Re: Will USCG fly over Cuba airspace?
When I was stationed at Guantanamo Bay in the 90's, we had a bad plane crash where the surviving member of the flight crew (civilian flight - it was mail if i recall) had to be flown immediately to the burn unit in Miami. At that time, Wash DC had to request permission from Cuba to allow the medical airlift to fly over Cuba in a direct route to Miami. Those kinds of things happened from time to time, and each time a request had to be made.
I don't know how it goes today, but at that time all flights to / from Gitmo had to fly around with the exception of the emergency requests I mentioned. The Coasties there were not allowed to violate Cuban airspace, either.
That was twenty years ago. I have no idea what the regs are these days.