Simon Le Bon of Duran Duran sailed a maxi called Drum. I believe they lost the keel during a race, capsized, and had to be rescued.

Crosby, Stills and Nash sailed. David Crosby had his own boat.

Before his accident, actor Christopher Reeve (Superman) had a 42 foot sailboat.

William Buckley Jr. political columnist and writer had several boats. He wrote several books about his saling adventires too. Airborne, Atlantic High and Racing through Paradise. Have your Thesaurus by your side if you read them.

Don't forget the obvious -- Jimmy Buffett.