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.
Back to Grenada in early December. Not sure I will remember how to sail. Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.