Re: how much experience do I need
FYI - here's an example of the kind of boat to be on the lookout for....good design, quality build, lots of example of this type of boat making the kind of trip you're contemplating. And a low enough asking price you should have the ability to make some repairs (and there will be some needed - there always are) and add some crusing gear and still be within your budget.
1980 CAL 2-27 Sail Boat For Sale - www.yachtworld.com
1981 Endeavour 32
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"At sea, I learned how little a person needs, not how much." Robin Lee Graham