How to Plan your DIY American Trip to Cuba before the Travel Ban is Completely Lifted

It’s an exciting time for Americans as we start planning our trips to Cuba, now that the travel regulations have been eased. But there are still a lot of questions before we start packing our bags. But don’t worry, even though no commercial flights are airborne from the U.S. just yet – it is perhaps the best time to go….before everyone else does.

Let’s breakdown the common concerns so you can plan your own DIY trip to Cuba now, without licenses, without a tour operator – all by yourself.

Is it legal?

Americans have been technically allowed to travel to Cuba for some time, given that the right licenses are obtained. Travel to Cuba is most simply arranged through government endorsed People-to-People travel agencies who are certified to take groups into Cuba for social missions on authorized charter flights. This may still be the easiest way, but not the cheapest…and certainly not the most flexible, since you are required to stay on the tour group’s agenda.

Although we cannot simply hop on a domestic flight to Cuba just yet, President Obama’s recent announcement to recover relations with Cuba has certainly made it easier.

Previously, if you fell within the 12 categories listed by the Office of Foreign Assets Control (OFAC), you would be allowed to travel with a “specific license” obtained through an authorized agent. This was a complex procedure (hence the need for group tours like People-to-People). Now, travelers who fall into these categories, no longer have to apply for a specific license. According to the White House Fact Sheet:

  • General licenses will be made available for all authorized travelers in the following existing categories: (1) family visits; (2) official business of the U.S. government, foreign governments, and certain intergovernmental organizations; (3) journalistic activity; (4) professional research and professional meetings; (5) educational activities; (6) religious activities; (7) public performances, clinics, workshops, athletic and other competitions, and exhibitions; (8) support for the Cuban people; (9) humanitarian projects; (10) activities of private foundations or research or educational institutes; (11) exportation, importation, or transmission of information or information materials; and (12) certain export transactions that may be considered for authorization under existing regulations and guidelines.
  • Travelers in the 12 categories of travel to Cuba authorized by law will be able to make arrangements through any service provider that complies with the U.S. Treasury’s Office of Foreign Assets Control (OFAC) regulations governing travel services to Cuba, and general licenses will authorize provision of such services.

This means that if you plan to travel to Cuba for educational/religious activities and support for the Cuban people, the trip can legally happen without any paperwork. This is great news! If you’re a reader of this site, chances are that you enjoy meaningful travel that includes time giving back to social businesses and charities, as well as loads of educational exploring. If you use the tips on The Global Commute for traveling to Cuba, than you can legally go now! But how?

According the White House, you are now able to individually book travel through an authorized travel provider, given that you fall in the 12 categories. This is because, right now, only chartered flights are running from the U.S. and Cuba. Therefore, a travel services provider is needed to assist with your flight arrangements. However, there is no legal issue with boarding a flight to Cuba from another country. Given that you can prove your travel involved educational/religious activities and support for the Cuban people, there should be no issues on your return to the U.S. after your trip.

In fact, the New York Times says that that Obama’s news is in effect, “removal of the ban.” The vague verbiage is really just a temporary statement until the kinks can be worked out and domestic flights can be launched.

What is the most economical way to fly to Cuba from outside the U.S?

There are lots of options for flying into Cuba. Perhaps the cheapest way is by connecting through Canada or Mexico (depending on where you live). Flights from Cancun are the cheapest from Mexico at around $250-$375 round-trip.  This may not seem cheap for a one-hour flight, but trust me…it’s a great value, considering the high price of chartered flights out of Miami (Once commercial flights are launched soon, the price will be much lower as well).

There are also plenty of flights from other Caribbean Islands. A great resource for booking travel is the Cuba Travel Network site – From here you can view all flights coming into Cuba from around the world. SkyScanner is also a great resource, but the U.S. version does not currently show flights (obviously, since no commercial flights exist yet). Switch to the Canadian site, to easily sort through flights.

How do I get past immigration?

Before you fly into Cuba from Canada, Mexico or another Caribbean island, you will need to get a tourist card. These are easily arranged at the airport. Just allow an hour or so to figure it out. They are not expensive.

Normally, Cuban immigration will stamp your tourist card and not your passport, so there really should not be any questions regarding your travel when re-entering the United States. Even if they do stamp your passport, there is no real reason to worry either. As long as you can prove your travel fell within the 12 authorized categories (which The Global Commute can help you with), than you are fine.

Where should I stay?

In order to have an authentic experience, I suggest staying in a guest house or “casa particular.” These private rooms in Cuban family homes are government approved, and a cheaper alternative to hotels. It’s also a great way to make friends with the locals. Even if you plan to spontaneously hop around the island, I suggest pre-booking your first few nights in advance. Immigration officers will ask you where you are staying when you arrive, and you will need an address on your customs form.

A great resource for finding and booking casas is Be aware though that traveling to Cuba requires diving into local life, as modern-day comforts may not exist. Expect no internet access and simple, but authentic accommodations. You could stay in a larger, touristy hotel for “western” amenities, but the price will be higher and you will lose the personal connection that you would have with a local guest house owner.

Transportation is often provided by casa particulares as well, so booking one in advance of your arrival is a great way to have a driver waiting for you at the airport. After a long journey – it’s a nice welcome.

How do I get around?

There are two forms of taxis: Turistaxis (western cars that are metered in US dollars) and Local taxis (mainly Russian-built Lada saloons). Although these official options exist, you can also flag down a ride from just about anyone. Normally strangers will agree to a favorable price. I wouldn’t suggest doing this as a female, solo traveler, but if you are with a companion and are going for a quick trip across town, don’t be shy!

Rental cars are also available. I think a great, fun option is renting an old American car for the day to road-trip out of town. A good reputable company is Gran Cars (

How do I make purchases?

Credit Cards cannot be used on the island, so bring lots of cash. US Dollars are widely accepted, but you can also exchange money at the airport.

What other things should I be aware of?

I suggest reading this article on Trip Advisor – it’s a nice summary of what to know before you go.

What types of activities should I do to make sure I comply with the 12 approved categories for travel?
How do I find out about these organizations, charities and social enterprises?

In the coming weeks, I will share my How to Journey beyond the Bucket List Guide to Cuba with you, so you will know what to do and how to get involved with charities, organizations and social enterprises while on the island. Come back next soon for the full details! But until then, don’t procrastinate. Book that ticket! The hardest part is deciding to go!


Feature Photo Credit: Thinkstock/istock/diego_cervo


35 thoughts on “How to Plan your DIY American Trip to Cuba before the Travel Ban is Completely Lifted

  1. Hi there, I am a graduate student studying tourism at Colorado State University in the U.S. I am looking to go to Cuba under the reason of “education” in the next few weeks. Any advice on what my university could provide me with prior to going to show that I am there for that reason or what to acquire while there to prove that?


    1. Hi Noelle,

      congrats on your upcoming trip! I would suggest you plan out your educational itinerary and have it in writing which shows where you will be going, what you will be seeing and what you will be learning about. You could also have them write a letter stating your intended reason for travel. I would bring both of these things with you on your trip.


  2. Hello Kari,

    I am a college student currently and I would like to travel to Havana under the support for people category. I’d like to plan this myself to save money.

    Cuba is on my Bucket list!!!

    Can you point me in the right direction for getting in contact with people so that I can arrange activities when we arrive?

    I enjoy salsa dancing, cooking, and sports events.

    I’m looking to go in early March, any helpful information is greatly appreciated.

    Also can you send me your email so I contact you about more questions?

    Thanks again!!


    1. Hi Anthony,

      Congrats on your upcoming trip! If you would like activities planned for you before you arrive, I would suggest contacting Travels by Design – Lee Lennon, the Principle Designer is very connected and experience in Cuba. You can contact her directly by using the contact form on their website.

      Good luck!

  3. Good Afternoon, I cant seem to find the answer to: What Types Of Activities Should I Do To Make Sure I Comply With The 12 Approved Categories For Travel?”

    W’e’ve looked into going with tour groups, but the prices are soooooo high and we would love the opportunity to plan our own educational trip.

    1. I am planning a trip to Cuba in May. I want to attend a one day salsa class and meet jazz musicians. Any recommendations of who to contact.

      1. Good afternoon Barbara,

        I would highly recommend Travel by Design. Lee Lennon the Principal Travel Planner there has years of experience and a wealth of knowledge and contacts in Cuba. Her email is Please tell her Kari from The Global Commute recommended you.

        Happy Travels!

    2. I am a teacher from the US and would like to travel to Cuba in April 2017. How can I arrange this?

      Thank you


      1. Hi James,

        Thank you for your question. There are now several commercial flights to Cuba from Miami, so it is very easy. Is there something specific you are concerned about so I can help you better?

          1. Hi James! I would recommend reaching out to Travels by Design. They can assist you with this specific need and help connect you with this opportunity. Best of luck!

    3. Can I teach primary school kids the game of baseball? I am a second grade teacher and I have taught baseball to elementary in the past.
      Thank you,

    1. Hi Brent,

      I am excited to hear that you are planning a “Journey Beyond the Bucket List” to Cuba! We haven’t posted an article with our normal “beyond the bucket list” title yet. However, we do have two articles giving you a wealth of information on how to plan a meaningful trip to Cuba here:

  4. Hello Keri,

    Your articles about DIY traveling to Cuba is the most helpful one I’ve ever seen. Thanks to all your tips and insights. Me and my friend have a small start-up focus on promote indie arts and music in greater NYC area and we are planning a trip to Cuba to explore their music, arts, life and also exchange ideas about arts and music.

    We believe this is totally under the “people to people” educational activities of the 12 categories. But we are not sure what kind of document should we prepare before we leave NYC to Cuba? Or we just simply keep all the records of who we meet and what we do in Cuba afterwards?

    Thanks for your help in advance.

    Again, your work here at Global Commute is extremely awesome.

    Denise & Yuxin

    1. Hi Denise,

      Congrats on your work to promote the music, art and life of Cubans through your startup. I would create a written document of your day-by-day itinerary that you print out and take with you on your trip. I would also bring business cards listing your company and individual titles to have on hand. You can also apply for a travel license for extra comfort. Here you can find updated information from OFAC from the U.S. Treasury on travel to Cuba including an application for the cuba travel license.

      I would love to feature your startup company and your trip to Cuba on The Global Commute! Would you be interested? If so send me an email at

      Look forward to chatting soon and following your journey.



  5. Hi a couple of friends and I are going but what to go In legally so we thought of people to people and educational . Would we need documentation to enter cuba in order to do this or go through a group ( they are very expensive) ?

    1. Hi Adaeze,

      Although I am not hear to give specific legal advice (please travel at your own discretion) – It is completely legal for you now to travel to Cuba without the need for people-to-people groups as long as the nature of your trip falls within one of the twelve categories (including educational activities) and you have the correct license. I agree that people-to-people groups are expensive! Here you can find updated information from OFAC from the U.S. Treasury on travel to Cuba including an application for the cuba travel license.

  6. Hi I am trying to plan a trip to cuba this year with 2 other travelers. I want to do it legally but am having trouble on how can i obtain proof or documentation to fall within the 12 reasons one can use to travel to cuba. I understand what they are but what exactly do they look for. I don’t want to travel with a guide and therefore have decided to find a way to fall within these categories without the people to people along with a full time guided trip. Any suggestions are welcome and great blog!

  7. Hello all,
    Quick question, I read above, (7) public performances, clinics, workshops, athletic and other competitions, and exhibitions;. I used to play professional baseball and my grandmother was cuban (even though lived in St. Petersburg, FL), but could I use some type of athletic/baseball reason to visit Cuba?

        1. Hi James,

          Yes you can! I would recommend volunteering while you are down there though to ensure you call with the 12 categories. You will then need to create your General License – There are now several commercial flights to Cuba through Miami who allow you to do this during the booking process.

  8. Have you posted about ” How to journey beyond the bucket list to Cuba.” I stumbled upon your information regarding traveling to Cuba “legit”. My boyfriend and I are going in two weeks. We are going as humanitarians but not through an organization. Through my business I’ve collected donations to bring to schools ect. I’m just looking for any other information to keep my trip legit:)

    Thank you

    1. Hi Ranye,

      Congratulations on your upcoming trip! It sounds like you guys fall within the 12 categories listed by the Office of Foreign Assets Control (OFAC), meaning you are allowed to travel without a “specific license” obtained through an authorized agent. You should be free to travel without any problems. If I were you, I would take some photographs of your humanitarian work at schools, just to have. Don’t take this as legal advice – just from one traveler to another in good faith! Have a great trip!

  9. Hello, I don’t see where the rest of the articles are explaining how to go on your own legally. Am I looking in the wrong place?

    1. Hey Briana,

      Thanks so much for reaching out and for your question. As long as your trip falls within one of the 12 categories you are free to travel to Cuba. The most common ones are: (5) educational activities; (6) religious activities; (7) public performances, clinics, workshops, athletic and other competitions, and exhibitions; (8) support for the Cuban people; (9) humanitarian projects.

      Did that clear up your concerns? Let me know if I can help in any other way!


  10. my boyfriend is from cuba. we havebeentogether for 14 years. he wants to see his parents and sisters that still live in cuba. he has his resident card and i was born here in the united states. he wants me to come along but i do not know if i can being that we are not married. can i go with hime without being married to him.

    1. Hi Carolyn,

      It is so exciting that you have the opportunity to travel to Cuba to meet his family! Technically right now the travel ban on U.S. citizens has not been lifted. However, there are 12 reasons for travel that exempt you from obtaining a special license – one being “family visits.” In the end though, you will need to do what you are most comfortable with. Hope this helps and good luck!

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