Best to buy a fairly well equipped boat in the Caribbean. They are usually fairly widely available, from people who have crossed to the Caribbean and decided that they weren't up to sailing anymore. The US Virgin Islands might be a good choice, since they're nominally part of the USA. Here is some info in their customs fees.
Articles imported into the U.S. Virgin Islands for use or resale in a trade or business are subject to an excise tax. Because the USVI is outside the U.S. customs zone, foreign (non-U.S.) made goods are also subject to a customs duty which is separate from the U.S. customs duty. The rate of excise tax on most goods is 4%, while the rate on certain products, such as cigarettes, is higher. Alcoholic beverages are subject to a flat rate based on volume. Certain other goods are subject to a lower rate of excise tax, and most tourist items, such as jewelry, watches, crystal, artwork, electronic goods, and leather goods, are exempt entirely. Tourist items are also exempt from the 6% U.S. Virgin Islands customs duty.
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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.