The Windwitch: Portland woman ready to sail her classic cruising sailboat

The epic journey's final piece came together in the past two months with the purchase of a classic sailboat commissioned for publishing mogul William Randolph Hearst in 1949. (KATU)

A Portland woman and her passion for art, travel, wooden boats and ocean sailing will take her across the globe in the coming months.

The epic journey's final piece came together in the past two months with the purchase of a classic sailboat commissioned for publishing mogul William Randolph Hearst in 1949.


Five years ago, Randi Whipple sold all of her belongings and crewed on a sailboat crossing of the Atlantic.

One trip turned into several, with stops in Portugal, Egypt and Israel.

“I thought I was just going to leave and do one ocean crossing, get it out of the system, come back go to work do my thing,” said Whipple. “But as soon as I got out there everything changed and just kept traveling and hopping on more boats..getting more experience because I wanted to get my own boat.”

The Syracuse, New York native moved to Portland in 2005 to go to fashion school.

But she dropped out to apprentice in an auto upholstery shop while pursuing art, leather work, and fashion on the side.

“I’m just an artist by trade,” she said. “I always made my own stuff. Everyone in my family’s a mechanic or works with their hands in some way. That’s just kind of who I am.”

She also crewed on racing sailboats on the columbia and joined the board of Portland’s RiversWest Small Craft center.

She also owned a series of small sailboats.

A few months back she helped a friend bring the boat to Portland from Warrenton on the Columbia River.

“As soon as she got her boat up here she was like we’ve got to get you a cruising boat so you can get out there.”

The friend searched for one and found "the windwitch" a 1949 wooden cutter in Cathlamet for sale.

“She said that her mother was going to give me a loan to get the boat. Initially I was like no way. I can’t do that.

But the seller was offering the boat for a good price.

Whipple was persuaded to accept the loan from the family to pursue her ocean cruising aspirations.

It was an emotional moment.

“They think I have what it takes which was more important to me than the money,” she said through her tears. “Because it’s hard doing this and it’s scary."

“To have a couple who sailed around the world on a wooden boat, raised four kids to think that I have what it takes to do it on my own is huge.”

The Windwitch, moored now on the Columbia near Jantzen Beach, was designed for ocean cruising.

The hardest part sometimes is just cooking a meal at sea.

“Because when you’re out banging in the ocean just having this right here,” she said of the small cubicle that held her body from moving. “I’m usually leaning up on something. This is a gimbling stove, so that moves with the motion of the ocean.

“The boat has all sorts of hand grips everywhere,” she said as she gave a tour of the small, but well-appointed cabin. “All of the edges been rounded which is really nice because you just get covered in bruises.”

One item tacked to the wall of the Windwitch's cabin may be more than a coincidence.

It's a drawing from fashion school, the only thing she kept from that time 13 years ago.

"What I drew is the character based on Marian Davies, who is the woman is said to have commissioned this boat to be built.

And she's already picked out the place to design and make "ditty bags" which she plans to sell and finance her ocean journeys.

“A ditty bag is by definition a receptacle for loose odds and ends specifically for sailors and fishermen,” she said of the small bags.

She expects to set sail after re-fitting the Windwitch, hauling it out for repairs and re-caulking.

Then it will be on to Mexican waters and beyond.

“From there I’m going to figure out whether I am going to go cross the Pacific or go through the Panama Canal and go to the Caribbean.

Now I have a boat that’s capable of going out in the ocean.”

Randi Whipple has been taking online classes and will pursue her Yachtmaster's license during her ocean journeys.

She plans to document her trips on social media and hopes to use the Windwitch in exotic places as a platform for fashion photo shoots.

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