Should I go to Cuba, and if so, how?
May 31, 2019 10:58 PM   Subscribe

Friends are going to Cuba and I'd like to meet them there. I'm American, they are not. I have passports from the US and Italy. I would like to know what's my best option, and for each option, what's the risk of getting in trouble with the US government.

Option 1: Fly direct from the US on my US passport and claim that the trip is in "support of the Cuban people" - this option may be a non-starter because I'm not sure the trip will include anything that fits into that category.

Option 2: Fly with a stopover in Mexico on my US passport.

Option 3: Fly direct from the US on my Italian passport.

I don't want to get into any trouble so if all three options are risky I will just skip the trip.

Thanks!
posted by anonymous to Travel & Transportation (8 answers total)
 
You can search online with your state's name and "bar association" as keywords to see if there is a lawyer referral service available, and consult with an immigration attorney. No answer obtained here can help you figure out how to 'avoid getting in trouble with the US government,' because the only answer is get a lawyer, because you are directly asking for legal advice.
posted by Little Dawn at 11:13 PM on May 31, 2019


I did Option 2, but through Canada recently. I was honest and transparent about going to Cuba at immigration checkpoints but I didn't get any questions about my itinerary from US, Canadian, or Cuban officials at any point. They were all typical border crossings, didn't seem different than any other country.

I belong to a lot of off-the-beaten-path travel groups and forums and have many US friends and family who have visited Cuba and I've never heard of anyone actually getting in trouble for traveling to Cuba. 10s of thousands of Americans go to Cuba every year, but personal accounts of fines or jail time from the US government are extremely uncommon (I couldn't actually find any in the internet research I did before my first trip.) The itinerary restrictions appear to be largely unenforced.

In April of this year, the Trump administration made a vague threat that travel to Cuba would become more restricted, but nothing concrete has come out of that yet. I'm planning on going through a third country when I make a return trip this summer, because I am a little worried that flights directly from the US could be canceled
posted by horizons at 5:11 AM on June 1, 2019 [1 favorite]


Option 3 doesn't really work as an American Citizen you'll have to leave and enter US with your US passport. You may choose to present your Italian passport in Cuba, but US authorities will certainly know that you went to Cuba.

I went with my family (wife and kids) to Cuba two years ago. At the check-in we declared that our travel was under the "Religious Exceptions" category. I chose that one as I thought that it would be the hardest for anyone to argue against. No questions asked on our arrival back to JFK.
posted by zeikka at 5:15 AM on June 1, 2019 [2 favorites]


Option 1. Staying at Airbnb is support for cuban people
posted by sandmanwv at 6:07 AM on June 1, 2019


I recently did Option 1 and found it very easy. I fretted and fretted about what qualified for "Support for the Cuban People." The law is so vague and (as far as I can tell) no one has actually been charged with violating it, so it was difficult to tell what was and wasn't permitted under this license. However, I eventually concluded this vagueness was a strength rather than a weakness. I bought a pre-packaged legal itinerary on the Internet from a travel guide, and updated it to suit my own interests. Upon re-entering the U.S. in the Orlando airport, I told the border agent that I had gone to Cuba to "support the Cuban people" and he asked me no further questions, although I was prepared to show up my itinerary and records from my trip.

FYI, "Support for the Cuban people" is not as simple as just staying in AirBnbs. If you look here, it says simply staying in privately-owned homes and eating in privately-owned restaurants are not enough; "in order to meet the requirement for a full-time schedule, a traveler must engage in additional authorized Support for the Cuban People activities." My friend and I visited art museums, took a bike tour of Havana, hired a guide to take us to the old Havana forts, hired a guide to take us birdwatching in the Zapata Swamp, hired a guide to take us hiking outside Trinidad, and hired personal drivers to transport us between cities. Most Cubans who work in the tourism industry knew about the "Support for the Cuban People" license and advertised their services accordingly; whatever your interest, you can probably find a qualifying tour/guide so that the activity counts as "Support for the Cuban People."

I met a lot of Americans on the trip who were going to straight up lie about their itinerary, and use the "Support for the Cuban People" license as an excuse to drink on the beach all week and visit the government-owned hotels and bars that are supposed to be off-limits. So many Americans do this that our Cuban guides even encouraged it! I'm too paranoid to do something like that, but it was sort of comforting because I came in to the trip worrying about the legality of my itinerary only to find that most American visitors were worrying far less than me. I figured if the Trump administration was going to make an example of someone violating Cuban travel policy, it would be with someone completely lying about their itinerary, not someone like me who made a good-faith effort to follow the license. Mostly, however, I was astonished with how many Americans were visiting Cuba even though the conventional wisdom now is that Cuba is "off-limits" again, and how little any Cuban or U.S. authority cared. I am not a lawyer, nor am I a travel agent, but in my experience if you take the trouble to print out and bring a physical itinerary that generally follows the concept of supporting private Cuban business, you're already being more careful than a lot of Americans traveling under this license.
posted by kingoftonga86 at 7:29 AM on June 1, 2019 [9 favorites]


What kingoftonga86 says matches my friends' experience. The only thing I would caution you about is if you have any intention of applying for any kind of federal job that requires security clearance--such a visit might cause difficulty during the investigation (you'd need to put it on your SF-86). But that's a specialized caution that won't apply to most.
posted by praemunire at 10:19 AM on June 1, 2019 [1 favorite]


In case anyone is still reading this...what about a combo of options 2 and 3? e.g.:

* Fly from the US to Mexico, showing my US passport as I leave the US and my Italian passport when I enter Mexico
* Fly from Mexico to Cuba, showing my Italian passport in both places

Then the reverse to return.
posted by sunflower16 at 2:59 PM on June 3, 2019


Today, Trump banned the People-to-People category of travel to Cuba.

WASHINGTON (AP) — The Trump administration on Tuesday imposed major new travel restrictions on visits to Cuba by U.S. citizens, including a ban on many forms of educational and recreational travel.

The Treasury Department said in a statement that the U.S. will no longer allow the group educational and cultural trips known as “people to people” travel to the island. Those trips have been used by thousands of American citizens to visit the island even before the U.S. restored full diplomatic relations with the communist government in December 2014.

Treasury said it would also deny permission for private and corporate aircraft and boats. However, commercial airline flights appear to be unaffected and travel for university groups, academic research, journalism and professional meetings will continue to be allowed.

“It kills the people-to-people category, which is the most common way for the average American to travel to Cuba,” said Collin Laverty, head of Cuba Educational Travel, one of the largest Cuba travel companies in the U.S.

Treasury Secretary Steven Mnuchin said the measures are a response to what it calls Cuba’s “destabilizing role” in the Western Hemisphere, including support for the government of President Nicolas Maduro in Venezuela.

“Cuba continues to play a destabilizing role in the Western Hemisphere, providing a communist foothold in the region and propping up U.S. adversaries in places like Venezuela and Nicaragua by fomenting instability, undermining the rule of law, and suppressing democratic processes,” he said. “This administration has made a strategic decision to reverse the loosening of sanctions and other restrictions on the Cuban regime. These actions will help to keep U.S. dollars out of the hands of Cuban military, intelligence, and security services.”

The new restrictions had been previewed by national security adviser John Bolton in an April speech in Miami to veterans of the failed 1961 Bay of Pigs invasion but details of the changed were public until Tuesday. Treasury said the sanctions would take effect on Wednesday after they are published in the Federal Register.
posted by apex_ at 10:38 AM on June 4, 2019 [2 favorites]


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