I haven't done this trip, but know the reputation of the trip to windward from the Canal eastward to Columbia
, and then NE from there - and would not look forward to it. One possible alternative to look into might be to head
north first, and cross to whatever point on the south coast of the Greater Antilles islands you can lay on a closehauled (but reasonably fast and not too uncomfortable or gear-busting) course; and then work your way along the south coasts of those islands.
Others might weigh in on where might be a reasonable landfall to expect; possibly no better than Jamaica, but if winds are more E than NE and your boat sails reasonably weatherly, hopefully S coast of Hispaniola - Haiti
or even the DR. From there the rest of the way E is upwind, but much more sheltered if you hug the coast, where you motor-sail in night-time calms and sometimes even reach in offshore
katabatic winds caused by the mountainous terrain and diurnal heating/cooling cycles. You may also get lucky with some fronts that will cycle the winds around to S-SW-W-NE-N before coming back into the NE-E. We made that passage along the S coasts of Hispaniola and PR to Ponce last winter, after transiting the Windward Passage coming S from the Bahamas
- and it was a relatively fast and easy passage.
This would be a significantly longer distance, but very often - especially in a sailing vessel - the shortest distance between two points is NOT a straight line!
If you do consider this, I would encourage you to take a look at Frank Virgintino's "Thinking Man's Guide to Voyaging South", and send him an email
to get his opinion and further suggestions. He has decades of Caribbean
experience and was quite helpful in planning our trip.