I don't think it makes much difference, but my preference would be to head
for the SE and NE Providence Channels through the Bahamas
to Fort Lauderdale. Less potential complications.
I made a passage
a year and a half ago from St Thomas, headed for the Moser Channel in order to pass through the Keys, then up to Tampa Bay. A weather
situation developed with a cold front approaching from the west and a tropical wave from the east, both planning to arrive just as we got to the narrowest part of the Old Bahama Channel between Cuba
and the Bahamas So we turned north for the open ocean and then went through the SE and NW Providence Channels. The nine hour Gulf Stream
crossing from Great Isaac Light to Hollywood, FL was pretty nice even with northerly winds at 15-18 kts. We were able to sail for the entire crossing.
Friends of ours made the passage
via the Old Bahama Channel several years ago. They were rather alarmed when a motor
vessel approached in the middle of the night, and hit them with a blinding spotlight. It turned out to be the Royal Bahamas Defense Force, who boarded them for an inspection
. I don't know if the Cubans do the same.