I've always wondered if the best way to the Caribbean from Miami (my home) is to go north. Looking at the pilot charts for November on into the winter, it would appear that one would be much better off leaving from the northern portion of Florida...going East (sometimes Southeast when winds permit) and then south at 65*. In that one can jump into the stream here and ride north like being on a rocket with East, Southeast or a Southerly winds, I wonder if the trip might not only be easier but perhaps even faster.
Yeah, Don Street also speaks of a departure from Jacksonville/N Florida, as being a viable route, but he's speaking of having come down from the N, of course... Only downside to that one, with the Stream being so far offshore at that point, you've got to make sure you're across before the arrival of a front...
Personally, I wouldn't think it would really be worthwhile to go THAT
far north... Maybe from around Ft Pierce, perhaps? If anything, I think I might be inclined to simply ride the Stream N in the SW-W breeze that typically precedes a frontal passage, sticking close to the E wall, and ready to bail at the first hint that the front is here... If that got you over the top of the Abacos, at least, seems that would still give you a pretty decent sailing angle for the remainder of the trip...
You've certainly got the right boat for the trip, from my experience running a sister ship last fall, she goes very nicely to weather... IMHO, even if you're only able to fetch the Mona Passage, that's not too bad... I've heard very nice things about working your way E along the S coast of Puerto Rico in stages, sounds like some very nice cruising, with plentiful stops not too widely spaced, to be found along that route...