As Canadians we too have visited Cuba. It is a beautiful island as are many of the surrounding islands. On our last trip there we were seated on the plane next to a couple from Texas who just happened to end up at the same resort we are staying in. While I know that one experience does not make up a norm, let me say that the Texans enjoyed the scenery and the beaches but not their stay in Cuba. There were many occasions where they were subjected to inconveniences that were based solely on the fact that they were American. It is my opinion that until things change "officially" taking so called "legal" trips through other countries is not the solution. IMHO things will change and people with brains will analyze this situation and Cuba will no longer be off limits for US citizens. Until that time I'd say just wait and dream. I know that this is harder for us since we are so accustomed to "living free" but sometimes there are rules and laws that we must follow even if they are based in a very demented version of reality.
Cuba is beautiful, but I found it disconcerting to get to the beach at the end of my resort to find armed guards asking us to turn back. But truth be told I didn't like this when I ran into it to a lesser degree in the Dominican Republic.