Americans still cannot not simply book a flight and head to Cuba, although that should be possible by the end of 2016. Most . citizens still travel with a Cuba travel organization that has an official license from the . State Department, like Insight Cuba and Central Holidays . Legal individual travel to Cuba is now possible if you fall under one of the 12 categories of permitted travel to Cuba , but remains (practically) difficult: you'll need to document your activities, and booking a hotel room -- while now legal -- can be a challenge due to high demand ... MORE and low supply. (Tour groups, on the other hand, have big blocks of hotel rooms reserved in advance.