Professional Sailor



“I love to take a kayak and snorkel gear and head out to the reef between Prickly Pear and Necker Island. I tie the kayak to my waist and snorkel while pulling it. Exercise and beauty all at once, with a little bit of adventure thrown in."

Dawn is one of the most recognizable and respected athletes in the sport of sailing. Her career has been outstanding: she was the first woman to manage an entire America’s Cup syndicate and was the first American—man or woman—to sail in three America’s Cups and two Whitbread Round the World races. When she’s not on the water, she’s working hard to provide access to sailing for people from all types of backgrounds and communities.
But beyond her resume, the Bitter End team loves Dawn because she cares for our home the same way we do. She recognizes its special place in the sailing community, and she participates in our annual regattas and events whenever possible. When visiting, if she’s not on a boat, you can often catch her swimming, diving or kayaking in the Sounds. Her incredible generosity of spirit is also always apparent, whether she’s holding court for hours with guests at The Crawl Pub or sending sailors our way from around the world.