Provided below is the technical advice I received from the insurance industry during the planning phase of the trip. I thought this would be helpful for those contemplating a trip to Cuba.
Tourist travel to Cuba remains prohibited except as authorized by the Office of Foreign Asset Control (OFAC) under the 12 general licenses categories. Each individual must qualify for authorized activities in his or her own right. If an individual does not qualify for one of the 12 general licenses, they must obtain a specific license from OFAC.