39 Airports, 1 Grand Adventure

Seventy-four-day Cirrus journey focuses on growing real-world pilot skills.

Monday, April 13, 2026 at 08:00 AM ET

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Pilot Blake Freedland (right) and co-captain Dylan Tamaroff flew across the U.S. and Canada in a Cirrus SR22. [Credit: Blake Freedland]

Key Takeaways:

The author and a friend completed a 74-day, 13,000-mile post-graduation flight across the U.S. and Canada in a Cirrus SR22, visiting 39 airports for adventure and skill development.
The journey exposed them to a wide array of airport personalities—from scenic favorites to challenging high-altitude or busy fields—each offering unique lessons in aviation.
Key takeaways from the extensive trip included the importance of flexible, regional planning, better financial budgeting, and the invaluable support of a network of aviation experts for guidance, significantly enhancing the pilots' proficiency, confidence, and overall skill.

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Like most pilots, I’ve always dreamed of a grand trip. A shared passion for challenge, adventure, and flying eventually drives all of us avgeeks to leave our comfort zones and explore.

So, to celebrate our graduation from Tufts University and Berklee College of Music in Massachusetts, I decided to fly across the U.S. and parts of Canada in my Cirrus SR22 with one of my best friends and copilot, Dylan Tamaroff. Our goal was to see new places, meet people, discover hidden gems, and most importantly, learn. I wanted to push myself, sharpen my skills, and become a better aviator.