The nice thing about the eastward route is that you can leisurely island hop, waiting for appropriate weather
windows as you go. If you want to do it as a passage
instead of a cruise
, then RayLChase's eastward route is still the most desireable.
The only reason to instead go west and south would be because you want to cruise
the Central American islands. The passage
from Panama would be a long slog of well over 1000 miles; you might get the benefit of some southeast winds; but mostly you would be bashing close to the easterly trades or even northeasterlies which in winter are quite strong.