I have seriously thought about this and was quoted about £7k each way for my 29-0 , which was less than I would probably need to spend on upgrades and gear to sail the Atlantic - yes I know there is the satisfaction of having "done it singlehanded" but a season in the Caribbean for the price of an expensive 3 week family holiday? hmmm, sounds pretty good.
Actually, as another option, has anyone ever bought a £14k boat over there for a season then sold it?
You could perhaps buy a boat like this - 36' Gulfstar 36 - BVI Yacht Sales
And then sell her on after a year or two, and the depreciation during that time should be a lot less than GBP 14k.