I’ll say it upfront: Being an American in Cuba is frustrating. There’s so much to see, so much to learn, so much to understand. You get to watch visitors from other countries explore as they like, while you’re constrained by government policies…on both sides.
Yet it’s totally worth it.

A three-paragraph history of U.S.-Cuba relations
By the time of the Cuban Revolution, U.S. financial interests included:
- 90% of Cuban mines, especially nickel
- 80% of its public utilities
- 50% percent of its railways
- 40% of the sugar production
- 25% of all bank deposits
With so much American influence, pre-Revolution Cubans embraced the culture. They drove American cars (you have wondered why nearly all of Cuba’s famous vintage autos are from Detroit, haven’t you?). They owned U.S. made televisions, watched films made in Hollywood, and listened to rock-and-roll. Baseball became–and still is–the national sport.
Then came Fidel Castro. Wanting to get out from under the thumb of the “U.S. Imperialists,” he looked to the Soviet Union for economic assistance, with a few dashes of political and military support, too. Khrushchev obliged. The aftermath of the Cuban Missile Crisis launched the Cold War.



The U.S. has strict regulations about going to Cuba
How strict? Check out the Federal Register, Part 515!
Naturally, the United States wasn’t happy about losing its sugar cane plantations; the Mafia hated giving up its IRS “exempt” gambling and prostitution operations; and then the U.S. tried to overthrow Castro. Ouch. No luck. And Castro did not take kindly to the effort.
Long story short, being an American in Cuba has been challenging for over half a century. Two governments at an angry stand-off, causing unnecessary grief for their citizens. For Americans, obstacles at every turn to visit the country. For Cubans, a nearly complete inability to get basic goods and supplies.
Then, things started to look up…
Relations were looking brighter under the Cuban Thaw (deshielo cubano) that began in 2014, under the Obama administration. Obama visited Cuba in 2016, the first U.S. President to set foot on Cuban soil since 1928. Obama and Raul Castro, in a process facilitated by Pope Francis, agreed to normalize relationships.
Hopes were high on both sides, as U.S. travel to Cuba became easier, remittances were freed up, and embassies were reopened–they had been closed since 1961–in Havana and Washington D.C. Cuba was removed from the State Sponsors of Terrorism list. Airlines and cruise companies started offering transportation and tour possibilities. All seemed bright…
But it all came crashing down…
Sadly, progress was abruptly halted. In June 2017, Donald Trump “cancelled” the deals. In November 2017, travel restrictions returned to previous levels, and new financial restrictions were put in place to eliminate transactions any support of businesses associated with Cuban armed forces.
In June 2019, the Trump administration announced that cruise ships would no longer be allowed to stop in Havana, a devastating blow to Cubans who had jobs at the port or in tourism. Not to mention Americans who had booked passage on a dream cruise to Cuba. On December 10–while I was in Cuba–flights from the U.S. were only allowed to land in Havana, severely limiting options for Americans and foreign visitors traveling from the U.S., in an attempt to repress Cuban trade with other countries, especially Venezuela.



What’s in store for 2020? Probably more restrictions. Although 187 United Nation General Assembly countries adopted a resolution in November 2019–for the 28th consecutive year–calling for an end to the economic, commercial and financial embargo imposed by the United States against Cuba, we can be fairly certain that the current administration will continue to add to the 190 new sanctions it has put into place. (BTW: Only the United States, Brazil, and Israel voted against the resolution.)



Some of the “restrictions” for an American in Cuba
Okay! Let me start by saying that, even with obstacles, travel to Cuba is worth every minute and dollar. There is nothing else like it on the planet and you will never, ever regret going.
Rules change constantly. Our itinerary was quite “fluid,” and had to be revamped, sometimes on an hourly basis, sometimes on the bus as we were headed to a place that was now off-limits. The tour guide and leader–both Cubans–never blinked. They simply referred to the “approved” lists and we changed course. It was all good.



As I write this in January 2020, here’s what I encountered:
- Absolutely NO American-issued credit cards or ATM access. This was a bit tricky for planning. We had to anticipate expenses and bring cash for the entire trip. There’s no “wiggle room” for error, so naturally, I brought more money than necessary. As it turns out, credit cards aren’t a good idea, anyway. Cuba doesn’t have the infrastructure to handle these transactions, and uses a third-party (read: non-secure) to process purchases.
- Most Americans travel under the “support of the Cuban people” category. Of course, we support the Cuban people, you say! What it really translates to is that the U.S. approves and regulates the itinerary. All activities on the itinerary are legally required, and attendance is taken for each event. No sneaking off to explore on your own.
- The itinerary cannot include any activities that support the Cuban military. Although a visit to the Che Guevara Mausoleum was on the initial program, I was crushed when it was eliminated, because the Trump administration deemed it a “show of military support.” (However, our guide and driver took a risk, and we drove by s-l-o-w-l-y…)
- The Cuban government-run travel company, Havanatur, had a few things to pile on, too. Our original plan to stop at a Jewish cemetery and Holocaust memorial was nixed, because we had been to St. John the Baptist Church (Iglesia Major of San Juan Bautista), the oldest church in Cuba, established in 1515. Apparently that was “too much religion” for the itinerary. Sure enough, any subsequent visits to plazas or sites with churches did not include entering as a group, although we could choose to go in by ourselves.
- Free time? What free time?? I knew this before I went, but it was still surprising. Independent exploration was limited to the evenings–when museums and attractions were closed–and for one three-hour period on the last day. Once you get a taste of Cuba, you want more, but have to settle for what’s given to you.
- Americans must keep receipts from travel to Cuba for five years. We also have to be able to provide “Proof of Compliance” for the trip, as dictated by 31 CFR § 515.574: Support for the Cuban People. We were provided with a daily list of activities, to show a full-time schedule (no free time, remember?) and evidence that we had meaningful interactions with Cuban individuals. Absolutely no mixing and mingling with Cuban government officials or members of the Cuban Communist Party, although I’m not sure how I would identify such a person.



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