scorecardA millennial who hates monotony didn't feel free enough living in a cave. He now hunts for treasure from a sailboat in the Caribbean.
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A millennial who hates monotony didn't feel free enough living in a cave. He now hunts for treasure from a sailboat in the Caribbean.

Jordan Pandy   

A millennial who hates monotony didn't feel free enough living in a cave. He now hunts for treasure from a sailboat in the Caribbean.
LifeThelife3 min read
  • Kyle Davis, 38, swapped living in a cave on a farm in Hawaii for living aboard a sailboat.
  • He loved feeding himself off the farmland but was frustrated by what he called a "lack of freedom."

Kyle Davis was living in a cave in Hawaii — and still wanted more adventure out of life.

The now 38-year-old planted and tended to fruits and flowers on a lava-filled corner of the Big Island while hosting rave parties and teaching volunteers how to farm.

It sounds like an exciting life for anyone confined to a cubicle. But Davis got bored. So he decided to sail the seas hunting for sea glass.

Davis, who calls himself Captain Ky or the Bored Pirate, said he's fulfilled by constantly staying on the move.

"The cool thing about going to new places and waking up with a different view inside your window every day is that every day is different, and you're able to make new memories," he said.

Davis was drawn to the idea of living off of his own land

Born in California, Davis grew up in Virginia and lived there until he enlisted in the Army. At 19, he was posted at Schofield Barracks on the Hawaiian island of Oahu.

After serving as a combat medic in Iraq for two and a half years, he returned to Hawaii in search of a unique place to live.

"I'd always been a big Batman fan as a kid, so I always wanted to have my own cave," he said. "How cool would it be to have your own underground lair?"

Davis was also motivated by the idea of living off the grid and off of the land.

"I just really liked having the idea of sustainability — of not having to worry about anybody else taking care of you," he said.

Davis found six acres of farmland with a large cave for sale on the Big Island, he said, and bought it in 2014 for about $65,000. Around the same time, he enrolled at the University of Hawaii at Hilo to study agriculture.

After three and a half years of life as a farmer, Davis had cultivated the self-sufficient life he thought he always wanted: He could wake up in the morning and harvest fruit from trees he planted for breakfast.

But it still felt too static, he said.

"The thing about having a farm is you have to be there every day, morning and night, starting first thing in the morning when the roosters start crowing and the pigs start screaming at you for food. And you can't skip a day — there are mouths to be fed," Davis said. "Your freedom is your self-sustainability on the farm, but also your lack of freedom is that same sustainability where you have to manage and take care of it at all times."

Davis traded the farm life for one at sea

Inspired by pirate movies this time, Davis sold his farm for about $400,000, he said, and set out on his next adventure around 2018.

With the proceeds from his land sale in Hawaii, he purchased a sailboat in Maine for $120,000 with the intention of leaving all his cares ashore.

"I always wanted to have the freedom to be able to go wherever you could want at a moment's notice," he said.

He took a 10-day sailing course in Thailand to learn the ropes. For the past six years, Davis said, he's lived aboard the 50-foot sailboat about 90% of the time, with breaks on shore here and there while the boat gets repaired.

His time is spent mostly in the Caribbean, sailing from beach to beach on islands including Aruba and Curacao looking for pieces of colorful sea glass to resell online. According to Davis, he's sold single pieces for hundreds of dollars. He also said he supplements his income by making videos he posts on social media. He earned about $1,000 in October from Facebook alone, for example, according to a remittance from Meta he shared with Business Insider.

It's a gig that keeps him island-hopping, fulfilling his desire for ever-changing surroundings.

No day looks the same for Davis anymore.

Once, he said, the boat's propeller fell off in the middle of the night, forcing him to grab a flashlight and hold tight to a rope while checking out the damage to make sure he didn't get swept away into the pitch-black ocean. Another time, he got struck by lightning.

After all, he added, a traditional house with a yard just isn't his thing.

"If every day is monotonous and kind of the same, going to work nine to five, five days a week, most of your life you can't even remember because it was always the same," he said. "Doing the same routine makes for a pretty forgettable life."




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