Flight Review: Tailwind Air Seaplane From New York to Boston(ish)

Flight Review: Tailwind Air Seaplane From New York to Boston(ish)

The northeast is a tightly compact space that makes it difficult to commute between the populous cities. You can take commercial air travel, but then you have to deal with security, long lines, and the pain of showing up early for your flight. You could take the high speed train service between these large cities, however they are often slower than it would be to fly commercial.

What if there was a third option? One that you could board from the downtown of these cities without traveling to the large commercial airports and go from downtown New York to downtown Boston (or the Cape) in just over an hour.

Meet Tailwind Air, a new commuter airline aiming to connecting New York, Boston, and much of the Northeast without having to step inside a commercial airport.

AvGeeks was given a complimentary ticket in exchange for this review.
Tailwind Air had no editorial input to our review.


Booking flights with Tailwind Air is pretty easy. You can pick your departure and destination and with a few clicks you have a ticket. For those that may choose to commute more often Tailwind Air also offers discounts via a membership club or you can buy a set number of tickets for a discount. I could see this being quite the value as not only does Tailwind Air have destinations like Boston but more seasonal touristy destinations like Bridgeport or Nantucket.


Currently check-in is done in person at your departure station. This day I was booked in on the New York Harbor to Boston Harbor route, one of the only routes that Tailwind Air operates during the non-peak season. However, you can charter the airline to go wherever you need them to go during these times. The plane that I was to fly on was coming in from Nantucket where it was chartered.

The check-in area also doubles as the lounge, there was a small cooler of drinks and a snack basket. This would be our only opportunity for snacks or drinks as there is no onboard service and there is no flight attendant, just the two pilots.

I ended up coming straight from JFK to the skyport, it took just over an hour by taking the Long Island Railroad and walking from Grand Central. I would not recommend arriving more than 30 minutes prior to departure as staff didn't seen to even be there yet and there was nobody to greet you.

Once someone did show up it was a quick check-in process and because I only had a backpack with me, didn't need to check any baggage.

Flight Cancelled

The day before my flight was supposed to happen, I received an email from Tailwind Air informing me that the flight I was supposed to be on was cancelled the next morning and thus they only had the afternoon flight open for rebooking.

The only problem with the afternoon flight was that it lands after sun down and due to harbor restrictions at Boston, lands at nearby airport Norwood (OWD). While I was really hoping to go from New York harbor to Boston harbor it just didn't seem like that was going to be the possibility for my schedule, so I accepted the change to the afternoon flight that landed at Norwood.

I later found out that the airplane I was supposed to fly on needed to go down for its 100-hour maintenance check, a critical maintenance item that ensures the single engine airplane is air worthy. While disappointing, I understand the safety and as I was told, the availability to do the check was limited.


Boarding was super cool, right outside the Tailwind Air lounge is a small pier where the plane pulls up and loads and unloads passengers.

It ended up being quite the windy day, and the plane was rocking back and forth in the water making it quite the experience to get on to the aircraft. Thankfully the pilots are there to help you, my advice is to take your step as the aircraft is rocking back up towards you to get a stable footing and use the momentum to hoist yourself into the aircraft. Just don't push a little too hard and bump your head against the ceiling.

The Seat

While not a full recliner or private suite, the seats in the Cessna 208 Caravan are perfectly padded and comfortable for the hour long flight up the coast. Unlike actual airliner seats, there is a shoulder harness and it acts more like a car set belt rather than something you'd find in a typical airliner.

The aircraft is laid out in a 1-1 configuration, with ample shoulder room. However for those who are over 6 foot, like myself you may find the knee room pretty tight but it's easy to angle yourself out into the aisle for a bit extra room.


As mentioned, there is no flight attendant onboard, you only have the two pilots onboard. The two that operated my flight were very pleasant to talk to and answered some cool questions about the job that I had. They also take care of everything when you arrive to the aircraft.

They give you a short safety briefing before pushing off of the pier for the float out to the takeoff area. It's quite the feeling to be in an airplane on the water. Being a windy day were got rocked around as we climbed out of New York but once past all the big buildings it smoothed out. As you can expect a smaller airplane picks up turbulence easier than a larger aircraft so I suggest you don't eat a lot of have too much of a queasy stomach.

One super cool thing about flying in a smaller aircraft is use of the general aviation corridors around the New York airspace, this means you get some wild views and do things you wouldn't think would be possible. On our departure out of New York we flew directly over the top of the LaGuardia Airport while aircraft were taking off and landing.

The whole experience was quite surreal, I don't fly in small airplanes much and on top of that I don't get to fly much in the Northeast except for just a handful of commercial airports.

Not Quite Boston

As we flew up the coast we crossed over some smaller airports on the outskirts of New York and the sun started to set quickly. About 20 minutes out of the Boston-area the sun had fully set and it was completely dark outside except for the lights of the cities below us. As mentioned, because of curfew restrictions at Boston Harbor we couldn't land and instead we landed at Norwood Memorial Airport, about a 30-40 minute drive from downtown Boston.

When we landed I was helped off the aircraft and into a small shared waiting room at the airport where I called an Uber to pick me up, during times when Tailwind Air has to land at Norwood they usually offer a $50 credit towards Uber/Lyft to get you into the city.

It's something I would make sure if I were ever to book this flight again is to make sure that the flight will be landing at Boston Harbor rather than outside of the city. I had a flight back home from Boston Logan and I ended up being very close to not making my connection due to the increased time it took for the Uber.

Final Thoughts

It's no doubt the fastest way to get from New York to Boston or the Cape is by seaplane. The ease of being able to fly directly from downtown New York and not having to deal with the general public at a commercial airport is paramount. You could get off of work in downtown and be in the Cape for dinner time. I expect that we'll see more great things when their service picks up in the spring time.

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