Randi Whipple threw her electronics into the stove, strapped herself to the slick deck, and watched boat parts float by. She was aboard a 36-foot Bavaria sailboat named Ocean Maiden, along with a grumpy German sea captain and a cat named Ska, getting thrashed by a massive electrical storm in the Bermuda Triangle.

“It was just like the Wizard of Oz—clouds started swirling, the sky went black, and there was a torrential downpour with thunder and lightning all around us,” she remembers. “You could feel electricity coming up your shins. When we finally came into port, there was a missing poster for the boat we were anchored next to before the storm. They had no survivors.”

That was Day 9 of the Portland-based hair and makeup artist’s three-week voyage across the Atlantic in 2014. And just the first leg of a two-year adventure spent globe-hopping with only her fashion and art skills to get her by.

Titanic storms, “semi-kidnappings,” getting haymakered on the streets of Turkey by a handsy creep—any conversation with Whipple can launch the kind of yarn that would charm a pirate. But it’s part and parcel for a local legend, known for her superfan love of Hooters restaurants and her knack for making anything from shoes to shelves, as well as for styling models for familiar Portland names like Nike and Wildfang. Her next adventure? Sailing the world again. This time with her own boat, chartered out for fashion shoots.

Rewind to 2007, and Whipple is sitting inside NW 21st Avenue dive bar Wimpy’s, where she not only bartends in between photo shoots, but has just convinced the owners to let her remodel the bar in the theme she loves more than anything: nautical. She uses her sewing skills to reupholster the leather booths, her artist’s hand to paint murals of mermaids and sea krakens on the walls. She even brings in a fleet of vintage miniature boats.

A friend notices her marine obsession and introduces her to a local sailor looking for some reliable shipmates—aptly named Capt. Randy Bauer. And with that, Captain Randy takes on Crew Randi.

Over the course of the next four years, Bauer and his band of old seamen relayed everything they knew. One shared the tale of how a whale took down his sailboat. Another claimed to be an ex-government agent who could burst clouds with his mind. They shared sea superstitions aplenty (never exit port on a Friday, don’t bring bananas on board, etc.). But beyond getting a good knife to cut yourself out of a rope tangle, their primary advice for the sailing novice was simple: stay on the boat.

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From left: Whipple aboard a camel in Egypt; into the drink; Captain Randi's mural in Tel Aviv

“I wasn’t born into sailing, but I was born to sail, with my skill set,” says Whipple. She’s referencing her childhood in Syracuse, New York (“where dreams go to die”). She learned engines, painting, and bodywork from her all-mechanic family and earned a full cosmetology license through her high school’s trade program. She found work in Portland doing car upholstery, bartending, and glamming up models on set, but she’d never been out of the country and dreamed of seeing the world.

In 2012, she quit Wimpy’s, told her styling clients she was taking a break, and sold off all her possessions through social media and a massive yard sale. She flew down to Antigua to globe-hop, earning money along the way by sewing, cutting hair, and painting.

Cue another trademark Whipple montage: Randi, sitting aboard the Stormvogel in the Azores—a boat famously used as the set of terrifying Nicole Kidman/Billy Zane thriller Dead Calm—and patterning a line of kimonos for the captain’s wife.

Randi, flat broke, selling watercolor paintings of the Wu Tang Clan holding tropical fish for $30 a pop on the streets of Amsterdam.

Randi, hard at work on a public mural of a dinosaur carrying Jesus in Tel Aviv while Vice News photographs her. In Israel, she spends six months living 200 meters from the beach in a makeshift camp, repairing ripped sails for a marina by day, doing acroyoga with friends by sunset. Alas, as 2015 came to a close, her visa expires, so she boat-hops to Martinique and flies home.

Back to present day. Now Whipple sits in the cabin of her own ocean cruising vessel, a 33-foot Fellows & Stewart wooden cutter built in 1949, originally commissioned by newspaper tycoon William Randolph Hearst and his movie star partner Marion Davies. And she’s realized that Portland land life isn’t for her anymore. “I got super-depressed when I first came back,” she says. “I was used to having so much adrenaline; the constant adventure. And then I came back to rain and sitting still.”

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A Whipple Ditty Bag

Image: Michael Novak

Her landlocked days are numbered. She’s currently working on using her nautical miles to obtain an Ocean Yachtmaster license, so she can officially charter paying customers across the seven seas. She’s also just launched her own line called Ditty Bags, taken straight from a sailing term for the little bags sea folks use to keep things from sliding about a choppy boat cabin. The soft leather bags are made using a cord that has a towing strength of three tons. Inside, the tag that might usually display country of origin proudly reads: “Made on a Boat.”

The crafty captain also plans to leverage her style background to offer even more for both her charter and fashion clients. “I can’t get out of the fashion industry. It’s a part of me,” she says. She’s scheming to become the first sea captain to offer major clients like Sports Illustrated and Victoria’s Secret both the stunning tropical locations they need and a stylist. She plans to obtain her license and set sail from the Caribbean in late 2019, with her Ditty Bags and her new photo shoot venture to fuel her sailing life.

“These big companies shoot on location 365 days a year. Not only can I sail the boat, I can do hair and makeup for them,” she says. “And I can MacGyver a bikini out of anything.”

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