The Caribbean has 28 islands, of which 13 are official UN countries. I had a good chance to go to the Bahamas when I was in Florida, but didn’t take it and so at time of writing in August 2013 I’ve only been to Cuba so far. The main problem with the Caribbean for a cycle tourist is the challenge of bouncing from one island to the next. Other than from Haiti to the Dominican Republic there’s no land border crossings so it’s all about either flying, very expensive, or finding boats, all about good luck and connections.
My idea for the Caribbean is after my time in South America to end up in Venezuela and hop over to Trinidad & Tobago on the official ferry. From there I’m going to try my best to find rides to take me the whole way through the chain with a few weeks in each country to get a glimpse. If I play it right, that’ll take me back to Florida, where it’s not only easy to hop over to the Bahamas, but I also figure I should be able to get some form of cheap transport across the Atlantic to either Africa or Europe.