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Assuming you are speaking of a sailing yacht:
Do you have sailing experience? If not I would recommend you get some. You can charter a sailboat with a captain aboard and/or you can take sailing classes on a boat of similar size.
Have you read any books on living the cruising lifestyle? If not I would recommend you do so. A good one is After 50,000 Miles by Hal Roth. With these two accomplishments in hand you will have answered all your questions and many many more that you have not thought of yet. Get reading and you will either get hooked or run for the hills.
 

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If you plan on leaving a boat in the Caribbean during the months away from her, you might want to check out the used boats for sale in the Virgin Islands. They are cheaper than the US. Typically what happens to the owners is, they buy their boat in the US and start their new sailing lifestyle sailing against the trade winds, island hopping down the Caribbean island chain. After getting beat up by sailing into the trade winds and into the waves generated by them, they decide it is not a lifestyle suited to them. So upon reaching the Virgin Islands they put their boat up for sale, leave it at the marina, and fly back to the US. Boat storage and maintenance in the Virgin Islands is quite expensive for someone who has lost their desire for sailing and are more than ready to sell their boat.
 
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