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:

A pilot and a friend completed a 74-day, 13,000-mile flight across the U.S. and Canada in a Cirrus SR22, visiting 39 airports to celebrate graduation and gain diverse flying experience.
Key lessons from the journey included the importance of flexible regional planning over rigid itineraries, managing costs, and having a strong support network of aviation experts for troubleshooting and safety.
The extensive trip significantly sharpened their piloting skills, proficiency, and confidence, enabling them to navigate varied terrain, airspace, and weather conditions, ultimately making them safer and more capable aviators.

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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.