I have a waterproof cooler with a built-in CD/radio. The best of both worlds! Keep the beer cold and be able to jam. I normally don't listen while sailing - just when we beach up and hang out. It's strapped to the front of the tramp under the wishbone and away from the downhaul lines.

... Or if the wind totally dies on me and I have to paddle a mile or two back to port. The music can at least make that bareable.