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Not a mistake I've made but one from my grandfather. Allow me to set the stage. Sailing a 21ft gaff rigged skiff under a bridge that's two feet too low. He's done it many times before and the idea is to tie the outboard to the spare halyard and lift it two feet off the deck. Then, as the bridge aproaches you lower the gaff and swing out the outboard to make th boat heel so you can get under the bridge. Sounds like a stupid idea to start off with but he was younge and it had worked several times before. As I remember, my future grandmother was aboard and my grandfather was showing off his master technique at getting a sail boat under a bridge. Anyway, the outboard comes untied at the apex of it's swing and the boat suddenly rights it's self. And due to gods incredible sense of humor the top two feet of the mast find themselves up a drain pipe that goes up through the bridge. So, how do you fix this situation? Well, sink the boat ofcourse. How did he explain it to my greatgrandfather? No idea.
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