You can circumnavigate Cuba now without help from the Obama administration. I recommend visiting Guantanamo Bay. It's beautiful this time of year and it's inhabitants are some of the finest people you'll meet anywhere.
I'd avoid the northern coast as much as possible given the large amount of unlit small boat traffic you can encounter there. The operators of these boats are, for some reason, never very experienced in seamanship. They're friendly enough but you should avoid them as they're a navigational hazard as well as somewhat obtuse. For instance, if you were to invite one on board, by way of helping him out with his leaking boat, you might find you have trouble getting him to leave your boat. if you sail towards the Florida Keys and tow his boat behind you, he'll tend to calm down and prove quite helpful about the boat. Usually they'll be willing to get back into their own boat when in sight of US land. You can spend quite an enjoyable summer sailing back and forth with these people if you so desire.
I hope this has been of help in your planning.
“Scientists are people who build the Brooklyn Bridge and then buy it.”
Wm. F. Buckley, Jr.