Re: Cruising Caribbean Single-handed
Sailing the eastern Caribbean alone is pretty easy, but if I were you (I did single hand this boat until I met my girlfriend) I would take at least one crew for any passage from the US to the Carib unless you leave Key West for Cuba, 90 miles, as the ocean passages are long and very tiring.
The north side of all the islands east of Cuba is a terrible and hard windward sail. Better to come into the Virgins, though there are a few who do the south coasts of those islands in tiny hops and love the trip.
Virgins to St. Martin is directly into the trades with a lot of current going north. After St. Martin, as stated above you can day sail to Grenada or Trinidad, but it not running, rather close reaching or beating unless you have a really fortunate weather window.
To give you some idea of the realities of eastern Carib sailing; almost everyone here sails with at least one reef (every day) in the main and more in the Christmas winds. Every channel funnels the wind and changes it's direction so that we seem to be beating more often than not, but the seas are manageable for a boat 40+ feet and more on the beam. Don't forget a good dodger and bimini; real comfort necessities down here.
We love the in mast furling for the main; it gives an infinite variety of sail sizes and does not require someone feeding the sail onto the mast track as I believe in boom furling does.
Good luck and I hope we can raise a few together when you get here.