New York and Boston are two of the largest cities on the East Coast of the United States. With around 200 miles between the two financial and business centers, one would expect travel between the two cities to be easy. 

In reality, however, traveling between New York and Boston is anything but easy. Driving? Well, the roads are good, but the traffic is terrible. Taking the train? Enjoy losing three hours on the highest-speed train in the United States. Flying? 

Enjoy savoring the stress of sitting in traffic to get to one of New York's three overcrowded airports and having to go through all of the other various airport time-consuming processes. In 2023, this is the predicament business-class travelers tend to find themselves in when traveling between the two cities. 

According to Westchester County-based Tailwind Air, business travelers should no longer fret over the stressful travel experience between New York and Boston, as the airline operates a unique service between the two cities that claims to save time but at a premium cost. 

Since August of 2021, charter and now commuter/air-taxi carrier Tailwind Air has utilized a fleet of modified Cessna 208 aircraft to operate commuter seaplane services between Manhattan's Lower East Side and Boston Harbor. 

According to the airline, those who take their flights can save upwards of one hour in travel time, not to mention the fact that the airline offers a complimentary free transfer from Boston Harbor to the city's bustling, new financial district. Quite the allure for business people. 

As I make my way to the 23rd Street SkyPort Marina, just a half hour away from Wall Street by bus or subway, I have one question. Does flying Tailwind make that much of a difference in saving time? 

The day before my flight, I received an email notifying me that there would be no Tailwind Air staff to assist me and the other passengers during check-in and before our flight to Boston. Besides, of course, the pilots coming in on the arriving flight into Manhattan.

In the email, explicit instructions were on how to access the inside of the Marina through an unlocked side door and where to wait once inside the Marina/Seaplane departure area. According to Tailwind Air, their departure lounges open for passengers 40 minutes before a flight's departure, while check-in closes 10 minutes before departure.

Upon arriving at the marina/seaplane terminal, I was surprised to find that the door to get inside was locked, unlike what was stated in the email. After a quick call with the fast and responsive customer service at the airline, I was told to wait outside for the pilots of the arriving flight to come to be let into the departure lounge and be checked in. This is precisely what happened. 

After a short wait under an overhang in the cold rain, I and the other passengers on my flight up to Boston were let in by the pilot of our flight into the departure lounge for check-in. The check-in process with Tailwind is rather rudimentary. All that's required is a photo I.D., and if your child (below 18) is traveling, minors traveling alone consent form.

One thing worth noting is that due to the nature of the airlines' operations, flying small commuter planes, Tailwind Air has a unique baggage policy. When one purchases a standard ticket with the airline, they are allotted one "normal sized" carry-on bag up to 25 lb (11.3 kg). If a carry-on bag is over 25 lb but less than 50 lb (23.6 kg), the passenger's bag will incur a fee of $250.

If one is looking for even more baggage allowance, they can purchase another seat on the plane (if available) at the "prevailing" rate (normal cost of an extra ticket of the airline). If a passenger chooses this option, Tailwind Air will allow passengers an additional 125 lb (56 kg) of luggage onboard. The Tailwind Air lounge features plenty of seating with power outlets and a mini-fridge stocked with soda and other drinks. 

Once check-in was complete, we were led out onto the dock to board our aircraft. In an email the day before my flight, I received the tail number of the plane I was supposed to fly on - N819BB. This aircraft was swapped out for another one of Tailwind Air's modified Cessna 208 seaplanes - N41TE. 

The airline's Cessna 208 aircraft features a 1-1 seat configuration in four rows for eight seats. The rows just behind the pilots and in the back of the plane are normal, while four seats face each other. Each seat is made of a comfortable, padded leather material with a comfy headrest.

The legroom is great, with me stretching out my legs fully. However, I can see there being problems with legroom should the flight be full and one sits on the four seats facing each other. Despite flying on a small plane, the aircraft still features the normal amenities of a power outlet (only on the right side of the plane in between the two seats facing each other) and the standard overhead controls of reading light and air vent.

The only problem with Tailwind Air's seaplanes is the low ceilings. One will hit their head when boarding and deplaning the aircraft. The only uncomfortable part about the experience was the loud engine noise coming from the engine in the front of the plane. 

Remember that during this entire experience, the pilots notified us (their passengers) of every detail about our flight. After waiting for one passenger to come (who never showed up) for around 20 minutes, we began on our way up to Boston. 

While one pilot started the engine of our seaplane, the other untied our seaplane from the dock as we began to taxi out into the middle of the East River. Within just 5 minutes of taxiing in the East River, we started our takeoff and climb out of Manhattan. 

One major perk that Tailwind Air doesn't advertise is the views, and even on a rainy day like the one I was flying on, the views of the NYC skyline were incredible. The views didn't stop here. For most of the way up to Boston, our aircraft stayed at a relatively low 5,000 feet above the ground, allowing us passengers to see the ground in detail - a two-in-one sightseeing tour. 

After just one hour in the air, we begin our descent and landing into Boston Harbor. One of the only downsides to flying on a small commuter aircraft with Tailwind Air is that takeoff and landing on water is a very bumpy and rough experience. If the air is turbulent or windy on the day you're flying, there can be more turbulence than normal due to the small size of the plane you're flying on.

Tailwind Air lands its flights in the Boston Harbor directly next to Logan Airport but taxis to a dock instead of a terminal stand. At the dock, passengers deplane and board a small boat directly to Boston's Fan Pier Marina, just a few minutes walk away from the city's financial district, downtown, and waterfront areas.

The time it took me from arriving at SkyPort Marina in Manhattan to making it to Boston's Fan Pier Marina took just under one hour and 45 minutes. This is exactly how long Tailwind Air claims their shuttle flights between NYC and Boston take. For comparison, my flight back to New York City, flying on a commercial airliner, took just under three hours from the airport entrance at Logan International Airport (BOS) to the airport exit at Newark (EWR). 

A Premium, Time-Saving Experience at a Premium Price 

A round-trip ticket with Tailwind Air is around $800 when purchasing the airline's "Advantage" or base fare, which is around $395 one way. While this price is twice that of flying First Class on a commercial airliner and about the same price of taking Amtrak's Acela high-speed train, the amount of time saved can be quite valuable to a business traveler, hence the higher-than-average price.

The higher ticket price includes a free boat transfer to Boston's downtown/financial district, a huge bonus for business class travelers. Unlike commercial airlines, Tailwind Air is quite generous with its base fare, offering flight changes up to 24 hours before a flight and cancellation options. Due to the small planes the airline uses, there are no advanced seat assignments. Whichever seat is open when one boards a Tailwind seaplane one can take. 

So... Is The Experience Worth the Price? 

In my opinion, yes. Compared to the competition - flying commercially, driving, or taking the train - nothing rivals Tailwind Air's time-saving nature and premium service. My experience with the airline, from the lounge to the included sightseeing tour of Manhattan, Long Island, and New England, truly makes Tailwind Air the best way to travel between New York and Boston. The price is worth the premium experience.