Bermudian Pilot Shares Aviation Journey

April 6, 2025 | 8 Comments

[Written by Stephen Wright]

Bermudian airline pilot Derek Anderson — who has worked on cargo flights, air ambulance flights in the Canadian arctic and passenger flights — vividly remembers the moment he fell in love with flying.

At just three years old, while playing outside at nursery, he stumbled upon a small toy airplane. Something about it – the bright yellow propellers, the black wheels – sparked a deep fascination within him.

“I was at Kids’ College on Dundonald Street during playtime when I looked down and saw this little plane,” he told Bernews. “From that day on, I knew I wanted to fly!”

Now a first officer for Flair Airlines, flying the Boeing 737 out of Calgary, his journey to the cockpit has been anything but smooth, requiring resilience, determination, and an unshakable passion for the skies.

“Tenacity has been a huge part of my personality,” Mr Anderson said. “There was never going to be anything that would stop me.”

From 2006 to 2009, he attended Sky Wings Aviation Academy in Red Deer, Alberta, earning a diploma in aviation management and a commercial license with a multi-engine instrument rating.

However, due to the financial crisis and the need to accumulate flight hours, it was not until 2016 that he secured his first job – flying cargo for Ameriflight in Seattle, Washington, as a first officer.

Before long, he moved to Calgary to work for Aries Aviation, an aerial survey company, captaining the Piper Navajo across North America.

“Those jobs allowed me to build a lot of flying time quickly,” Anderson said.

His next career move took him to Ken Borak Air, where he piloted air ambulances across the Canadian Arctic, serving remote hamlets such as Paulatuk, Tuktoyaktuk, and Ulukhaktok.

“I’m the first and only Bermudian to go to some of these places – there’s no reason for anybody to go there!” the former Berkeley Institute student said.

Derek Anderson 3 March 26 2025

“I was based in Calgary, but we would do two-week rotations in the Canadian Arctic, where there would be 24 hours of daylight. That does something to your body!

“We’d go to these remote communities where people were sick or injured and didn’t have the facilities for continued care and offer them immediate transport to larger medical facilities in the south – to Yellowknife or, if things were really bad, to Edmonton.”

In 2018, Mr Anderson joined his first passenger airline – Sky Regional Airlines, which operated under Air Canada Express.

However, his career took an unexpected hit when the Covid-19 pandemic forced many airlines to lay off employees or declare bankruptcy.

“I remember flying from Toronto to Washington, D.C., with no passengers,” he said. “It wasn’t long before we were all laid off.

“I had to find other means of income to keep the lights on at that point.”

At the time, he was in the process of upgrading from first officer to captain, having completed his training and preparing for in-flight assessments.

“The difference between first officer and captain is the physical seat you sit in and one additional bar on your shoulder,” he explained.

“A co-pilot doesn’t really exist anymore. The stark reality is, if at any point the captain becomes incapacitated, I’m now the captain. We’re doing the same role. The captain puts his signature on the paperwork; I don’t – that’s the difference.”

Derek Anderson 2 26 March 2026

One of his most memorable moments was his first entry in his pilot’s logbook as an airline pilot.

“I was flying from Toronto to Newark, New Jersey – one of the busiest airports you can go to – on September 17, 2018,” said Mr Anderson, who is now working towards his goal of becoming a captain.

“It was an amazing feeling. To hear a Bermudian voice via the radio, having my hands on the controls with all those people behind me – it was pretty special.”

Mr Anderson was among a handful of Bermudian pilots who shared their knowledge with Bermuda College students via Zoom during the Aviators Alliance Bermuda’s inaugural aviation information session.

“When I started flying, there was nobody you could talk to or any footsteps to follow,” he added.

“You had to make it happen. It’s definitely viable [for Bermudians], but you need a thick skin, and you must be able to tough it out.

“If you can do your training in the US, that’s the way to go.

“For anybody that has an interest, the best thing you can do is take a discovery flight. It’s going to tell you one way or the other what you need to know.”

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Comments (8)

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  1. Terry Cabral says:

    Good on you my man.
    Best of luck.
    Get that fourth Bar on you shoulder.

  2. Lion Paw says:

    What an amazing history Mr Anderson you are definitely an inspiration. May you goal becoming a captain be a shorter flight
    Congratulations and all the best

  3. Joe Bloggs says:

    Thank you, Derek Anderson, for sharing. All the best for the future.

  4. Nicky says:

    Mr Anderson your determination shines through your passion. Thanks for sharing your story and good luck!

  5. Computer Guy says:

    This has always been my dream job. Never actually ended up pursuing it but it’s awesome to see other Bermudians out there doing it. All the best and stay safe out here.

  6. Pondering says:

    Great article & great guy!

  7. Positives Vibes says:

    Thanks for sharing your inspiring journey.

  8. Ladeej says:

    What a great story! This will inspire the next generation of Bermudian aviators. We are so proud of you, Derek II!! Next step, Captain Anderson!

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