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I think the rule is that you are not allowed to fly directly from the US to there. You can fly into cuba from any other country, just not the US. So for example, take a plane to Mexico, and then take another plane from Mex to cuba.
well if you are american it wouldn't be a good idea to fly to canada to get to cuba because your entrance and exit would be in the same day and that would raise questions.
mexicans don't stamp american passports so you don't have to worry.