Originally Posted by
PLeblond
On this point. I know of a lot of US Citizens who travelled to Cuba by way of Canada, Mexico, Caribbean on separate tickets. Cuban immmigrations officials were 'nice' enough not to stamp their passports. In fact I once had to ask them to stamp my Canadian Passport. Haven't been to Cuba in a few years, so I'm not sure if they still extend this courtesy or if it extends to other countries.
The Cubans do this, but given the hostility with which CBP greet aliens I would not chance it. A denial of entry would be a monumental annoyance.