It all begs the question of "Why?"
How many people do you know that have been to Cuba? For me the attraction is less about the sailing race and more about experiencing the culture of a place that very few people in the US have ever seen. Once Cuba becomes an approved travel destination for US travelors, much of the Cuban culture will be changed forever, it will be paved over by big US hotel chains and developers. I'd like to see Cuba before that happens.
Add in a relatively short distance race (its not 500miles), and it gets even more compelling.