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For 16 years, travelers have been treated to the comfort and convenience of private jet service for the cost of a single seat through Tradewind Aviation, based out of Waterbury/Oxford, Connecticut. Skipping the hustle and bustle of commercial airline terminals at such major airports in the Northeast as Logan, Newark, JFK, and LaGuardia, passengers can hop on one of the company’s Pilatus PC-12s at Westchester County Airport in White Plains, New York, or Teterboro Airport in New Jersey and head to Nantucket or Martha’s Vineyard; shuttle service is also offered between Stowe, Vermont, and White Plains or between Boston and White Plains.

Tradewind was founded in 2001 by brothers and aviation enthusiasts, David and Eric Zipkin, who grew up in Bedford (part of Westchester County), New York, flying a Cessna four-seater for fun; the idea for Tradewind came to Eric when he was working for a private charter operator in Westchester.

“He saw that there really was this need for service that fell between the private jet world and the more rustic small companies,” says co-owner and co-founder of Tradewind, David Zipkin. “We offer high service in smaller airplanes…better aircraft traveling shorter, smaller routes.”

And so, in 2002, Tradewind was officially certified as an air carrier. Tradewind’s first scheduled route was Westchester–Nantucket. The service, which started as a shared private charter, organically grew into the more structured, scheduled shuttle routes. Eventually Tradewind began offering scheduled shuttle service to other locations such as Martha’s Vineyard, driven by the high demand for private charters already flying to these locations.

And in 2006, the airline started flying regionally throughout the Caribbean to such locations as St. Barths, Anguilla, Antigua, and Nevis from Tradewind’s hubs in San Juan, Puerto Rico, Antigua, and U.S. Virgin Island St. Thomas. Passengers that fly out of San Juan to one of the Caribbean destinations, David says, usually take a commercial airline to San Juan and then connect with Tradewind. Just over a year ago, Tradewind added Boston–New York and Westchester–Stowe, Vermont, shuttle service.

Passengers on the Boston–New York shuttle service are mostly business commuters, says David, adding that even though that service is already there (via commercial airlines), you’re spending a lot of time waiting around in airports for what is only a 45-minute flight. “We wanted to solve this problem for business commuters,” David says. “When you board in White Plains, you’re off the ground in five minutes, as opposed to departing from LaGuardia, which could mean you’re wasting two-plus hours in the process—to check in, on the runway, etc. It should be a lot smoother of a process for such a short flight,” David says.

Additionally, David adds, Westchester Airport is located only 10 minutes from the Metro North commuter rail station and from there it is only a 35-minute train ride into Grand Central—perfect for commuting into the city.

Shuttle flights fly from private charter fixed-based operators (FBOs), avoiding commercial terminals and TSA screenings, which are not required in the private charter world. “These are scheduled flights with the comfort and convenience of a private charter,” David says. Background checks on passengers are performed, however, which is a requirement for private charter flights, David adds.

Flights to New York from Boston fly out of a private terminal in Logan called Signature Flight Support (Logan has only one; other airports have several), and a seat typically costs around $395. If you purchase shuttle tickets in bulk, however, the price goes down, David adds. Pricing for private charter flights start at $4,000. (You can effectively rent the entire plane and fly anywhere.) Currently, Tradewind operates 50 percent private charter flights and 50 percent shuttle service.

David explains the company also has plans to expand and is considering adding shuttle service between Boston and Nantucket, Boston and Martha’s Vineyard, and Boston and Stowe. It’s also looking to fly to Washington, D.C., and Philadelphia, either from Boston or by way of New York. And in the Caribbean, Tradewind is considering potentially flying to other destinations such as the British Virgin Islands.

In addition to being a convenient and comfortable flying option, Tradewind is also a safe option. The airline has a fleet of 21 airplanes—18 Pilatus PC-12s for scheduled shuttle service and three Citation CJs for private charter flights. The Swiss-designed Pilatus PC-12s are very well known for safety, David says. They were designed for harsh environments and are capable of landing on short runways, which comes in handy for Tradewind passengers. “It gets the person closer to where they are going, whether it be a summer home or a child’s summer camp,” David says. 

He adds that the turbo prop-powered Pilatus PC-12s are “very reliable” and contain pressurized cabins for short-range flights. “We fly high and we fly fast,” David says. “This means there will be less turbulence because the aircraft is flying above the clouds.”

Tradwind has about 200 employees, 90 of whom are pilots. Pilots run the gamut in age, but a good portion of the pilots are early in their careers. “This is not to say that they are inexperienced,” David says. “In fact, many have had previous jobs, often at another private company, in addition to training.” He adds that the regional type of flying that Tradewind does is beneficial to pilots, especially those with families, because they get to go home every day. “They value the ability to stay in the region,” David says. There is also a lot more customer service involved; pilots get up close and personal with passengers and even check them in. David says. “It’s good for pilots interested in more than just flying the plane.” 

Tradewind Aviation