A good rigging knife or pocket multi-tool, a good whistle, a good water-resistant or water-proof flashlight... a good PFD with harness, are all things that I think every sailor should have. A handheld GPS is a nice toy to have. A water-resistant digital camera is too.
You might want to get David Seidman's The Complete Sailor, if you haven't sailed much or at all. It is very easy to read and covers a lot of material.
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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.