Why I’m Not Traveling to Cuba… And You Should Consider This Before Going There, Too.

If you write a travel-related blog, you’re supposed to have a sense of adventure,. This post is how my sense of adventure is actually outweighed by risk, legal risk, that most will never face. Hear me out, and I’d love it if you just tell me I’m being paranoid. I’d love it if you’d help to change my mind on this.

There’s virtually no legal risk for the average American in traveling to Cuba now, it would seem.

While the categories of allowable travel haven’t changed, it’s no longer required to obtain a special permit from the US government to travel. Americans have a general license, and those who do go are presumed to fall into an eligible category.

As for as those categories go, I arguably could go as a ‘journalist’ and blog the trip. I haven’t consulted with legal experts, and I’m not certain how well-tested that area of law is.

Even MasterCard will allow US-issued cards to be used for payment in Cuba starting March 1.

So it’s for all intents and purposes open season for Americans to travel to Cuba, even if it isn’t strictly legal for all to do so. And even if scheduled flights by US carriers to Cuba are on hold.

Here’s the concern I have, and how the legal grey area of Cuba travel might come up. Say you’re being investigated by a US attorney for completely unrelated activity. For the purpose of this hypothetical post, let’s say the investigation is for ‘structuring’ bank deposits in a manner that appears to avoid the required reporting of amounts over $10,000.

You have a pretty good case you weren’t doing what you were accused of. The prosecutor offers you a deal, because they know their case is weak. You’re inclined to roll the dice with a jury. But during discovery, the US attorney’s office comes to learn that you traveled to Cuba — and may not have fallen into an allowable category to spend money there. So if you don’t take the plea, the prosecutor will pile on with charges … for something that most Americans would get away with.

Put another way, it looks fine to travel to Cuba — unless you catch the ire of a prosecutor for something else entirely. And then every grey area move you’ve made is on the table.

I suppose I’m super cautious by nature. Heck, I could be a lot more aggressive on my taxes than I am. But I don’t think I’m ready to travel to Cuba. Many others, of course, will be!

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. You raise valid points. I guess I’m not ready for other reasons (which I won’t share here, but, being DC-based, you can imagine). I’d hope prosecutors wouldn’t try to pile-on, but that’s more an idealistic approach. All that said, it certainly is beneficial to be cautious with traveling to Cuba. Yes, it might be more “ok” but, ask yourself, would you like your visit to Cuba to be posted on the front page of the Washington Post or NY Times? If not, its probably not the right time.

  2. What in God’s name are you talking about? “Just in case you’re being investigated by a US Attorney, you should be careful of traveling to Cuba!”


    Don’t jaywalk, because Just In Case You’re Being Investigated By A US Attorney…

    Don’t have lots of credit cards, because Just In Case You’re Being Investigated By A US Attorney…

    Don’t look suspicious, because Just In Case You’re Being Investigated By A US Attorney…

  3. @gustav if you were not qualified for an eligible class of visitor, you could still be charged, in which case it would be very relevant. No one is going to be charged for this alone. But if they were otherwise the target of an investigation, a prosecutor could still go after this.

  4. Maybe it’s more far-fetched for some than for others..!

    Although jaywalking doesn’t carry substantial penalties. And having lots of credit cards doesn’t fall within a legal grey area, either.

  5. I am pretty sure Chase has a language against signing up for credit cards for sign up bonus. But that is what you effectively promote everyday. Many bloggers even advocate signing up for ink bold without a relevant business. I presume all these would be a bigger issue if a prosecutor was up against a miles/points blogger. Cuba is peanuts.

  6. Gary, you sound awfully paranoid. Makes me wonder what else you do besides this? Anyway, the novelty of going to Cuba will wear off in about three months

  7. I’m married to a US Attorney, so I could neutralize the threat by taking him with me. You can borrow him, Gary. He’s a great guy, and we live in Virginia.

  8. The only way I can see a trip to Cuba, becoming an issue, is if you run for public office. Or perhaps the GOP manages to change this policy back to what it was…. Since blogging is justly defined as journalism, I really don’t see a problem. Unless you feel you need to make excuses for not wanting to go. You won’t be earning miles and points by going to Cuba.

  9. Just go. You are a journalist. I went as an educator with my educator husband. It is not like any place I have ever been (have been to over 80 countries). Go before it opens up. Everything has risk, but this is not something to be that concerned about. I cannot wait to go back again.

  10. even before restrictions were relaxed, this was small potatoes. i have had friends who have gone via YYZ or MEX and had their cuban immigration stamps on a blank piece of paper instead of in their passports. out of maybe a dozen of these people, i know of only one who was busted. the US immigration agent mentioned he looked really tan for a trip to toronto and smirked. that was it.

    even if they do bust you, it’s a fine — and anecdotally that’s rarely imposed. they have to suspect you’ve done some money laundering or drug-related stuff to get harsh on you.

    now myself, i won’t ever do it because i have several close family with security clearances for work and i wouldn’t want to jeopardize that. otherwise, i wouldn’t worry about it at all.

  11. If I were really worried about being investigated for structuring financial transactions at the top of my list of what NOT to do would be to publish an article that might as well be titled “Do You Think Going to Cuba Would make It Less Likely I Could Skate on a Charge Of Financial Structuring?” Just sayin’

  12. The one issue I haven’t see anyone raise that I’m worndering about is how would this affect one’s standing with a trusted traveller program like Global Entry?

    Is it possible that the CBP can use an unauthorized trip to Cuba against you as an excuse to revoke Global Entry?

  13. I was hoping to use “small potatoes” on this post regarding Cuba. I was beat to it. Good job, pavel.

  14. I travel a lot out of the U.S. I really enjoy having Global Entry when I come back home. Although I would like to travel to Cuba, I know that I could have my Global Entry revoked and my TSA pre check would go with it. Not worth pretending that I have a license to visit Cuba unless I truly have such a license.

  15. @LarryInNYC my concern isn’t actually about financial structuring investigations

    @Ben of course, and this will be an issue for some folks who seek security clearances

  16. Really? What a stupid narrow-minded (and uniquely American) way to think about travel to Cuba. Everyone else in the world except the US is already travelling to Cuba without an issue, many large multinational companies have significant interests there. The health, medical and academic communities are already linked. No-one’s going to give a rats-a** whether you went to Cuba or not. The current categories can fit in pretty much anyone anyway. You run more risk entering a country for a conference visit on a tourist visa instead of a conference visa (i.e. not very much)

  17. Gary — if you truly have a basis for believing you may be indicted for a federal offense, then, yes, wait a while to go to Cuba. But the Cuba question really has no place in this discussion. The bigger problem is doing something you believe will draw an indictment. Stop doing that thing. If you’re pinning your hopes on convincing a “jury” that you’re not really a criminal, Cuba has nothing to do with whatever the hell you’re talking about. Put simply if you merely have a “pretty good” case you aren’t commiting federal crimes, but not a good enough case to convince a prosecutor, stop worrying about Cuba and start worrying about doing whatever you need to do to avoid being accused of federal offenses that will make prosecutors seek to get you to plead guilty.

  18. WAY too paranoid but, that said, I’m now on the TSA’s SSSS list for having visited Istanbul at Christmas (and I’m not the only one — see Flyertalk and other blogs for the ridiculous details). So if a visit to IST can “get you in trouble,” who really knows what a visit to Cuba would do. 🙂

    Personally, I’m not going to Cuba until regular tourists can visit independently. Before then, I figure I’m just going to get ripped-off buying some “education” tour or something.

  19. Despite wearing your politics on your sleeve far too frequently for a travel blog, I tend to doubt the President is going to sic Eric Holder on you for it.

  20. Moot argument.

    Most of the world are not Unitedstatesians, and Americans — which means people who live on the continents of two Americas (Canadians, Argentinians, Brazilians, what have you) — always could and still can travel to Cuba without any restrictions whatsoever.

  21. I’m with iahphx. I’ll wait to go when I can go on my own terms, just as I did in the cases of Russia and China.
    I’m not one to accept propaganda gladly, and would probably say something that would embarrass someone. I suppose hopping on a plane from Cancun would get me more freedom of activity than one of those highly priced “tours”, but I still have dozens of other places on my list of things I want to see, and there’s no need in my mind to prioritize Cuba over them at this point.

  22. Just go. When I was a Florida resident, from 1989-2005, I made 22 trips to Cuba without any visas. It was so easy to just go Nassau-Havana. I was caught twice and threatened with getting a letter from the Treasury Dept. The ACLU said that if I did get a letter just to forward it to them, but that the US gov’t will not put people in jail for being tourists in another country.(How would that look?) The novelty never wore off. I continued going, but never received any letter. I’m planning on going again in March but its a much longer trip from Arizona.

  23. I didn’t realize that the USA is more like the old USSR than a country where its citizens are truly free.

  24. WHAT?

    Why get on a plane? It might crash or you could be falsely accused of wrongdoing/lawbreaking by a flight attendant or fellow passenger.

    I can see how some may look at travel to Cuba as a moral dilemma due to political or human rights concerns, but this post borders on the absurd.

  25. I agree with Larry. If you’re worried about a hypothetical financial structuring charge [or some other potential federal investigation], then that is the activity to stop doing, clean up, make amends, and prepare a legal defense.

    The Cuba discussion is a red herring, even if you view it as the straw that breaks the camel’s back.

    I hope for your sake this is all hypothetical.

  26. Jaja I’m traveling. .Everybody should. People go to your travel agent for reliable information. He must be distant family member of Batista or the Dia-Baliart family

  27. Given that the average person commits three felonies a day, if you have a Federal prosecutor determined to convict you, a trip to Cuba is likely to be the least of your problems.

  28. What the heck are you doing that is making you so paranoid?! As Larry says, “stop doing what your doing” that’s making you paranoid!

    Jeez…there are probably other more serious issues you’re facing than going to Cuba! And “hypothetical”? Heck of a detailed “hypothetical” scenario.

  29. 1. Can someone explain what structuring bank deposits is and why it’s a crime? Seriously, I don’t know what he’s talking about.

    2. I’m with Larry. If you’re being investigated by the Feds, you’ve got bigger issues to deal with.

    3. I’m also with John Tarik. How ironic that people are afraid to go somewhere as a tourist because the government might use the trip as leverage against you in an unrelated case. Home of the free indeed.

    4. As a Canadian, one of the best things about Cuba (compared to Mexico, the DR, etc.) is the lack of Americans, particularly the underage drunken students. I suppose it’s only a matter of time now before Señor Frog and Jimmy Buffett open their first branches in Havana.

  30. Your fear of being investigated by US Attorneys makes me wonder what the heck you have been up to lately.

  31. I know a lawyer who has helped others with these structuring charges. Very effective. Don’t let it cost you your job…or worse, your CC links. Banks won’t work with you if you have that sort of felony background.

    Email me when you can.

  32. Gary – save all the legal risk and stress! You can just fly to Miami and see the novena provincia de Cuba – Calle Ocho.

  33. You can’t call yourself much of an adventure traveler if you don’t go to Cuba. Definitely a must-see before it gets commercialized.
    Are you really that terrified of your own government? How many people have been prosecuted for being a tourist somewhere?

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