I flew in and out of Guantanamo a few times. Usually we landed straight in with a tailwind and took off the other way.
A DC-8 tried to approach and land into the wind but had to make tight turns downwind to base to final, then stalled
and crashed. (This is all from memory 27 years ago, but at the time the distance to Cuban airspace was only 3 NM or so, hence
the tight turns)
The airspace may have changed but we had special procedures and frequencies to get in there, can't post
it here as none of it was on any public charts.
I flew civilian planes on contract to the DOD, B-747-200 pax.