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Old 08-21-2013
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Re: how much experience do I need

A reasonable plan would be to sign up for an ASA 101-103 course or equivalent. Then a few seasons of sailing on other people's boats - ideally with some more experienced sailors. Then if that isn't enough sailing for you, buy a boat, something you can handle with your usual number of crew. Sail her for a year and then if this plan is still appealing to you (as others have pointed out, this isn't a particularly fun route), go.

Sailing, even day-sailing, is a ton of fun. Take some classes, join a sailing club, rent boats for day sails - gaining sailing experience is fun. There's no need to skip over this part - enjoy it!

E.
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