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Flying The Seaplane Between New York and Boston: What to Know

Boston is only around 200 miles from New York City, and there is no shortage of options to get between the two (Amtrak’s Acela and Northeast Regional service, multiple direct flights every hour out of Laguardia, Newark and JFK; or simply braving the traffic on I-95). Recently, a new possibility has entered the mix: seaplanes. After the operator Tailwind announced expanded service and new destinations, I tested out the experience. Here’s what it’s like to fly in the seaplane between New York and Boston. Plus, how the service stacks up to other options, where else it flies, and what it costs.

Contact your Trip Designer or Indagare, if you are not yet a member, to learn more about planning your next travels. Our team can match you with the itineraries, accommodations, reservations and guides that are right for you.

The Check-In:

Tailwind operates its New York flights from the Skyports Seaplane Base (NYS) on East 23rd Street by the East River. For many New Yorkers, getting to the skyport along FDR Drive is significantly more convenient than making the trek to any of New York’s airports. That alone is a major time saver. Another time saver: no lines, no security, no walking down large airport halls... no airport whatsoever.

Instead, guests enter a small lounge in the historic, though slightly crumbling, skyport building (it was a seaplane hub in the 1930s, but fell out of use after World War II and the rise of jet planes). Inside, expect a couple of sofas, light snacks (fresh fruit and granola bars, for example) and not much else, with a bathroom down the hall. The American Express Centurion Lounge, this is not. But unlike at commercial airports where passengers need to arrive early (and wait for inevitable delays), guests aboard Tailwind’s seaplane service can show up mere minutes before departure.

Once the plane is close, a Tailwind employee escorts passengers outside along a dock. In Boston, the pick-up is at Fan Pier, where a water-shuttle takes passengers to a floating dock in Boston Harbor.

On-Board Experience

Tailwind’s Seaplanes are Cessna Caravans, with room for a maximum of eight passengers along with two pilots. Comfortable leather passenger seats are in single file (a spacious three feet apart from each other) along both sides of the aircraft, with an aisle in between.  There is no service aboard the flights. The seaplane is noticeably louder than a normal plane, so talking to another passenger requires some leaning in and speaking up.

As for the views, they’re exhilarating—and unique. No other flight service (apart from helicopter tours and airport transfers) offers the same proximity to the skyline. We took off northbound over the East River, gaining altitude as we passed above Midtown, with the U.N. immediately on our left. We continued along the river, passing Roosevelt Island and the Upper East Side and Central Park. (Out the right side, the skylines of Williamsburg in Brooklyn and Long Island City in Queens were impressive as well.) From there we flew directly over Laguardia before continuing  along the northern shore of Long Island, with fabulous views of its Great Gatsby-esque homes. Then came the Long Island Sound, Connecticut and, eventually—after about an hour—Boston. We circled in from the north over the Charles River (with the Back Bay, the Common, Beacon Hill and downtown high-rises on the right, and the campuses of MIT and Harvard in Cambridge on the left). We swooped in and landed on the harbor close to Logan International Airport, where we deplaned onto a floating dock before taking a water shuttle to Fan Pier. (Note that wind patterns impact which direction the seaplanes take off and land, so sitting on the left as you leave New York does not guarantee a Manhattan view.)

Where Tailwind Flies

Tailwind currently operates non-stop service between New York and Boston, as well as Shelter Island, Bridgeport, CT and Newport, RI.

There is also continuing service—or, for Bostonians, non-stop service—to Provincetown, Nantucket and Plymouth, Massachusetts.

Come this fall, Tailwind will begin non-stop service between New York and Washington, D.C.

The Cost

Prices for the seaplane vary, but begin at $350 each way for Boston flights. This usually puts it as a slightly more expensive alternative to business or first class commercial plane or Amtrak tickets.

The Take-Away: Who Should Take the Seaplane

At about an hour and 10 minutes (depending on the winds),  the seaplane ride is longer than your typical flight between New York and Boston. But the central take-off and landing locations coupled with zero actual airport experience mean that—door-to-door—the entire trip should actually clock in below an average flight (or Amtrak ride or I-95 drive). Plus, flying at a lower altitude makes for more interesting views.

For leisure travelers heading from New York to Bridgeport, Newport or the Hamptons, the seaplane is a game-changer that avoids traffic. Likewise for New Yorkers or Bostonians looking to travel between the two or get to Cape Cod and Nantucket, it is a fun, easy and reasonable alternative. The experience also makes for a splashy gift, even as a day excursion. On my flight, a father with a plane enthusiast for a son was taking him on a day-trip to Boston purely for the purposes of enjoying the seaplane.

Tailwind has also found a loyal following of business travelers between New York and Boston who want to avoid airports but arrive faster than on Amtrak.

Contact your Trip Designer or Indagare, if you are not yet a member, to learn more about planning your next travels. Our team can match you with the itineraries, accommodations, reservations and guides that are right for you.

Published onMay 9, 2023

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