Tailwind Air's seaplane tempts with thrilling NYC-BOS short hop

For many travelers, a low fare is the most important metric when booking transportation. For others, a premium experience tops all other requirements. And then there are those who have the need for speed — above all else.

In 2021, Tailwind Air started operating pricey seaplane services between Manhattan’s East River and Boston Harbor, offering arguably the lowest possible trip time between the two major Northeast US cities. Just days before its launch, I took Tailwind for a spin around Manhattan.

Fast forward to this fall and the Part 135 operator invited your author and a travel companion to experience a flight between New York and Boston.

Alas, my initial attempt was thwarted by poor weather conditions. A day before the flight, it was clear that a seaplane ride off the East River was going to be unlikely. But this gave me the opportunity to see how well Tailwind communicates with its passengers.

To its credit, Tailwind shared robust and concise information via email and SMS in the day leading up to departure. After initially bumping up the departure time by 15 minutes, it imposed a deadline of 7pm the night before to make a final decision and ultimately opted to cancel in the 4pm hour.

Unlike a traditional airline, no alternate routing is possible with Tailwind. Any impacted passengers would have to figure out another way to Boston and use the credit issued by Tailwind another day.

I settled on another attempt a month later and lucked out with a perfect fall day. Tailwind operates out of a spartan space at the East River and 23rd Street, but the entire concept of Tailwind is about speed of travel so I bypassed the small lounge and went straight to the dock to where the Cessna 208 Caravan taxied (ferried?) after landing.

With just one other revenue passenger, the experience was extremely laid back. Boarding began early and took just seconds.

Background Reggae music played over the pilot’s bluetooth speaker, creating a fun and chill vibe.

A pre-flight safety briefing was conducted and we were informed that our flight time would be approximately one hour and twenty minutes. The average commercial jet flight between LaGuardia and Boston Logan hovers around 40 minutes from wheels up to wheels down, but that excludes the hours of additional time that the entire commercial air travel experience adds.

We departed to the south and made a 180 degree turn around the battery of Manhattan, enjoying stunning views as we climbed out over the Hudson River before making a turn to the northeast.

From here the flight was about an hour of staring out the window while cruising at about 10,000 feet and 200 MPH.

This is all the entertainment passengers could need. Power outlets would, however, be a welcome addition as I drained my phone’s battery taking many photos and videos.

Unlike in New York, Tailwind’s seaplanes are not able to taxi up directly to the actual “terminal” in Boston. Rather, a connecting boat shuttles passengers on a five-minute journey between Boston’s Seaport District across the Inner Harbor to East Boston. This last leg may prove slightly annoying during poor weather conditions.

The total travel time from boarding the seaplane in New York to disembarking the connecting boat in Boston was approximately one hour and thirty five minutes.

A quick walk (with brief stop at a popup shop with kittens to play with) had us enjoying a lobster roll lunch at exactly noon.

For comparison sake, the journey back to New York on board an Amtrak Northeast Regional train clocked in at four hours and twenty three minutes, a 277% longer trip time. While the Amtrak ticket cost just $31, Tailwind’s fares start at $395 and climb to as much as $895 for a flexible fare. Those views, though…

It’s clear that Tailwind’s service is not for the cost conscious, but for those who value time above all else and don’t have their own helicopter at the ready, there is simply no faster way between New York and Boston.