A lot of people have forgotten about this, but you could once drive to Cuba. Catch the ferry in Key West and disembark in La Habana.
Al, John Huston, and I used to drive down regularly. Huston had this wino buddy, Ernie, who was always bumming rides and booze. He smelled just like that pack of six toed cats that was always following him around. We tried to make him ride in the back with Al's pet goat, but the goat wanted nothing to do with him. We usually ended up tying him to the roof.