Just so you know, we haven't drunk the Kool-Aid. Cuba is not a free country; people are not free to criticize their own government, and information and travel out of the country is strictly controlled. At the same time, education is free to all citizens, and Cuba is the most literate country in Latin America. They have incredible support for the arts, much better than we have in the US (as far as public support goes), and a beautiful country that pretty much everyone on the planet is free to visit except for US citizens.
And therein lies the problem. When Castro drove out the incredibly corrupt Batista government in 1959, he declared a socialist state. Eisenhower went on a golfing trip to avoid having to meet with anyone who even smacked of socialism, and so when Castro visited the US shortly thereafter he met with (of all people) Nixon. Needless to say, we offered no support for the fledgling government, and so being a pragmatist he turned to the Soviet Union. When that country collapsed in 1990, Cuba went through a "bad" period of time, and we didn't help then either. Today, they have a thriving tourism industry, but things are difficult for the average Cuban on many levels, although not as bad as 20 years ago.
Why has the US been such a hard ass on Cuban relations? The answer goes back hundreds of years, when we had designs on making Cuba a US territory because of it's strong sugar and tobacco industries. We even trumped up a cassus belli for the Spanish-American War in the late 19th Century mostly so that we could incorporate Cuba, but the one concession the Spanish managed to get was that Cuba be an independent state (as opposed to Puerto Rico, the Philippines, and the other territories we stole from the Spanish). For the first half of the 20th Century, Cuba was a defacto US territory, although one that we didn't need to worry about little things like democracy, civil rights, or any of the regulation that was becoming de rigeur in the US.
When Castro's revolution was successful, he nationalized all of the US and Cuban holdings, in particular the sugar and tobacco plantations. And there is the reason that the US is still pissed off about 1959. It wasn't communism, it was that Castro kicked us out and gave the country back to the Cubans. It has taken 50 years for the interested parties to have largely died off, and it is now that we start to see normalized relations with the country.
Having been to Cuba, I will say that it is indeed a totalitarian state, although one that does some things right. Universal health care and education are some of the laudable things the Cuban government does for it's people. On the down side, there are a lot of very smart people who are forced to take jobs doing things that would seem crazy in the US. I met a cab driver there who had been a social studies teacher, but made so much more money in tips that he changed jobs!
Now that Obama has lifted restrictions on Cuban ex-pats visiting and sending home money, we will start to see major changes in a year or so. I predict that there will no longer be restrictions on any US citizen traveling to Cuba by the end of 2010, perhaps sooner. The painful thing is that over the last 50 years, the people who have traveled to Cuba have had good intentions. Cuba AyUUda, the organization associated with the Unitarian Church that my wife is involved in, goes not only to help Cubans, but to let Cubans and Cuba change those who visit, and it's been effective for both sides.
Once the restrictions are lifted, however, the quality of American in Cuba will change. As one of the people we met there said, "Now, Americans come who love Cuba. Soon, Americans will come who want us to serve them drinks and who won't care about the Cuban people." I think he's got it just about right. I think that as our relations with Cuba normalize, we'll start to see Cubans lose the good things about their revolution and it will become just another Latin American country with corrupt politicians, ugly American tourists, and where the dollar reigns supreme. That will be a shame, because while the youth of Cuba certainly are looking for any way they can to improve their lives, it will be through quick and easy money rather than hard work.
For those who say that we shouldn't have relations with any dictatorship, I suggest you pull your head out of your ass. We have many many relations with countries that have similar or worse governments than Cuba. Cuba also hasn't been a military threat for decades, and in fact I saw military *officers* hitchhiking on the side of the roads, repeatedly. This is a country that offers no threat at all to the US, unlike North Korea.
By opening up US travel to Cuba, we destigmatize this wonderful and beautiful country, introduce a flood of desire for greater freedoms, and right at least 20 years of boneheaded political policy engineered more to keep the Cuban ex-pats in Florida voting Republican than to "stop Communism". The Bush administration actually tightened restrictions on travel, despite there being not the slightest reason to do so, and I'm glad to see that we are finally getting to a point where we stop acting like a bunch of spoiled children who got kicked out of a sandbox that wasn't theirs to begin with.