This has to do with the stupid idea that if we cut off all trade with Cuba, they will become a democracy. They prove otherwise and haven't fallen yet. I srongly feel that we should start moving toward opening up trade and tourism to leverage the desire of the population to live a little more free.
I think that the skewed thinking by the JFK administration was promoted by the self-exiled Cubans who lost their property by Castro (and still trying to sue Cuba over it) as a hope that when a change in government takes place, the self-exiled Cubans will get their land back - which I think is wrong after 48 years.
As a Canadian, it seems that you have the advantage. You can actually go there.