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
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
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.