We were in Cuba a couple of years ago and found it a wonderful place to sail.
Few of the magizine articles that I have read regarding cruising in Cuba have been accurate or even handed regarding dealing with the officials in Cuba. I was amazed that the Cuban officials were so polite and considerate, given the efforts that our government to ruin their economy. Obey their regulations regarding taking photos of military subjects, etc and keep in mind that they live in a virtual state of siege. They aren''t being paranoid. Our government has sent agents into their country many times to disrupt and sabotoge their economy.
The people there were great. The food and rum excellant. (You will never be satisfied with Baccardi again!) Walking thru Havana one afternoon, we steered around a group of men engaged in a violent discussion in a public park. Fearing that there might be trouble, but curious, we discreetly inquired what was the problem. It turned out to be an argument about American baseball! We felt safer there than in our own hometown. It is quite unlike typical third world countries. Everyone has a job, a place to live, food to eat and an education. Their resorces are scarce, but evenly distributed. The historical district in Havana is crumbling. Heartbeating. But investors from other countries are moving in. While the US is frozen out, our "allies" are developing tourist attractions right next door to us.
It''s a fantastic sailing destination. You will have a great time.