NOW! Ok, there is hurricane season at the moment (check National Weather Service) and it is better avoid it. But if you are considering trip to Cuba sometimes, you shouldn’t delay it for too long. Why? Because after B. Obama became president of USA relationship between Cuba and USA became much warmer. It is good sign for Cubans and should make their life easier if economic embargo would come to the end. I wish them to achieve this ASAP, but from point of the tourist it will be big lost. With all money which will come from US, it will became just another Caribbean resort. Even in these days some parts of Cuba already are like this. For example: Varadero or Coco island. Some tourists are fly in to these resorts and don’t see anything else. If you want to see real Cuba avoid these places as much as possible. Of course everything won’t change instantly, but you should consider it will be changes in the future. Probably in the near future.
Here some resources should be useful for preparation for you trip to Cuba:
P.S. Unfortunately this suggestion doesn’t apply to Americans. They still can’t [legally] visit this island.