Fly The Whale: Westchester pair's charter flights to Cape, Hamptons, thriving

Andrew Clark was walking along the East River one summer day several years ago when a seaplane touched down on the water in front of him.

“There was something about watching this huge powerful machine that was incredible,” recalled Clark, a Scarsdale resident.

Clark, now 35, was working as a real estate developer, but hoping to switch careers and start his own business. After seeing the plane, he thought about the hassle of driving to Nantucket on Friday afternoons during the summer and making the long trek back on Sunday. He knew other New Yorkers also dreaded the traffic-clogged journey.

“A light bulb went off in my head — if we could get people there from the city and Westchester in 45 or 55 minutes (by plane) — I felt it was a really good business idea,” said Clark, who grew up in Scarsdale and has always been fascinated with flying.

That idea would turn into Fly The Whale, an aviation company he launched in 2011 with his business partner, Melissa Tomkiel, a Bronxville resident.

The company — which operates flights from Westchester County Airport in White Plains as well as Teterboro Airport in New Jersey and Manhattan’s East River — specializes in trips to upscale vacation destinations, such as Nantucket and East Hampton. People can also reserve chartered flights to locations within about 700 miles of the area and between Caribbean islands.

To meet growing demand, the company will offer shared charter service this summer from Westchester’s airport to Nantucket and East Hampton. Rather than one group booking an entire plane, under the new option travelers can buy individual seats — a less expensive way to fly privately with all of the same perks, Tomkiel said. The service starts Memorial Day weekend.

“This is a much more affordable way to do it and get there conveniently,” said Tomkiel. “We did it because our clients asked for it.”

They expect to provide 120 to 150 shared private flights this summer. Each plane typically carries eight passengers and two pilots. Tradewind Aviation also operates chartered flights from Westchester’s airport to the Nantucket area.

Fly The Whale currently manages five planes, a mix of traditional aircraft and amphibious planes, and oversees a full-time staff of 14 employees.

“We’re not committed to any certain routes, and as soon as our clients express demand for a new service, we are able to be flexible, and I think that’s how we got popular quickly,” said Tomkiel, 32.

The company’s quirky name is a nod to Nantucket’s whaling history, though it didn’t catch on right away, Clark said.

“At first we were laughed at in the business,” he said. “We struggled with it at first, but if someone sees Fly the Whale on the tail of the plane, you remember it.”

The pair’s Westchester connections have contributed to their success, they said.

“A lot of people we know — our family and friends — are our clients and help us tremendously to get the word out,” said Tomkiel, who previously worked full-time as a corporate attorney.

People who charter flights want to make the most of their relaxation time, Clark said.

“They don’t have time to sit in a car on a Friday afternoon for four to 6 hours to try and get to East Hampton. A flight from Westchester County Airport to East Hampton airport takes 18 minutes,” he said.

For a shared private flight, passengers will pay roughly $800 to $850 for a round-trip weekend ticket from Westchester to East Hampton. The same type of ticket to Nantucket goes for about $900, though travelers going to either destination get discounts for buying multiple trips, she said. People can also book early Monday morning flights from those places to extend the weekend.

By comparison, a roundtrip commerical ticket to Nantucket for a weekend in June costs about $530 on Cape Air, for example, not including taxes.

Tomkiel acknowledged that starting an aviation business was a big risk, but she said she enjoys the challenge. In addition to handling legal aspects, she is in charge of development and marketing.

“This was an opportunity to build my own company and exercise my own creative abilities and not be in the confines of other people’s ideas,” she said.

Clark said he believes Fly The Whale has brought fresh energy to the business of chartering planes.

“I never thought it would grow this quickly,” he said. “It helped me being that young and fearless, because now having kids, I probably never would have done this.”