“Our mother still doesn’t believe that we’re able to work together, because we spend so much time as rivals,” says Eric Zipkin, President of Tradewind Aviation.

He and his brother, Vice President David Zipkin, founded the company in 2001, building on a lifelong passion for aviation. Raised with an entrepreneurial mindset, the brothers had always known that they would work together and embarked on several ventures before identifying the need for high-quality, regional flights in the Northeast.

Both were private pilots at the time, and Eric was working for a charter company (a position he attributes to his wife, who said he should probably get paid if he was going to spend every day at the airport). After learning the ins and outs of the charter business, it didn’t take Eric long to determine that there was a niche opportunity waiting for them.

“When we first started,” he says, “if you needed to go from New York to Nantucket, the options were – put bluntly – not the greatest. They were small airplanes, not necessarily well maintained, very inconsistent quality standard.”


While larger jets (like those made by Gulfstream) offered a pampered experience for charter fliers, with luxe interiors and exceptional service, the options were very limited for small aircraft. The planes available for travel to Nantucket and similar destinations were outdated, and many offered only a single pilot.

“We used better airplanes,” says David of the company’s first charter flights. “Two pilots, full service, just like you would in a big jet.”

And it wasn’t long after inception that Tradewind clients began asking if they could share a flight, only needing one or two seats each. The Zipkins said absolutely, and the idea for scheduled shuttles with single seat purchase was born.

“That was really the big break,” says David. “That’s where it turned into something that was accessible to a larger portion of people, because it’s a lot cheaper, of course, to buy one seat on a charter plane than the entire plane. The word really got out. One plane turned into two planes turned into three planes, and the rest is history.”

The company expanded to various destinations in the Northeast and Caribbean, with the favorite for both brothers being St. Barth, hands down. A challenging approach – which they will tell you brings out the best in pilots – and the culture of the island itself make it a memorable place to land again and again. (During a stay, David recommends enjoying the secluded Saline Beach, kite surfing Grand Cul de Sac, and indulging in some of the island’s world-renowned cuisine.)


Today, Tradewind flies 30 to 40 flights to Nantucket alone on a summer day, along with any number of flights to other shuttle and charter destinations. Approximately 70 percent of the flights are shared, and the other 30 percent are private. But with any one of Tradewind’s flights, you will find the quality of service to be the same.

“We are an airline,” says David, “but we consider ourselves more of a charter company than we do an airline. Because everything we do with our scheduled flights is done with an eye for private charter – asking ourselves what would someone expect from a private charter and trying our best to deliver that on an airline flight.”

Throughout the journey, both Zipkins will tell you that the most memorable experiences came during times of struggle – like in the fall of 2017 when Hurricane Irma decimated Puerto Rico, St. Barth, and the surrounding islands.

One day after the storm, Eric and David were in the Caribbean coordinating much-needed relief flights and evacuating visitors and islanders. And St. Barth recovered quicker than anyone could have imagined. David attributes the restoration to the incredible spirit of the people, saying, “In just a short five months or so – besides some of the hotels that are still closed – they’ve really recovered almost completely.”


Tradewind’s efforts in Puerto Rico and St. Barth closely mirrored another natural disaster years before: the devastating earthquake in Haiti in 2010. “We were delivering relief supplies, landing on a closed road in rural Haiti right at the epicenter of the earthquake,” says Eric. “It’s always good to feel like you’re having an impact, that you can do something.”

“We were in a position to help people who didn’t have anything,” adds David, “and that was really, really rewarding.”

Looking to the future, the Zipkins only see continued expansion for Tradewind in both the Northeast and Caribbean. The concept of high-end, premium short flights is one that would work in many places, they will tell you, as they note the possibility of shuttles to Newport, Montauk, and Cape Cod as well as additional Caribbean islands.

“We’re really looking at an exciting summer season going forward,” says Eric. “We’re looking at a lot more flying and a lot more opportunities for growth.”

Eric and David both joke that running the company together only works because they are only in the same room every two weeks or so, but they also speak about the implicit trust between family. “[The] rivalry bleeds through from time to time,” says Eric. “But more importantly, you know you’re working with someone that always has your back. There is never, ever any question about that.”