There are a lot of strange replies and stuff in the above posts along with some very good answers - you need to do more
research. As to the reality in the
Caribbean, as mentioned by some only the "Territorial/Outlying" islands of
France and maybe the U.K. are sticky about have Federal "level"
documentation. Most of the independent little countries are not very strict about it although you will have a much easier time with USCG
documentation.
- - There are a huge amount of small powerboats and older sailboats that are purchased in
Florida and other
east coast States by people from the little island countries and then brought down to the islands without anything more than the last State
registration. These little countries do not even look to see if the vessel is has a
current registration (especially if a little
money is passed before checking in as a "service incentive"). There are thousands of expired US/State registered boats in the islands that are not even "registered" with the
government of the island.
- - But as others said you will need a
current passport for yourself. For the boat you just say you are taking it to the island of "XX" - somewhere beyond where you are. All of this is possible because there is very, very little actual examination/checking of what you put on the "entry" form for the island.
- - From the US
east coast you will have no problems going to
Bahamas with a State registration and then you can go to the
Turks and Caicos and re-register the boat there. Or even work your way to the BVI although you have to pass by
Puerto Rico and the USCG and there is a good chance you will be intercepted for "inspection" which would be embarassing if not a major problem.