I commute between Boston and New York City up to three times a week on a seaplane. Here's why it beats taking the train or flying commercial.

• Rob Biederman commutes between Boston and New York City up to three times a week via seaplane. 
• He pays $2,995 for an annual Tailwind Air membership, which unlocks access to $295 one-way fares.
• Here's why he thinks the seaplane shuttle is the best way to travel between the two cities right now. 

This as-told-to essay is based on interviews with Rob Biederman, a Managing Partner at the venture capital firm Asymmetric and co-founder of Catalant Technologies. The following has been edited for length and clarity.

I've been using Tailwind Air, a seaplane shuttle service, to commute between Boston and New York for almost two years now. 

I live in Boston and go back and forth between the two cities a tremendous amount, sometimes as many as two or three times a week. I run a venture capital firm with offices in both Boston and New York. I also help teach a class at Harvard Business School, and I'm still chairman of a company I founded that's based in Boston. 

The challenge is when you don't have full schedule control — I might wake up in Boston on Monday, have to come down for dinner in New York on Tuesday, then have something in Boston on Wednesday. 

The reality of traveling between those two cities is that you essentially have four choices: you have driving, bus, train, and commercial flying, which all have pretty specific drawbacks. If you go between Boston and New York once a month or once a quarter it doesn't really matter, but when you're going back and forth multiple times a week, it really puts a lot of stress on how convenient and pleasant the trip is.

It's the most efficient and productive way to commute between the two cities

I think Tailwind really helped solve the challenge with the bus, train, and driving, which is that they all take a really long time.

Tailwind is most relevant for people who need to go back and forth between Boston and New York in a single day. If you have a bunch of stuff you have to do on both sides, but you take the bus or train or drive or fly with a traditional airline, it just eats up a lot of your day. 

With Tailwind, I can have a full business day minus 90 minutes. I'm usually on calls right up to the departure time of my flight and I'm picking another one up the minute we land. 

I totally get why people take the train, I just don't know that I have the attention span to be sitting on the train for three and a half hours. It's my belief that the train is actually quite overrated for productivity because they make so many announcements between New York and Boston, even on the quiet car. Plus, the WiFi service can be unreliable. 

It's much less stressful than flying with a mainline carrier

I typically book Tailwind flights a week out. The Boston seaport is only a 10 minute walk from my apartment and I get there one or two minutes before take-off since you don't have to go through security.

During the Winter, when Tailwind doesn't run, I fly Delta or United. Going to any airport in New York is a pain (I think Logan is a fantastic airport and is super convenient). But on the New York City side, whether you're going to or coming from Laguardia or JFK, it's quite annoying. The Tailwind departure point in New York is on 23rd street and I stay in an apartment on 30th, so it's a quick shot across the city.

The Tailwind flight is maybe 60-65 minutes in the air, whereas the commercial flights are around 45 minutes. But if you think about what makes this trip stressful, Delta and United are great airlines, but there's a lot of things that are kind of out of their control like security and timing. So I'm happy to trade an extra 15-18 minutes in the air in exchange for not going through all the hullabaloo on both sides. 

For Tailwind, if you're scheduled to be dropped off at Boston Harbor or 23rd Street at a certain time, that time is pretty reliable. Door-to-door, the trip typically takes 90 to 95 minutes. Another benefit is you don't have to pay for an Uber or a cab on either side. You can walk right on and off, which is great from a health and sustainability perspective. 

It also lets me travel with my dog, Duke. With Tailwind, it's just so easy to have him along. They love having dogs on board and he took to it pretty quickly. It's not an easy thing getting a dog onto a seaplane, particularly in Boston when we're out in the dock in the middle of the water. But when you take off on the river, It's not choppy at all. It's pretty exciting. It's like being on a boat and it suddenly becomes a plane. 

If you fly frequently, the cost difference isn't that huge compared to commercial 

I use Tailwind's Fast Lane membership, which costs $2,995 a year and gives you access to reduced fares. 

Obviously, it's not inexpensive. And so I think my hope is that over time, they scale their volume and reduce prices to make it an option that makes more sense economically for a larger group of people. 

If you do Fast Lane, and you're not getting an Uber or cab on either side, I don't think the cost difference is all that huge compared to flying commercial. Anytime you have to book a commercial flight one or two days before, it gets pretty expensive — I've seen United flights go for $400 or $500. And then you have to account for transportation to and from the airport. 

The customer service experience is seamless 

One thing that makes Tailwind so attractive is their customer service. When there's inclement weather or you have to change your flight, their team is incredible. You call their number and you talk to a real person that helps solve your problem. I think with a lot of the traditional mainline carriers that's a more complicated story. 

One time, we left a package behind in New York and we were already in Boston, so we called and they said if somebody brings it to the dock, they'll make sure it gets on the plane to the other side. They're super flexible. That kind of personalized customer service is hard for a mainline carrier to pull off when they're processing millions of passengers a week. 

For the long-term, it's not a sustainable commute 

It's not very sustainable to commute this frequently between two different cities. I would certainly love to have a more conventional life that 99% of Americans have where it occurs in a single city. I think it's my goal within a year or two to really settle down in one place. 

I think if you want to be performing at the highest level professionally, you want to minimize distractions. The reality is moving back and forth between two cities creates a tremendous amount of excess mental load. 

The reality of business is that a lot of business is face-to-face, so there's always going to be a role for traveling to important meetings. But I wonder if, over time, people will potentially realize that a lot of the time spent moving around day to day is actually not very valuable. 

I think short-hop travel will look totally different in 50 years

I think in 50 years short-hop transportation between cities like New York and Boston will look totally different than it does today. 

For commercial jets, there's a lot of overhead for moving 50 or 100 people between New York and Boston. I think over the long term, the right solution is probably ultra high-speed rail. It's only around 215 miles — Japan and France have trains that go 200 miles an hour. There's no reason why New York to Boston shouldn't be a one-hour train commute, except for the fact that they have grade crossings all throughout the Northeast. 

In the short term, if you have to move this set of atoms from this zip code to that zip code, Tailwind is certainly the best alternative until high-speed rail is a possibility, which I think is going to be a long time.