But that seems a very lawerly parsing of the question. We all know they are asking for every country one visited on their trip. Come on. :)

Isn't the whole point here that thousands of Americans travel to Cuba through third countries every year and get by with it? They are not prosecuted. They are not even discovered. That doesn't mean that there isn't some risk. It's up to the individual traveler to decide if that risk is worth it. Apparently, thousands do. I must be the only American I know in Costa Rica who hasn't traveled to Cuba, but I want to be the first one in my circle to make a licensed trip there.

We all know that's what the government probably meant to ask. But that's not what the government did ask in this form. All such ambiguities are resolved against the government when we're talking about criminal statutes and criminal prosecutions.

Americans and Cuba Travel - the Facts, Resources, Related Experiences [only]
 

I'm an American expat living in Canada. My wife (she is Canadian) and I are flying to Holguin this week for her brother's wedding, returning to Canada next week. I am the only American attending the wedding and I'm getting a little paranoid reading some things on this board and elsewhere.

I guess my only real concern is getting my passport (USA) stamped or upon entry into Cuba, Cuban Customs having a problem with my American passport among a plane full of Canadians'. I read further up that Cuban policy is to specifically avoid stamping US passports; this is comforting.

I shouldn't have to worry about completing a US immigration card b/c I'm not returning to the US until probably late February for business.

Any advice to ease my concerns or warnings to reaffirm my paranoia would be most appreciated.

As I mentioned previously, this is policy - but my wife and I both got two exit stamps on two different pages of our US passports in late November 2013.

The quite noticeable 9 cm wide, 2.5 cm high square exit stamp is scarlet, and the header says "REPUBLICA DE CUBA", the footer "JOSE MARTI" and a date in between, with the agent number (168) in upper left and lower right corner.

Nobody said anything, they just stamped; I don't know if others with US passports were getting these exit stamps or not. I have no idea why the woman behind the immigration counter gave us (and two on different pages, seemed to me she was conveying some kind of message, probably not sanctioned by the Cuban Secretaría de Relaciones Exteriores), and being licensed I wasn't worried - other than when getting our passports renewed, which we did this month.

I annotated each Cuban exit stamp with the OFAC license number before sending them in to the Passport Agency (we had no problems other than the atrocious reproduction of our photographs - hardly any contrast and very high key, so much you can't really tell we have ears other than outlines or hair color).

The chances you will somehow be held accountable by the US authorities are probably minimal, but it's a risk factor you have to analyze and make an informed decision about.

Enjoy - the wedding will undoubtedly be a huge blowout event!

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Would it be worthwhile to ask the Cuban border agent not to stamp my passport? Or could this trigger concern?

AFAIK, they are NOT SUPPOSED to stamp your passport, entering or departing. They usually (as indicated in the OP) stamp the paper form you are issued as a "tourist visa" alone. If you think someone is making a move to stamp, indeed, do ask they not do that. (In my case, nobody asked, the woman, "immigration agent 168" at José Martí International Airport, just did it without asking or anything.

Americans and Cuba Travel - the Facts, Resources, Related Experiences [only]
 

JDiver, thanks for putting all this information together and responding to my questions. I will report back when I get home.

The difference with your situation, JDiver, is that you went on a licensed trip. You have nothing to conceal.

Exactly. Those not on a licensed trip need to make a risk assessment and make an informed choice - and hopefully they will not have arrivals or departure stamps entered into their passport as I did.

I suspect Cuban immigration agents are not supposed to, and the woman did so with some hidden agenda or upset toward US passport holders - and "erasing" such a stamp from a passport is virtually impossible without anything showing at some level.

did

Americans and Cuba Travel - the Facts, Resources, Related Experiences [only]
 

I just returned from a wonderful 7 day trip to Cuba. Again, I'm an American expat living in Canada. I traveled through the "back door" and arrived with a plane full of friendly Canadians (even though about half of the plane was from Quebec... only kidding, they're also quite friendly).

Upon entry and exit at the airport in Cuba my passport was not stamped. I was only asked if I live in Canada by a Cuban border control officer, not sure if this was his own personal interest or something they're encouraged to ask. But all together everything went smoothly. Also no hiccups crossing back into Canada. Between my wife and I we declared over $800 of goods, mostly Cigars (about 80). Now I just need to get a humidor to keep these babies fresh.

A new question: I have a business trip to the US next week followed by a long weekend with some friends before retuning back to Canada. I have Global Entry which I plan to use upon entry into the US. Is there any chance I might get tagged at the GE kiosk for my trip to Cuba? I'd like to bring a handful of Cubans back to share with my buddies but that might be too much to risk at this point.

In addition, I recently applied for Nexus and was conditionally approved for an interview (applied before going to Cuba). Planning to schedule this interview on my return flight to Canada in 2 weeks.

Possible, but quite unlikely. Since Obama took office, OFAC has essentially stopped pursuing penalties for unlicensed travel to Cuba. See http://www.fas.org/sgp/crs/row/RL31139.pdf (p. 22). It's hard to see why they would go to the effort of tagging unlicensed visitors when they aren't pursuing penalties.

Still, your cigars are contraband. You're rolling the dice with those.

I agree with dhuey - and cigars, well, those re invitations to confiscation at this time. CDs, DVDs, posters, books, art, etc. are fine; rum, cigars - no dice. And certainly, if I chose to make the attempt, I would not lie about possessing these - especially if one has Global Entry or the like.

It is possible you could get a curmudgeonly CBP agent with political beliefs who could choose to be nasty - I have seen this over the years, whether it is about Cuba or something else. I think that's the equivalent of what I got in Cuba, and why I got exit stamps in my US passport.

Indeed, lying to a law enforcement officer, border agent, or any public official is a really big deal. You mentioned Martha Stewart, upthread. Indeed, had she just kept her mouth shut, it's highly unlikely she ever would have been convicted of anything. She thought she was talking her way out of something, but in fact she talked herself into an obstruction of justice conviction. Ironically, she was never convicted of insider trading, which was the focus of the investigation.

I would never counsel someone to import Cuban cigars unlawfully, but I would emphatically discourage anyone from lying about possessing such contraband if asked by a CBP agent. Don't risk turning a very little problem into a big one.

Agree. The only real issue when returning from Cuba is carrying contraband though I've heard this is not such a big deal in Miami anymore. The one time I was pulled over at a US airport was when I had cigars. Luckily I had a Specific License at the time that allowed $100 worth of booze or cigars. The reason they did that was probably because of the stamp that Cuban Immigration used to put on Page 16 of the US passport, but perhaps they were able to sniff out the cigars.

I just returned from a week and a half in Cuba, as a non-resident US Citizen traveling from Germany via Canada to VRA on a US passport.

Unlike most of the other posters to the thread, I flew into Varadero. Upon presentation of my US passport to the doors at immigration, was turned away for a fairly thorough secondary screening with questions about my visit to Cuba. The questioning took place in the main arrivals hall, and was conducted by three uniformed immigration officers in Spanish. The hall was half full when I was pulled back, and the questioning took about 15 minutes. By the time I was finished, the hall was mostly empty. One of the immigration agents copied my passport details, and took fairly detailed notes, while the other two asked questions.

The questions were:

-Where were you born?
-Are you a German citizen as well?
-Why do you live in Germany?
-How long have you lived in Germany?
-Why did you not take a direct flight from Germany?
-What were you doing in Canada?
-Where did you learn Spanish?
-What is your occupation in Germany?
-What company do you work for?
-Where did you live in the United States?
-What company did you work for in the United States?
-What are you doing in Cuba?
-Where will you be staying in Varadero (and later in Havana)?

I had printed reservations of my hotel, casa particular, (German) insurance, return tickets, and showed them at various times to the immigration officers.

Overall, the order of the questions seemed somewhat haphazard, and not very structured. My feeling was that I was being evaluated on my perceived honesty than the actual answers to the questions.

As a side note, for anyone considering going to Cuba, go before it's too late. The Cubans walking around in Central Havana with brand-new, bright yellow, Nike shoes and Lacoste shirts in state-run commodities stores, alongside their compañeros who aren't as lucky is an outstanding contrast to see. The number of Geeley and Lada cars, alongside the occasional modern E-Class Mercedes or Audi A4s is unforgettable.

I did not have an OFAC license for this visit. When entering the US, I have Global Entry, so don't speak to an immigrations officer. Since I'm a non-US resident, I always leave the "Countries visited on this trip prior to US arrival" blank on the customs declaration form.