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 recent graduates embarked on a 74-day, 13,000-mile flight across the U.S. and Canada in a Cirrus SR22, landing at 39 diverse airports to gain extensive flying experience and personal growth.
The journey exposed them to a range of airports, from stunning and favorite locations like Aspen and Key West, to challenging ones due to terrain, weather, or traffic, with each stop offering unique lessons.
Key takeaways for future adventures included the importance of flexible, regional itinerary planning, using a base airport for day trips, intentional budgeting, and the critical value of a dedicated support network (especially for maintenance).
Ultimately, the trip significantly enhanced their piloting proficiency, confidence, and detailed flight planning skills, transforming them into more capable and aware aviators by pushing them beyond their comfort zones.

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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.