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This Seaplane Is One of the Fastest Ways to Get From NYC to Boston — and It’s Surprisingly Affordable

The Tailwind Air trip takes 75 minutes, and the best part is you get to check in for your flight at an oyster bar.

One of the Fastest Ways to Get From NYC to Boston

By Stefanie Waldek

For those who have traveled between New York and Boston, you’ve probably taken the train, driven, or maybe even flown on a commuter jet. But we’re willing to guess you probably haven’t made the journey via seaplane. Well, now you can.

Tailwind Air just relaunched its seasonal route between New York and Boston, flying eight-seat Cessna Caravan seaplanes between the cities twice daily in each direction: once in the morning and once in the evening. The flights depart from and arrive at the New York Skyports Seaplane Base on East 23rd Street in Manhattan and the ReelHouse Oyster Bar – Seaport in Boston Harbor (yes, you’ll be checking in at an oyster bar). All in, you’re looking at about a 75-minute flight in each direction.

This seaplane experience differs significantly from regular flights. For starters, the flights are designed for daily commuters or single-day sightseers, as luggage is restricted to a single bag weighing less than 20 pounds — it must fit beneath the seat in front of you or in one of the small baggage compartments on board. And then there’s the fact that you only have to show up 20 minutes before your flight, no TSA security check necessary. (If you’ve ever flown out of a private terminal on a semi-private jet, these seaplane terminals operate similarly.) 

“Demand for our flagship service between Manhattan and Boston Harbor, which takes just 75 minutes, continues to grow. Last year, our overall ticketed revenue grew by over 400 percent,” said Peter Manice, Tailwind Air’s vice president of scheduled service, in an interview Travel + Leisure. Beyond the New York–Boston route, Tailwind Air also flies to Provincetown, Sag Harbor/East Hampton, Shelter Island, Bridgetown, Plymouth, and, as of this summer, Nantucket. The airline will also fly between New York and Washington, D.C., starting this fall.

Rates for the New York–Boston flights start at $395 each way (which is pretty reasonable when you consider an Amtrak ticket for a train from New York to Boston costs $161 to $327 this month). You can also buy commuter books (multi-flight packs) for a discount. There are also two membership programs — Fast Lane Club and Fast Lane Club PLUS — that provide even better discounts. With Fast Lane Club PLUS, which costs $4,495 per year, members have access to last-minute flight deals as low as $1 per seat. Availability for that deal is, of course, quite limited. 

To book your next flight on Tailwind Air, or to sign up for a membership, visit

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