Sailing to Cuba...need advice on Government and expenses
Jim, you are asking a question with a highly variable, complex answer since, in one broad sweep, you are inquiring about the practices which exist in a mix of island nations at a diverse number of ports, islands and remote areas. If you really want a good explanation of the wx pattersn, where anchorages exist, clearance fees & practices info, etc., your best source of info without a doubt is Passages South by Bruce VanSant, now in it''s 7th or 8th edition I believe. It is excellent.
WRT Cuba, if you and/or your boat is from the U.S. this simply isn''t a good time to consider visiting there, altho'' this has been done many, many times by boats leaving from S Florida over the last few decades (when the Treasury Dept. didn''t have Dubya poking it in the ribs about enforcing the Trading with the Enemy Act).
Another alternative is to arrive in Cuba from a 3rd country (e.g. Belize or Mexico, after visiting there) and departing for yet another 3rd country (typically the Bahamas).
For this area, with sustained reinforced tradewinds and any to/from route including some sailing to weather and against wind-driven current and lots of wave action, a boat your size would need to think very carefully about which seasons offer less opposition from weather (usually late spring thru early fall), how you''ll deal with the inevitable storms during that part of the year, and you''ll need a stoutly rigged, well equipped boat (good anchoring systems, most especially).