If you go to Cuba, remember that there are no facilities as we consider a "marina"--even at Hemmingway. Look at the experience of the recent "international" fishing tournament. Power available sporadically, and voltage often very low. At that time severe restrictions about going anywhere without permission. Water questionable quality, and again not always available. Not a fancy "yacht club"…
My concern would be the size of our boats--I would be much more likely to go in a larger boat--which is fully self contained--and were I would not need any shore side support. (Saying this after having spent 3 1/2 weeks, totally independent on Lake Powell, except fresh waterl…--but not a privacy, or security issue there--as there might be in Cuba.) I have a number of friends who have cruised Cuba (some illegally). They had issues with the bureaucracy, time of check in and check out. If I was to cruise Cuba, I would prefer the more remote South Coast. (We had planned this in 1996, just before the two US light planes were shot down after dropping leaflets. After this incident, we were concerned about how we would be accepted. As it turns out, it would have been OK. (we met several US boats who were there at that time, and no problems).
Hopefully things will sort out eventually.