Made the trip once in a 36'
Morgan. It was no picnic but doable, even in the
winter trades. We were actually going to the USVI so even more upwind
work than trying to make the Bahamas.
I assume your planned route would be through the Windward
Passage? If the easterly trades don't have too much northern component you could make the
Passage on a
single tack.
I would probably keep options open and go the way conditions dictate. Try for the Windward Passage with
Jamaica as a possible rest stop. If it gets too bad then yes,
head off to the
Yucatan and up the Keys. You still have a beat from the
Yucatan to FL but will have the
current with you.
I ended up making landfall about the border between
Haiti and the DR. The trades were running ENE-NE so I stayed close enough for the islands to blanket the trades and used the land/sea breezes and a lot of
motor sailing to make St Thomas.