Depends... a friend of mine buys a box of Cohiba lanceros every three months and drives them right on into the US, he never really gets inspected... if you want to CYA, remove any indicators they are cuban, the labels, the box, etc. Just stick them in a plastic bag if need be, there's no real way to prove it beyond that.
I'm debating smoking my Opus X or a Cuban tonight... decisions, decisions.