Meet Paradise Helicopter Chief Pilot, Kalei Gregory - Paradise Helicopter
Home/news/Meet Paradise Helicopter Chief Pilot, Kalei Gregory
Company & Team

Meet Paradise Helicopter Chief Pilot, Kalei Gregory

Jan 01, 1970

Meet Paradise Helicopters Chief Pilot, Kalei Gregory

Meet Kalei Gregory, Paradise Helicopters Chief Pilot. Kalei was born and raised in Hawai’i, and went to school at Mauna Loa Helicopters to get his rotorcraft pilot’s license. After Kalei built his hours with Mauna Loa Helicopters, he began to fly MD 500’s full time for Paradise Helicopters out of Hilo which eventually brought Kalei to becoming a Chief Pilot & check airmen for Paradise Helicopters. Kalei currently works full time in search and rescue for the Fire Department and continues to oversee the Paradise Helicopters pilots as Chief Pilot.

**Q&A with Paradise Helicopters pilot, Kalei Gregory: **

Where are you from?

  • I was born at Queen’s in Honolulu, Hawaii

How did you end up in Hawai’i?

  • My family moved back to Kailua-Kona when I was 2 years old. My dad was originally from Kona and my mom is from Rhode Island, they slowly made the trip back to Kailua-Kona from California and Oahu.


  • Travel, food, and relaxation (spa days!!)

Why did you become a pilot?

  • Growing up, my best friend and I watched a movie called Eragon, about a boy who became a dragon rider. From there on we were both obsessed with dragons. Flying helicopters is the closest thing I could get to that.

What’s your background in flight experience? Where did you get the bulk of your hours?

  • After serving in the military as a ______ for ___ years, I enrolled in pilot school with Mauna Loa Helicopters in Kona. After graduation, I moved to Honolulu where I continued to fly for Mauna Loa as an instructor, accruing around 2,000 flight hours. At this point, I received a call from Paradise Helicopters chief pilot, Steve Kitrell, asking if I wanted a job flying MD 500’s out of Hilo on the Big Island. One of my instructors from flight school, Jesse Hudson, was working at Paradise Helicopters and had recommended me. I flew for Paradise Helicopters for six years after that doing tours, film, utility, OAS, instructing, as well as being chief pilot and check airman, flying both MD 500’s and Bell 407’s. With the extensive utility experience that I acquired doing all this, I was also hired on with the Hawai’i County Fire Department to do Helicopter Air Ambulance (HAA) or Helicopter Emergency Medical Services (HEMS), search and rescue, and fire suppression. I’ve been working with the fire department for the last six years in combination with also working for Paradise Helicopters.

What do you do for fun (besides flying helicopters)?

  • I feel like flying is so much fun that when I’m off, rest and relaxation is my fun. Chilling at the beach isn’t the worst thing to do.

What is your favorite tour to fly and why?

  • Anything that involves the valleys, I just feel so awestruck anytime I fly there.

What’s your favorite place to eat on the Big Island?

  • Canoe House at the Mauna Lani, hands down the best food on the west coast of the Big Island

Is there a flight you’ve done that sticks out to you as a favorite?

  • I can’t say that there is any one flight that is my favorite. But I do really enjoy it when I have an on-scene HAA call or a rescue and you know that there’s no way they would have lived if we didn’t have that resource. To get updated that night or the next day that someone is going to make it truly is the best feeling.

The Paradise Blog

Hawaii Lava Update 

The latest happenings at Kīlauea, Mauna Loa, and Hawai'i Volcanoes National Park

Read More