The Bahamas-Windward Passage-Jamaica is not a bad option. That's how I came to the NW Carib in 2004-2005. Conditions can get pretty sporty in the Windward Passage
(WP) so chose your window carefully. When we came through, systemic winds were about 25 knots or so between the Bahamas
(Acklins) and the approach to the WP. In the WP it amped up to a good steady 35 knots with 8-12 foot seas. But it was all from NW so it was a fun ride (if you like that sort of thing -- which I do).
I think the route selection depends on how much you want to really "cruise" and how much you want to get there. You could just run straight from Jamaica to Panama at that point or do a more "cruiser-ly" route.
In our case, from Jamaica we went to Bay Islands Honduras
and then about a 5 year detour to Belize
. This year finally made it "around the corner" to Panama. If getting to Panama is your objective then I might skip the Bay Islands, because the stretch from Bay Islands "around the corner" to Providencia, Colombia
(a common cruisers stop on this route) can be a challenge (against normal prevailing winds). You could just run straight from Jamaica to Providencia and take a break there (great place). From Providencia it is all down wind or no wind to Panama. Once you get south of about 11N then you will probably have little or no wind depending upon the location of the ITCZ at the time. We spent several weeks cruising the Bocas del Toro area this season and never had enough wind long enough to justify raising sails
Note that late October you are still technically in hurricane
season and Nov - Feb (at least) you can still get strong cold fronts pushing down as for as the NW Caribbean
. This year, we did not leave Guatemala
until April because the cold front season was so active so late into the season.