I'm only going on second hand info, but the descriptions of cruisers who have headed west south west from
Florida have suggested that it's a rough old
passage, hard on the boat and hard on the crew.
An old, small,
cheap boat is not going to have a good time of it.
Would it be possible to start from the western end of the
Caribbean and sail back to
Florida, maybe even drifting all the way up to
Canada if the weather Gods are willing.
To me the question that you need to ask is can I find a suitable boat in the Western Caribbean?