Originally Posted by
SJOGuy
Dual citizenship does not make you two different people. As long as you have a U.S. passport, you are a U.S. citizen and are bound by all U.S. laws governing travel to Cuba. As VNP says, you'll have to have everything in order as a U.S. citizen to be able to book and board your flight to Cuba.
Not exactly. Speaking in practical terms, if he went through Mexico City, for example, he wouldn't need to fill out the form and could use a cheaper green tourist card/visa, and either passport. He could also buy insurance once he landed, if he were asked if he had it (which is apparently not always happening).
And the US government has not been interested in checking up on anyone for quite some time, according to those who travel there regularly.