We just traveled from Key West
to Santa Marta, Colombia. First of all - Cuba is SO in the way, isn't it? We decided that it didn't make sense to go west of Cuba - even though, from KW, we were already much further west than you are in Ft. Lauderdale. If you go west, then you will have to sail east once you get south of Cuba, beating into seas/winds that are commonly BIG.
Based on our experience:
We did our easting through the Bahamas and then went to Great Inagua. As President of the International Great Inagua Fan Club, I must ask you to disregard the comment to avoid Matthew Town.
We were in Great Inagua for 8 days. Click here
for the noonsite report. And here
for a blog post about our visit.
And here is a taste of what you might see in Great Inagua:
After an easy sail through the Windward Passage and a detour to the extraordinary Ile a Vache, Haiti
, we had winds and waves forward of the beam, both increasing as we approached Colombia (30-35 kn and 12-14 ft seas on the evening before we arrived in Santa Marta).