

Tailwind Air launched in 2014 and provided short seaplane flights operated from the 23rd Street Seaplane base in Manhattan (NYS). The routes included New York City (NY), Shelter Island (NY), Bridgeport (CT), Boston (MA), Nantucket (MA), Plymouth (MA), Province Town (MA), Newport (RI), and Dulles (VA).
Upon its launch in 2021, the New York–Boston route was particularly popular. It took less than 90 minutes and proved to be a more efficient travel choice than a standard flight between the main airports. At the time, sales were high, and the outlook for the airline was positive.
However, since then, Tailwind Air has been unable to turn a profit. The fleet’s aircraft, the Cessna 208 Caravan, could seat eight passengers and two pilots, yet many flights were less than half full.
As reported by the Boston Globe, Chief Executive Alan Ram said, “Tailwind needed an average of five passengers per trip to cover the costs. […] We had a base; they tried it, they liked it, and it was kind of growing, but even then, the awareness was still pretty low. To make something sustainable at this time scale, it does take seven-figure or eight-figure investments, which we haven’t generated yet.”
Ram told the Boston Globe that he had been looking for a partner to revive the Boston Harbor service, but this fell through. Ram is still hopeful that the seaplanes could return with the right investor in 2025.
“This was a great time-saver for people. If we can find the right partner, we’ll keep doing it,” said Ram.
At this point in time, Tailwind is continuing to operate chartered services with a sister company, Tailwind Air, LLC, that operates private land planes.
Photo: Tailwind Air






