The Tailwind difference

We leverage modern and efficient FAA certified 2 pilot seaplanes to help you bypass the New York area and the Northeast’s congested airports. Punctual, comfortable, and available to meet you anywhere on water or land. We have decades of combined aviation experience and an impeccable safety record so you can feel confident in placing your trust with us. Experience the wind at your back – experience Tailwind. 


We operate Cessna 208 Amphibious Caravans, the most popular, modern, and comfortable turboprop seaplane in the Northeast. We are FAA certified for Part 135 Charter and Taxi Operations. Flights have two experienced 2 pilots and feature complimentary water, sodas, and beer.




    Our New York flights operate from Manhattan’s Skyport (NYS). Located at East 23rd Street and the FDR drive access road. Flights depart from the East River’s FAA approved waterway.

    Flights to Nantucket Airport use the general aviation terminal. Flights to Boston Logan use the Signature General Aviation Terminal. Other destinations may use a land airport- or water arrival. We always prefer a splash.

    Before Your Flight/FAQ

    Flying with us sometimes yields a lot of questions:

    We have put together an FAQ answering the most common:

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