Your heart is good and your goal is admirable but you are one person. Tourists going to Cuba aren't flying down there to go on a humanitarian mission, they're there to soak up the sun. Most of them are from Europe. The Cuban people do have interaction with them, prostitution is one way many Cubans support themselves. Do you really think Castro would allow a FReep on his island? There is no dealing with a tyrant. The Cuban people know what they don't have.
Sorry I didn't make myself clear. When I said an "informal" freeper trip, I meant a non-freeping trip made up of good hearted conservatives meeting people and just chatting with them about America and it's values. As you know, I did that a couple of years ago with 3 friends, and it was simply amazing what we learned from our new Cuban friends and what they learned from us. We still correspond with them, they cling to their friendship with us as it gives them "courage to go on." Meaning, the courage to live their grim lives and wait as long as it takes for Castro to die and their beautiful country to be free. Yes, most tourists want to soak up the sun (I soaked up plenty), but many get absolutely enthralled with life there and interact as much as possible with people on the street, not just those serving them in hotels.