Years ago my wife and I visited Cuba. As a Canadian it was perfectly kosher, although I met several Americans there pretending to be Canadians as well. I bought a box of cigars from a guy on the beach (40 cigars, I think), brought them home and passed them around at my club. I was a popular guy that day! (No problem getting them through customs.)
Years ago I visited Cuba and brought back a box of cigars. I forget what I paid for them, but it wasn’t much. I sold them to a friend for 4 times what I paid and he still got a bargain.