Hi there,
You have to approach this situation from two sides - the Cuban “government” side and the U.S. government side.
CUBAN GOVERNMENT
If your father left Cuba prior to January 1, 1959, he will have no problem returning on a U.S. passport. There’s no issue there whatsoever. Might as well be travelling to Jamaica.
Now, if your father left after 1/1/‘59 he’ll need to obtain a Cuban passport - -as his U.S. passport and citizenship will not be honored. This does not mean they’re going to kidnap him and conscript him into the military or anything silly like that. It’s merely a power-play on the part of the Cuban government. Totally hollow.
I’ve heard from some folks that if you left after 1970, you need the Cuban passport - but before ‘70 it is not necessary - conflicts with what I listed above, I know. In my aunt’s case, this was not true. She left in 1961 and when we were getting her paperwork together for a trip in 2003, she was obliged to get a Cuban passport. This could be because her last name tripped an alarm bell and they simply wanted to give her a hard time, however (our family is very well know in Cuba).
Just call the Cuban Interests Section in Washington, DC (you can google them). They’ll be able to assist you with this.
As for you, again, there should be no problems. If your dad left pre-‘59 it’s a breeze. If he left after ‘59, the folks in customs (Havana) might give you this silly speech on how you are a duel Cuban/U.S. citizen since your father is still considered a Cuban citizen, blah, blah, blah but again, it’s all hollow nonsense meant to simply intimidate you and, to be honest, I think they’ve stopped using a lot of these intimidation tactics in Racho Boyeros (the airport) in the last two years. I only say this because I have not had the problem at all during my last two visits.
U.S. GOVERNMENT
It’s simple, to travel to Cuba (under current Bush laws) legally, you need to have either a parent, child or sibling on the island. Other family is not considered “family,“as George Bush, in an incredible scientific breakthrough, actually altered the human genome.
So, you’ll have to go through a third country like the Bahamas or Mexico. If you go this route, make sure you buy your ticket from, say, Mexico to Havana - in cash in Mexico. you don’t want a paper trail. And for god’s sake, don’t bring ANYTHING back that says you’ve been to Cuba. Cuban customs will not stamp American passports by the way.
I’ve never had to travel illegally to visit family as, I am also a journalist and fall under the general license provision meaning I simply sign an affidavit, send it to the OFAC office in DC and just buy a ticket from Miami.
If I can give you any more advice, just let me know.
Cheers, and good luck.
Anatasio