Beyond Wellesley—we get to New York City via a speedy seaplane

There are many commercial outfits that can take you from Boston to New York City, but I’ve just experienced the quickest way to make that trip—via Tailwind’s seaplane service, which gets travelers from Boston’s Seaport area to midtown Manhattan typically in under 75 minutes in-air travel time.

The Federal Aviation Administration last summer gave the thumbs up for flights out of Boston Harbor after Tailwind spent almost ten years coming up with solutions for every problem that busy Logan airport’s flight patterns presented. For now, Tailwind is the only seaplane game in Boston, but others will likely take advantage of the regulatory legwork already done and try to enter the market.

Tailwind, Boston
Mrs. Swellesley is ready to try out a seaplane for the first time on Tailwind.

As part of a press tour to try out the service, my round-trip flight was paid for by Tailwind. Trust me, I wouldn’t have been able to experience the flight any other way. Prices range from $395 to $795 one-way, depending on advanced purchase and available inventory. There is a bargain option of $595 roundtrip if the passenger stays over on a Saturday night. Flying by seaplane from Boston to New York is for those for whom time is money.

Farewell for now, Wellesley

I hopped the Wellesley Square commuter rail into South Station and walked the 15 minutes to Tailwind’s check-in area at Boston Harbor at Fan Pier Marina in the Seaport area. The secret to finding this tucked-away spot is to put Davio’s Northern Italian Steakhouse into your GPS. Keep Davio’s to your left and look for Tailwind’s small brick building on the harbor. That’s where staff will greet you and you’ll get your bag weighed (20 lb. maximum) and relax until the ferry arrives at the dock. The seven-minute ferry takes passengers to a floating pier for take-off.

Because Tailwind screens passengers and confirms IDs in advance in compliance with all regulatory requirements, the check-in process is incredibly civilized. Nobody shouts at stressed-out passengers to take off their shoes and remove all electronics from their bags, and I didn’t have to remove my baseball cap and reveal the truth about my second-day hair. Passengers can show up at the dock well under 30 minutes before the ferry leaves, and be on the plane in short order.

Tailwind, Boston
Above Boston en route to NYC.

Getting on and off the ferry and the plane, a Cessna Caravan EX amphibian aircraft with eight passenger seats, isn’t difficult, but it also isn’t accessible. The flight is staffed by a pilot and a co-pilot, who are in full view, as are their flight instruments and the plane’s GPS screen. There’s enough leg room and headspace in the functional and spotless, but not luxurious, cabin. So far so good, but I’d received disappointing news shortly before take-off. Due to low cloud cover, the flight wouldn’t be landing in New York Harbor. We’d be landing in Westchester County Airport in the lovely suburb of White Plains, about a 1-hour and 15-minute drive from midtown Manhattan. Sadly for me, no water landing. This time around I would experience a run-of-the-mill runway landing, not a problem for the aircraft, since it can handle both paved and water surfaces.

Don’t sweat the small stuff

I, too, can manage myself on both land and sea, but the White Plains landing presented logistical problems. Anxiety triggered, I briefly considered bagging the whole adventure. But I’d already booked my hipster-cool hotel, and the refund window had slammed shut. And I really wanted to wander through some shops and bookstores, and go to the Whitney Museum of American Art. Plus Riverside, a Polish rock band, was expecting me in the audience at The Gramercy Theatre. I couldn’t let those guys down on their 20th anniversary of rocking on, hell no. What was I? An intrepid traveler, or a wimpy traveler? So what if I didn’t have any idea how I’d escape from a leafy green suburb quite similar from the one I’d left. I’d figure it out.

“This is unfortunate,” a fellow passenger sighed about the detour to White Plains. I agreed, and together we hatched a ride-sharing plan into the city, which Tailwind paid for. Problem solved.

Time to take off and enjoy the flight. Lifting up into the air was an easy experience with just a few bumps. As we banked right I got up-close amazing views of Boston’s easily identifiable landmarks—the State House, Beacon Hill, the Charles River, and more. Soon we were at one with the clouds. A little over an hour later, we touched down nice and easy in White Plains. I clambered down the aluminum ladder to the tarmac, far from the midtown hotel I had chosen because it was a mere 6/10ths of a mile from Tailwind’s drop-off point at 2430 FDR Drive and 23rd Street. Ah well, my driver had me at the front doors of the Freehand Hotel in about 90 minutes, and the city was my oyster. Time to have some more fun.

Freehand Hotel, New York
Freehand Hotel, New York, about $350/night.

I chose the Freehand Hotel in midtown’s Flatiron District for a couple of reasons—its proximity to Tailwind and because before the Freehand was a hotel, it was home to many  writers, musicians and creatives, so that seemed inspirational. Nearby were a couple of bookstores, some shopping, and the Gramercy Theatre, where I could catch a show and still stay safe while traveling solo.

The city is back in action

That evening, I headed over to The Gramercy, a 2,000 square-foot space with 375 theater-style seats, and standing room for about 125 more. The historic venue was built in 1937 and mostly served as a movie house and live theater spot over the years until Live Nation (which also owns several venues in Boston) bought the building in 2006 for use as a concert space. The closest comparison in this area might be The Paradise in the Boston University area.

Riverside was in the house for their 20th anniversary tour. “We were going to play all our hits,” lead singer Mariusz Duda told the crowd. “Then we realized we don’t have any hits. So we chose the longest ones. I hope you have time for that.”

Riverside, rock band, New York
Riverside, a progressive rock band based in Poland, showed the crowd a great time.

The audience, made up in large part of dudes who looked like they were in their own bands and who didn’t much care about “hits,” most definitely had time for that, as the quartet rocked the house. To see these musicians back on their first tour since COVID did my own rocker heart and soul good, and made me glad that I didn’t let a little thing like travel logistics scare me off.

My two-night stay also included  a visit to The Whitney Museum of American Art, about two miles from my hotel, but I really didn’t need to leave the Flatiron District for a museum visit. I found myself wishing I’d stayed in the neighborhood and explored The Fotografiska (281 Park Avenue S), a branch of the Swedish photography museum by the same name. Anyplace with a tag line, “Have fun. Stay late. Get deep. Spill your drink,” sounds intriguing.

Whitney Museum, New York
Found art outside of the Whitney Museum of American Art. But no, The Swellesley Report won’t stop delivering news!

With area dining options both fancy (the Freehand has several including a very popular rooftop bar/restaurant) and casual (I could get a steaming bowl of dumpling soup, Mexican fare, and great breakfast options literally steps from the lobby), I was all set in the meals department.

A shopping jaunt took me to the Strand Bookstore (828 Broadway at 12th street), the last such indie outpost standing on what was once known as “book row”; Housing Works thrift shop (157 E 23rd street), where you just might find the perfect mid-century modern home accent item; and Fishs Eddy (889 Broadway corner of 19th), with its endless collection of  dishes and glassware from defunct restaurants, as well as other odds and ends they just happen to come across.

Before I knew it, two days in the city had passed, and it was time to catch my early flight back to Boston. I showed up at the SkyPort seaplane base at the very eastern end of 23rd Street and relaxed in the small, nondescript lounge area. “We just got the OK to renovate the lounge,” a Tailwind team member told me. “It’s going to look a lot nicer soon.”

Tailwind, New York
Tailwind, New York

This time the weather cooperated and I did, indeed, get to experience a seaplane takeoff from New York (the views!) and a seaplane touchdown in Boston Harbor. The flight was a little bumpy ascending and descending due to windy conditions, but nothing scary. Splashing down was great fun and felt nice and smooth. A 15-minutes walk later, I was back at South Station where, with fortunate timing, the Worcester rail commuter line into Wellesley Square was boarding.

I could get used to this

Wish I could take the seaplane every time I wanted to pop into New York City, but alas, this was probably a one-off adventure for me. Unless we open up a Swellesley NYC bureau, which would, of course, necessitate frequent business travel. Now there’s a thought…

Tailwind, New York
Tailwind, above NYC.

Starting May 25, Tailwind will start up its seaplane service from Boston Harbor to Provincetown Harbor, with pricing that starts at $275. The nonstop flight takes about 35 minutes dock-to-dock.

With the addition of Provincetown Harbor, Tailwind Air now serves four destinations from its Boston Harbor base. Manhattan is served three times daily, seven days a week. Plymouth, MA is served daily. One-stop same plane service to East Hampton (HTO) is also available.

A complete schedule for all flights operated by Tailwind Air can be found at