Today, the Office of Foreign Assets Control (“OFAC”) amended the Cuban Assets Control Regulations to, among other things, expand the general licenses authorizing travel by U.S. citizens to Cuba. Under the new amendments, U.S. citizens can travel to Cuba under the people-to-people general license without doing so under the auspices of a sponsoring organization. As long as the individual arranges for himself or herself a “full-time schedule of educational exchange activities that will result in meaningful interaction between the traveler and individuals in Cuba,” the trip is authorized under the general license for educational activities in section 515.565. The amended rules still exclude travel that is “primarily tourist-oriented” but eliminates the exclusion for “self-directed educational activities that are intended only for personal enrichment.”

A new example tries to grapple with the distinction between a trip that is primarily tourist-oriented and a permitted self-directed activity that involves a meaningful exchange with individual Cubans:

An individual plans to travel to Cuba to rent a bicycle to explore the streets of Havana, engage in brief exchanges with Shopkeepers while making purchases, and have casual conversations with waiters at restaurants and hotel staff. None of these activities are educational exchange activities that will result in meaningful interaction between the traveler and individuals in Cuba, and the traveler’s trip does not qualify for the general license.

In that case, go directly to OFAC jail; do not pass go. As you might imagine, it may be difficult for individuals, anxious to swill down a few mojitos in Old Havana before there is a Starbucks on every corner and an Olive Garden in every storefront, to grasp the difference between a meaningful exchange and a pub crawl. The checks and balances of a sponsoring organization will be absent.

Worse yet, consider this: under the rules for the people-to-people license, the individual will need to “retain records sufficient to demonstrate” a “full-time schedule of activities” that result in a meaningful interaction with Cubans (other than waiters, bartenders and hotel staff). Forgive my cynicism (or not), but a large number of individuals engaged in self-directed people-to-people (other than waiters, bartenders and shopkeepers) travel are not going to have a clue as to how to do this. Unless this is intended to be a requirement that is never enforced and a concealed license for tourism in Cuba, this is not going to end well for many people relying on this self-directed license. Don’t get me wrong, as you can imagine, I’m all for unfettered travel to Cuba. But I really don’t relish the possibility that, 18 months from now, I’ll be getting calls to help out a friend whose kids went to Cuba and thought that their Instagram account qualified as adequate documentation of their self-directed people-to-people trip to Cuba.