Update 2019:  Given the recent changes, we are currently researching the process for Americans to travel to Cuba.  Check back for updates.

Only a short distance from the United States, but hidden just out of reach for most us Americans, this island has lived only in my dreams for years… actually over a decade.  

In 2014 restrictions eased, and many more Americans began making their way to the island.  I started planning, but hadn’t actually made it there when, in 2017, the rules tightened somewhat again.  But independent travel to Cuba for Americans is still possible.  In fact, it’s actually much easier than you might think!  You need to understand the requirements and keep some additional documentation, but that’s it.  My whole family just got back from Havana in May 2018, so I’ve got all the latest details.

There are 12 categories of travel that allow Americans to travel to Cuba, depending on what type of activity you will be engaged in.  Previously the people-to-people license was one of the most general categories to travel under.  After the new rules came into effect on November 9, 2017, you must travel with an official tour group if you choose this license.  But you can still travel independently, under another relatively general license called Support for the Cuban People.  This is the license we used, so this information is based on travel under that license.

When booking your flight, the airline will ask what general license you are traveling under.  Then, upon arrival at last airport before your flight to Cuba you will be given a document to mark the appropriate license category and sign.  (If you have a layover, you’ll do this then, but you can probably pay the $50 visa fee at the ticket counter when checking in.)  The gate agent will give you your tourist card, and you’re all set.  You don’t need to apply ahead of time, or seek any sort of special approval.

Check with your airline, but most major airlines include the cost of health insurance in the price of your ticket.  You will be required to keep your boarding pass on you while in Cuba as proof of insurance.

Make sure you pack everything you'll need, including plenty of cash.  I think everyone knows this, but American credit and debit cards WILL NOT WORK in Cuba.  I took $2,000 cash to cover five days for our family of four.  We only spent a few hundred (not including our Airbnb), but I wanted to be prepared.

We heard the same refrain over and over again during the planning process, and even on the flight down.  "What you bring is what you have."

So, parents, this means that you need plenty of diapers, wipes, and formula (if your kids need them).  I've heard that you can buy disposable diapers at the supermarkets, but they are very few and far between.  On top of that, diapers are very expensive and often hit-and-miss on sizes.  So, if you're going for a shorter trip, just pack what you need.  For an extended stay, you'll want to secure some way before you actually need them.

Once you've arrived, you'll want to make sure you know what requirements must be met while traveling.  The official documentation is HERE, but in general this license requires you to keep a full schedule of activities with independent businesses and organizations that promote civil society and result in meaningful interactions with the Cuban people.  Make sure to keep all receipts and records for five years.

Example 1 to §515.574:

An individual plans to travel to Cuba, stay in a room at a rented accommodation in a private Cuban residence (casa particular), eat at privately-owned Cuban restaurants (paladares), and shop at privately-owned stores run by self-employed Cubans (cuentapropista) during his or her four-day trip. While at the casa particular, the individual will have breakfast each morning with the Cuban host and engage with the Cuban host to learn about Cuban culture. In addition, the traveler will complete his or her full-time schedule by supporting Cuban entrepreneurs launching their privately-owned businesses. The traveler's activities promote independent activity intended to strengthen civil society in Cuba.

Because the individual's qualifying activities are not limited to staying in a room at a rented accommodation in a private Cuban residence (casa particular), eating at privately-owned Cuban restaurants (paladares), and shopping at privately owned stores run by self-employed Cubans (cuentapropista) and the traveler maintains a full-time schedule that enhances contact with the Cuban people, supports civil society in Cuba, and promotes the Cuban people's independence from Cuban authorities, and that results in meaningful interaction between the traveler and Cuban individuals, the individual's travel qualifies for the general license.

Having read all that legal bit, these are the things my family did to make sure we were following the rules.

Rented an apartment from an individual through Airbnb

THIS was our place, and it was perfect.  A great location in Old Havana, air-conditioned bedrooms, and a beautiful terrace.  Our wonderful hosts worked with us to arrange any transportation, reservations and other activities we wanted.  They even got us in for a last-minute spot at Paladar San Cristobal.

Shopped with local vendors

Tried an Airbnb Experience 

We did a "Walk my Neighborhood" tour with Jose, a photographer who gives a guided tour of his neighborhood near Revolution Square.  He introduces you to local shopkeepers and business owners, and explains in great detail what daily life is like in Cuba.  It was so incredibly interesting learning about everyday life there and, BONUS, he photographs the whole experience for you.

Ate at paladares

Had breakfast at our apartment and interacted with our hosts

Brought toiletries and toys to hand out to people  

We took along school supplies, toiletries, toys, and games.  Handing things out gives you a chance to interact with the local people, and everyone was incredibly grateful.  We met an American with Cuban relatives on our flight down.  He said that the Cubans go crazy over spices and seasonings.  This idea was confirmed by one of our tour guides, who told us the variety of food in the shops is very limited.  So next time we'll bring spices too.

Played at local playgrounds  

Playgrounds are fantastic places to interact with the locals, no matter where you are.

When you add up the hours eating breakfast, lunch and dinner, plus making purchases from vendors and going on independently-run tours, it’s not hard to create a full-time schedule.

Check out our video

Even for Americans traveling under one of the general licenses, certain government-run establishments and businesses connected to the military are still prohibited.  Take a look at the official list and make sure you plan accordingly.

Easy! I think I’ve been checked harder coming back from Europe.

I spent lots of time rehearsing what to say at immigration, carefully organizing my notes and receipts, and making sure everything was in perfect order.  And then at immigration:

Immigration Officer: Where are you coming from?
Me: Cuba
Officer: What was the purpose of your travel?
Me: Support for the Cuban People

Stamp, stamp, and we were on our way!

Customs was the same story. No one looked at of our luggage in customs.  The checked bag that contained all our cigars was held up and arrived a day late, and we were told by the airline that sometimes they will pull bags that need additional checking.  You can legally bring back $800 worth or 100 cigars, whichever is less.  (And, American Airlines delivered the bag within 24 hours, as promised.)

Cuba will require a bit more planning than most other island escapes.  But when you’re strolling through Old Havana listening to music pulsating from every corner while children run playing through the street, you will know it was worth it.  If you have questions about logistics or anything else you can’t find here, please shoot me a message.  I’d be glad to give you any information I have.

*This is based on my personal experiences, and does not constitute legal advice.*