I'd point out that unless you're independently wealthy, hiring a captain to sail your boat from SFO to Hawaii is going to be a fairly expensive proposition, especially if you can find one that is willing to teach you along the way and take a new-to-you boat that may or may not be seaworthy for the voyage.
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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.