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I was just thinking about it and winter is a great time to take the US Power Squadron or US Coast Guard Auxiliary Boating Skills and Seamanship courses. These basic classes will teach you most of the skills you need to be a competent boater and these classes are dirt cheap.

Once you've got these skills under your belt, you could take a sailing class at your local marina. Then you might be able to meet the right people and bum around enough to go sailing for free as a crew member. :dunno:

How To Go Sailing For Free
 

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Wow, haven't done that since Boy Scouts. THAT's been a while. I can see where seamanship skills would be very useful in certain situations. Could be fairly geographically specific though. I'm barely a mile from the Illinois river, and I don't think there's another lock/dam downstream from me, so, if it came to it, it'd be smooth sailing from me to the sea.

Edit: There is, I believe, one lock and dam between me and Mississippi River. Would have to navigate that.
 
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