I never sailed with him, but I worked with him. My first job out of college in corporate relations at the studio in Burbank. What a ride! Many great memories at "The Mouse" as a fly on the wall whilst some of my heroes changed Hollywood and film business. Roy had the coolest office...down the hall from from Eisner and Katzenberg, and he inspired me to make my office more like a home away from home.
Remembering Roy: "I think Roy Disney liked sailing in part because, on a boat, he was just one of the boys, not the gazillionaire who ousted Michael Eisner and revived animation at the Disney studios. Those who have heard only of his high-profile racing yachts would not know that he started with modest cruising boats, got hooked, and just got steadily deeper into the game. I first sailed with him in the 1980s when he brought his shiny new Shamrock to a Big Boat Series and discovered that she was not at all right for the job. Shamrock was a lovely boat, as green as Ireland, but an S&S centerboard yawl best put to uses other than broaching around the buoys on San Francisco Bay. He loved that boat and never sold it."