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Welcome to Cuba!
The regulations are in such a flux, the embargo is on the paper but nearly 200 000 americans came to Cuba last year as tourists.
From the point of USA, individual travellers can now travel to cuba for "cultural reasons", that could be anything from learning from cuban bartenders to see management of marina hemingway where you may berth your boat in La habana. So no problem there.
Waiting for Cuban government to change their rules for most foreign visitors (except some like canadians) where the visa is issued for one month and renewable for another month. Many foreigners overcome this by going for a day trip to nassau or cancun, but you could just sail out for a day and come back the next.
As I mentioned, things are changing at a fast pace that no one can be sure what is happening but the only thing I can tell you is that Things are much better for ALL cubans since Obama opened the relationship.
I just arrived in Miami from London and will be going back to Havana soon, if I can be of help please let me know
You have a spanish sounding surname, it would be SO MUCH better if you can speak Spanish, in Cuba

Yes, you can sail to the water of Cuba and visit the Island but for what I have read and seen in YouTube sailors doing that wonderful trip have to ask for documents required to enter by water plus when you get to the Cuban water you will be hours before you can park your boat and enjoy the beauty of the Island because everything is still done by hand writing and not yet updated like in other places. Check out in YouTube for (going to Cuba) look for a man getting his hair trim or shaved video, he did the trip and I believe it was his second time.
I will look it up for you, I will write again but with the Infor.

Good Luck, great experience you will get.
Ely from AmericaninCuba.WordPress.com