I agree with this. The Cuban people desperately need to talk to us, one by one, and hear what our lives are like. I don't agree that spending $600 for a week in Havana is putting too much money into Castro's coffers, when you balance it against the number of people you can talk to in a week. Tourists go to Varadero and other beach resorts by choice. If you get on a plane in Nassau or Mexico and fly into Cuba on your own, you can travel around at will. They keep an eye on you, but don't stop you from going where you want to go and speaking with everyone in your path.
The embargo shouldn't be lifted until Cuban exiles and other Cubans get their property back and free elections are held. But that's quite different from individuals visiting and making friends with Cubans. Stay off the state-sponsored tours, which take you only to those model hospitals and schools, and you have the run of the place.
I can just imagine an informal Freeper trip to Havana. Besides bringing in clothes and aspirin and other articles that the people would appreciate, we'd have the opportunity to speak up for democracy, which they all yearn for, and for capitalism, which they do not understand at all. We'd do them a world of good.
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.