In July of 2015, I boarded a plane (legally) bound for Havana, Cuba from Cancun, Mexico. For many years I had dreamed of visiting Cuba, but I had no idea how I was going to make the trip possible.

As an independent traveler, I knew that I did not want to take an organized tour to the country and have every single day of my trip dictated to me, so I decided that I was going to find a way to make the trip possible by going on my own.

Cuban Flag

A Brief History of US-Cuba Relations & Why Americans Were Unable to Travel to Cuba

According to the U.S. Department of State, Cuba’s current authoritarian regime assumed power by force in 1959 during the Cuban Revolution and then proceeded to restricted the freedoms of Cuban people, repressed political opponents, and violated human rights.

In 1962, a few years after the Revolution began and tension began to rise between Cuba and the United States, President John F. Kennedy placed a permanent embargo on trade with Cuba. The embargo was strengthened further in 1992 and then again in 1996 with the Helms-Burton Act.

From the 1960s when the permanent embargo was put in place, Americans were not legally allowed to visit Cuba until 2011 when the a licensed educational program called People-to-People allowed travelers to visit the country on an educational-basis.

In December 2014, President Obama eased restrictions for traveling to Cuba for people falling under one of the following 12 categories:

  • Family visits.
  • Official government business.
  • Journalism. (*Me)
  • Professional research and meetings.
  • Educational activities.
  • Religious activities.
  • Public performances, clinics, workshops, exhibitions and athletic competitions.
  • “Support for the Cuban people.”
  • Humanitarian projects.
  • Activities of private foundations or research for educational institutes.
  • Exporting or importing information or “information materials.”
  • Travel related to some authorized export transactions.

Since Congress has the ultimate power to end the embargo, unless travelers fall under one of the aforementioned categories, traveling to Cuba is still not legally (meaning: general tourism is not allowed).

Further Reading:

travel cuba

This guide covers the following topics:

  • The Planning Phase: Booking Flights
  • The Entry Phase: Visas, Passport Stamps, Health Insurance
  • The Traveling Phase: Money in Cuba

Read More: Accommodation & Travel in Cuba

*Please Note: The following information is valid as of July 2015, and as the nation moves closer to lifting the embargo, the information below is likely to change.

The Planning Phase: Booking Flights

Many Americans that enter Cuba do so through Mexico or Canada. There are other ways to enter the country however including flying directly from the United States or traveling through an alternate country that flies directly into Cuba.

Airplane Cuba

Traveling through the United States: Currently, JetBlue is the only major U.S. airline operating weekly chartered flights into Havana from New York City, Tampa, and Fort Lauderdale-Hollywood. Time Magazine reports that starting in late 2015, there will be additional ways for Americans to enter Cuba including via ferry, cruises, and flights out of BWI, Miami, and Tampa.

Traveling through Mexico: While I was planning a vacation to the Riviera Maya area of Mexico, I decided that since I was going to be a mere hour and a half away from Cuba, that I would travel directly from Cancun into Havana.

Booking my ticket from Cancun to Havana from the United States without using an agency turned out to be a little trickier than I had thought it was going to be. When I went to purchase tickets online on the Cubana website using my American credit card, the transaction was denied, which meant that I had to wait until I got into Cancun to pay with cash.

There are currently two airlines that operate directly between Cancun and Havana: AeroMexico and Cubana.

  • Aeromexico has daily mid-morning flights between Cancún (CUN) and Havana (HAV) and daily afternoon flights from Havana–Cancún.
  • Cubana operates flights daily between Cancún and Havana (3:05PM) and also daily between Havana and Cancún (1:45 PM).

I purchased my ticket at Cubana’s Cancun location (Ave Tulum 232 local A1 y A3) and the ticket cost 5,623 MN pesos (about $350 USD).

The Thrifty Traveler, a points and miles blogger said that his American card was also declined when trying to purchase a ticket via the Cubana website, but that he had success purchasing one with his credit card for $340 USD via the third party website Cuba Travel Network, so this is another option to book your flight before you travel to Mexico.

Traveling through Canada: Air Canada operates flights to Cuba out of Montreal, Toronto, Windsor, and Vancouver.

Traveling through a different country: Flying into Cuba can be done from a number of different countries including England, Panama, and Brazil. A complete list of countries can be found on the Cuba Jet website.

The Entry Phase: Visas, Passport Stamps, Health Insurance

Cuban Visa

A visa is required for all international travelers entering Cuba.

Visas: For Americans traveling through Mexico, visas can be purchased directly at the Cancun airport at the Cubana ticket counter directly across from the Cubana check-in area. If you are flying through another entry point, such as the United States, contact your airline carrier to determine how to obtain a visa for Cuba.

cuban passport stamp

Passport Stamps: Most Americans traveling through Cuba will have their tourist card stamped and not their passports, however in some instances, a Cuban immigration officer might stamp your passport. If you are traveling to Cuba legally, there is no need to worry, however if you are traveling to Cuba illegally (and do not have Global Entry), you may be questioned by immigration officers upon your return to the United States.

Health Insurance: The Cuban government states that “travelers shall have a travel insurance which covers medical expenses or a policy for medical expenses with coverage in Cuba…Residents in the United States traveling to Cuba will have to take out their insurance policy at their home country of departure from Cuban insurance companies.  The arrangement shall be made through agencies associated with Havantur-Celimar Company. US insurance companies do not provide coverage in the Cuban national territory. Upon demand after their arrival, travelers shall present a policy, insurance certificate or travelling assistance card valid for the time span they will stay in Cuba.”

When I booked my ticket in Mexico, I was not asked whether travel insurance, and when I arrived to Cuba, I was not asked either. For the six days I spent in the country, I did not have insurance, but I would not advise traveling in the country without any.

The Traveling Phase: Money in Cuba

Cuba has a dual currency system: one for Cubans (CUP) and one for tourists (CUC).

Cuban Convertible Pesos

CUC – Cuban Convertible Pesos

The CUC (pronounced ‘kook’) are Cuban Convertible Pesos, and is the type of money that is issued to and used by tourists. 1 CUC = 1 USD and can only be obtained within Cuba. The CUC comes in values of 1, 3, 5, 10, 20, 50, and 100.

Cuban Peso

CUP – Cuban Peso

The CUP (or moneda nacional) are Cuban Pesos, and is the type of money that is used primarily by Cubans. The CUP is about 25 times less valuable than the CUC (1 CUC = 25 CUP) and can only be obtained within Cuba. The CUP comes in values of 1, 3, 5, 10, 20, 50, and 100.

*Note: ‘1’ CUP and ‘1’ CUC come in both bill and coin form. CUP coins are always gold and CUC coins are always silver. Make sure you pay attention to the change being given back to you to avoid getting scammed.

Exchanging Money: When you arrive to Cuba, you will need to exchange your cash into CUP. The American dollar will be charged a 10% penalty, so it is advised to carry a different form of currency into the country, such as Euros, Pounds, or Canadian Dollars. The airport will not give you the best rate for your money, so exchange the majority of your money at Cuban banks or Cadecas (currency exchange shops).

For more information on exchanging money in Cuba, check out this great article on TripAdvisor.

Credit Cards and Debit Cards: American credit and debit cards do not work in Cuba, so make sure to bring cash – lots of it.


Have you been to Cuba before? Share your experiences!