I just booked Tailwind’s seaplane flight between Boston and New York. Will the much-awaited service finally launch?

Jul 25, 2021

This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. Terms apply to the offers listed on this page. For an explanation of our Advertising Policy, visit this page.

A-plane, B-plane, seaplane.

A terrible joke. I know, and I’m sorry (not that sorry).

I’ve always thought seaplanes were exceptionally cool, ever since I was a little kid in Brooklyn watching them leaving and approaching the East River.

There’s just something exceptionally fun about seeing a plane flying low carrying pontoons that are almost as big as the fuselage itself, with the ability to go where other aircraft can’t, with a unique mix of grace and clumsy awkwardness.

Want more airline-specific news? Sign up for TPG’s free new biweekly Aviation newsletter!

Modern seaplanes (technically “floatplanes”) are a far cry from the Pan Am Clipper flying boats of an era gone by, but there’s still something about them that’s just cool, and useful; seaplanes arguably make the Maldives viable as a vacation destination, for instance.

Now, I’m excited to fly on a seaplane a bit closer to home.

Tailwind, a small scheduled shuttle and charter operation based in New York, this week announced new seaplane service between Manhattan’s New York Skyport, on the East River at 23rd Street, and Boston Harbor.

The carrier typically runs shuttle routes from Manhattan to summer hotspots on Long Island — East Hampton, Shelter Island and Montauk — as well as Bridgeport, Connecticut — using a fleet of eight-seat Cessna 208 Caravan turboprops with an amphibious configuration, meaning they can land and take-off on both paved runways and water. For charters, the airline can also arrange for other types of aircraft.

Tailwind will be the first airline to launch seaplane service between the two cities in modern times, after Cape Air pulled back on plans that it had set in February 2020, which were derailed by the COVID-19 pandemic. Both Cape Air and Tailwind have been working on launching seaplane service between the cities for more than half a decade. Tailwind won final approval from the Federal Aviation Administration earlier this month.

The airline will start with two round-trips per day on Aug. 3, before increasing service to four daily round-trips on August 23. The seasonal service will run through November, and resume in March.

Tailwind argues its seaplane service to Boston will be faster overall than the train or a traditional plane. (Screenshot via Tailwind)

Flying time will be about 75 minutes, with a total of fewer than 90 minutes “dock to dock,” the Boston Globe reported. That beats the fastest train option — about three and a half hours on the Acela — and while the flying time is longer than on the regular airline shuttles, which are blocked at 80 minutes, the seaplane will eliminate the airport travel time.

On the Boston side, the flights will dock remotely near the East Boston shoreline, with a 7-minute water taxi connecting passengers to Fan Pier

The service is mostly geared towards business travelers — flights start at $395 one-way, and go up to as much as $795.

Flights between New York and Boston start at $395 each way, but can go up to as much as $795. (Screenshot via Tailwind)

I lived in New York for most of my life but recently moved to Boston, so the new service is particularly exciting for me — even if it will be prohibitively expensive. Still, more options are always a good thing and being Boston-based, I’m the perfect candidate to check out Tailwind’s first flight for TPG when it launches in August.

Plus, I’ll finally get to be on one of those seaplanes in the East River that I used to watch as a kid.

More: You could soon redeem miles for flights to space — here’s how

Be sure to check back on Aug. 3 for the full review!

Featured image courtesy of Tailwind Air.

Chase Sapphire Preferred® Card

WELCOME OFFER: 80,000 Points


CARD HIGHLIGHTS: 3X points on dining and 2x points on travel, points transferrable to over a dozen travel partners

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

Apply Now
More Things to Know
  • Earn 80,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $1,000 when you redeem through Chase Ultimate Rewards®.
  • Enjoy benefits such as a $50 annual Ultimate Rewards Hotel Credit, 5x on travel purchased through Chase Ultimate Rewards®, 3x on dining and 2x on all other travel purchases, plus more.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards®. For example, 80,000 points are worth $1,000 toward travel.
  • With Pay Yourself Back℠, your points are worth 25% more during the current offer when you redeem them for statement credits against existing purchases in select, rotating categories
  • Count on Trip Cancellation/Interruption Insurance, Auto Rental Collision Damage Waiver, Lost Luggage Insurance and more.
Regular APR
16.24% - 23.24% Variable
Annual Fee
Balance Transfer Fee
Either $5 or 5% of the amount of each transfer, whichever is greater.
Recommended Credit

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

Disclaimer: The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser’s responsibility to ensure all posts and/or questions are answered.