Closest I've been is Miami
I have been to Key West. There are areas of Miami that might as well be a part Cuba.
True, that!!
I've been to Jamaica, Puerto Rico, Haiti, Dominicam Republic, Turks and Caicos, several other ex-British colonies on tour, but I think that Miami is just about as close.
It's like Cubans don't exactly jump in boats and purposefully row to the other isles as much as they do Florida.