Comment Re:So will he go to jail upon return to the US? (Score 5, Insightful) 190
The whole purpose, for the US government’s perspective, is to intimately experience the day-to-day lives of residents while learning about Cuban cultural, social and religious organizations firsthand. For this reason, all participants are required to adhere to the approved full-time schedule of activities – beg off to relax by the hotel pool and OFAC could pull the company’s license.
So there are restrictions: you have to travel with a tour guide, and your trip agenda has to be filled with culturally-relevant activities rather than just random tourist stuff. It wasn't clear from TFA if Schmidt's visit was under this particular license, but his trip agenda ("to get a tour of Cuba’s University of Information Sciences in Havana and discuss life within the country") certainly sounded like it would have qualified.