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Re: Will USCG fly over Cuba airspace?
dawg, oddly enough the DOS OFAC guide says that you don't need specific permission to visit a close relative (3 generations) who is a Cuban national. Doesn't say a word about dead or alive so "I'm going to visit my grandfather, I've never met him" might actually be all you need to say.
Could be worth looking into, because visiting family gravesites isn't on the slim list of allowed reasons, but the rules don't say anything about the relatives having to be living.