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.
In South Africa doing lots of boat stuff. Departure north from Cape Town around December 15th. Arrival in the Caribbean around the beginning of February, after 5300 miles or so.