Rum Runner
 

Back before - way before - the U.S. embargo of Cuba, my father, a Commander in the United States Naval Reserve, was instrumental in the quasi-legal if somewhat surreptitious importation of Cuban rum. His choice of transport was the venerable DC-3; in Naval nomenclature, an R4D-2. The craft flew VIP's - Admirals and their (lady) companions - regularly between Miami and Havana. These sturdy craft had a fuel capacity of 822 gallons U.S. Dad greased the proper palms of the appropriate authorities and arranged to have the starboard wing tank filled with 400 gallons of high-proof rum. After a number of successful and highly profitable forays, Dad decided to go along on a flight to enjoy the bountiful beauty of that then-unspoiled Caribbean paradise. And he did... :)

Two days later he boarded the "Pack Rat" to fly back to Miami. He noticed a line boy mounting the starboard wing, laboring under the weight of the shoulder-slung fuel hose. Suppressing a grand mal epileptiform seizure and an inexorable urge to follow through, Dad lept from his seat and ran out of the plane onto the apron. "STOP!", he screamed at the top of his lungs. Too late! The line boy, missing a number of teeth, smiled broadly. He chortled: "Señor Capitan! Ju weel be glad to know that I have topped off jour right tank! Eet was theerty gallons low!" Ron Rico plus 100 LL do not a fine drink make, orange slices and miniature umbrellas notwithstanding. And thus came to an inglorious end my beloved and clever father's career as a rum runner! :=

- Ed :}

Now that is the kind of stories I like!

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?