For travelers looking to make a quick trip from New York City to Boston, Tailwind Air offers a comfortable and convenient ride with views you can’t get from any other mode of transportation. It is the first scheduled seaplane air shuttle service to connect New York with other major cities from the Kips Bay Skyports Seaplane Base on the East River. Tailwind Air’s New York to Boston seaplane shuttle has been operating for nearly two full seasons. Scheduled New York-Washington service will begin in Spring 2024.
The Tailwind shuttle is all about minimizing end-to-end travel time. Downtown New York to downtown Boston dock-to-dock time is under 90 minutes. Gone are the usual airport ground transfers, traditional TSA screening, and runway congestion. The eight-passenger plane quickly loads and unloads. But, it’s the overall seaplane shuttle experience and views that delight.
From New York, the personable Tailwind pilots add a few extra items to their pre-departure checklist. The position and behavior of East River maritime traffic — barges, ferries, jet skis, and random pleasure boats — and the river’s notorious tidal flows and currents provide technical challenges.
Often the morning flights head upriver. Those departures quickly ascend over Roosevelt Island. The United Nations and Long Island City rush by. On my recent trip, however, Tailwind delivered a premium sightseeing tour.
We departed South, rising above the Williamsburg Bridge. Our flight path wrapped around the Battery and up the Hudson River. The Cessna Grand Caravan presented us with amazing views, as we then turned right across Central Park.
In several more minutes, the Tailwind shuttle was above the other more famous (former) seaplane base — the Marine Air Terminal — now LaGuardia Airport, Terminal A. The Queens structure opened in 1940, one year after the Lower East River seaplane base. It sits at the opposite end of the river in Queens. In the 1940s, Mayor Fiorello La Guardia championed the more humble NYC seaplane base to transfer passengers and mail between Floyd Bennett Field and Manhattan, with the hope of undercutting Newark Airport’s then-dominance.
Unlike modern seaplanes which make use of pontoons, the “flying boats” of the 1940s had a bloated fuselage built specifically for buoyancy. This allowed the planes to land safely in the water and float despite their heavy loads. The popularity of flying boats for international travel increased in the 1930s and 40s as seaplanes offered a much faster transatlantic journey than luxury ocean liners, at least for those who could afford it. As paved runways and faster jets became standard in the mid-20th century, the popularity of seaplanes dwindled, but today they still offer convenient service for short distances.
In Boston, Tailwind’s air shuttle arrival and departure paths present even more intimate and uncommon commercial aerial perspectives. The close-up views of Chestnut Hill, Back Bay, Downtown, and North End landmarks — such as Boston College, Harvard, Fenway Park, Prudential Tower, and the Charles River — are not possible from Logan Airport flights.
New York and Boston seaplane air shuttle terminals offer different vibes. In New York, Tailwind uses the rather basic Skyports Seaplane Base at the Eastern end of 23rd Street in Kips Bay. It is well located at the FDR Drive and also a short distance from the Stuyvesant Cove NYC Ferry dock.
In contrast, Tailwinds established a new, very different base in Boston Seaport, adjacent to Fan Pier Marina. What the Boston Seaplane Air Shuttle terminal lacks in history, it makes up for with a modern, elevated experience. Check-in is at an Oyster Bar! A brief boat ride transfers passengers between land and the seaplane air shuttle dock.
The Tailwind shuttle offers a premium, semi-private experience. It provides value for money to time-squeezed travelers, AvGeeks, and others who wish for a unique travel experience. Among my hundreds of trips between these two cities, my travel on the Tailwind Seaplane air shuttle stands out as the most efficient and enjoyable.
Next, check out Kick Your Feet Up Above NYC on a Helicopter Tour