I'll have to break up my bonehead moves by era and boat. I'll start at the beginning with the 14' Hobie turbo that I purchased from my then boss when I was 16. He told me when he sold it to me that the trapeze wires needed to be replaced. But hey, I was 16 and knew everything. Sometime later I was hiked out, flying a hull in the Gulf of Mexico off of Indian Rocks beach. The trapeze wire gave way and my whole upper torso dropped into the water while my legs wrapped around the shroud. I lost my favorite hat and nearly drowned before the boat rounded up.
Lesson learned: never wear your favorite hat sailing! : )