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:

Two pilots embarked on a 74-day, 13,000 sm cross-country flight across the U.S. and Canada in a Cirrus SR22, visiting 39 airports to celebrate graduation and seek aviation adventure.
The journey provided diverse experiences, from discovering favorite and beautiful airports to navigating challenging terrains, weather, and busy airspaces.
Key lessons learned included the importance of flexible, regional planning over fixed itineraries, the necessity of strong support from aviation experts, and better budgeting.
Ultimately, the trip significantly enhanced the pilots' proficiency, confidence, and skills, transforming them into more capable and aware aviators through continuous practical experience.

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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.