Flight Review: Tailwind, New York Skyports Seaplane Base to Stratford, CT, USA


On that particular day, I could have strolled up to the airport – seaport? – and boarded two minutes before take-off. After having logged no less than 600+ flights taken, this was not only the first where I was the sole passenger, but also the only one where the pilots asked me “when do you want to depart?”

Good times.

As I’ve noted on my previous two flight reviews, the customer service throughout has been great. Sure, the people who originally helped me make the reservations were privy to my role as travel blogger, but random check-in staff and phone agents were just as pleasant and helpful.


I’ll give you a brief walkthrough of the boarding process at the New York Skyports Seaplane Base, and then show you the photos that we’re all here to see.

First, do you see that DOCKNYC sign above? Ignore it. Rather, if no one is waiting outside, someone inside will walk you to the pier where the Tailwind seaplane (a Cessna 208 Caravan single-propeller) awaits you.

Then, the pilots will greet you, and may tell you that you should leave soon, in the event that it looks like too many boats will be causing havoc – leaving the seaplane in their turbulent wake – in the East River.

Oh, right, the whole seaplane thing. I think this photo tries to sum up the unusual juxtaposition of an aircraft purposefully on water…


and out of the starboard side, you’ll see a boat.

Surprisingly, Tailwind provides – you can take them whenever you’d like – drinks and snacks.  No TSA/security check either, so the soft product is already that much better than legacy US carriers.  In other words, if only Tailwind flew to more places than Stratford and Boston.  More on this later.  As in, right now.


We took-off heading towards the Williamsburg Bridge, then made a sharp easterly turn to complete the 25-minute flight to Sikorsky Memorial Airport. Which is on land. In the town of Stratford. You see, my only complaint is that I believed we were going to land in the waterfront of the city of Bridgeport – I timed my Metro-North train that way – however, we made it a bit further northeast, with Stratford being the closest Metro-North station. Tailwind, please clarify this on your website.

Enough of the quibbles, it’s photo time:


I still prefer the Chrysler Building.


The 59th St. Bridge and Roosevelt Island.  Towards the foreground is Four Freedoms Park.


Central Park


Long Island City…skyline???


LaGuardia (LGA) Airport?  Or…


…the USS LaGuardia?


That looks out-of-place. My shadow, that is.

After the brief flight, we made it to Stratford, from where I was escorted by a Tailwind employee to the train station. Sikorsky Airport has a lounge with refreshments and periodicals, for those of you looking to take the flight going to Manhattan.

I asked the representative if rides to the train station are normally included in the cost of the ticket, though I’m still waiting on that reply. Additionally, I asked if Tailwind offered something similar from select points in Manhattan to the seaplane base, though that would be rather anticlimactic, no? In other words, you might spend more time getting to your flight than sitting on the seaplane. Not an unusual scenario in the least, but considering that this is a niche airline, I was curious.


Thanks again for the memorable trip, Tailwind!

Source: buildingmybento