This depends on the sailboat...
165 weight is nothing to sailboat rigging.
if you only need to get up 14 feet how about tying it to the pier and using a halyard to pull the boat over so the mast is over the pier. then you can use a normal step ladder on the pier, by the time its over far enough you might only need an 8 foot ladder
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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.