You are in-house counsel for a large commercial cruise line based in Miami, Florida. The company was founded in Miami by a Cuban family that established routes in Miami in the late 1950s. The cruise line started with small routes to the Florida Keys and the Bahamas in the 1960s and is now a household name with route all over the world leaving for various ports. While the family no longer runs the company, they still hold a significant equity stake in the business and have a seat on the board of directors of the company. The CEO of the company wishes to establish a route from Miami to Cuba with stops along the way in Puerto Rico and the Bahamas.

The CEO of the company has asked for help to make memo of her detailing some of the sanction related considerations in connection with establishing this commercial route through Cuba. The CEO would also like yours thoughts on the business and reputation considerations with establishing a route through Cuba. Of course, if there are any other considerations that the CEO did not mention, please feel free to touch on those in your memo as well.