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Going Through US Immigration And Customs After Visiting Cuba

Yeah, they messed with me a little.

Airplane landing
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ASTORIA, NYC- While I wasn’t particularly concerned about returning to the US after visiting Cuba — the days of the strict embargo on travelers are over — I did wonder if there would be any residual hiccups when going through immigration.

Spoiler: there were.

Technically, I believe I’m supposed to keep all of my receipts, only stay in local-run accommodation, only eat at local-owned restaurants — basically, not purchase anything from any entity owned by the Cuban government. There is even a prohibited accommodation list on the US Department of State website.

Did I follow these rules?

I have no idea — I’m not asking who owns what everywhere I go.

Did I keep the necessary documentation?

Of course … I … did.

I came into Miami on a flight from Havana and stood in line to be processed, as usual. I looked around and it seemed as if I was one of the only blatant tourist around — everyone else appeared to have had some deeper form of connection to the place (i.e. being / having family from there).

When it was my turn I approached the booth and a young, kind of tough looking Latino dude looked through my passport and began his interrogation.

Where did you go?

Havana.

What did you buy?

Nothing.

What do you do?

I’m a camera operator.

Where do you work?

Newsmax.

Are you freelance?

No.

What did you buy?

A magnet for my mother in law.

Fuck.

I fell for it.

There seems to be a common tactic among immigration officials to ask you the same questions twice to see if there is any discrepancies in how you respond. It’s kind of like how you need to type a new password in twice before changing it. Any difference and you get stopped in your tracks by that bright red X with a message that your responses don’t match.

That’s basically what I received when the guy printed out a little ticket, handed it over to me, and directed me to go to tier 2 customs.

Maybe he thought that by magnet I meant cigars and rum? Honestly, I don’t think he thought anything — I just tripped a wire in his standard operating procedure.

Or maybe it’s just customary to mess with American tourists coming back from what were obviously trips of leisure in Cuba on principle?

To be honest, I don’t really mind being sent to tier 2 customs in the US. Tier 2 immigration can be a pain in the ass. But customs, well, I may be naive but I don’t have any fear of the agents in this country trying to scam or extort me. In a weird way, going through situations like this almost makes me appreciate being from here. All over the world people live in fear of their governments and public servants. And while the US government isn’t necessarily something to not fear — like any other government they do whatever the fuck they want — it is not my impression that this sentiment should be directed towards those poor saps digging through people’s bags in customs.

When you go to tier 2 customs you also often get to see all the weird shit that other people are trying to bring into the country. I’ve seen entire suitcases full of of meat, a small stuffed deer, and all kinds of random shit that makes you truly wonder about the mental disposition of the people carrying it. The question often isn’t why did they think they could get that through customs but why would they even want to?

On this trip to tier 2 customs my intrigued was captured by a guy who was trying to bring in a full size flat screen television. He had it wrapped in black garbage bags that were cinched around it with duct tape. What? Did this guy think we don’t have TVs in the USA? Did he really just spend all day(s) carting something so big and heavy across the world — more than likely paying additional checked baggage fees — that is readily available and dirt cheap just about everywhere here?

But the immigration officials didn’t seem baffled. This was probably one of the more ordinary things they see on a daily basis.

I’d really love to interview one of these guys sometime about all the weird shit they confiscate.

The other people around me in the customs area were from other countries and had massive amounts of stuff. I seemed to be the only US citizen and I just had a small rucksack and a shoulder bag. I kind of stood out.

When it was my turn the guy took my ticket and sent me over to the inspection table, but another dude intervened and waved me over to the x-ray machine. I ran my bags through. On the other side I looked up at the dude for further direction. Did he want to inspect my bags further? He just kind of grunted and did a hand motion for me to take my stuff and get out.

“I have no idea why they sent you here,” he said.

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Filed under: Cuba, Travel Diary, USA

About the Author:

I am the founder and editor of Vagabond Journey. I’ve been traveling the world since 1999, through 91 countries. I am the author of the book, Ghost Cities of China and have written for The Guardian, Forbes, Bloomberg, The Diplomat, the South China Morning Post, and other publications. has written 3720 posts on Vagabond Journey. Contact the author.

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VBJ is currently in: New York City

2 comments… add one

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  • Rob March 24, 2024, 6:50 pm

    I’m always interested in customs stories, it’s maybe an odd thing to be curious about but your story was a good one.

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    • VBJ March 25, 2024, 9:17 am

      Haha, yes, those guys have to have a very unique view on humanity after doing that job for a while!

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