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Lifting up your spirits
Next Level Training Starts Here
Accelerated Instrument and Flight Instructor Courses are our specialty!
Earn Your Rating in as little as five days!
We're open seven days a week booking into 2022!

Your New Office View

Step aboard the One-Fifty... 
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The one-fifty is the leader in flight training. And that's why we selected it for the mission. Ours is fully IFR and ready to help you get your next instrument or flight instructor rating!

Meet Your Instructor

Allow us to introduce you to Kyle. He is the founder of Fly Upwind, currently serving as an Airline Pilot and Instructor, as well as a Flight Instructor certificated in single and multi-engine airplanes. He holds an Airline Transport Pilot's License with type ratings in the Embraer 170 and 190 variances with Pilot in Command privileges. Kyle grew up hanging on the airport fence as a young boy, longing to one day become a pilot. It wasn't long before the friends he made at the airport offered to take him up flying. He was hooked. After earning his ratings while in school, he gained experience as a Flight Instructor before moving onto the airlines. Shortly thereafter, he became an instructor at the airline he flies for, and then went back to his roots in general aviation - Fly Upwind was born.

Conveniently Located...

Fly Upwind

63 Tom Harvey Road B

Westerly, RI 02891


Learn to Fly with Us!

Have you ever dreamed of flying an airplane? Have you ever thought about becoming a pilot? If so, we're ready to get you flying! Enjoy our "Take the Wheel" experience, a one hour introductory flight with one of our talented flight instructors who will show you what it's like to be a pilot. Explore the beautiful sights that Watch Hill has to offer from our Cessna 150, high wing airplane so you can see all of the sights below you, while at the controls of an airplane!

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