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