Making a Splash

Tailwind Air links New York City and Boston by seaplane.

Tailwind Air’s fleet of turboprop planes provides transport to coastal destinations in New York and New England.

By Howard Goodman

Before You Fly, You Float

At the end of a pier jutting into the East River off 23rd Street, you step carefully onto a bobbing Cessna Caravan EX, taking care as the wing just inches above your head rises and falls with the waves.

You strap yourself into one of the eight leather seats. Soon, the plane’s door is shut and you are bouncing on the water, the New York City skyline

doing trampoline jumps in the windows. Then the Pratt & Whitney engine roars and you are gaining speed, the plane cutting through the water like a motorboat. Near the United Nations building, you lift off, the pontoons shedding foam as you rise.

Manhattan is clear as cut glass in the morning light. You are suddenly eye-level with the buildings’ upper floors, then above them as you make out Central Park and the Jersey side of the Hudson all in the same magnificent vista. It’s a Hollywood view of America’s greatest city.

Boston Harbor is just an hour and 10 minutes away.

This is travel by Tailwind Air, the only scheduled seaplane service in the US Northeast. Since 2021, this mainly-charter company based in Port Chester, NY, has provided service two or three times a day from early April through mid-December,

offering exceedingly scenic transit from midtown Manhattan to downtown Boston that is hours faster than trains or other airlines.

It’s not the cheapest way to go: fares usually range from US $395 to US $895 one way between New York and Boston, depending on booking times, discounts, and packages. During summer months, from late May to mid-September, Tailwind’s seaplanes also plop down off the Hamptons and Shelter Island in New York’s Long Island; Newport, Rhode Island; and Provincetown, Plymouth, and Nantucket, Massachusetts. This fall, they will resume flights to Washington, DC. The network has terrestrial destinations, too, including Westchester Airport in New York and Bridgeport, Connecticut.

Boarding the plane at New York’s East River in the morning light. Photo Howard Goodman © 2023.

Tailwind utilizes Manhattan’s
New York Skyport (NYS), which is a dedicated seaplane base located at
the eastern end of 23rd Street along the East River.

This year, Tailwind announced something new for high- flyers who make frequent trips between the Big Apple and Beantown—a plan called Fast Lane Club Plus. For $4,995 a year, members can take unlimited flights for $1 when select seats are available. Fast Lane members also have everyday access to seats on other Tailwind flights at discounts of 30% to 70%.

“For our Boston-Manhattan route, about 60% of passengers are business travelers,” said Peter Manice, Tailwind co-founder and executive vice president, “with that number increasing as the pandemic pauses recede and people are out there meeting face to face again.”

“Business is good,” Manice added. “We’ve expanded to daily service and launched some new routes. We’ve still got some work to maximize load factors, but our base of frequent fliers is encouraging, showing the value we deliver over commercial airline and train options.”

New York City looked dazzling as we climbed. Photo Howard Goodman © 2023.

The route to Boston look us directly over LaGuardia Airport (LGA). Photo Howard Goodman © 2023.

On April 21, Airways flew as Tailwind’s guest from New York to Boston and back as the company opened its 2023 season. We were among six passengers, none happier than an aviation-smitten 6-year-old named Victor who had been taken on the trip by his father as a birthday present.

Tailwind’s office at the Skyport Seaplane Base, on the old New York piers, is so nondescript you have to look hard for it; the place used to be a stockroom. Boarding is a throwback. You can show up 10 minutes before departure time, and there’s no security machine to walk through.

Passengers can carry only 20lb of luggage, so these flights might be best for short visits. No food or drinks are served on the flight, but you can bring your own or grab some of the pretzels, chips, and bottled water that Tailwinds lays out in the waiting area. And there’s no onboard lavatory. A pit stop is advised before boarding.

In Boston, a dedicated seven- minute water-taxi ride connects passengers to
the South Boston waterfront. Photo Howard Goodman © 2023.

Onboard, the eight seats are in a 1-1 pattern, each one next to a window with the aisle down the middle, and there’s nothing separating passengers from the Pilots. You get a good view of the cockpit instruments and the front windshield, as you would on a bus. The generous seat pitch runs up to 36”.

All of Tailwind’s planes can land on the ground as well as water, which comes in handy when visibility is poor or the winds severe, Manice said.

Our flight was called for 08:50 and we were in the air at 09:09.

No one seemed to mind being a few minutes slow in getting started, possibly because we were so agog at the views. Just minutes after rising from the river, the Bronx and Queens stretched before us and, soon, we were flying directly over LaGuardia, the parked planes posed at perfect angles below us. Then, we were looking down on the lush reaches of Gatsby’s northern Long Island, crossing Long Island Sound to Connecticut, and flying almost perfectly north by northeast through mostly rural stretches of New England.

As we climbed, the 41ft, 7in plane was a little shaky but, once we hit the 12,000ft cruising altitude, the ride settled in a smooth and easy glide.

Connecticut and Rhode Island sped below us in a hurry. Unbelievably soon, we were swooping past Boston office buildings and curving into Boston Harbor, the plane bouncing a bit on the water as it scudded to a stop. We passengers applauded and Captain Luca Solari turned to us with a big grin, clasping his hands like a boxing champ. Then, he piloted us over the water to a landing raft not far from Logan International Airport. Co-Pilot Brody Carlson stood on the plane’s left pontoon, ready with a rope to tie the plane to the raft, boating-style.

From the raft, we boarded a motorboat for a 10-minute ride to Fan Pier, a newly developed section extending Boston’s downtown to the south. It was only mid-morning. If we’d had a business appointment, we would have had plenty of time for it.

Captain Luca Solari gave the thumbs-up as he told passengers that the route ahead looked clear. Photo Howard Goodman © 2023.

Later that afternoon, we retraced our steps, our return flight called for 16:00. This time, we checked in not at an office but at a bright, little waterfront restaurant, the ReelHouse Oyster Bar, where an upbeat employee in a Tailwinds ball cap worked from a laptop at the bar.

The trip started with the water taxi ride. The takeoff was quick—smoother than the morning’s. We flew so low for most of the flight that it was easy to make out individual cars, trucks, even people moving around a soccer field. Our course took us right over the old street scheme of Providence, Rhode Island. We crossed the Connecticut River north of where it empties at Old Saybrook, then the Sound, then miles of Long Island exurb and suburb until there, again, lay the expanse of New York—its bridges, its haze to the horizon, its densely compacted towers.

The plane descended on a parallel to FDR Drive and we splashed down between Manhattan’s East Village and Brooklyn’s Greenpoint. We looped around in the East River’s waters to putter back north to 23rd Street as a long, stately barge glided past us on its own New York voyage.It was an impressive vessel, but it was never going to leave the water and sail through the air. You had to feel sorry for it.

Heading back to New York, we flew directly over Providence, Rhode Island. Photo Howard Goodman © 2023.

©2023 Airways Magazine.