Tailwind Air LLC
IATA ICAO Callsign
HubsNew 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 size16[4]
HeadquartersRye Brook, NY[3]
Key peopleShane Reynolds
Michael Siegel
Alan Ram
Peter Manice
Wensley Barker

Tailwind Air LLC is a commuter scheduled air carrier and charter airline based in Westchester Airport and Sikorsky Memorial Airport. Its main seaplane base is New York Skyports Seaplane Base (NYS) and it also owns its own Boston Harbor seaplane base (MA17), near Logan International Airport in Boston.[5] The airline has a sister company named Tailwind Air, LLC, which charters and manages a fleet of land planes.


Tailwind Air seaplane leaving the dock at the New York Skyport

Tailwind operates scheduled and charter seaplane services out of the 23rd Street Seaplane base in Manhattan (NYS).[1] Tailwind services 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 include Amtrak and Delta's and American Airlines' hourly shuttle services. Tailwind intends to move its routes to all water airports after regulatory approval. The routes are not serviced by any existing seaplane operator. In-flight service includes complimentary snacks and beverages.


Tailwind operates flights to the following destinations:[6][7]

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[8]
Nantucket United States (Massachusetts) ACK Nantucket Memorial Airport Service began on May 17, 2023[9]
Plymouth United States (Massachusetts) PYM Plymouth Municipal Airport
Provincetown United States (Massachusetts) PVC Provincetown Municipal Airport Service began on May 25, 2022[10]
Newport United States (Rhode Island) NPT Newport State Airport
Dulles United States (Virginia) IAD Dulles International Airport Service began on October 14, 2022.[11]


The Tailwind Air fleet consists of the following aircraft:

A Tailwind Air Cessna 208 Caravan

Former fleet


  1. ^ a b c Bachman, Justin (2014-05-02). "A New Airline Wants to Land Business Travelers on the Water". Bloomberg.com. Archived from the original on May 21, 2014. Retrieved 2014-05-21.
  2. ^ a b c "Tailwind starts service". Archived from the original on 2014-05-21. Retrieved 2014-05-21.
  3. ^ a b c "Tailwind Flights". Tailwind Airlines. Archived from the original on 2014-05-21. Retrieved 2014-05-21.
  4. ^ Federal Aviation Administration (29 April 2018). "Title 14 Code of Federal Regulations (14 CFR) Part 135 Operators and Aircraft". Retrieved 3 April 2019.
  5. ^ "Tailwind Boston Seaplane Base". Airnav.com. August 13, 2020. Retrieved August 20, 2020.
  6. ^ "Shuttles". Tailwind Air. FAQ. Retrieved May 26, 2023.
  7. ^ "2023 Seaplane Schedule" (PDF). Tailwind Air. May 2023. Retrieved May 26, 2023.
  8. ^ Zea, Tibisay (July 30, 2021). "Puddle Jumping To New York In 75 Minutes: Seaplane Service Set To Launch From Boston Harbor". WBUR. Retrieved May 26, 2023.
  9. ^ Palma, Kristi (April 5, 2023). "Travelers can soon take a seaplane from Boston to Nantucket". Boston.com. Retrieved May 26, 2023.
  10. ^ Palma, Kristi (April 29, 2022). "Travelers can take a seaplane from Boston to Provincetown beginning this month". Boston.com. Retrieved May 26, 2023.
  11. ^ Sachs, Andrea (2022-10-27). "We tried the new seaplane flight from D.C. to New York". The Washington Post. ISSN 0190-8286. Retrieved 2022-11-01.