Traveling to Cuba as an American (Trump Era)

Old School pink 1960s car in front of the Cuban Capitol building in Havana ,Cuba.

I am a Florida girl and for the longest time it killed me that it felt like Cuba was at my fingertips, but I wasn’t allowed to go. 90 miles off the coast of Florida, less than an hour flight, and a past between our countries that seemed ages ago was holding back cultural exchange between the people of Cuba and the USA. When Obama lifted travel restrictions to Cuba, I rejoiced, but now with a tightening grip hold by Trump Era Regulations it looks like it is getting a lot harder. 

Recently there has been widespread confusion about how to travel to Cuba legally, and it has begun to deter Americans from visiting this scenic Caribbean Island. Don’t worry while cruise ships have stopped going to Cuba from the USA, THERE IS STILL A LEGAL WAY (and it is simple)! You have come to the right place for everything you need to know about visiting Cuba as an American. 

Current Regulations for Americans Traveling to Cuba

Sarah Fay sitting on ledge in front of bright colored building and Cuban Flag in Trinidad Cuba.
In Trinidad, Cuba exploring the brightly colored colonial architecture.

Recently there is no question that Trump is tightening travel to Cuba, after a brief honeymoon of Americans traveling to Cuba with ease during the Obama era people are confused on the legality of traveling to Cuba. 

Recently Trump banned cruise ships in June 2019 from traveling to Cuba under new restrictions on travel to Cuba for Americans. The State Department said the United States will no longer allow travel to Cuba via recreational vessels, cruise ships, yachts, and private/corporate aircraft.  

After the January 2019 travel restrictions there are Twelve Categories of travel to Cuba and “Tourism” is not allowed. Also, the “people to people” category was eliminated (this functioned as a proxy for tourism) by Trump. 

I was combing the internet looking for the precise information that I needed in order to go to Cuba. And in truth it was not easy to find. The information on the State Department’s site is vague, not clearly defined, and I have never heard of it being enforced amongst my friends. 

Many Americans feel the easiest way to stay in compliance is to travel with tour groups. However, I would highly recommend you avoid the large tour groups, that will take you to tourist traps and sub-par overpriced restaurants. 

I suggest going on the “Support For the Cuban People” Category (this is what I did). This category gives you the flexibility to choose your own itinerary, travel freely within Cuba, and create an experience that connects you with locals and local businesses. It may seem daunting but it is actually quite easy to do on your own. 

What does “Support for the Cuban People” entail?

Horseback riding with local guide to waterfalls and coffee farms near Trinidad Cuba
Horseback riding with a local to a National Park near Trinidad, Cuba.

The best category in my opinion is the “Support of the Cuban People”, but I am partial because I love planning my own adventures and itinerary. Also, this category promotes socially responsible travel, since the main purpose of your visit to Cuba is to benefit in part financially and socially with locals through cultural exchange. 

This category is definitely vague, but works on an honor system. When I arrived back to the USA, no one asked to see my itinerary when I came back (although you are supposed to keep records of your travel for 5 years). 

It is important to create an itinerary with a full program of activities aimed at strengthening the civil society of Cuba. Mainly the USA does not want any American dollars ending up in the Cuban Military’s hands. Also, the aim is to increase contact between Cuban people and American citizens. The best resource I could find on the regulations other than the State Department’s site is HERE.

There are two options that are available under “Supporting the Cuban People”: 

A: Support Locals and Local Businesses 

Supporting a local in Cuba by riding in their pedi cab in Havana.
Supporting the local pedi cab industry and avoiding walking in the heat in Havana!

It is impossible to use sites, such as Booking.com/Hotels.com while I was in Cuba, so it was an easy choice to look on Airbnb for Casa Particulares. Casa Particulares are family owned homes that offer rooms at very affordable rates, and often include breakfast! Basically, my friends and I ate at paladares (family owned restaurants) and stayed at Casa Particulares in order to stay in compliance with the USA State Department’s regulations. 

Also, when we traveled to other parts of Cuba we organized Taxi Collectivos and taxis from our Casa Particular hosts to avoid the state-run taxis. On Airbnb experiences, you can also find some very entertaining local guides, salsa lessons, and foodie experiences that will have you interacting with locals that are just as excited as you to share their culture. 

As a general rule of thumb, connect over conversations with you host about life in Cuba and the culture over a meal, find a local to give you a tour, and find local businesses to support through buying souvenirs, eating at locally owned private restaurants, and you should be A-Okay! 

My favorite Casa Particulares: 

Trinidad landscape in Cuba.
View from the roof of my Casa Particular in Trinidad, Cuba.
  • Havana- Colonial Guesthouse B&B in Vedado makes you feel like your at home, with breakfast included this is the best place to start off your day!
  • Trinidad- Stay at La Casa Cubana is a beautiful Casa Particulars in the center of Historic Trinidad, Cuba.

Virtually all Casa Particulares are on Airbnb, but book in advance or be at risk paying more for dingier headquarters, since Cuba is very popular right now! Click here for $30 USD off your first stay when you sign up for Airbnb. 

Favorite activities in Cuba: 

  • Get a private driver to give you a lift in a vintage car and tour Old and Central Havana. 
  • Take a salsa class. 
  • Private tour guide of Trinidad to teach you about the history, culture, and daily life in Trinidad. 
  • For $20 USD get a full day tour to a coffee farm, waterfall, and swimming hole in a national park from Trinidad. 
  • Have a cooking lesson at a casa particular with the host. 
Old school red cars from the 1960s in Havana , Cuba.
Hire a private driver in an old school car in Cuba!

B: Volunteering 

While I did not get to volunteer when I was in Cuba, I do love to try and leaving a positive impact when I go to places by supporting social enterprises. However, this would be a great way to support the Cuban people and to be compliant with the regulations. But it is important to make sure that the organization is a nonprofit and non-governmental organization. 

Volunteering allows you to see another side to a country and is more intimate than any other way of traveling. The conversations you will have will be priceless from important issues, to understanding what life is really like in a country. Also, you will often find the best information on local places to eat, things to see, that you would not otherwise have found in any guide. 

What activities don’t qualify? 

The Support for the Cuban People category does not include relaxing at the beach at an all-inclusive resort, what ever excessive “free-time” means, and/or spending money at enterprises on the Cuba Restricted List( state run entities the U.S.A. thinks has military ties). 

Visa and Immigration Process 

This process was the easiest that I ever dealt with in my honest opinion. If you have any questions related to the visa, immigration process, and/or flights to Cuba check out the answers below. 

Booking your Flight

Many major airlines fly to Cuba, including: Delta, Jetblue, American Airlines, and United. Generally, you will have a layover in Florida, before heading off to Cuba. I found my flights using Google Flights, but I also recommend checking out Kayak and Skyscanner. 

Getting A Visa

When entering Cuba as an American, you will need a pink/or green visa card for entry into Cuba. Pink cards are for entry from the USA as an American and green cards are for entry for Americans from another country (think entry from Mexico or Canada). 

You can preorder the visa online that is good for 180 days after issuance for trips up to 30 days in length. However, the cheapest and most efficient way is to purchase the visa through one of the major U.S. airlines flying to Cuba (Jetblue, Delta, Southwest, United, and American Airlines). The price ranges from $50-100 USD, and requires a passport, boarding pass, and credit card. I booked my flight with Delta, since there visa only cost $50 USD. 

The only thing you have to prove before you get on a flight to Cuba is that you have a flight out. See piece of cake! 

On completion of your trip to Cuba and reentering the USA, Cuba immigration will ask to see your pink/green tourist card and then USA immigration asked me nothing about my trip (so stop sweating it!). 

I was prepared with a little itinerary of my trip to be safe, but it was unnecessary. 

Currency and Exchange, Credit/Debit Cards, and ATMs 

There is no putting it nicely, as an American with US currency you are going to be ripped off on the exchange rate. With a penalty of 10% off the get go when you exchange money. Also, take all the cash you have and want, since American credit and debit cards do not work in ATM’s or anywhere in Cuba for that matter. 

Another interesting thing I found was that Cuba has two currencies, the Cuban Convertible Peso (CUC) and the Cuban Peso Nacional (CUP). The CUC is what the tourists use and has an exchange rate of $1 USD to 1 CUC, whereas the CUP has a 25 CUP to 1 USD exchange rate. I mean seeing that things were 100x more expensive with the CUC, no matter where you are from as a tourist you will be spending a lot more for everything. Cuba is not as cheap as you would think. So be warned! 

Watch your change. Sometimes you maybe given CUPs as change, which means you could lose a lot of money. For instance, someone may give you 20 CUPs change (about 1USD), instead of 20 CUCs ($20 USD). 

Sarah Fay travel blogger in Trinidad Cuba.
Trinidad, Cuba

Where to exchange money in Cuba?

As an American in Cuba, prepare to come with all of the cash that you will need or want during your stay. Why you ask?

Currently US banks don’t do business in Cuba. American bank cards simply do not work in Cuba. Thus, you must carry an uncomfortable amount of cash with you at all times. Finally that money belt my mom is always trying to get me to wear came in handy! 

Well the deal is you cannot get CUCs in advance of your visit. Right off the bat you will have to exchange some money at the airport in Havana in order to get a taxi into the city ($25 CUC= $25 USD). Then you have some choices when you are in the Havana. You can exchange money all your money at the airport, major banks in the city, most hotels, and get lucky like I did and get a 1:1 deal at your Casa Particulares and/or Airbnb. (Foregoing the 10% penalty of exchanging USD for CUC.) 

Some people recommend exchanging USD for Euro and then exchange Euros for Cuban Pesos. But with exchange fees, it will most likely cost the same. So, I decided to wait to exchange there. Also, the question is now how much do you need to survive in Cuba. I would recommend $700 USD for 9 days. I spent less than that, because I booked Airbnb’s and paid for accommodation with a card via the app.  

Also, be warned you cannot exchange CUC when back in the USA, so you need to exchange this at the airport before you leave. When I was leaving I needed a minimum of 22 CUCs to exchange back to USD, don’t know why but I thought I would leave you that tid bit. 

Will your credit and debit cards work in Cuban ATMs?

While my Australian friend was able to take out money using his Visa card at a Cuban ATM machine in Havana. I was not able to because U.S. bank cards do not work. So here is just ONE MORE REMINDER TO BRING CASH!!!! 

I also exchanged as I needed more CUC, because I did not want to get stuck with a lot of money that I would get possibly penalized more for exchanging back to USD. 

Pack your bags and GO! 

Sarah Fay on the Malecon Havana, Cuba
Sarah Fay on the Malecon in Havana, Cuba

I though traveling to Cuba was going to be difficult as an American, but it was actually extremely easy and a smooth process. Trust me if I could travel to Cuba with only a day’s notice and get there and back safely, you can too! Hopefully, with the information in my blog post, you will be able to navigate the legal requirements for entry, find the best local places to stay, and really find activities that allow you to interact and enjoy Cuban culture and people. Enjoy Cuba from a genuine perspective by staying with a local, living like a local, and experiencing the delightful food and colorful culture.  90 miles away, but a world apart, Cuba should be at the top of your list! 

Travel to Cuba as an American.Are you an American looking to travel to Cuba? Here is everything you need to know to comply with Trump regulations and legally travel to Cuba from the US.

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2 comments

  1. This is great information! My Spanish is pretty rusty, how difficult is it to use English there?

    1. Hey there. I always found someone that spoke English. Especially in Havana. But when you are in smaller towns it can be more difficult, but with patience and google translate you will be fine!

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