Tailwind seaplane at the dock prepping for flight.

Taking Tailwind for a spin before it begins NYC-BOS seaplane operation

Seaplane operations are not a new idea for New York City. Small airlines have been utilizing the East 23rd Street Skyport since the 1930s. What’s new, though, is having the option to take a seaplane flight from Manhattan directly to another major city rather than a weekend getaway destination like The Hamptons.

Tailwind Air will begin operating flights between Manhattan’s seaplane base and Boston starting 3 August, offering what should be the fastest overall trip time between the two cities. What Tailwind lacks in amenities and service is made up for by sheer speed.

I joined Tailwind for a demo flight out of its Manhattan seaplane base to get a feel for the departure experience in the days leading up to the launch of Boston flights.

Seaplane terminal entry doors.Much like flying private, there is no TSA checkpoint or screening. Passengers are advised to arrive at the seaplane base just 20 minutes before their scheduled departure time, the same as the American Air Shuttle minimum check-in window at LaGuardia.

While I arrived on one of the two frequent New York City Bus routes that stop just outside the entrance, I suspect most passengers will arrive by car service.

Tailwind offers a small departure lounge for all passengers, though most passengers should really aim to arrive close enough to departure time so that they won’t have to wait long.

The Tailwind lounge windows have signage saying: "Birds of a feather stay cool together"

Inside you’ll find a few couches and chairs, along with a small mini fridge loaded with complimentary beverages.

Seaplane departure lounge with assorted seating.Boarding takes place on a dock in the East River and can be a bit challenging. As large boats and ferries pass and create wake, transferring from the dock to the small ladder and rear entrance door can be a difficult task. Tailwind seaplane at the dock prepping for flight.

Passengers with reduced mobility are going to have a difficult time boarding this aircraft. The flight crew is there to assist boarding passengers, but there is no ramp from the dock to aircraft.

A large door enables people to board, but boarding is not PRM friendlyThe aircraft operating our demo flight was a 2019 Cessna 208B Grand Caravan EX Seaplane configured with eight passenger seats and operated by two pilots.

Tailwind seaplane's cockpit, with two pilots at the controls

Each passenger seat offers about 35 inches of pitch and is perfectly comfortable for a flight of this duration.

Interior of the Tailwind seaplane, with cream seats in 1-1 config I suggest sitting in the forward most right seat for the best views of Manhattan.

Interior of the Tailwind seaplane. The author's knees are shown in this pic as he is showcasing the ample legroom in front of him Speaking of views, this is the entertainment offered, and it is all passengers should really need. It is spectacular.

A glorious view from a Tailwind seaplane in flight over Manhattan

I did notice that the middle section of seats had DC power ports on the sidewall, but I’m not sure if they are active for anyone who brings along their own DC power adapter.

Interior of the Tailwind seaplane.Takeoff and landing on the East River is an interesting experience and can be a bit bumpy due to the current and wake from boats.

View from a Tailwind seaplane which has just landed on the water

Once in the air, however, the ride was mostly smooth, though an aircraft of this size is going to be more susceptible to small bumps than a larger commercial aircraft.

view from a Tailwind seaplane in flight.

The Cessna is also far louder in the cabin than commercial jets, but I found it quite pleasant as a part of the experience.


Weather for this demo flight was ideal, but summer in the Northeast can be challenging.

Tailwind says that if conditions do not allow for landing on the East River or Boston Harbor they will divert to Teterboro or Logan, respectively, and provide alternate transportation in the form of a prepaid card for a car service.

Overall, Tailwind is offering a very unique transportation option that some may find worth the high fares.

The time saved in a flight can be very real, and some people value that above all else.

Tailwind seaplane at the dock prepping for flight, with a pilot standing in front of the aircraft, smiling

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All images credited to the author, Jason Rabinowitz