Dawn Riley remembers being desperate to race sailboats in 1977 when she was 13, growing up on the shores of Lake St. Clair near Detroit, Michigan. She did anything she could to get on a crew.
“I would go into the bar and accost old people and say, ‘I’m going to race with you tomorrow,’” she said. “The bar owner would tell me, ‘Get out of here!’
“I went sailing with people that were old, but I was much better than them,” she added.
Much of that was due to the fact that she grew up in a sailing family. She began racing at 4 and her family spent a year at sea, sailing down the East Coast and around the Caribbean. That trip, she said, gave her an obsession that she has not lost.
Ms. Riley, known as a pioneer in women’s sailing, spent the past weekend in Grand Cayman, speaking to and meeting with young sailors and taking advantage of the island’s offerings, including a stint sailing a hydrofoil catamaran on Saturday.
Saturday evening, she spoke to the Cayman Islands Sailing Club.
“I’m just going to talk about my background and about Oakcliff,” Ms. Riley said in a Friday morning interview.
Oakcliff is a U.S. Sailing training center she founded four years ago on New York’s Long Island. Students at Oakcliff learn the ropes of professional sailing and can train for various jobs in the sailing industry.
Ms. Riley’s own sailing background includes competing in four America’s Cups, including being the first woman crewmember on an America’s Cup yacht, the winning America³ in 1992. In 1994, she raced with the first all-woman crew in the event, and was CEO and captain of a co-ed team that finished fourth in 2000.
She has also captained two boats in the Whitbread Round the World Race, one of which, the Maiden, had the race’s first all-woman crew in 1989-1990. Ms. Riley wrote about her experience with that race in her 2013 book “Taking the Helm.”
She is a public speaker and has a small foundation, America True, which provides advice to people starting sailing programs and advocates for getting at-risk youth out onto the water.
By Friday morning, some of Cayman’s youth had already dropped by the home where she was staying.
“I’ve already had some kids stopping in asking me questions: what boat they should sail; how they can get into the Olympics; how many pushups can I do?” she said, with a laugh.
The answer to the last question is 30 “pretty easily.”
Ms. Riley said the sport of sailing is moving from a traditionally elite activity to a more egalitarian footing. She is helping that trend as much as she can, she said.
“Community sailing in the U.S. is huge,” she said. “The very elites are continuing to tell me the sport’s dying and there aren’t as many people. They need to look outside their bubble and see where the demand is.
“I would like more people of all different backgrounds to come to Oakcliff,” she added. “My biggest thing is gender equality and ethnic diversity.”
She planned to address those aspects of sailing when she spoke Saturday evening. Part of the focus of her visit was to promote and possibly recruit sailors to come to Oakcliff, which she called the epitome of everything she’s done in sailing.
“I get to see young, hungry athletes who are obsessed with the sport,” she said. That devotion is more important than anything else.
“I don’t believe in this mystical natural talent,” she said. “I want someone who’s interested and motivated … and quirky. We have our characters.”
But her biggest message was just to enjoy sailing. Doing so, she said, is a no-brainer.
“It’s a sport,” she said. “It’s on the water. Especially around here, it’s gorgeous. Just have fun.”