The Trump Administration’s Changes to Cuba Travel

A lot of folks have been asking me my opinion on the legal changes to Cuba travel announced in June 2017, by President Trump. I’d been quiet about it for many reasons: 1) I’ve been busy traveling throughout Central Asia since the announcement; 2) The changes were still pending official implementation by the Treasury and Commerce departments; and 3) It’s a complex question to try to answer casually. But here are my thoughts on Trump and Cuba travel.

The Embargo Was Never Lifted

First, some background… it’s important to note that the embargo was never lifted under Obama. Only an act of Congress can do that. Second, however intricate the US-Cuba issues may be, there are a few things that are crystal clear: the embargo against Cuba is counterproductive and deleterious to both U.S. and Cuba interests. The only people who benefit from the embargo and its related policies are:

  1. The businesses built around it (i.e. people-to-people tours)
  2. The older generations of understandably traumatized Cuban-Americans.
  3. U.S. Politicians vying for the Cuban-American vote in Florida.

That’s about it.

Read more about why the embargo should be lifted here – it’s a bipartisan topic.

Why Did Trump Make these Changes to Cuba? Because the Cuban-American Vote is Critical

Politicians have continued to uphold these anti-Cuba policies out of fear of losing Florida, one of the most important states in U.S. elections. Where most Cuban-Americans live. No politician would risk their entire election by standing up for a tiny island that often shoots itself in the foot. So for decades, politicians have continued catering to the Cuban-American vote by upholding the embargo and sugarcoating it about the Cuban people while never pushing for any embargos to the rest of the communist countries or dictatorships committing far worst human rights atrocities around the world.

Many argue that Trump’s anti-Cuba stance helped him win Florida in 2016.

Who Suffers From the Embargo/Travel Restrictions to Cuba?


These policies barely make a dent to the well-being of the Cuban government or its officials, the U.S’s allegedly intended targets. These guys will always be in the “front” of the food ration lines, driving new cars and connected to their free internet at home.

The ones that will always suffer from these sanctions and embargos are the Cuban people. Who in turn resent the U.S. and end up supporting their government even more, despite their short-comings because the Cuban government will always get to say “it’s the U.S.’s fault” every time something goes wrong.

Fighting Totalitarianism with Totalitarianism

These policies also further deplete the Cuban people’s will and power. Without the embargo limiting extra tourism income to the people’s pockets, they could have more access to income to better build some self-autonomy for themselves.Without the embargo restricting the Cuban people’s contact with Americans via travel restrictions, Cubans could have more access to information from the other side of this political war instead of only hearing what the Cuban government says.

I saw these changes happening after Obama loosened restrictions. I saw Cuban entrepreneurs cashing in on the waves of American travelers, I saw Cuban families engaging in hour long debates with Americans where both sides left enlightened.

What I saw was a boost of empowerment for the Cuban people and powerful cultural exchanges between Cubans and Americans. I saw the government having to catch up to their people’s renewed sense of independence, however small it may still be.

cuban entrepreneur fruit stand

But instead, under the embargo and by adding more restrictions, the Cuban people will continue to remain poor because of their government’s inefficient policies but also, in addition, because there’s a world giant adding to their problems. And instead, they will continue to view the U.S. government as a detriment to their well-being. Even when they see something wrong with their country, there is nothing they can do because they’re caught powerlessly in the middle of a political war and at the mercy of their government.

The Embargo Empowers the Cuban Government

In turn, the Cuban government is empowered (the very thing the U.S. says the embargo serves to destroy) because they can rest assure that little to no opposition will happen if the Cuban people are primarily focused on basic day-to-day surviving while seeing their government as a victim of U.S. bullying. Good job, U.S. government.


Now you know what I think of the Trump’s changes and the still-standing failure that is the U.S. embargo against Cuba.

But what do these recent changes actually entail? Here’s my analysis…

The Legal Changes for Traveling to Cuba in Trump’s America

cuban rickshaw entrepeneurs

Here is a quick summary of the key points to know, directly from OFAC’s latest FAQ, published June 16, 2017:

1. No legal amendments have been officially implemented into the Treasury or Commerce department’s regulations. So these rules aren’t even in effect yet.

2. If you’ve booked anything pertaining to Cuba travel before June 16, 2017 – Trump’s changes don’t apply to you. You can still go as an individual seeking an educational experience.

3. The most hurtful change that will restrict individual travel to Cuba is that you will no longer be able to go as an individual on your own people-to-people self-created tour.

Somehow, the Trump Administration thinks that forcing U.S. travelers to go in tour groups owned by American companies will empower the Cuban people and promote entrepreneurs? The logic here is baffling.

4. In the future, the easiest category for everyone may be to go on your own self-created tour under “Support For the Cuban People”. We will have to wait on the amendments to see if they change what this category entails, but currently, the category serves to “provide support for the Cuban people, provided that:

(1) The activities are of:

(i) Recognized human rights organizations;

(ii) Independent organizations designed to promote a rapid, peaceful transition to democracy; or

(iii) Individuals (you!) and NGOs that promote independent activity intended to strengthen civil society in Cuba;

5. The second major change will be that you cannot engage in certain entities/businesses owned by factions of the Cuban government. The list of these businesses is supposed to come out soon.

This will almost certainly mean that it will be illegal to stay at a hotel (all are owned by the Cuban government). However, many people rarely stay in Cuban hotels since they are almost always overbooked, overpriced, and horribly run. Casa particulares (homestays) and Airbnb are the way to go. They’re cheaper, have better food/service, and directly support the Cuban people. So this is not much of a loss in terms of travel.

6. All other requirements/Obama’s changes are still in effect. You still don’t need to apply for a license if you meet one of the 12 categories of travel. You can still book your flights or cruises independently online.

7. Itinerary auditing will be enforced. As Fabiola Santiago of the Miami Herald so kindly puts it:

Such control might help streamline the Big Brother work of the Treasury Department, which will audit itineraries from now on instead on relying on the Obama-era honor system that allowed people more open engagement under the 12 categories of permitted travel.

For help creating an itinerary or travel planning, feel free to contact me.


If you have any questions, feel free to post a comment below!