Tailwind Air

Not to be confused with Tailwind Airlines.

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.^[5] The airline had a sister company named Tailwind Air, LLC, which charters and manages a fleet of land planes.

Tailwind Air LLC

IATA ICAO Call sign TQ PGN PEREGRINE
Founded	2014[1][2][3]
Ceased operations	2024
Hubs	New York–Skyport Sikorsky Memorial Airport (Connecticut) Boston Harbor Seaplane Base
Focus cities	New York Skyports Inc. Seaplane Base New York City Boston Harbor Seaplane Base Westchester County Airport
Fleet size	16[4]
Destinations	5
Headquarters	Rye Brook, NY[3]
Key people	Shane Reynolds Michael Siegel Alan Ram Peter Manice Wensley Barker
Website	http://flytailwind.com/[2][3]

History

Tailwind operated scheduled and charter seaplane services out of the 23rd Street Seaplane base in Manhattan (NYS).^[1] Tailwind serviced Boston Logan Airport, Boston Harbor Seaplane Base, Shelter Island, Bridgeport, and the East Hampton Airport and Nantucket Airport^[1] with multiple shuttle flights.^[2] Initial competitors on these routes included Amtrak and Delta's and American Airlines' 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 is currently charter-only. The airline reported that scheduled operations had not reached profitability, and they failed to get a large enough investment to continue slow growth in ticketing.^[6]

Destinations

Tailwind operated flights to the following destinations:^[7][8]

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)	SH1	Sunset Beach
Bridgeport	United States (Connecticut)	BDR	Sikorsky Memorial Airport
Boston	United States (Massachusetts)	BNH	Boston Harbor Seaplane Base	Service began on August 3, 2021[9]
Nantucket	United States (Massachusetts)	ACK	Nantucket Memorial Airport	Service began on May 17, 2023[10]
Plymouth	United States (Massachusetts)	PYM	Plymouth Municipal Airport
Provincetown	United States (Massachusetts)	PVC	Provincetown Municipal Airport	Service began on May 25, 2022[11]
Newport	United States (Rhode Island)	NPT	Newport State Airport
Dulles	United States (Virginia)	IAD	Dulles International Airport	Service began on October 14, 2022.[12]

Fleet

Tailwind Air seaplane leaving the dock at the New York Skyport

A Tailwind Air Cessna 208 Caravan

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