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‘Manhattan In 75 Minutes’: First Look At Boston-New York Seaplane Service

Tailwind Seaplane Flying Over New York City

Angus Loten

Prior to the app, bookings might often be done by phone. Since its introduction, ‘we’re seeing double the digital engagement with our brand from last year’s high watermark,’ the CEO says

Tailwind Seaplane Flying Over New York City

Tailwind Air, serving mostly New York, Boston and nearby vacation spots, is planning to add more short-hop rides.

Seaplane operator Tailwind Air LLC is pushing further into the air-taxi market with more short-hop flights between downtown New York City and Boston, with a new mobile app drawing more passengers, the company’s chief executive said.

The Rye Brook, N.Y.-based startup, launched in 2014, this month plans to add direct flights from Boston’s Fan Pier Marina to Provincetown on Cape Cod, Mass., promising a 35- minute trip dock to dock, said Chief Executive Alan Ram. The company has also added flights from Manhattan’s SkyPort Marina on the East River to Provincetown via Fan Pier, he said.

Each of the company’s three Cessna Caravan EX amphibian seaplanes has eight seats. Passengers are allowed one bag weighing less than 20 pounds, which is then stowed under a facing seat or in the rear baggage compartment.

In addition to seaplanes, the company also operates 17 land aircraft under management, ranging from Gulfstream and Falcon jets to King Air and Pilatus turboprops. Its crew of 40 pilots includes 10 seaplane captains and co-pilots.

Tailwind currently offers direct flights to seasonal havens like the Hamptons on New York’s Long Island, and Plymouth, Mass., among others. Last year, it began testing direct flights between New York City and Boston, and now offers commuter packages of 10 one- way tickets starting at $5,950, going up to $26,250 for a 50-ticket book.

Since March, the company offers three to four daily flights from New York and Boston to various destinations. Flights only run during the daytime from early spring to late fall, and are grounded in winter months.

“You could leave your office on Wall Street and be in downtown Boston in less than two hours,” Mr. Ram said. He refers to the service as an air taxi, in part because it bypasses the long lines, baggage-claim scrum and transit time to and from sprawling airports at the edge of town.

But software also plays a key role, Mr. Ram said. Late last year, he said, Tailwind launched a mobile app, developed in partnership with a third-party vendor, on which travelers can scan daily flight schedules and reserve one of eight seats onboard.

”We generally close flights 90 minutes or less before takeoff, and if there’s an available seat you can hop on,” Mr. Ram said. With no Transportation Security Administration or baggage checks, passengers need only arrive at the pier around 10 minutes before their flight, he added.

Before the app, bookings tended to be done manually, with many regular passengers calling in reservations instead of going through the company’s website, Mr. Ram said.

Tailwind Site from iPhone Screen

Tailwind’s mobile app allows passengers to scan daily light schedules and reserve one of eight seats onboard its amphibious planes.

“Right now, we’re seeing double the digital engagement with our brand from last year’s high watermark,” he said. He expects to add a fourth seaplane by the end of the year, and three more by the end of 2023, he said.

The company, which operates on a 50-50 mix of angel-investor funding and earnings, saw its revenue double last year, Mr. Ram said, declining to give specifics.

Like Tailwind itself, the air-taxi industry is in its infancy—along with the fledgling efforts of the biggest players in aviation, which are adding electric and autonomous elements to it.

In January, Boeing Co. invested an additional $450 million in its air-taxi joint venture with Google co-founder Larry Page. The project looks to develop small, pilotless aircraft for short passenger trips in and around cities. Rival plane-makers Airbus SE and Embraer SA are also developing electric air taxis.

Last year, four startups designing ride-hailing aircraft known as eVTOLs—it stands for electric vertical takeoff and landings—went public through special-purpose acquisition companies. They include U.S. firms Joby Aviation Inc. and Archer Aviation Inc., Germany’s Lilium N.V. and Britain’s Vertical Aerospace Ltd. None is planning to start services before 2024.

Uber Technologies Inc., which floated its vision of flying taxis in 2016, two years ago sold its aerial ride-hailing division to California-based Joby, while taking an initial $75 million stake. Joby went public through a combination with Reinvent Technology Partners, a blank-check company backed by LinkedIn Founder Reid Hoffman.

On Wednesday, Mr. Hoffman said the company is on track to launch operations within the next two years. “We’re on plan,” he said, adding that air taxis—especially in the form of electric helicopters—represent a chance to rethink the urban transportation space in a way that is cleaner and more efficient.

Smaller-scale firms operate on models similar to that of Tailwind. On Blade Urban Air Mobility Inc., headquartered in New York, customers can also book trips on helicopters and jets through a smartphone app, taking passengers to destinations roughly 100 miles away or more. (For comparison, Boston to New York is around 190 miles.)

Unlike eVTOLs, Mr. Ram said, Tailwind’s advantage is that its underlying infrastructure and technology are already in place—and have been for more than a century.

“The idea of an air taxi being able to land on every building or on the corner creates challenges of airspace integration and customer acceptance,” he said. “We’re concentrating it around existing infrastructure.”

Write to Angus Loten at angus.loten@wsj.com

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Need to Get From New York to Boston Fast? Hop on a Seaplane.

A speedy—and highly scenic—new way to travel from New York City to Boston is also one of the oldest: the storied seaplane

By Barbara Peterson Aug. 31, 2021 8:16 am ET

THE FIRST seaplanes in 50 years to fly scheduled service between Boston and New York City splashed down in their cities’ respective harbors this summer, and even the most jaded travelers took notice. These partly waterborne journeys clock in at about 90 minutes, beating traffic jams at an airport checkpoint—or on I-95—any day.

Tailwind Air promotes its flights as the fastest downtown-to-downtown trip in the market. But you can also think of them as time-travel back to the golden age of flying. Seaplanes have been around for more than 100 years. The terminal on the East River in Manhattan where you take off was built in 1936, when scarce airport runway space favored these maritime depots.

The 1930s was also the heyday of the flying boat—a bulky vessel whose fuselage acted as the hull, floating it when the plane was in the water. These flying ships plied Pacific and Atlantic routes and reached their apogee (or nadir, depending on your viewpoint) with Howard Hughes’ Spruce Goose, a gigantic wooden flying boat that required eight engines to get aloft—which, on its first and only flight in 1947, it managed for just 26 seconds. Though modern aviation advances ended the flying boats’ run as passenger planes, a few still operate today, fulfilling industrial functions such as carrying water to fight fires.

The amphibious Cessna Caravans operated by Tailwind hardly resemble the glamorous “Pan Am Clippers” of the past; they’re diminutive, single-engine floatplanes with pontoons. Capable of landing on land as well as water, they are mainly drafted for sightseeing excursions or, in Tailwind’s other market, ferrying well-heeled weekenders and commuters from Manhattan to the Hamptons in a mere 40 minutes.

With a capacity of eight passengers—arranged single file, so everyone has a window—neither Tailwind flight offers much luxury but they’re still not cheap. Fares start at $395 one-way for the New York City to Boston route, which, as of Aug. 31, will offer four flights every weekday. And because the fleet doesn’t include flying icebreakers, the seaplane will only take off March to November.

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

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David Slotnick

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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.

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.