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Kyle Curtis

President, Founder, and CEO

Kyle Curtis is the President and Founder of Fly Upwind with over 15 years of aviation experience. He also serves as a major U.S airline pilot domiciled at Boston-Logan International Airport.


Kyle is the holder of an Airline Transport Pilot certificate with type-ratings in several jet transport aircraft, many of which he currently flies today. Kyle also holds flight instructor certifications for both single and multi-engine airplanes and still teaches students to fly in his spare time. 


Before founding Fly Upwind, Kyle served as a flight instructor in Connecticut. He acquired experience and flight time to later join the ranks as an airline pilot for Republic Airways at the age of 21 in Indianapolis, IN. While at Republic, Kyle became an instructor pilot for the airline. When he wasn’t "flying the line", he taught aircraft systems, indoctrination classes, ground schools, aircraft procedures and also developed training curriculums requiring FAA approval for the airline. He later moved on to a major U.S carrier to operate Embraer 190 and Airbus A320 equipment.


Kyle’s entrepreneurial spirit pushed him to start his own aviation outfit in 2019. After organizing the company, he purchased the first aircraft for the business, a Cessna 150. Fly Upwind began as a flight school in Westerly, RI, later growing into the air charter brokerage house that still exists today. Kyle currently manages all of the day-to-day operations of the air charter department. He also oversees the increasing fleet of privately owned aircraft that Fly Upwind manages and maintains for its customers located throughout the country. 


In his free time, Kyle enjoys flying tailwheel aircraft, running, having campfires in his backyard, and playing acoustic guitar.

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