

We are thrilled to announce that we have officially begun working with Tradewind Aviation. The company was founded in 2001 by brothers Eric Zipkin and David Zipkin on the premise that every flight deserves the highest quality aircraft, crew and service.
Headquartered in Oxford Connecticut with operational bases at Westchester County Airport in New York and San Juan International Airport in Puerto Rico, Tradewind operates both on-demand private charter and scheduled “Shuttle” service throughout the U.S. and Caribbean.
We recently sat down with both Eric and David to get to know them a little better and learn more about Tradewind Aviation, and they did not disappoint! Read more about our conversation below:
- Can you tell a little about the history of Tradewind Aviation?
We founded the company in the dark days after September 11. We recognized that the new reality of commercial air travel was bleak and that people needed safe, discreet and high quality transportation that wasn’t the cattle car that traditional airline flying had become. Our original routes centered around the NYC area to Nantucket. We had a core group of people who would charter every weekend and share the plane. That concept eventually grew to become today’s Shuttle.
- What inspired you both to go into business together and found this company?
We come from an entrepreneurial family. Our father and grandfather were serial entrepreneurs, exploring hundreds if not thousands of opportunities throughout our lives and it was really the only thing we ever knew.
- We know you are both trained pilots – where did your passion for aviation stem from?
Our father learned to fly after WWII under the GI bill. Aviation was always a gateway to excitement and progress for us and that is still true to this day.
- Where is one destination that you never get tired of flying to?
We can confidently state that St. Bart’s will never get old!
- We know Tradewind Aviation just launched some new routes – could you fill us in a bit?
Our newest scheduled routes are White Plains to Boston and White Plains to Stowe VT. The Boston route is centered around the business traveler and brings them our signature service and convenience. Passengers avoid the traditional terminals and depart from private facilities, needing only to arrive 20 minutes in advance of their flight. Because of the private nature of our flying, passengers bypass traditional TSA checkpoints. Flights run 8 times a day throughout the work week. Our service to Stowe is aimed toward the weekender on both ends; New Yorkers looking to experience some of the best skiing in the northeast and Stowe residents planning a weekend retreat in New York.
- Overall, what would you say makes your company stand out from the competition?
Our 110% dedication to service.
- What is one amenity that customers are most excited to learn about Tradewind Aviation?
The family atmosphere and the benefits surrounding that; the pilots know you by name, the avoidance of the TSA security machine, the personal touches. All of it comes together for a one-of-a-kind experience unlike any other.
- What has been the highlight of Tradewind Aviation’s journey thus far?
The incredible people we have had the privilege to work with since beginning this adventure nearly 15 years ago.
- What does the future hold for your company? Any big plans in the works?
Aviation attracts some big dreamers…some would say fantasists. We are about solid, measured growth that keeps the company healthy. We plan to grow our existing routes throughout the Northeast.
- What is the one take-away you would like our readers to know about Tradewind Aviation?
In many ways we’re a throwback to a time when traveling was more civilized. Private lounges, no TSA security hassles, no change fees, no bag fees and our reservations team and pilots are actually accessible and helpful. We’re obsessed with service and constantly looking for ways to improve the passenger experience. In a world where traditional airlines have conditioned us to expect less, our passengers are thrilled to see that we add more.
Follow along with Tradewind Aviation on Facebook, Twitter, Instagramand YouTube. To learn more about this amazing company, you can head to their website and check out some upcoming flights!