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Will somebody please move this thread to the motorboat forum?
It just amazes me that so few of you armchair salts seems to believe it possible to actually use a sailboat for it's intended purpose, which, last I checked, is to move across water using sails and wind.
I mean Jesus. It's a sailboat. The young salt has balls and work ethic and a sense of adventure. He doesn't need a holier-than-thou lecture. What he needs is a couple of good hands to help him sail, actually sail, the boat for a day or two. It's kind of pathetic that none of you have stepped up to help. If I lived nearby and spent all of my waking hours pontificating about sailing on the internet, you bet I'd take the chance to do a trip with a real sailor--by which I mean the dictionary definition: "One who sails," a/k/a the Kid.
If the weather is right any half-decent sailor should be able to put it on the dock. Then you tell the dude at the marina to haul it out. It's really not that hard. I am pretty much exactly a one-half decent sailor, and performed said maneuver last weekend in a boat I'd never sailed before. Coincidentally, I was about about one-half drunk at the time.
Crux, here's your plan: Get a couple of bros to help you out. Tell them it should take a couple days but might take four. Check the weather report before you go. Stay out of the shipping lanes. Double-check that anchor. Then go.
There's a good chance something will happen that will be a pain in the ass at the time, and a good story later. It's almost sure to be a lot of fun. Almost no chance you'll make the Darwin list. Sorry.