Sailing down memory lane

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As a member of the Hobie Cat crew, Kim Pitts fondly recalls her days of combining the gulf with the arts

By Hannah Wallace

“Do you know how many weddings photos have been taken on our boat,” asked Kim Pitts, “standing there in their gowns like they’re ready to become a pirate?”
Plenty of people who visit Siesta Key fantasize about living this kind of unbridled island life — tan skin and wind-tangled hair, days spent in artists’ studios and afternoons out on the water rigging sails tacking wind, sliding the Hobie Cat’s hull back onto the sand just after sunset, in time to paint the afterglow.
But for a community of Sarasotans these days, the free-spirited Siesta Key lifestyle isn’t so much fantasy as recent memory. They still hold their big Easter gathering on the beach at Access 3, where upwards of 100 people gather every year for a potluck lunch to remember the friends they’ve lost and celebrate the memories they have.

Kim Pitts is flanked by sailing friend Jim Houghton (left) and her husband, Rip Pitts.

Pitts, 67, is one of them. She’s been sailing the Gulf and Sarasota Bay for more than 40 years.
“If you were to go down there [on Easter], you will see the essence of Siesta Key,” said Pitts just two weeks before another Easter get-together on the sand. “These were the beach people, people who rode their old rusted bikes down the road, the Hobie Cat sailors.
Pitts comes from a family of artists. Born and raised in New Jersey, she visited the Sarasota area’s artists’ communities as a kid in the 1950s and ’60s. She studied art at Bard College and even started her own garment business with a friend in their early 20s, counting Bendel’s department store on Fifth Avenue among their customers.
Eventually she came to Sarasota in 1980, married “local boy” Rip Pitts, had two sons and settled into small-town life. Most importantly, he taught her to sail a Hobie Cat, a famously beachy brand of catamarans that flew onto the sailing scene in the late ’60s.
Pitts found a home in the community. “Hobie Catters, we’re kind of a wild bunch,” she laughed. “Most Hobie Cat sailors will take a stranger, a newbie out on the water to see what we see — turtles, manta rays, we’ll have dolphins follow us. You can set a Hobie to where it won’t move, and everybody but one hops off, swimming in crystal-clear water a half a mile out. There’d be four or five boats all together. It’s that community of sharing the adventure for everybody. It kind of rolls over into the art, the music, the camaraderie.”

Pitts displays a denim jacket featuring her artistic touches. Below, a sailboat-inspired painting she created on Siesta Key. (submitted photos)

New friends would come ashore afterward and immediately seek out their sailing partners’ artwork in local galleries and boutiques.
“The rule is, you have to be good soul,” Pitts added. “Well, you have to at least try.”
Hobie Cats are made of relatively lightweight fiberglass hulls connected by an aluminum alloy frame that holds a mesh “trampoline.” In races, members of the crew can also lean over the side — called “trapezing” — to counter-balance against the wind and maintain maximum speed while keeping the boat flat. Hobie Cats are made to go fast.
While her husband manned their 20-foot boat, Pitts would assemble a boisterous crew to sail their 18-footer. “I called it ‘the girl boat.’ I would take four other women, all in bikinis, bright red toenails,” she said. “We would play chicken with the guys. I was a real taskmaster with those girls, and we all had a blast. These friends would still remember that for 20 years.”
At the end of the day, conditions are often just right for an energetic appearance on shore, as Pitts described it: “You’ll see people sitting at the edge of the water. We’ll be coming in on a nice strong evening wind, and we’ll just scream right onto the beach. The boats are like sleds.”
Pitts also found new artistic inspiration in the sunsets, which featured colors and textures she’d never seen up north.
“Sailing to the little sand dollar island, sitting there until sunset. Everything would be magentas and reds, just brilliant colors,” she said. “It was like, ‘OK, I have got to paint this.’ The beach just gave me this backdrop, and this vastness. I remember being out there on the water when it was so glassy it was pink, like pink satin. It felt like you were in another world.”
Pitts began painting large-scale recreations of Siesta sunsets, and also creating artwork on denim jackets. (Her creations can still be purchased at Key Salon and Boutique, formerly on Columbus Boulevard and now on the South Trail.)
At one point, the Pitts family rented a small backyard apartment on Beach Road, where they ran an air conditioning company and still found ample time to get out on the water.
“Every morning, we would look at the flag that Capt. Ralph Styles flew there on the northeast corner,” remembered Pitts. “We’d look at his flag flying and ask ourselves, ‘Is it a work day, or is it a sail day?’” As 1- or 2-year-olds, their sons could fall asleep on rolling seas. Later they served as first mates. Nowadays, Pitts has been introducing her grandkids to the remaining Siesta Key Hobie Cat crew.
But recent contention over catamarans being stored at Beach Access 8 has made uncertain an already dwindling way of life on the Key. For her part, Pitts hopes to keep sailing for as long as she can. She and her husband currently own just one Hobie Cat, its 31-foot-tall mast sporting a sky-blue sail with orange and red highlights, like a Siesta Key sunset just getting started.
“He and I sail together now, a little more sedately,” said Pitts. “But in our dreams, we’re still hanging off the side of the hull, screaming onto shore.”

The Pitts’ sailboat in action. (submitted photo)
Hannah Wallace
Author: Hannah Wallace

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