I Tried It: The Boston Harbor Seaplane

Get to New York in two hours, complete with ample Instagram bragging.

By Lisa Weidenfeld· 7/29/2021, 6:30 p.m.

Photo by Lisa Weidenfeld

If you were taking a stroll along Boston Harbor on Wednesday to enjoy a brief glimpse of the sun this summer, you might have spotted the newest attempt to solve the Boston to New York commute. That would be Tailwind Air’s new seaplane service, which aims to get business travelers from Fan Pier to Manhattan in around two hours. The service begins in earnest on August 3, but this week the company offered the media a chance to test the waters, so to speak, and as an intrepid traveler who is now willing to leave the home, I was keen to see what all the fuss was about.

The plane, a petite eight seater, takes off from a platform in Boston Harbor in between various yachts and harbor cruises. Nearby is the similarly petite Tailwind lounge. It’s not exactly a place you’d want to spend hours of time (picture a couch next to a wall-unit air conditioner and a fridge stocked with Fiji water, all in a space the size of a kitchen island), but then again, you won’t have to. That’s because Tailwind will let you check in for your flight up to 10 minutes before it takes off. If you’re coming from an office in the Seaport, you’re looking at leaving your desk perhaps 20 minutes before the scheduled flight time to downtown NYC.

So what’s the actual journey like? From the dock, a water taxi takes you to a small wooden platform floating in the harbor, a far cry from the Dunkin-bedecked terminals of Logan (though at least there are no liquid limits on a Tailwind flight—feel free to waltz onboard with your Dunkin iced pre-purchased on the way over). The plane itself pulls up right next to the platform, at which point you climb aboard via steps that split the difference between a ladder and stairs. These steps are, in my personal opinion, not UN-intimidating, and I can’t say visions of plopping off into the harbor didn’t cross my mind, but we all managed to navigate the boarding process with aplomb, and the pilot took the lead on hauling bags on and off.

Once onboard, you’ll be guaranteed a window view, as there are four rows of two seats divided by a narrow aisle. It is at this point that I must issue my strongest warning to those considering this flight: If you are at all prone to seasickness, take a Dramamine before flying, or, if you really struggle with it, just get off the plane and head straight to Amtrak. I had not fully anticipated that we would get a brief boating trip around the harbor before takeoff. The plane has to find a clear space to take off between all the boats, and while that space doesn’t have to be enormous, the plane can’t just hover up into the air like your average chopper. So for a while, you’ll be stuck inside a cramped interior, bobbing around on two large skis over wakes generated by passing yachts, as you wait for clearance for takeoff.

If you’re willing to brave the seas of Boston Harbor, though, the sightseeing you’re going to get out of the seaplane is pretty jaw-dropping. You’re flying much slower and much lower than you would in a jet, so the views of iconic Boston buildings are amazing. Gawk at the red seats of Fenway Park from the air, snap the perfect skyline photo of the city, or, in my case, take the nicest picture of the Cambridgeside mall that you’re ever going to get. It’s also a smooth flight—if you’ve taken a small, rattle-y plane before, know that this doesn’t really feel like that. Sure, it’s noisy, but the actual flight was smooth-going, in my experience. The return landing was quick and gentle, and if the water taxi is there to meet you at the platform, you could conceivably go from the plane to the Seaport dock in about ten minutes. If you’re up for spending $800 for a round trip flight to New York that you can accomplish within one day, you may be the target audience for Tailwind.

As for me? As a person who is not often called upon to race to Manhattan mid-day for a Business Meeting (invite me any time, fancy New York people), I was most interested in the overall experience of traveling by seaplane, something I’d never tried before. And I have to say, it’s not a tough call between a seven-minute water taxi ride to a floating dock and crawling through Logan-bound traffic in a Lyft, all the while experiencing anxiety spikes as my flight departure time creeps nearer. Plus, because you’re leaving from the Seaport, you’ll get a phenomenal view of the skyline behind you even as you putter out to the platform in the water taxi. I had the pleasure of doing so on a gorgeous July day, but if you were taking this thing in October, you might want to pack several sweaters for the trip.

On that note, because this is a seaplane, it is definitely a fair-weather-only method of transit. As Peter Manice, director of schedule operations at Tailwind explains, “Seaplanes need to land in daylight and they need to see where they’re landing.” That means no rainy flights, no night flights, and the service will shut down completely during the wintry days between Thanksgiving and the third or fourth week of March.

Right now, anyway, the company is currently offering four flights to New York every day, Monday through Friday, but that number may decrease as sunset arrives earlier and earlier—Manice said the schedule would compress as the days shorten, given that they can’t fly at night. And although destinations are currently limited to New York, Tailwind hopes to expand to other cities as well. Eventually they’ll even board passengers right at Fan Pier, cutting out the water taxi ride. It would be more convenient, I suppose, but that view of the harbor as you head out to sea? It’s hard to beat.