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American traveling to Cuba: Current info needed

Hi all,

Does anyone have any recent experience or a source on current information regarding US citizens getting exemptions for traveling to Cuba?
I have a friend that is a US citizen, but currently lives and works here in Canada. He wants to go to Cuba next year but is worried about problems crossing back into the US, which he does regularly for work and to visit family.
He is a corporate exec, so issues with US customs would jeopardize his position. This must be done through appropriate channels.

Any suggestions where I can start to look to find current information about the exemption process? Goggle returns a lot of out of date info and it’s hard to determine what’s still valid.

I think there still is a voluntary fine you can pay for breaking that silly law.
I’m sure I saw it on one of the threads here and others will know the details, but last I saw, it wasn’t all that bad, considering.

First of all, it’s a (slightly) complicated question that is better handled on other forums (like Lonely Planet) that are geared towards independent travel and address American tourist travel in particular, but here’s a thumbnail sketch of the situation your pal faces…

Quite simply: It is illegal for an American to visit Cuba as a tourist. There are no loopholes or exceptions. The, “not illegal to travel there, it’s only illegal to spend money” is an urban myth. Your buddy is breaking the law, period.

That said, let’s consider the worst case scenario…

Imagine your pal completely loses his mind and upon crossing the border back into the US he goes insane and admits to US CBP (Customs and Border Protection) that he visited Cuba or he was silly enough to somehow give the CBP irrefutable proof that he went to Cuba.

What would happen?.. He would negotiate a settlement of $250 - $1,000 with the Office of Foreign Assets Control (OFAC), pay the fine, and forget about the entire episode. No trial. No prosecution. No criminal record. Nothing.

Lastly… if he’s living in Canada, how would the OFAC ever discover he went to Cuba? Cuba doesn’t stamp Passports and he’s flying in and out of Canada. I don’t see the issue…

My understanding is, since 9-11, there are flight manifests of every aircraft that fly over US airspace. This is the bugbear that has my friend spooked.
Again, he’s more worried about his ability to freely cross the boarder without being stopped or delayed because of this. Delays could cost him his job, which is the big fear.

At one time, there were humanitarian exemptions that you could get from the Red Cross if you took a nominal amount of aid with you to Cuba. I suspect this loophole was closed up but, again, I can’t find current information on this.

I’ll take a look on Lonely planet.

Thanks for the input.

As I said above he can forget exemptions of any kind. The reason you can’t find any info is because they don’t exist for anyone trying to enter as a tourist.

There has never been a single OFAC case that has been initiated by a name on a flight manifest. Not one. Imagine the incredible expense and investigative man-hours it would take to tie someone into a flight manifest. The payback of a civil fine of a few hundred dollars would never justify the cost.

Tens upon tens upon thousands of Americans living in the US travel to Cuba illegally every year with zero problems - and they have to deal with the US CBP. An American living in Canada who will never see the CBP during his trip has even less issues.

Since your pal now knows that any problem would be a simple civil issue with no criminal record and he’s still a Nervous Nellie he should probably just forget Cuba. It’s illegal, and there’s no way around that.


Americans also enter Cuba via a flight from Jamaica. He would not be crossing U.S. soil to get there but being American, he is still going against that silly U.S. law. Cuban immigration will not stamp his passport so unless he verbally says something to U.S. customs when he returns, it could remain his secret.

Flying from Canada to Jamaica to Cuba is crazy. Unless you’re a suspected terrorist named on the No Fly List the flight manifest is a complete non-issue.

On the Lonely Planet Altahabana recently posted a link which reported that in the last few years OFAC had levied fines on 30-40 people per annum for Cuba violataions - and most of those were cigar related. (And I suspect most of the rest were guys wearing Che Guevara T-shirts when entering the US !).

It was pointed out to me that travelling under a humanitarian licence when the real purpose of the trip is something else is actually a federal offense - and probably a worse crime than breaking the OFAC travel rules.

The rules are/were so convoluted I don’t know what the truth really is/was.

Back in 2000, a group of us flew into Havana (1 was an American). We had some baggage issues to sort out and while we were waiting, a little league baseball team (I think from Baltimore) flew in. They brought in boxes and boxes of medical supplies that they left in the middle of the floor at the terminal.
While chatting with their chaperon, he told me that the team was there to play baseball with the Cubans and that the medical supplies were their ticket back into the US. This was the Red Cross humanitarian exemption thing.

Anyhow, I now see that those rules have been tightened, but I heard yesterday that Obama is loosening some of the rules from the Bush administration. Perhaps this is the beginning of the end?

Thanks all for you input.

“… Perhaps this is the beginning of the end?..”

The beginning of the end of what is at the present time a complete non issue for a smart, normal American traveler living in Canada…

According to OFAC itself, in 2007, a total of 17 Americans had fines levied against them by OFAC. In 2008 the number was 30+. “The vast majority” were fines of a few hundred dollars levied against people who bought cigars on the Internet. Therefore, the vast minority of fines OFAC levied involved Americans for having visited Cuba. Maybe 20 Americans out of the 100,000 that visited Cuba illegally faced ANY repercussions for having visited there, and none were for more than a few hundred dollars.

It’s time to kill this dead horse that there is any reason for any American to fear going to Cuba. It’s pure bullshit. If it doesn’t happen in the real world then it doesn’t happen, and it doesn’t happen in the real world.

It’s reasonable to speculate that US Customs has standing orders NOT to pursue ANY US citizen for having visited Cuba UNLESS they fall on their own guilt-sword and bleed on the table, admitting having gone, so as to and mandate a response from US Customs.

The statistics suggest you are as likely to be struck by lightning than to face the modest fine from OFAC should you visit Cuba illegally as an American. I am offended by people who know these simple truths for suggesting anything otherwise. That there are laws on the books fail to realize how many other laws that millions of us break every day but which are simply never enforced in the “real world”.

I have more than enough “real-world” things to worry about. Visiting Cuba is not one of them.

Then we have the folks who quote Jiminy Cricket.
“and always let your Conscience be your guide”

Martian and pelodorado nailed this one.