It depends... if you took some solid sailing courses, you could probably get there in a few months. But you really need to learn a lot to go cruising effectively—fiberglass skills, mechanical skills, plumbing skills, etc., are all really necessary to have to go long-term cruising. The better you know the boat and the more you can repair on it, the better off you'll be.
A good foundation to build your cruising skills on would include the ASA 101, 103, 104, 105 and 106 courses.
It would help if you had a boat after taking the courses so you could practice what you learn in them...
You might want to read Donna Lange's story
, as she went from being a novice to circumnavigating in a relatively short period of time.
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You know what the first rule of sailing is? ...Love. You can learn all the math in the 'verse, but you take
a boat to the sea you don't love, she'll shake you off just as sure as the turning of the worlds. Love keeps
her going when she oughta fall down, tells you she's hurting 'fore she keens. Makes her a home.
—Cpt. Mal Reynolds, Serenity (edited)
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Still—DON'T READ THAT POST AGAIN.