Homeless Travel Blogger Advises Readers To Violate OFAC Rules

Posted by at 6:03 pm on January 10, 2017
Category: Cuba SanctionsOFAC

Ben Schlappig via http://onemileatatime.img.boardingarea.com/wp-content/uploads/2008/01/Ben-Schlappig-10bw-cropped-e1427813265841.jpg [Fair Use]
ABOVE: Ben “Lucky” Schlappig

A homeless blogger named Ben “Lucky” Schlappig, who makes his living flying on airplanes and staying in hotels, has decided to take up the practice of law along with advising fellow travelers on the intricacies of the airline and hotel reward programs. The result is pretty much what you would expect when Lucky opines on the legality of traveling to Cuba as a tourist.

Technically Americans can only travel to Cuba for one of about a dozen approved reasons. … In practice, most people traveling to Cuba as tourists choose either “Support For The Cuban People” or “People-To-People Exchanges” as the reason for visiting.

So technically you can’t go if tourism is your stated reasons [sic], though in practice there are tens of thousands of American tourists going. That’s because they keep the categories intentionally broad, and you won’t generally be asked about the details of why you’re going to Cuba. Arguably when you’re a tourist somewhere you have “people-to-people exchanges” and also “provide support” to the people.

Without hesitation I’d feel comfortable recommending people visit Cuba as tourists and just state one of those as the reasons.

Arguably, when you’re relying on a pretend lawyer, your mileage may vary.  Also, never trust anyone who goes by the name of “Lucky.”

Of course, OFAC anticipated that amateur lawyers like Lucky would say that all tourism in Cuba was inherently a people-to-people exchange, so it gave an example here, in the actual rules (which Lucky clearly did not bother to read), to put the kibosh on such silliness:

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.

So, just as you should not trust my opinions on how to get the most frequent flyer miles from your airline, you probably shouldn’t trust Lucky when he tells you to travel to Cuba as a tourist.


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I had taken a break from practice for about year now and decided to come to your blog for some much needed updates as I ease back in. Really happy to see the sharp humor and insight that I remembered from being a regular reader continues to be on full display. Thanks for the great commentary!

Comment by Erin on January 11th, 2017 @ 3:01 pm

I agree that Lucky would have been wiser if he was more discreet about his purpose in traveling to Cuba. He should not provide unqualified legal advice which puts his readers at a significant liability risk.

But I agree with Lucky that the OFAC Cuba travel rules are overly broad, vague and, in many cases, open to interpretation. The people-to-people (P2P) licenses, especially, evade clear legal definition.

The main requirements of P2P licenses are that (1) they must involve some type of educational exchange that can occur outside of an academic setting; (2) the contacts and interactions with the Cuban people must be “meaningful”; (3) these activities must be conducted on a full-time basis while in Cuba; and (4) these interactions cannot be conducted with a Cuban govt official or Communist Party member.

Given that criteria, visiting a girlfriend in Cuba probably could satisfy all four of the above elements as long as the pair talk about philosophy, science and other high brow topics and the other regulatory requirements are met. As alternative evidence of a P2P exchange, simply practicing and perfecting Spanish and English skills could satisfy the educational requirement. And as far as “meaningful” is concerned, I can’t think of any other types of interactions that are more meaningful than those between boyfriends and girlfriends (or significant others to use the PC terminology).

I would like to hear OFAC’s opinion on this hypothetical situation.

Comment by Daniel Zim on January 12th, 2017 @ 1:30 pm

    I don’t believe visiting a girlfriend in Cuba and discussing philosophy or practicing Spanish would be “meaningful.” They might be other things, however.

    Comment by Clif Burns on January 13th, 2017 @ 3:29 pm

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