Air Charter Logistics | Flight Training | Aircraft Sales

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Safety...

defines our very operation. At Fly Upwind, our aircraft operators are FAA, Part 135 approved Air Carriers. Additionally, all of the certificate holders we work with are "ARGUS" rated carriers, evaluated by the most respected and rigorous safety rating system in the industry. Rest assured, you're in good hands.

Reliability...

is the key to our credibility. And yours. Enjoy increased business productivity, prompt ground handling and transportation services, and experienced aircrews handpicked by Fly Upwind to serve you and your party. Allow our highly trained and experienced aviation professionals to handle even your most complex transportation needs, so you can focus on what is most important.

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Go your own way.
Experienced | Available | Invested

Private aircraft management solutions custom fit for your needs. Purchase a share or a whole aircraft, we're with you every step of the way

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Looking to take flight?

Whether you are interested in flying as a hobby, or as a career, now has never been a better time to become a pilot! Fly Upwind's roots stem from a passion of safety, and continued professional development in aviation. So naturally, our team of flight instructors and office personnel are true aviation enthusiasts - and we look forward to connecting with you soon!

We offer...

Private Pilot Training, Instrument Ratings, Commercial Pilot Courses, CFI, Aircraft Rental, Time Building and much more!

Please feel free to contact our office with how one of our pilot programs can work for you! One of our team members will be happy to assist you!

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Meet your broker...

Learn more about Fly Upwind's President, Founder, and CEO, Kyle Curtis. Our humble beginnings and bright future, all detailed below.

Meet Kyle

What we do best...

Fly Upwind is a flight school and air charter logistics service located in Westerly, Rhode Island arranging charter flights in piston, turbo-prop and light to heavy-jet aircraft throughout the United States, Canada, and overseas. Our customers benefit from our logistical expertise and industry-wide connections to network their ever-changing needs. We pride ourselves on customer satisfaction and repeat business with over 15 proven years in the aviation industry. Whether you are traveling for pleasure or business, Fly Upwind has the ability to find you the right aircraft for your next mission.

Available Scheduled Flights

Every time we book a charter flight with one of our operators, one of the flights to or from the destination becomes available as the aircraft repositions to pick up passengers or return to it's home base. These flights are referred to as "empty legs". We are excited to have the ability to offer these flights to you. With some flexibility in your travel plans you may save up to 75% in total cost by utilizing our service, as compared to a typical charter flight. We can also tailor these "empty legs" at an additional cost to more conveniently cater to your traveling needs. Simply contact one of our Customer Service Representatives below to inquire about our many "empty legs" that might benefit you!

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