Legal Travel to Cuba for the U.S. Citizen Explained

I’ve traveled most of my life and have been fortunate to have visited over 50 of the world’s countries. Some travels were on tours (both as a guide and a participant) and some travels were independent.  I’ve traveled by airplane, car (renting, taxi and hitchhiking included), bus, train, ferry, ship, yacht, horse, camel, raft, kayak, bicycle, and foot.  There are countries where travel is simple and straightforward and others where that is not the case.  Cuba falls into the latter category.  Mostly this is because of two factors.  Internal infrastructure and, if you’re a U.S. citizen, the U.S. laws pertaining to travel to Cuba. Even though travel to Cuba can be challenging, it’s also very rewarding and worth the effort!  This article is not meant to discourage you, but rather, spell out some options and considerations.
Cuba mountains in the distance
Legal Considerations
If you are a “person of U.S. jurisdiction” (citizen, green card holder, etc.) it’s important to understand the U.S. laws pertaining to travel to Cuba. Because of the U.S. embargo, travel for touristic purposes is not allowed.  However, there are 12 categories of permitted travel for persons of U.S. jurisdiction, and your travels must be in compliance with one of these.  This means having a full-time agenda of activities related to the category of travel.  As of June 2019, most people now travel under the “Support for the Cuban People” category.
The United States Department of Treasury, Office of Asset Control (OFAC) has a very useful FAQ that answers many questions and was updated according to new rules put into place in June of 2019. Note also that the U.S. State Department has a list of Cuban government-owned hotels where U.S. persons are not allowed to stay. This is called the “restricted list.”  
Cuba street at night
Getting to Cuba
There are many flights from the United States to Cuba every day.  Almost every major airline flies to Havana.  A few also service other cities in Cuba, including Santa Clara, Camaguey, Holguin, and Santiago de Cuba.  Use a search engine such as to find the best routing from your city.  When you fly on a U.S. airline, the health and accident insurance required by the Cuban government is included. It’s also possible, and perfectly legal, to travel through a third country to get to Cuba.  Sometimes flights via Mexico, Panama or Canada might be more convenient.  
Cuban bicycle taxi
Travel Within Cuba
If your goal is to visit Havana only, or a city with direct air service from the U.S. (listed above), then it is relatively easy to travel to Cuba on your own.  However, if you want to travel to various parts of the country, it gets more complicated. 
Unlike many countries, there is not much in the way of public transportation in Cuba, so getting around is a challenge, or expensive.  Public buses are woefully lacking. There is a new train service from Santiago de Cuba in the east to and from Havana in the west, but it is so new there is not yet much information or reliable traveler experience to know how dependable it is.  
Car rentals are possible, at a cost of $80-$120/day or more.  Finding fuel for the car can be problematic.  Hiring a taxi and driver is also possible, and this will cost from $100-$160/day plus the expenses of the driver (meals, accommodations, etc.)  
There are a few good roads in Cuba, but many are in a bad state of repair.  If your map app says it will take 3 hours, count on at least 5-6.  There are a few exceptions to this such as the A-1 highway that runs from Havana to Santa Clara.  Or the road from Havana to Vinales.  Beyond these, however, the roads are generally slow due to potholes, slow-moving vehicles, animals, pedestrians, and cyclists, etc.
Finally, it’s best not to use air travel within Cuba as the flights are not dependable.  Delays and cancellations are common.  
Rolling a cuban cigar
Communication and Money
U.S. cell phone companies don’t yet offer any “travel plans” for mobile coverage in Cuba, so expect to pay $2.99/minute for phone calls.  You can get around this by buying a phone and sim card when you get to Cuba but you need to allow a few hours for the process. This will then allow you to more easily communicate within Cuba with Cuban phone numbers.  Canadian and European cell companies do have more reasonable rates and plans.  Because the internet is not as widely available as it is in many countries, using apps while on the road to make accommodation bookings, etc. is not realistic.  
Cuba is a cash economy.  U.S. credit cards do not work in Cuba and very few places accept credit cards at all.  This means you need to carry all the funds you need in cash.  In an emergency, friends or family could send funds via Western Union or a similar service, but it’s expensive and cannot be sent to you, but only to a Cuban national.
When considering the costs of traveling to Cuba be aware that when you exchange U.S. dollars there is a penalty fee of 10% in addition to the exchange fee.  Be sure to add at least 10% when calculating your estimated expenses.  It’s also possible to buy Euros or CAD before you go, but bank and currency exchange fees reduce your savings considerably.
Cuban native playing the drums
Health Insurance Requirements
The Cuban government requires all visitors to have health insurance.  Fortunately, most airline tickets include the $25 fee that includes Cuban health insurance that covers you in-country.  Just have a digital or printed copy of your ticket with you to show if necessary.  In many major cities in there is usually an international visitor clinic, or Clinica Internacional designed specifically to treat visitors. 
Pink flamingos in Cuba
Here are some thoughts on the best ways to tour Cuba.
Most Convenient – The easiest way for Americans to visit Cuba is on an organized tour through a legal U.S. company.  Since foreign companies do not comply with U.S. law regarding travel to Cuba for U.S. citizens, traveling with a foreign tour operator is not legal for U.S. citizens.
An organized tour, or a custom trip organized via a U.S. company, is especially practical if you want to visit a variety of places in the country since all transportation and accommodation logistics are included.  It’s also the simplest way to comply with U.S. law.  As noted above, there are only 12 categories of permitted travel for persons of U.S. jurisdiction, and your travels must be in compliance with one of these.  A reputable tour operator will have a tour specifically designed to meet the legal requirements. 
If you want to get off the beaten path to kayak in Cuba, this is the only way to travel due to Cuban government restrictions regarding boats and boat travel.  If you want to cycle or hike, you could do this on your own, again, making sure your agenda is in keeping with the legal travel requirements of the U.S. government.  However, knowing where to go, trail or road conditions etc, would require a lot of homework and research.  Thus an organized cycling tour, or walking or hiking tour, would be easier and meet the U.S. legal requirements.
A custom tour to Cuba organized by a legal U.S. company is another great way to go.  In this case, you are placing your trust in a company that has an extensive and reliable network of guides and drivers, to plan and execute a tour taking you to the exact places you want to go, and the activities you want to do. As well, since a group tour or custom tour to Cuba is prepaid, it eliminates the security issue of carrying a lot of cash.
Moderately Convenient – As mentioned above, if your plan is to visit only Havana or another city with direct air service to and from the U.S., this is reasonably straightforward.  You can buy an air ticket on many U.S. airlines who also sell the required Cuban visa or “tourist card” at the airport on your way. You can book accommodation on a service like Air BnB or similar.
If you did want to explore outside of Havana or the other airline-served cities, it is possible to rent a car or hire a car and driver, as detailed above.  Be aware that any vehicle accidents can create all kinds of legal hassle within Cuba and could delay your travels considerably.  
Least Convenient – If you have lots of time, it is possible to travel around Cuba using public transport.  There is a government bus service for tourists called Via Azul.  They have a station in each major city and route they follow.  It’s best to buy your tickets at least a day in advance.  If you get off in a small place, like Playa Larga by the Bay of Pigs, it will be hard to know (perhaps impossible) if the next day’s bus will have seats available or not.  Within the cities, there are shared taxis. Some cities and towns also have motorcycle taxies or horse-cart taxis.  Walking is always a good option for exploring towns and cities as well.  As mentioned above, there is also some limited train service in the country.  In the recent past, this has been very, very slow.  But new equipment from China may change this on certain routes.
enjoying cuban street art
Your Travel Helps Ordinary Cubans
While travel to Cuba does present some interesting challenges, it is certainly worthwhile.  The economy in Cuba is suffering due to the U.S. embargo and travel restrictions.  When you travel to Cuba your money has a real and positive impact on the people there.  For you, the reward is also great!  Cuba has a vibrant culture of music, art, architecture, and history that awaits the intrepid traveler.  The people of Cuba will welcome you warmly.  And as noted, your travels, however you may choose to do them, will have a very real and positive impact on the lives of Cubans.
I firmly believe that travel builds connections and bridges and in Cuba especially, you will find a country where we have much to learn, and much to give.

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