Originally Posted by
KARFA
I would not suggest this is a way around it. Airlines provide information to the US CBP even on itineraries which do not touch the US. Basically the US will know you went to Cuba whether you like it or not, they are not relying on searching for stamps in your passport.
Originally Posted by
Swanhunter
The Cubans do this, but given the hostility with which CBP greet aliens I would not chance it. A denial of entry would be a monumental annoyance.
I'n not suggesting anyone try this, simply adding data points. Though if US citizens are frequently flying to Cuba, not sure who much information is being read by CBP.
Added data point, I have Cuban, Turkish, Egyptian stamps in my passport and frequently travel to/through the US both land & air and have never had any issues. Perhaps it's because I am enrolled in the Nexus programme, but I think Fears of Cuba travel are slightly overblown. But I understand those who do not want to poke the bear.