Travel Tips

Travel to Cuba Independently & Legally

By on March 2, 2016

For decades, Americans have been barred from traveling to Cuba but we still continue to dream of visiting our neighbor in the Caribbean. Thanks to the easing of sanctions by the Obama Administration, Cuba is no longer the forbidden fruit of travel for US Citizens. Since the restrictions have loosened, tour companies have lied to Americans, misleading them to think that they cannot travel to Cuba independently and legally. Recently, my own travel dreams took me to Cuba. That trip is proof that Americans can travel to Cuba independently, have a meaningful experience and not fear prosecution.

Who Can Go To Cuba

It’s not Cuba who is excluding Americans, but our own government who puts limitations on travel to Cuba. These rules seem to be changing fast and furious as relations between our governments continue to normalize. As of December 2015, when I traveled to Cuba, you had to qualify for one of 12 categories of authorized travel. The Treasury Deparment, or more specifically OFAC, has issued general licenses within these 12 categories:

  • 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 information materials and
  • Travel related to certain authorized export transactions.

Each traveler determines whether or not they qualify for these categories. The best part is that you do not need to apply for or receive a paper license. The most recent amendment, published in the Federal Register on January 27, 2016, continues to ease tensions and pave the way for full fledged normalized travel to Cuba. With the upcoming visit to Cuba by President Obama in March 2016, I’m sure travel to Cuba will become even easier and hordes of Americans will soon be arriving in Havana.

Why Independently?

Traveling to Cuba independently is by far the most economical option. Tour companies charge an outrageous amount to visit and tour Cuba. Like most Americans, I was unable to afford this egregious option. Most tour companies fall under the “People to People” license which is only one of the 12 qualifying licenses or reasons to visit Cuba. Also, due to this requirement, tour companies have heavily structured itineraries. It’s not that I’m against tour companies, but I’m against bad tour companies that keep fellow travelers in the dark. Additionally, in Cuba, there are plenty of opportunities to hire your own tour guide or join various excursions and day trips set up by either your hotel, B&B or centrally located tourism bureau.


How to Book Airfare

Booking airfare was the most frustrating part of the process because booking travel to Cuba is unique. You could book a flight from Mexico to Cuba online with no problem. Remember, foreign airlines will still verify your citizenship jurisdiction and certify under which section of the OFAC license you are authorized to travel to Cuba. If you want to fly direct from the USA, there are several flights now available from various cities like Miami, New York, Los Angeles, etc. These flights are considered chartered flights because there are currently no regular commercial flights to Cuba. Charter flights to Cuba must be booked by a licensed and approved travel agency. I used an agency listed on the American Airlines website. The whole process reminded me of booking travel before the internet age. These travel agencies often do not pick up the phone and respond to email vey slowly. Once the details and paperwork are sorted, your agency will mail you an envelope with your paper airline ticket, Cuban Tourist Visa, medical declaration, copy of your signed OFAC affidavit and insurance documents. This process is surely to  become obsolete when regular commercial flights to Cuba resume and travelers can book online. Currently, the Department of Transportation has allowed the airlines to begin the process of restoring commercial flights to Cuba.


A panorama from the balcony of my flat. Vedado, Havana, Cuba

How to Book Accommodations in Cuba from the USA

Since American credit cards still do not work in Cuba, I chose to pre-book my accommodations so I didn’t have to carry around loads of cash. Airbnb allows travelers to pre-book accommodations in Cuba and pay with American credit cards. Also, since Airbnb is a partner with American Express, I was able to use points. Double win! There are no hotels listed on Airbnb but you have your choice of self catering flats, private rooms and B&B’s. Registered B&B’s in Cuba are commonly known as casas particulares and will give you the best local experience in Cuba. On Airbnb it may appear that one person has several listings for Cuba. This is very common as that person is acting as the booking agent or managing the online listings for that property and the owner. I booked various types of accommodation, with the amenities I wanted, and enjoyed each of them immensely. For booking a hotel, which are all officially state owned, you will have to book through an agent. Oscar Jacas, of A Nash Travel in Canada, was very helpful in booking my all inclusive beach side resort. They charge in Canadian Dollars and were much cheaper than the approved agencies in the US. When booking hotels and resorts, beware that many can be big soviet style buildings making it seem like East Germany on the Sea.


With an air ticket in hand and your accommodations booked, you have the biggest expenses sorted, a place to sleep every night and a rough outline of your Cuban itinerary. At casas particulares especially, you will have a local contact, basic tourist information and an in house concierge readily available to make your life in Cuba more enjoyable.


Check out this sample 10 Day itinerary 

For update government rules by the Trump Administration for American travelers going to Cuba check out my recent article here. 


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Angel Castellanos
Pasadena, CA

I'm a US based travel expert and spend my time teaching people how to travel well, smart and often. I'm passionate about travel and helping people save time & money. This blog, or travel lounge, is a collection of my practical travel advice and experiences from traveling 8-10 weeks internationally each year. I believe that travel has never been easier and that everyone can achieve their travel dreams. Happy Travels!


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