Re: annual cost of crusing Carib 2012?
As was pointed out, it can vary enormously. We did it for about $1500 a month a few years ago on a 45' with full boat insurance and no health insurance (we are Canadians and paid as we go in the Caribbean and could fly home for major things. A lot depends on what you are after in terms of lifestyle - do you want expensive restaurants, visits to marinas (there aren't that many in any case). Can you do your own repairs of most things.
One good thing is that you have a large amount of capital if you need it - for example if you needed a major engine repair or a new piece of gear. Many folks have a monthly budget that is adequate but nothing in reserve and that would worry me.
Finished the circumnavigation in early February in Grenada. Have to work on a book project for the next several months so the boat will be waiting for next year.