It all began with a dream. literally.
Richie Olsten, currently serving as the Director of Operations for both Air Maui and Air Kauaʻi Helicopter Tours, has been flying over Hawaiʻi for more than five decades.
It’s earned him many awards and titles — and even more once-in-a-lifetime experiences and stories.
Stories that are worth sharing.
His journey began long before he ever took the controls of an aircraft.
As a kid, Richie constantly dreamed (literally — he had dreams, and still does to this day) of flying.
where it all STARTED
1970s – The Dream Takes Flight
Richie Olsten’s passion for flying was sparked in childhood when his dad — a private pilot — took him on his first flight at age 12 in an old Piper Cub over Wisconsin. That feeling of floating — no radios, just air and instinct — never left him.
After moving to Hawaiʻi at age 13, Richie chased that dream. In 1971, the first flight school opened its doors on Maui, and he became one of its first students. He also worked there, fueling planes and helping in the office just to earn flight time. He began flying Cessna 150s and 172s, and by 1977, he was flying rental aircraft around the islands.
His creativity took flight too — starting the first banner-towing operation in Hawaiʻi for his family’s t-shirt business. He even helped launch radio promotions where listeners could win shirts by calling in the number from the banner flying overhead. He also became the first person to have a golf cart on airport property (which is an entire story in itself).
1980s – Skywriting and Showmanship
In the early '80s, Richie dove headfirst into aerobatics. In 1980, he bought a Citabria — “airbatic” spelled backward — and installed a smoke system, setting the stage for a new era of air shows across Hawaiʻi. By 1981, he was flying a biplane and performing high-energy routines with smoke trails, loops, and dives — all choreographed to music.
He became a fixture at annual air shows, sharing the sky with legends like the Blue Angels and even taking on wing-walking stunts. Richie’s goal was simple: to be the greatest aerobatic pilot in the state of Hawaiʻi — and he left smoke trails across the sky chasing that dream.
1990s – Mastering the Skies of Hawaiʻi
By the '90s, Richie’s expertise in the air was unmatched. Having flown over every island and through almost every type of weather, he developed an instinctive understanding of the terrain, wind, and weather patterns unique to Hawaiʻi.
He continued banner towing, aerobatic shows, and started building a reputation not just as a skilled pilot — but as a trusted figure in the aviation community. His dedication to safety and preparation became a defining trait in his approach to aviation. His go-to motto says it all:
“The only time you have too much gas is when you're on fire.”
2000s – The Storyteller Pilot
With thousands of hours in the air, Richie began to focus more on sharing the story of Hawaiʻi from above. He curated flights that weren’t just scenic — they were deeply emotional experiences, where the views of places like Haleakalā Crater, the Hāna Rainforest, the West Maui Mountains, and the sea cliffs of Molokaʻi were paired with Hawaiian music, perfectly timed to the landscape.
People began asking for his playlist — and sending him heartfelt letters and emails after their flights, sharing how his tours became defining moments in their lives.
He wasn’t just flying — he was giving people something to feel, remember, and carry with them.
Listen to his playlist here:
2020s – Legacy in Action
In 2023, when the devastating Lahaina fires struck Maui, Richie was the first in the air the following morning. As he approached Lahaina from the south, he saw — and recorded (see the video here) — the full scope of the destruction before emergency responders arrived. His video quickly spread, prompting national news coverage.
Over the following days, he helped fly in critical supplies: water, baby formula, breast milk, and more — supporting families in need. Community is everything to him.
Even after decades in the cockpit, Richie still gets a rush during the first hover of the day. His favorite route? West Maui to Molokaʻi, with a long, slow hover in the Keyhole — his personal favorite landmark.
“It never gets old. You lift off, clear the trees, and you’re just... blown away by how beautiful this place is.”
Being a pilot isn’t just what he does — it’s who he is. He’s never stopped flying, never stopped learning, and never lost the feeling he had as a 12-year-old kid in that Piper Cub.
2010s – A Lifetime in the Air
Richie continued flying tours while also assisting with emergency flights and search operations. From spotting overturned sailboats off Kanahā to tracking missing vessels after Kona storms, he always stepped up when the community needed help.
With a sharp eye and decades of instinct, Richie became a go-to pilot for tricky missions, difficult weather, and community support.
Legacy & Philosophy
Richie believes flying isn’t just about getting from point A to B. It’s about being one with the aircraft. Feeling everything. Trusting your instincts. And creating once-in-a-lifetime moments for those lucky enough to fly with you.
If there’s one thing he wants to be remembered for, it’s this:
“That I made a difference in people’s lives. That decades later, they’ll remember that one flight — and how it made them feel.”
Richie is always working on something.
submit the form field below to be the first to know when a new project, item, or event is happening.
We will never use or sell your information, period. By submitting your contact information, you are agreeing to be contact by Richie Olsten, LLC for marketing and informative purposes.
