Join Date: Jun 2005
Location: New Orleans
Thanked 48 Times in 45 Posts
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I like your dream, but being a conservative type, if I were you I'd try some coastwise cruising before trying to cross any of the really big "ponds". Several sailing schools offer cruising classes, or you can charter a boat with skipper, who will teach you and let you do as much (or little) of the sailing as you want.
Plenty of "high seas" out there 30 miles offshore to learn on, before you go 2000 miles offshore, and it's just as authentic, it's just that the "safety net" is closer if you need it.