If you were tasked with taking a boat say Sunseeker 68, Leopard 24 or the like from the Gulf Coast would you jump off from Southern Lousiana or go Key West via Cuba? The straight line distance is about 500 NM, long range cruise on any of these is 8-11Kts The current from the west is more favorable but it is open ocean in all directions? Either route is well within range with internal fuel.
I've done the trip MANY times from Key West to Cancun/Isla. I'd most likely leave from Louissiana but it would have to be a GOOD weather window. You're talking 500NM versus 350NM from Key West, but takes thousands of miles to get to Key West from LA.