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.
Some insurance carriers are now offering coverage to Cuba as long as the travel is authorized, meaning all Office of Foreign Asset Control (OFAC) and Bureau of Industry and Security (BIS) licenses (export licenses for the yacht) are obtained. Keep in mind that all travelers will also need VISA's from Cuba. Marsh and the insurer would require written representation from the owner that the owner/yacht and each traveler accompanying the owner/yacht are authorized to travel to Cuba. (see Marsh authorization form).
Also note that vessels and/or private aircraft may require authorizations from other agencies such as the Department of Transportation or the Department of Commerce to travel to Cuba. Vessels are only authorized to travel directly from the US to Cuba and back to the US and can only stay in Cuba for up to 14 day sojourns.
It will take you some time to obtain the appropriate General Licenses from the government and some clients are obtaining a maritime attorney to assist with the task. When you submit the OFAC application to the USCG, please copy me as well as sending me the complete marsh form and I will ask Marsh Legal for approval at that same time that you are getting approval from USCG. Once you have the appropriate OFAC licenses in place, we can submit a request to the ACE underwriters; ACE will then have to obtain approval from their compliance office if they are even offering terms for Cuba. If ACE does not offer terms, we will have to try [others].