Not as short a flight as you think. I did that flight from Miami, and it is several hours in a CASA. Reason is you can’t enter Cuba’s airspace.
Kind of a bummer.
An “Aviocar” CASA or a C295 CASA (twin engine transport, c130-like)— both Spanish made?
Guess it would take a while— prop flight, out over Great Inaqua then around the end of Cuba (East) then up to Gitmo airfield.
It was a different era in the 60’s (obviously)— friend said they could see Russian freighters come in drafting high and then leaving weighted to the gunnels. Barter— no cash. And a show with Cousteau’s son interviewing Fidel— he opened a drawer full of US treasury checks for annual rent of Gitmo, honored since the Spanish American war victory over Spain for a “free” Cuba. Such a shame how it ended up.