For the few Americans I know that have illegally been to Cuba (as recently as last year), there is a subtle, but obvious threat that you'll get a stamp if you don't offer up a bribe. The fines imposed by the US Governenment for illegally visiting cuba are very steep.
I understand that this may be different for Canadians, as we're all aware, it isn't illegal for Canadians to visit Cuba.
I've never been, so this is second hand.