Cheap Travel Hacks

How to travel to Cuba from the USA










In January 2015, U.S. President Barack Obama expanded the categories of authorised travel to Cuba for Americans – 55 years after it was first put in place. So now the hot topic in question for all American travellers who have longed to visit this forbidden island is: How to travel to Cuba from the U.S.A.?

But before we get into how Americans can travel there, let’s take a look at the history of:

Why Americans could not travel to Cuba



Dwight D. Eisenhower

Fidel Castro

Fidel Castro

John F. Kennedy

John F. Kennedy






During the height of the cold war between the Soviet Union and the United States of America, former Cuban dictator Fulgencio Batista, ally to the United States, was forced into exile and was replaced by 26th July Movement led by Fidel Castro. The beginning of the Cuban-American conflict began when Castro expropriated American economic assets and started to develop strong links with the Soviet Union. U.S. President Dwight D. Eisenhower started to become alarmed of these ties and in March 1960, he allocated 13.1 million dollars to a CIA-lead invasion to overthrow Castro’s government (Bay of Pigs invasion). This April 17, 1961, invasion was unsuccessful, and the CIA-sponsored paramilitary groups surrendered, which in turn, further strengthened the Cuban-Soviet relations.

Communist Influence

By this time, Cuba had already entered into trade agreements with the Soviet Union, East Germany, and Polland, which was viewed by the U.S. as:

“an extension of Communist influence in the sphere of American influence”

Once Castro nationalised all American owned refineries without compensation (after the U.S. had refused to refine Soviet petroleum due to an outstanding debt owed by Cuba), the U.S. retaliated by cutting all sugar imports from Cuba. And by October 19, 1960, the first of the American embargo was placed on Cuba for all exports excluding food and medicine. On February 7, 1962, under the Kennedy administration, the embargo had been extended to include almost all imports and a complete travel ban for all U.S. citizens visiting Cuba.

Has the embargo been removed?

Not exactly.  But congress is working on lifting it once the two countries can resolve their differences on issues such as democracy and Human Rights issues.

So then, how can Americans travel to Cuba?

President Obama has made travel into Cuba legal for Americans if they engage in activities in one or more of the U.S. Department of Treasury’s 12 Categories of Authorised Travel:

  • Public Performances
  • Professional Research/Meetings
  • Religious Activities
  • Educational Activities
  • Family visits
  • Athletic Competitions
  • Public Performances, clinics, workshops
  • Certain authorised export
  • Jouralistic Activites
  • Supporting the Cuban People
  • Official business of the U.S. government
  • Activities for private foundations or educational or research institutions

Where previously it was required to obtain a license which was subject to approval on a case-by-case basis, most Americans can now visit Cuba by “self-licensing” and by stating that your visit falls within one of the 12 categories.

However, visiting for the purposes of tourism is still prohibited.

Ways to fly into Cuba

While there still hasn’t been an Aviation Agreement drafted between the two countries as Cuba is still suspicious of another potential CIA invasion.  There are a few ways to legally fly into the country.

American Airlines and JetBlue Airways are offering a number of daily flights departing from Miami, Tampa and Los Angeles. But because there is no Aviation Agreement, they cannot sell tickets and they must be purchased through a Charter Company.

Below is a list of Charter Companies that are offering daily flights which can be booked either online or by telephone:

ABC Charters – 866-4ABC-AIR or 305-263-6829

Cuba Travel Services – 310-772-2822

Marazul – 800-993-9667 or 305-559-7117

Xael Charters, Inc. – 305-643-2200

How to visit under the 12 categories

Unless you are a journalist, professional athlete, professor or government official, the Office of Foreign Assets Control (OFAC) has implemented strict guidelines as to who qualifies for travel licenses under the 12 categories.

The easiest way to qualify is either by visiting family members who resides in Cuba, or to visit for the purposes of Supporting the Cuban People.

However, if you do not have any family members who reside in Cuba and are interested in visiting under the humanitarian category, the OFAC guidelines for Supporting Cuban Peoples is:

Travelers utilizing this general license must ensure they maintain a full-time schedule of educational exchange activities intended to enhance contact with the Cuban people, support civil society in Cuba, or promote the Cuban people’s independence from Cuban authorities, and that will result in meaningful interaction between the traveler and individuals in Cuba

So what does all this mean…

It means that staying in a 5-star hotel and sipping cocktails on the beach all week is not going to happen! In order to gain a cultural experience and to give back to the Cuban people, you need to stay in non-government facilities, eat at locally owned restaurants and markets, and be engaged in the Cuban community.  Airbnb is a good way to go as you will be essentially staying in a local’s home and submerged into the Cuban culture. 

The Charter Companies listed above also have accommodations offered that they can assist you with booking that will fall under the required criteria.


It also means that you are legally allowed to bring back $100 worth of Cuban cigars.


What to expect when you arrive

Cuba is hands down, one of the most beautiful islands in the Caribbean. Miles of white sand beaches and turquoise water, surround this tiny island paradise. The people are extremely friendly and the nightlife and entertainment are remarkable.

However, after a more than 50-year ban on American imports, there are quite a few things that will not be customary to U.S. visitors. 

Food in the resorts and some restaurants is not always delectable.  Common staples such as ketchup and cola, are the Cuban versions. Most of the vehicles that are driven around the country were built in the 50’s (which is actually pretty awesome to see. It’s like being at a car show for your entire vacation!). The Internet is comparable to the old Dial-up version – and some places still have it!

But if you can get past the transition to new tastes and you have no problem with rolling up in a classic car, you will find that Cuba is one of the most stunning island countries you could ever visit. And the Cuban people are forever trying to welcome you and help you enjoy your stay.

Veradero – 2012

15 thoughts on “How to travel to Cuba from the USA

  1. Pj

    Wow, I never thought of visiting Cuba because I wasn’t familiar with the change implemented by President Obama. This sounds like a fantastic way to visit and truly get immersed into the culture. Fantastic information on how to travel to Cube from the USA.

    1. Nicki Post author

      Thanks, Pj!

      I have been to Cuba a few times, and I can tell you that it is an extremely friendly, and beautiful country. If you like Latino culture, it is definitely somewhere you need to check out. And now that Americans can legally visit, now’s the time to head on over! 🙂

  2. Ashley

    Wow, your post is so cool! I’m not an american, but I never knew you guys were’t allowed to travel in Cuba. i haven’t thought about visiting this country, but this travel hacks are so useful 😀
    Do you know that if they’re available for Europeans too? I mean, first of all, do you know if we are allowed to travel to Cuba? Because I guess there’s no difference between Europe and America when it comes to visiting Cuba, because of their system. So I guess these tips could apply in our case too.

    1. Nicki Post author

      Hi Ashley,

      I’m actually Canadian, so I’ve been there a few times. I’m also in two of the pictures posted which were taken in Varadero. 🙂

      Yes, any citizen can visit Cuba from any country in the world. The embargo was just between the United States and Cuba. It’s actually the only country in the world where American’s were not allowed to visit!

      I’ve met a lot of Europeans from all over Europe while visiting Cuba. It really is a grat country to visit and cheap! I highly reccomend visiting. And if you ever do decide to go, I can give you some tips on some really good resorts to stay at! 🙂

  3. Jonathan

    Omg! Thats all I can say. What a fantastic article! I absolutely love it. Not only did we get a history and great offers to Cuba but the way you described it felt like i was right there. I can’t wait to visit Cuba! Better yet it will be an even better day when they can open up their country for tourists. I don’t quite understand why wouldn’t Cuba want tourists or the other way around. What are your thoughts on that? So you went to Cuba too? How was your experience?

    1. Nicki Post author

      Hey Jonathan, thanks for much for that!!

      To answer your question, there’s two reasons:

      1. Cuba is still a communist state, and we all know how much the U.S. government doesn’t like communists! lol So as much as the U.S. is loosening the reins on the embargo (it’s the U.S. who placed it there), there still is a lot of tension between the two countries. And Cuba is still worried and doesn’t really trust the U.S., so it’s a dicey situation. I’m sure Cuba would more than welcome the revenue from American tourists, but there’s still that tension.

      2. Cuba is a very poor country. Their resorts and getting better, but it’s not like most of the other islands down south. They really don’t have the infrastructure to accommodate a huge flux in tourism. I’m sure it will happen soon enough though with Americans now being allowed to visit there!

      As for my experience there: Cuba is kind of like the Vegas of the Caribbean! lol It’s so much fun! Everyone party’s and has a great time. The Cubans really know how to entertain their guests. There’s also a TON of Europeans, so you really get to mix in with people from all over.

      I haven’t been to Havana yet, but next time I go, I will for sure be going to Havana and checking out more of the old history of Cuba. Like I say, it’s such a fun culture and Cubans are so warm and friendly. You never feel unsafe or out of place! 🙂

  4. Kyle Jones

    Enjoyed seeing this page get better and better! I wonder if similar rules used to exist for those in the UK? I’m from wales (and proud) and definitely going to follow this page as my online career climbs so i can go away and my online business in the sun! lol

    This is an awesome page!

    1. Nicki Post author

      Hey Kyle, thanks for your comment and no, it’s was only for the U.S. Europeans can easily travel to Cuba!

      Thanks for your support on my site!


  5. Richard

    I am impressed! I knew that it was now possible to go to Cuba, but I have never read an article like this that discussed how to do it. I assumed that the biggest problem would be flying there. Do they do it with puddle-jumpers from Key West?

    I am from the mid-west but have recently moved south and I love it. One of my favorite places to go is Key West and I have often wondered about getting over to Cuba. I might just try to get that done now! Thank you!


    1. Nicki Post author

      Thanks Richard!

      Yeah, you can definitely go there now. But like I mentioned, you have to book through a charter company. Or, you could always just fly here to Canada and go on one of our flights without hasstle. I would assume you can take a smaller plane over if that pilot as the required license to be able to land there. You can check out all the regulations here:

      I have never been to Keywest, but I know you can see the lights from FL in Cuba. So, I’m assuming it’s there same there as well. Sounds like you’re not too far. You could always swim as well! lol I heard a lady just made it not that long ago!!

  6. Barry

    All this time I thought the Bay Of Pigs was a Kennedy thing. I have seen the car show in Cuba on TV and have read that some of the vehicles have the latest Toyota engines in them.

    Since there is so much beach i would expect to see more rust on the cars but I guess not. How much money will a trip to Cuba cost and what kind of money?

    It’s really too bad that the people are always the ones that suffer because of Governments. People never go to war any more just Governments.

    See you on the beach.

    1. Nicki Post author

      Thanks Barry!

      Yeah I always thought Bay of Pigs was all Kennedy as well, but it was a joint effort between Eisenhower and JFK.

      They do have a lot of newer cars as well, but a majority of the cars are classics.

      Well the two times that I’ve gone to Cuba, it cost me $550 all-in (that’s airfare, hotel, food and drinks) and $675 all-in. And that’s leaving from Toronto. Depending on where in the U.S. you are coming from, I would say you can easily go there for a week for under $1000. They have their own currency which is the Peso but there’s two currencies – CUP (National Peso) and CUC (Convertable peso). THe CUC is the currency that tourists use and the CUP is used by the Cuban people and what they’re generally paid by. The CUC is almost on par with the U.S. dollar.

      And you’re right -it’s always the citizens who suffer from their governments issues!

  7. Andy

    It’s great that there’s steps being made to open up Cuba to Americans again. I’m from Canada so have no problem visiting Cuba however I have never been there. It’s interesting how they have a lot of classic cars since they weren’t allowed to trade with the US so I’m thinking it would feel like a trip going back in time. It’s amazing how they’ve been able to maintain the cars and kept them running for so long!
    Definitely will be an interesting place to visit.
    Thanks for this post!

    1. Nicki Post author

      You definitely need to get out there and check it out Andy! Cuba is a beautiful country and the people there are so friendly. It’s the Vegas of the Caribbean!! 🙂
      It is kind of like travelling back in time when you go there. There are so many things that they don’t have because of the embargo. But it is pretty cool seeing all the older cars. They do have a lot of newer ones as well, but you see tons of older cars.
      I’m not sure how they manage to keep them all in such great shape, but whatever it is they’re doing it’s working!

  8. Lanta Eco News

    This is so interesting. What a shame that Americans have missed out on the beauty of Cuba for so long. It’s great that they can experience it now though and also fantastic that, if they do visit for tourism, they have to do it in a way that benefits the locals by supporting local businesses. Surely that will also be a benefit to the Americans tourists, as they’ll have a much more authentic experience than they would if they stayed in a 5* resort. It’s a shame more countries don’t enforce this rule. Holidays would be totally different and you would actually get to experience the real country instead of the watered-down version most resorts and tourist places offer.

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