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

July 25, 2021
4 min read
I just booked Tailwind's seaplane flight between Boston and New York. Will the much-awaited service finally launch?
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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.

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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.

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

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  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
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TPG Editor‘s Rating
Card Rating is based on the opinion of TPG‘s editors and is not influenced by the card issuer.
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3XEarn 3 Points per $1 spent at Restaurants and Supermarkets
3XEarn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
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  • Intro Offer
    For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening

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    60,000 points
  • Annual Fee

    $95
  • Recommended Credit
    Credit ranges are a variation of FICO© Score 8, one of many types of credit scores lenders may use when considering your credit card application.

    670-850
    Excellent, Good

Why We Chose It

The Citi Premier’s 3 points per dollar spent across a wide range of popular categories is one of the more lucrative offerings in the world of points and miles. The Citi Premier comes with a $95 annual fee and is currently offering a solid sign up bonus of 80,000 points after you spend $4,000 on purchases within the first three months. It also has some valuable transfer partners to make the most of your rewards. Add in access to Citi Entertainment plus a $100 hotel credit for any single-stay hotel booking that exceeds $500 or more, excluding taxes and fees, booked through the Citi travel website, there are few reasons why the Citi Premier should not be in every traveler’s wallet.

Pros

  • Earns 3x points on restaurants, supermarkets, gas stations, air travel and hotels.
  • $100 annual hotel savings benefit (on single hotel stay bookings of $500 or more, excluding taxes and fees, booked through thankyou.com)
  • Points transfer to 16 airline programs, from JetBlue to Virgin Atlantic.
  • World Elite Mastercard benefits, extended warranty, damage and theft protection.

Cons

  • $95 annual fee
  • Lacks travel protections that other travel rewards cards come with
  • For a limited time, earn 80,000 bonus ThankYou® Points after you spend $4,000 in purchases within the first 3 months of account opening
  • Earn 3 Points per $1 spent at Restaurants and Supermarkets
  • Earn 3 Points per $1 spent at Gas Stations, Air Travel and Hotels
  • Earn 1 Point per $1 spent on all other purchases
  • Annual Hotel Savings Benefit
  • 80,000 Points are redeemable for $800 in gift cards when redeemed at thankyou.com
  • No expiration and no limit to the amount of points you can earn with this card
  • No Foreign Transaction Fees on purchases