For most people, a summer road trip means packing up the car and hitting the highway. For pilots Blake Freedland and Dylan Tamaroff, it meant something entirely different — charting a 12,767-mile flight plan across North America in a Cirrus SR22. Over the course of 74 days, the pair landed in 32 cities, crossed 19 states and four Canadian provinces and logged 100 flight hours along the way.
A Lifelong Dream
For Blake, aviation has always been more than a hobby. “I’ve loved planes and flying since my earliest memories,” he said. “I would dream of flying as a kid and always knew I would become a pilot.”
After years of persistence, Blake began flight lessons at 15. By 17, he had earned his Private Pilot License, followed by his Instrument Rating at 20. “I always wanted a challenge in the plane,” he explained. “I wanted to become a better pilot and see the entire country from above.”
Dylan’s path to aviation took shape later in life, but the pull was just as strong. “I always enjoyed being at airports when I was a kid, but it wasn’t until college that I met a private pilot who took me on my first discovery flight,” he said. “That one flight changed everything.”
Planning the Ultimate Journey
The idea for the trip started as a shared goal to test their skills, see the country and grow as pilots. “We spoke with everyone we could before taking off — our A&P, our CSIP, airline pilots and even a former F-16 instructor,” Dylan said. “They helped us prepare everything, from weather patterns to mountain terrain and airspace differences. We wanted to make sure we were ready for any situation.”
They mapped out their route carefully, taking into account runway length, fuel availability, airport elevation and nearby accommodations. Their circular journey began in Boston and wrapped up in Fort Lauderdale.
“Every flight taught us something new,” Blake said. “By the end, I was far more proficient in IFR flying and flight planning than ever.”
The Journey of a Lifetime
From the Atlantic to the Pacific, each leg of the trip revealed something unforgettable. The pair landed in Aspen surrounded by mountain peaks, went whale watching in Monterey and fished the salmon run in British Columbia.
“For me personally, seeing Mount Rushmore in person was incredible,” Dylan said. “And visiting national parks like Canyonlands and Arches — those were moments I’ll never forget. Seeing the West Coast for the first time was definitely a highlight.”
Their favorite memories weren’t limited to the skies. They toured FBOs, met fellow pilots and mechanics, and stayed with friends and family along the way. From fresh lobster in Nova Scotia to fireworks over the water, every day brought a new story.
Growing as Pilots
The trip offered constant opportunities to learn. “Flying around new terrain like the Rockies was intimidating at first,” Dylan admitted. “But as the days went on, I became more comfortable and learned how to anticipate what the wind and terrain would do. By the end, I was far more confident.”
It was also a test of endurance. “With the amount of flying we were doing, we had to stay disciplined about getting rest and managing fatigue,” Dylan said. “It really pushed us to practice strong crew resource management. Me and Blake’s CRM is pretty much down to a science now. There’s no other pilot I would have rather done this with.”
The Meaning of the Cirrus Life™
For both pilots, this journey was about embracing what the Cirrus Life™ stands for. “It means charting your own path,” Blake said. “Cirrus provides the tools and technology, and it’s up to us as pilots to make something amazing out of it.”
After covering thousands of miles, Blake came home with a renewed sense of gratitude and a goal to give back. “This trip made me realize how fortunate I am,” he said. “I want to inspire kids who dream of flying but might not have the opportunity. Aviation gave me so much and I want to share that joy with others.”
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