Florida is a very bad place to start from to go to the Caribbean. It is something like 600 miles downwind from the Virgins. The current
is also against you. I would be surprised if you could carry enough fuel
on a sailboat that size to make it in any kind of a reasonable time frame. Better to sail offshore and get there in one shot.
I just did this in a 33 foot boat - and was the smallest boat in the Carib 1500 fleet. Sure, it can be a bit rough, but it was rough for the larger boats too and some of them bailed when we didnt. If I do it again, I might go to Bermuda earlier in the season and then head south from there in November to avoid the colder weather
on the US coast - But if you leave from the CHesapeake on a favorable forecast
you will be across the Gulf Stream
and in warmer water by 24-36 hours after you start so it is doable.
Coming back was an easy downwind sail from st. maarten to the the Abacos - took about a week - and then four days from there to Beaufort
. The weather was better and the current
is with you and the wind
steady and reliable at least until the trade
winds die somewhere in the middle of the Bahamas.
you will see that virtually all of the boats in the carib 1500 are big. but we saw quite a few smaller boats - many europeans - down in the islands