The Gulf of Mexico
should take you south along the gulf coast
, though most of those waters are shallow close to shore. You might be better off staying a ways off of the Florida
The Florida and Loop Current
will take you east between Florida and Cuba
, however form there you'll bang into the gulf stream
and Antilles current which you'll fight all the way to Tortola.
From there you might want to look at 'The Thorny Path' and 'The Thornless Path'.