnited States BDRSikorsky Memorial Airport
BostonUnited States BNHBoston Harbor Seaplane BaseService began on August 3, 2021
NantucketUnited States ACKNantucket Memorial AirportService began on May 17, 2023
PlymouthUnited States PYMPlymouth Municipal Airport
ProvincetownUnited States PVCProvincetown Municipal AirportService began on May 25, 2022
NewportUnited States NPTNewport State Airport
DullesUnited States IADDulles International AirportService began on October 14, 2022.

Fleet

The Tailwind Air fleet consisted of the following aircraft: