How to Travel to Cuba as a U.S. Citizen
“HOW?” That was the first question every single person asked when I told them I was planning my annual New Year, New Country trip to Cuba.
There is a common misconception that U.S. citizens cannot travel to Cuba. However, travel to Cuba has been legal for Americans since JetBlue’s flight 387 left Fort Lauderdale, Florida and landed in Santa Clara, Cuba on August 31, 2016. Flight 387 was the first commercial flight to Cuba since 1961!
So, what happened?
Simply put, President Obama.
During Obama's presidency, significant strides were made in re-establishing diplomatic relations between the United States and Cuba. In 2014, Obama announced the beginning of a historic thaw in hostility, marking the start of efforts to normalize ties. This led to the reopening of embassies in both countries in 2015. And in 2016, Obama became the first sitting U.S. president to visit Cuba in 88 years. Before then, the last sitting U.S. president to visit Cuba was Calvin Coolidge in 1928! Other important strides made included easing travel and trade restrictions, as well as allowing limited financial transactions between the two nations. Obama's administration also removed Cuba from the U.S. list of state sponsors of terrorism. As such, many Cubans refer to Obama’s presidency as the “good times.”
However, much of the progress made was quickly unraveled during the following administration of He Who Must Not Be Named. Under Captain Combover, the terrorism designation was reinstated and new sanctions were issued to keep U.S. citizens from staying in certain hotels, eating at certain restaurants, and supporting businesses owned, affiliated, or funded by the Cuban government. Despite these rollbacks and continued sanctions, Cuba remains accessible to Americans but there are rules and regulations (literally) that must be followed to do so legally.
Overall, it’s a six step process. First, you need to determine your travel authorization. This determination will need to be disclosed in the next five steps required which are booking accommodations, booking a flight, getting health insurance, securing an E-Visa, and completing a D’Viajeros form. I know, I know. It sounds like a lot. But I promise, it is very manageable if you follow the information laid out for each step below.
Travel Authorization
Under the guidelines established by the U.S. Department of Treasury’s Office of Foreign Assets Control (OFAC), there are 12 categories of activities that permit travel to Cuba. These categories are:
Family visits;
Official business of the U.S. government, foreign governments, and certain intergovernmental organizations;
Journalistic activity;
Professional research and professional meetings;
Educational activities;
Religious activities;
Public performances, clinics, workshops, athletic and other competitions, and exhibitions;
Support for the Cuban people;
Humanitarian projects;
Activities of private foundations or research or educational institutes;
Exportation, importation, or transmission of information or informational materials; and
Certain export transactions that may be considered for authorization under existing Department of Commerce regulations and guidelines with respect to Cuba or engaged in by U.S.-owned or -controlled foreign firms.
Outside of the 12 categories listed above, there are two additional ways to enter Cuba: (1) with a license issued by OFAC or (2) as a Cuban National returning home.
The category used most often is Support for the Cuban People because it is a general authorization. And it is the category I used for my New Year’s trip to Havana. However, as mentioned, rules and regulations apply. For example, you must stay in a private Cuban residence (casa particular), eat at privately-owned Cuban restaurants (paladares), and shop in privately-owned stores run by Cuban entrepreneurs (cuentapropista). Additionally, you must maintain a full-time schedule (meaning 6-8 hours per day) of activities that promote and strengthen Cuban civil society and connect with Cuban people.
Accommodations
As I mentioned above, you cannot stay anywhere owned by the government. ALL, and I repeat, ALL hotels in Cuba are owned by the government. Even hotels operated by well-known brands like Iberostar do not actually own their hotels or operate independently. Instead, Cuba retains ownership of the property and splits the profits. This is usually a 51/49 split with the government retaining the larger portion.
However, it is extremely easy to find private accommodations through Expedia and Airbnb. And the rates are very reasonable. I used Expedia to book a room at JM7, a casa boutique in Old Havana. It’s essentially a privately owned boutique hotel and it was incredible. A double room was only $656 (which is crazy over a holiday) and included a full breakfast every morning. Highly recommend!
Flights to Cuba
Now, you need to book a flight to Cuba. Only a handful of commercial airlines fly from the United States to Cuba – United Airlines, Southwest, American Airlines, and Delta. More airlines used to offer flights, like JetBlue, but have ceased operations due to lack of demand. Naturally, most of these flights have a layover in Florida. And this was the most expensive portion of the entire trip. My Southwest flight to Havana was $964.01.
Health Insurance
Booking your flight also handles your next travel requirement – health insurance. When you book your flight, you’ll notice a $25 health insurance fee. To demonstrate proof of insurance, you’ll need to maintain your boarding pass. Essentially, your boarding pass is your insurance card. Keep it and protect it!
E-Visa
Your fifth requirement is securing a visa. However, this process is not done through the embassy like most countries. Instead, you will use a third party to secure an E-Visa. I used Cuba Travel Services. The E-Visa costs $85 and should be secured in advance of your travels. You will need five pieces of information for the E-Visa:
Flight Date,
Airline,
Airline Confirmation Number,
Cuba Province (i.e., Havana), and
OFAC Category.
Once you place your Cuba Visa Services order, you will receive an email that contains a PDF. This PDF is proof that you purchased an electronic visa. So, it needs to be printed. It will also provide another key piece of information – your E-Visa number. This E-Visa number must be entered into the D’Viajeros form which is your sixth and final requirement.
Entrance Form
The D’Viajeros form must be completed to enter Cuba. It’s a simple form and should be completed within seven (7) days of your departure. The form itself requires the E-Visa number you received, asks some health questions, and includes a customs declaration form. After you submit the form, you will receive an email containing a PDF containing your entrance form which must be printed and presented at the airport before boarding and upon arrival to Cuba.
