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 friends embarked on a 74-day, 13,000 sm flying trip across the U.S. and parts of Canada in a Cirrus SR22, visiting 39 airports to gain experience and explore new places.
The journey provided diverse experiences with airports, categorizing them into "overall favorites," "most challenging," and "most beautiful," with some, like Aspen, appearing in multiple lists due to their unique characteristics.
Key takeaways included the importance of flexible trip planning (preferring regional bases for day trips over rigid itineraries) and the invaluable role of a strong support network for maintenance and expertise.
The most significant outcome was a substantial increase in the pilots' proficiency, confidence, and skill, preparing them for varied terrain, weather, and airspace, and fostering a meticulous approach to flight planning.

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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.