A Trip to Cuba
I have traveled to Cuba six times now. I studied in Cuba in 2003, for a month, and in 2004, for a semester, with a few other more recent trips mixed in here and there.
All of my trips were legal ones; a point that should not be overlooked.
The fact that many of my trips came years apart should also not be overlooked. After several changes in the law and regulations, I was unable to return to the island legally. In the past few years, however, these restrictions have eased and I'm allowed to return as part of "people to people" exchanges approved by the U.S. Treasury Department. The upshot of all this is that apart from money and free time, there's no reason why Americans can't legally travel to Cuba these days.