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?