I was a navigator on a Coast Guard C130 and Cuba is very protective of their airspace. Violating it will be a MIG photo op!
The way the runways in Guantanamo were setup required a really tight turn in order to stay on the US side. It was amazing to see the Airforce Galaxy make this turn and quickly land. Even on a C130, it was entertaining at times.
One of our pilots suffered an eye injury from a Cuban laser when landing. Ended his career.
Cuba is beautiful, the government is bad and the people suffer terribly - it's sad. Not that this bothers anyone outside the US that takes advantage of cheap vacations to be had. BTW, the money skips over the "regular" Cubans and is directed to the Communist Party elitists. Even in poor countries there are wealthy people. The wealthy are picked by the elite ruling class in Cuba, you can't earn your wealth.