Here is somebody's story who took his twin Bonanza from the US to Cuba and back.
How To Fly To Cuba - Plane & Pilot Magazine
Some more info:
https://generalaviationnews.com/2016...i-fly-to-cuba/
I somewhere read all general aviation in Cuba is military. However the state travel agency gaviota seems to be military owned as well. Maybe you can get some dual or aerobatic instruction for hard currency?
Last edited by Less Hair; 26th Feb 2018 at 12:35.