Does Cuba allow American planes to fly over its airspace on the way to Jamaica or the Caymans?

Definitely. I fly over Havana countless times. There is a certain service ceiling that Cuba would not allow American carriers to fly below. I believe that no. is 15000ft.

Yes. They encourage it actually & try to shoot us down to steal our pre-packaged peanuts & life rafts.

Good luck!!

Yep

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