Q: Now that the Trump administration has done away with People-to-People travel to Cuba, is there any legal way for our agency to arrange a tour to Cuba for members of the general public? If so, do we need any permission from the U.S. government? What would we have to watch out for?
A: You can organize and operate a tour for the general public under the category called Support for the Cuban People. This is the term used by the Treasury Department's Office of Foreign Assets Control (OFAC) for one of the authorized categories of travel.
To qualify under this category, your tour must meet the following criteria:
First, it must be in conjunction with "recognized human rights organizations; independent organizations designed to promote a rapid, peaceful transition to democracy; or individuals and nongovernmental organizations that promote independent activity intended to strengthen civil society in Cuba."
So, using any independent organization that intends to strengthen civil society in Cuba will work. In practice, this means that you can use a privately owned Cuban destination management company (DMC) to organize the tour for you if the DMC uses private suppliers, since such suppliers are part of "civil society."
Second, the tour must consist of "a full-time schedule of activities that: (i) enhance contact with the Cuban people, support civil society in Cuba or promote the Cuban people's independence from Cuban authorities; and (ii) result in meaningful interaction with individuals in Cuba."
The OFAC regulations don't define "full-time schedule," but they note somewhat circularly that such a schedule should "not include free time or recreation in excess of that consistent with a full-time schedule." In any case, my review of the rules indicates that you would probably need to have the DMC organize all meals and day-long activities every day.
Notably, your tour can operate with as few as one participant, as group travel is not necessary.
The rules provide a few examples of trips that would and wouldn't qualify. The first example that would qualify can be summarized as staying in private residences, eating at privately owned restaurants, shopping at privately run stores, engaging with Cuban hosts to discuss Cuban culture and supporting owners of other private businesses.
The example of what wouldn't qualify is the traveler who "rents a bicycle to explore the neighborhoods and beaches and then engages in brief exchanges with local beach vendors." According to the OFAC, "the traveler's trip does not qualify because none of these activities promote independent activity intended to strengthen civil society in Cuba."
You don't need any OFAC permission to organize, sell and operate a tour that qualifies. All you have to do is to follow the requirements. You have to make sure that the DMC and all its suppliers and hosts are not government-owned. You can find a definitive list of all government-owned enterprises at this State Department webpage.
Finally, you need to make sure each traveler maintains a diary of all activities and keeps the diary for five years.