It depends on a lot of variables. The size of the boat is one major variable. The boat's ability to be self-sufficient is a second. A large boat with a water maker, solar panels and wind generator, may be able to stay out at anchor far longer than a boat without those abilities—making the costs of staying out lower in the long run. Staying in marinas will increase your costs quite a bit IMHO. A larger boat will have higher haulout and maintenance costs.
Also, where you're located in the Caribbean is going to affect your costs.
Without more information, I'd say it is almost impossible to give even a rough ballpark.
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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.