I just booked Tailwind's seaplane flight between Boston and New York. Will the much-awaited service finally launch?
A-plane, B-plane, seaplane.
A terrible joke. I know, and I'm sorry (not that sorry).
I've always thought seaplanes were exceptionally cool, ever since I was a little kid in Brooklyn watching them leaving and approaching the East River.
There's just something exceptionally fun about seeing a plane flying low carrying pontoons that are almost as big as the fuselage itself, with the ability to go where other aircraft can't, with a unique mix of grace and clumsy awkwardness.
Modern seaplanes (technically "floatplanes") are a far cry from the Pan Am Clipper flying boats of an era gone by, but there's still something about them that's just cool, and useful; seaplanes arguably make the Maldives viable as a vacation destination, for instance.
Now, I'm excited to fly on a seaplane a bit closer to home.
Tailwind, a small scheduled shuttle and charter operation based in New York, this week announced new seaplane service between Manhattan's New York Skyport, on the East River at 23rd Street, and Boston Harbor.
The carrier typically runs shuttle routes from Manhattan to summer hotspots on Long Island — East Hampton, Shelter Island and Montauk — as well as Bridgeport, Connecticut — using a fleet of eight-seat Cessna 208 Caravan turboprops with an amphibious configuration, meaning they can land and take-off on both paved runways and water. For charters, the airline can also arrange for other types of aircraft.
Tailwind will be the first airline to launch seaplane service between the two cities in modern times, after Cape Air pulled back on plans that it had set in February 2020, which were derailed by the COVID-19 pandemic. Both Cape Air and Tailwind have been working on launching seaplane service between the cities for more than half a decade. Tailwind won final approval from the Federal Aviation Administration earlier this month.
The airline will start with two round-trips per day on Aug. 3, before increasing service to four daily round-trips on August 23. The seasonal service will run through November, and resume in March.

Flying time will be about 75 minutes, with a total of fewer than 90 minutes "dock to dock," the Boston Globe reported. That beats the fastest train option — about three and a half hours on the Acela — and while the flying time is longer than on the regular airline shuttles, which are blocked at 80 minutes, the seaplane will eliminate the airport travel time.
On the Boston side, the flights will dock remotely near the East Boston shoreline, with a 7-minute water taxi connecting passengers to Fan Pier
The service is mostly geared towards business travelers — flights start at $395 one-way, and go up to as much as $795.

I lived in New York for most of my life but recently moved to Boston, so the new service is particularly exciting for me — even if it will be prohibitively expensive. Still, more options are always a good thing and being Boston-based, I'm the perfect candidate to check out Tailwind's first flight for TPG when it launches in August.
Plus, I'll finally get to be on one of those seaplanes in the East River that I used to watch as a kid.
More: You could soon redeem miles for flights to space — here's how
Be sure to check back on Aug. 3 for the full review!
TPG featured card
Rewards
| 2X miles | 2 miles per dollar on every purchase |
| 5X miles | 5 miles per dollar on flights and vacation rentals booked through Capital One Business Travel |
| 10X miles | 10 miles per dollar on hotels and rental cars booked through Capital One Business Travel |
Intro offer
Annual Fee
Recommended Credit
Why We Chose It
The Capital One Venture X Business Card has all the Capital One Venture X Rewards Credit Card has to offer and more. It offers an incredible welcome bonus and requires an equally impressive spend to qualify. In addition, the card comes with premium travel perks like annual travel credit. (Partner offer)Pros
- The Capital One Venture X business card has a very lucrative welcome offer.
- In addition, the card comes with many premium travel perks such as an annual $300 credit for bookings through Capital One Business Travel.
- Business owners are also able to add employee cards for free.
Cons
- The card requires significant spending to earn the welcome offer.
- Another drawback is that the annual travel credit can only be used on bookings made through Capital One Business Travel.
- LIMITED-TIME OFFER: Earn up to 400K bonus miles: 200K miles when you spend $30K in the first 3 months, and an additional 200k miles when you spend $150k in the first 6 months
- Earn unlimited 2X miles on every purchase, everywhere—with no limits or category restrictions
- Earn 10X miles on hotels and rental cars and 5X miles on flights and vacation rentals booked through Capital One Business Travel
- With no preset spending limit, enjoy big purchasing power that adapts so you can spend more and earn more rewards
- Empower your teams to make business purchases while earning rewards on their transactions, with free employee and virtual cards. Plus, automatically sync your transaction data with your accounting software and pay your vendors with ease
- Redeem your miles on flights, hotels and more. Plus, transfer your miles to any of the 15+ travel loyalty programs
- Every year, you'll get 10,000 bonus miles after your account anniversary date. Plus, receive an annual $300 credit for bookings made through Capital One Business Travel
- Receive up to a $120 credit for Global Entry or TSA PreCheck®. Enjoy access to 1,300+ airport lounges worldwide, including Capital One Lounge locations and Priority Pass™ lounges, after enrollment
- Enjoy a $100 experience credit and other premium benefits with every hotel and vacation rental booked from the Premier Collection
- This is a pay-in-full card, so your balance is due in full every month
Rewards Rate
| 2X miles | 2 miles per dollar on every purchase |
| 5X miles | 5 miles per dollar on flights and vacation rentals booked through Capital One Business Travel |
| 10X miles | 10 miles per dollar on hotels and rental cars booked through Capital One Business Travel |
Intro Offer
Earn 200K miles when you spend $30K in the first 3 months, and an additional 200K miles when you spend $150K in the first 6 monthsLIMITED-TIME OFFER: Earn up to 400K bonus milesAnnual Fee
$395Recommended Credit
Credit ranges are a variation of FICO® Score 8, one of many types of credit scores lenders may use when considering your credit card application.740-850Excellent
Why We Chose It
The Capital One Venture X Business Card has all the Capital One Venture X Rewards Credit Card has to offer and more. It offers an incredible welcome bonus and requires an equally impressive spend to qualify. In addition, the card comes with premium travel perks like annual travel credit. (Partner offer)Pros
- The Capital One Venture X business card has a very lucrative welcome offer.
- In addition, the card comes with many premium travel perks such as an annual $300 credit for bookings through Capital One Business Travel.
- Business owners are also able to add employee cards for free.
Cons
- The card requires significant spending to earn the welcome offer.
- Another drawback is that the annual travel credit can only be used on bookings made through Capital One Business Travel.
- LIMITED-TIME OFFER: Earn up to 400K bonus miles: 200K miles when you spend $30K in the first 3 months, and an additional 200k miles when you spend $150k in the first 6 months
- Earn unlimited 2X miles on every purchase, everywhere—with no limits or category restrictions
- Earn 10X miles on hotels and rental cars and 5X miles on flights and vacation rentals booked through Capital One Business Travel
- With no preset spending limit, enjoy big purchasing power that adapts so you can spend more and earn more rewards
- Empower your teams to make business purchases while earning rewards on their transactions, with free employee and virtual cards. Plus, automatically sync your transaction data with your accounting software and pay your vendors with ease
- Redeem your miles on flights, hotels and more. Plus, transfer your miles to any of the 15+ travel loyalty programs
- Every year, you'll get 10,000 bonus miles after your account anniversary date. Plus, receive an annual $300 credit for bookings made through Capital One Business Travel
- Receive up to a $120 credit for Global Entry or TSA PreCheck®. Enjoy access to 1,300+ airport lounges worldwide, including Capital One Lounge locations and Priority Pass™ lounges, after enrollment
- Enjoy a $100 experience credit and other premium benefits with every hotel and vacation rental booked from the Premier Collection
- This is a pay-in-full card, so your balance is due in full every month

