The answer Walter, is yes...downwind... but you want to go to windward.
Lowcountry has it right.
Going east, north or south of Cuba is all into wind
, and the Windward Passage
can get exciting.
I did Panama to Grand Cayman going north in November...basically the same trip as Jamaica
to Panama going the other way.
That would be a very hard trip in a boat with an outboard
if the winds were not friendly and there are some very nasty shallow areas en-route that can get very ugly.
I sailed a light F31 tri with a 15hp outboard
for 6,000 miles, but it would have disintegrated going the route