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· Master Mariner
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I would suggest you offer yourself up as free delivery crew (not captain) on cruising boats doing crossings or whatever. This will give you a number of cruising designs to sample w/o spending your own money and a chance to learn from those who are actually cruising. Whatever your skill level from schooling, the practical will be an eye opener and a variety of captains will hopefully broaden your knowledge, as there are as many ways to skin a cat as... you get the idea.
 
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