Originally Posted by skofarrell
"average" Americans are not allowed entry. The embargo is economic, you simply aren't allowed to spend money there. Makes a holiday somewhat difficult. There was a US company that exploited a loophole by parking a cruise ship in Int'l waters, shuttling visitors in and out for the day. The US government shut it down.
Flying in thru Canada or Mexico is possible. A $20 tucked in the passport will prevent it from being stamped.
I have been to Cuba a few times. As a Canadian they don't stamp your passport. It used to be that you could pay $25 for them not to stamp your passport. Now you just pay $25 CUC when you depart. Maybe they treat American passports differently - this is my experience with a Canadian passport.