This begs the question as to how the Congressional Black Caucus was permitted to visit Cuba earlier this year to hobnob with Castro and friends. The guess here is that the travel restriction doesn't apply if you're a black congressional Democrat!
Isn’t Congresswoman Maximum Waters supporting a wanted cop killer in Cuba? There was a letter posted here a couple of years ago. She wrote to Castro asking him not to extradite.
In the halycon (or was it “Hellspawned”?) 1970s, Americans traveled to Cuba via third countries (usually Mexico); the Cubans processing their arrival would stamp a separate slip of paper (showing they’d been processed in and were in the country legally) and paperclip it to their passports, so the visitors could avoid trouble when they got back to the US customs. Unless someone there found the cigars of course. ;’)