It’s time for another installment in our occasional series exploring new airlines you’ve likely never heard of. This time, let’s shine the spotlight on Tailwind, an airline with big plans for the Big Apple. Right now, however, it’s starting out very small.

If you live in New York, you may have seen Tailwind’s fleet of Cessna Caravans (8 passengers plus two pilots) buzzing around. The airline has been flying for more than 5 years primarily operating charters and as a lift provider for Blade (a company which may need to be featured in this column some day) taking people from Manhattan out to the Hamptons. But now Tailwind is getting into the game using its own brand, and it’s moving into new markets.

This summer, the company is beginning by flying from New York to both Boston and Nantucket. It’s not cheap with fares beginning at $549 one way to Boston and $795 one way to Nantucket with a 14 day advance purchase. On top of that, flight frequency is very light. Nantucket operates as you’d hope it would: out Thursday and Friday late afternoon with returns Sunday afternoon and early Monday morning. But the schedule to Boston is abnormally light. Flights leave for Boston only Monday, Tuesday, and Wednesday afternoons with returns Tuesday, Wednesday, and Thursday mornings.

What kind of ridiculous plan is this?! Oh wait, I forgot to mention one thing.

Those aren’t just run-of-the-mill Caravans. They’re equipped with floats. And these floatplanes are arriving and departing from the Manhattan Skyport in the East River at East 23rd St and FDR Drive. Take a look…

Ah, ok, that’s a different story. I’m always curious when someone comes up with creative ways to serve an already well-served market, so I decided to dig in more. I spoke with Tailwind VP Peter Manice so I could better understand the idea here since it’s clear to me that even on floats, three times a week to Boston isn’t a winning formula.

Let’s start with the easier one to understand, the Nantucket operation. There aren’t a lot of commercial flights in that market anyway and the times aren’t perfect. The last one each day in the summer leaves at 5:25pm from Newark on a United turboprop and the first one doesn’t get back to JFK until after 10am. Tailwind’s schedule is set up perfectly to get the person who really wants to spend that extra night on vacation with his or her family but can’t do it with traditional commercial options due to work commitments. This schedule makes sense, and it’s a leisure market. It wasn’t hard for me to see how this could work, but then there’s Boston. This is a business market with many flights and trains every hour all day long. How is that going to work with three weekly flights?

As you’d expect, this kind of service is clearly aimed at the traveler whose time is very valuable and books at the last minute. Being able to fly from Manhattan saves a ton of time over LaGuardia, especially now that it’s under perma-construction for the next several years. It saves journey time over Amtrak Acela as well since the flight is much shorter than the train ride. If you assume most people will be booking at the last minute, then the fare difference isn’t as great as it would be for someone who could take advantage of advance purchase fares on existing options.

That’s all well and good, but how does operating 3 flights a week make sense? It doesn’t. It may feel like a joke, but it’s not. It’s more of a trial balloon.

As of now, Tailwind is flying into Boston’s Logan Airport so the time savings are primarily on the New York side. (There are still savings on the Boston side since they fly into a private terminal and there is no security screening slowdown.) The company is actively working on being able to land in Boston Harbor, however, and hopes to have that going next year. In fact, starting next spring, Tailwind expects to ramp up its Boston schedule significantly with multiple daily flights so that it can be far more useful than it is today. I’ve never seen the “dip the toes in the water” strategy work in a business market, but maybe this is about proving the operational capabilities while also being able to show off the possibilities to potential clients. Regardless of whether it makes sense or not, it’s not supposed to be a success from a commercial perspective this year.

With a more robust schedule, can this work? You can imagine the appeal of operating a flight directly from Manhattan. When you have only 8 seats, you don’t need to fill that many to be a success, so there is a chance. But there are also some serious issues that are hard to overcome.

The biggest issue of all is that the aircraft can only land on the water during daylight. That’s obviously less of a concern during the summer when the days are long and flights can operate when you want them. But in the winter, that’s a huge problem. There’s also the issue of not being able to operate with fog and low visibility. This seems like it will be a hard operation to maintain in the winter.

So how does the company deal with this? Well for now it’s not even operating from November to February. That’s not a problem for a summer destination like the Hamptons or Nantucket, but that’s going to have to change to make for a meaningful schedule in a business market like Boston. The plan going forward appears to be that it’ll operate as much of a schedule as it can in a market like Boston during the winter. That means the latest flight won’t be all that late. It could operate the aircraft on land, but it doesn’t sound like that’s in the cards. Instead Tailwind will likely partner with airlines on land to fill in the gaps. Don’t expect to see them partnering with the likes of American and Delta. It’ll be more about the commuters in the region. A company like the similarly-named Tradewind, which is flying from Westchester to Boston today, could be a good partner in that respect.

There’s no question this is risky, but the company has a cash cushion and think it can make this work. It’s about more than New York to Boston. Once it can fly into Boston Harbor, there will be other routes to follow if that time-sensitive business traveler demands it. I can easily see how this would work in a summer-only leisure market like Nantucket or the Hamptons, but the jump to the business market is going to be a much larger challenge.

I want to hear from you all on this one, especially those in New York and Boston. Does this sound appealing?

[Photo from Tailwind.com]