How to Easily Travel to Cuba from the US

Here’s the tl;dr – Americans can easily travel to Cuba from the US, they just have to do culturally enriching activities, save their receipts, and avoid certain hotels.

Can Americans travel to Cuba? Short answer: yes! Long answer: yes!!! The thought of traveling to Cuba from the US can be pretty daunting for many Americans, but it doesn’t have to be. Cuba is so close to the US and yet so culturally different that you really get to immerse yourself in a new culture without an overnight flight or $1000+ airfare.

Americans can travel to Cuba from the US by entering under Support of the Cuban People general licensing without having to pre-apply for a visa.

If you are someone that likes to immerse yourself in culture and explore when you travel, Cuba (and Havana in particular) is a great place to visit, and you’ll have no problems complying with the visa requirements.

If you’re an American wanting to visit Cuba to sit on the beaches and drink cocktails all day, I absolutely love that goal for you, but you should definitely find a different Caribbean island to go to (though the piña coladas probably won’t be as good tbh).

One of the things former President Obama did in his final term as president was to take huge steps forward in normalizing relations with Cuba in 2015. He ended the trade embargo and eased restrictions on travel, allowing Americans to plan their vacations to the island for the first time in decades. There were concerns about how much restriction Trump would put back in place during his administration, but ultimately the changes during his term do not significantly reduce the ability of US citizens to travel to Cuba from the US. 

My husband and I traveled in Spring 2019 and did so under the Support for the Cuban People category. This travel is legally allowed without prior authorization of either government. If you are seeing anything in books or blogs about the “people to people” travel option, that has not been a valid option for multiple years, so don’t plan to pursue that avenue.

There are also a couple of other types of approved travel such as family visits and religious activities, but for most people that won’t apply.

Culturally Enriching Activities

What does it mean for an activity to be “culturally enriching” in this instance?For our purposes, this refers to activities that “enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities; and result in meaningful interaction with individuals in Cuba.”

Examples include:

• Staying in a room at a rented accommodation in a private Cuban residence (casa particular)

• Eating at privately-owned Cuban restaurants (paladares) i.e. any eatery that isn’t state owned. This is very easy to do, and the seafood in Cuba is some of the best I’ve ever had. As were the piña coladas.

• Shopping at privately-owned stores run by self-employed Cubans. Again, any shop that isn’t state owned will cover this, and it’s pretty easy to avoid.

There is so much to do in Havana that meets this criteria! When we were in Cuba, we took a salsa class in Havana through Baila Habana. I booked ours via email exchange with Sabine, the manager, and scheduling was super easy – she let us pick the 2-hour window between 9am to 8pm that worked best for us. We had an absolute blast with the two instructors who spoke great English and had a great sense of humor. I have absolutely no rhythm, so I was unfortunately unable to pick up or retain much (ok, absolutely nothing at all), but that was not for lack of excellent instruction, and we both had a great time.

We also did an architecture-focused walking tour through Havana. This was booked with our B & B host’s son who did a wonderful job of pointing out all of the influences of colonial Spain while talking excitedly about the future development of the city as one that locals love and travelers want to visit. Once again this was booked via email and very flexible on timing.

Later in the trip, we took a day trip to Viñales where we visited a tobacco farm, rode horses around the countryside, and toured a cigar production facility. That was a full day private trip with our Cuban guide and Cuban driver. We drove around in a vintage car that didn’t have a working speedometer or gas gauge. Or seat belts. The landscape outside of Havana was stunning. More about that in a future post!

If you are a Conan O’Brien fan, he was one of the first American TV personalities to visit Cuba after the restrictions eased for his “Conan without Borders.” While quietly filming the episode, he took a Spanish class, joined a Salsa band, toured La Corona cigar factory in Havana, and toured a rum factory. All of these would count for activities in support of the Cuban people. He also discovered rum in a box, which is popular on the island. And while that is not necessarily a Support for the Cuban people activity, I highly recommend it. Or sangria in a box for that matter. 

Note: Viator and GetYourGuide do not have activities in Cuba at this time, so you’ll have to do a little bit more legwork to book your experiences. Trip Advisor will be your go-to for pre-trip research.

Saving Receipts

This is going to be the easiest part. Just hang onto them in case you’re asked for them while going through US customs upon your return. We were not not asked about our itinerary or asked for our receipts at all. The only question we had to answer was how many cigars we were bringing back with us. Note: if you want the border agent to think you’re cool, the answer should not be zero.

Avoiding in Certain Hotels

If you want to travel to Cuba from the US, don’t plan on a 5 star luxury accommodation. If that’s the only way you travel, you may want to sit Cuba out for awhile. If you’ve ever stayed in a Bed & Breakfast, Airbnb, or VRBO, you’ll do just fine in Cuba. Refer to this list to determine which hotels you should not stay at if you decide to travel to Cuba from the US.

We stayed at El 81 Guesthouse which is now ranked the #1 B&B in Havana. It is hosted by Melba and Alberto, who, as far as I can tell, are the sweetest people you will ever meet. The flat was quiet, clean, well-decorated, air-conditioned and had both ocean and city views from the roof-top.

We had the option to dine-in one evening on the terrace with a multiple course meal prepared by Melba, and it was genuinely one of the cooler experiences we’ve had. Highly highly recommend. Did I mention nightly rates are under $60 USD?

Bonus, it was also a 3-minute walk away from multiple paladares (privately owned restaurants for those of you paying attention). Our favorite was Castas y Tal. When I say their piña coladas changed my life for the better, I mean it. And 5 years later I can still taste the seafood pasta.

That’s basically it! Plan fun culturally immersive activities like you would any other trip, stay with the world’s sweetest hosts (or people just like them – I also recommend using Trip Advisor specifically for Cuba accommodations and experiences), and hang onto to your receipts in case anyone asks what you did each day. 

Other tips for Travel to Cuba from the US:

American debit cards and credit cards do not work in Cuba. You will need to bring cold hard cash with you to exchange, and bring enough to last you for your full trip.

Not going to lie, this was a little stressful and we were running on a couple of dollars by the time we got to the airport to return to the U.S. I’m not saying you should pull cash out of your 401k and carry it around with you, but I am saying you should give yourself more of a buffer than you think. You never know how many cigars you’ll want to bring back with you.

American cell phones don’t have access to cellular data in Cuba, so you’ll be sticking entirely to WiFi while there. This might sound a little frightening if you were never a broke college student abroad that refused to turn on data and pay the extra daily fee, but reliable WiFi is everywhere.

If you happen to dip into a café for an afternoon mojito (which you will), just log onto their WiFi, get your bearings straight, and continue on with your day. If you are someone who might get very anxious without having cellular data, you may want to join the others that picked a different Caribbean island. 

To sum, Cuba is a wonderful, unique place to travel to from the United States. The Cuban people are incredibly warm and friendly and the history and culture is rich. With a little advanced planning and an openness to new experiences, you will have a very enriching and fun vacation. 

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