As long as your visit is a "cultural exchange" or a visit to relatives and not a vacation, you can get permission to go.
http://news.yahoo.com/s/a...a/cb_cuba_more_americans
 Clinton allowed visits, Bush stopped them and now Obama is allowing them again.
All I know is that my Cuban friends have told me that unless you are visiting family, stay away from Cuba. They've told me that the Cuban government does their best to make things look good for tourists, having nice hotels and medical care. But any money tourists bring into the country never makes it into the hands of the citizens but gets taken by the government. My one friend told me that her sister in Cuba was a tour guide and at the end of her tours she was tipped by tourists. As soon as the tourists were gone, a government official would come to her and take any money she had on her person. Her sister developed the trick of having a nephew brush past her in the crowd and pass some of her tip money to him to sneak home.
 So, in my opinion, there are other tropical islands to visit, just as poor as Cuba, that at least your tourist money might make a difference to the locals.
Ida