I understand your desire, and hope you don't take this the wrong way.
I'm probably one of the few folks around here who has first-hand, on-the-ground experience of living in Cuba. And yes, I'm a US passport holder.
First, you will drive yourself crazy trying to apply reason as an argument relating to the US-Cuba political relationship. It's a very emotional subject on both sides, and pragmatism rarely prevails in discussions. Just accept things that you cannot change, while keeping your hope alive that policies can and will change. (For the record, I'm not advocating radical change or full repeal of the current policies -- they will almost certainly evolve at their own pace.)
Second, don't take the glowing reviews of Cuba as a cruising Mecca at full face value. The people of Cuba are warm, friendly, and for the most part great folks. Yes the waters are beautiful. Scuba diving, particularly on the southern coast, is great. However, keep in mind that Cuba remains a very bureaucratic and fairly strictly regulated state particularly in regards to foreigners. Many of the vacation resorts catering to foreign tourists, which is a very important source of hard currency income for the government of Cuba, are closed "communities" that keep tourists in and locals (other that the staff) out. This is intentional. The Cuban government maintains its grip on power, but remains cognizant of what Glastnost did to the Soviet Union.
Third, maritime facilities are somewhat spartan and in less than tip-top condition. The Coast Guard and maritime Border Patrol organizations have in some instances proven themselves to be less than friendly, less than helpful, and in some instances complicit in screwing cruisers -- and avenues for seeking redress or compensation for an American are very, very limited.
Fourth, you run a very significant risk of losing your vessel if US authorities determine that you have violated US travel restrictions. Is your desire to visit Cuba so strong that you're willing to take that risk?
In the long run, my guess is that sanctions will ease and travel will become possible. Until that day comes, I for one wouldn't even consider going there.
Sorry to rain on your parade, but I hope you take this to heart.
Last edited by PorFin; 11-02-2010 at 09:02 AM.