Looks like I may have been corrected within this thread and it's pretty easy if you just only use cash and semi lie. If I were American I dunno if I'd fuck with it to be a tourist. If you don't have any contacts in a place you're visiting who live there, you're never really seeing the place. You'll be spending your tourist dollars well, better to give your money to Cuba than most places, though I'm pretty sure American money won't really get you anywhere, this is from people I know going in the past. Canadian money is very readily accepted, or was, most of my Intel is pretty old.

One of my friends went while he was homeless, it was around Christmas so he made like a grand in a couple days (dude is amazing at panhandling) and since he was trying to get clean off heroin, he looked into other ways to spend the money and just prior to 9/11 he spent about $600 on the round trip flight and $400 to stay at a resort. He couldn't be a recovering addicted and homeless with $1000 so that was his move. Cuba is a super super common vacation place for Canadians, I don't know if I've ever met someone who's done the typical Carribean vacation thing anywhere else. Mostly cause it's cheap as hell.