One of the first places to go to for planning your route
is the "Pilot Charts" - in this case for the N.Atlantic, November, page 3 (Caribbean/Gulf of Mexico).
- - The historical trend is for predominant NE Winds during this period of time. From Colon planning to head
NNW towards St Andres and Providencia should give you a hard beat but doable when motor-sailing. You will also be getting assistance from the current
(green arrows) until you are WSW of Jamaica. Depending upon the real life wind conditions you might be able to pinch some and gain some easting. If not falling off a hair still gets you north.
- - Then the tough part (magenta line) is turning east to pass below Jamaica - as the shortest route
- and motor-sailing to the south coast of the D.R. and on to Puerto Rico
. The basic idea is to stay away from the "red circle" region between Jamaica and Columbia
- - Plan "B" (black line) would be to continue NNW toward the Caymans and then turn ESE to run the north coast of Jamaica and onto the D.R. and P.R. Some like this route as there are places to stop and also to try to take advantage of any "Lee-effect" that Jamaica might offer.