There are tons of boats that are delivered from the U.S. to the Caribbean, or back from the Caribbean, or to other far away places. To get them around, each boat needs crew, or hands, to do the sailing. Commonly the boat owner will pay your airfare, and meals on board the boat (housing - sleeping aboard is included too), but you pay all other expenses - booze, cabs, etc. And you get to sail a lot!
Here's my story of sailing from Bermuda to St. Thomas, VI over Thanksgiving on a 63' wooden Herreshoff "Fish Hawk", built in 1930 for the Governor of Maine at the time -
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