Legal Travel to Cuba for Americans
Coming up on the 11th of January, I will be going with an Arts & Culture Delegation to Cuba through the organization, Witness for Peace.
I have asked for a new DSLR camera for Christmas/My Birthday (it is the 29th, unfortunately) and will be posting some great pictures from Cuba!
The first link above has a lot of information on how you can take a similar trip to Cuba as an American citizen without having to fly through another country and asking them not to stamp your passport.