How to Travel to Cuba as an American Citizen 

Having just returned from my trip to Cuba, I am excited to share the research I did prior to my trip and anecdotes from my experience abroad to help you decide which ways of traveling to Cuba works best for you!

Although restrictions for American tourists traveling to Cuba are gradually changing it is still not the easiest place to visit for leisure and many people have asked me how I traveled there on my recent trip. It’s fairly easy for students, journalists or people with relatives, but if you are just hoping to travel as a tourist, it’s a still little onerous. It’s designed that way so it should come as no surprise.

There are however 4 main ways that Americans can visit Cuba as a tourist:

  • Organized tour
  • Build your own tour
  • Cruise
  • Through an international destination

Note: With each new day, there may be adjustments to US regulations so please check the State Department website for the most up-to-date information on traveling to Cuba.

Organized itinerary

  • Pros: Easy, legal, convenient
  • Cons: Expensive, typically group tours, fixed itinerary

By far the easiest way to visit Cuba as an American is by signing up for an organized tour through an American or Cuban based travel agency. These tours are specifically designed to meet the requirements of the US government’s visa restrictions and typically have robust & well-detailed itineraries. They provide support every step of the way to ensure you have the visa, insurance and travel details that you need in order to be admitted into the country. This is the way that I traveled to Cuba.

There are tons of options of travel providers to choose these days. In the past, you had to use multiple agents to book flights and tours, but now with open flight access on US airlines, it is much easier. I booked my flight directly on Southwest and with frequent flier miles no less!

I would recommend setting your budget early in the process since prices vary widely and the organized tours are not cheap — my tour alone was over $3000. Trips typically range from a few days in Havana to a 2 week trip around the island, so there are ways to make it less expensive by choosing a shorter duration. There are definitely cheaper options than the one I did, but organized tours are not the type of experience for the thrifty traveler.

If you haven’t done a group trip before, don’t rule it out just yet. There are some really great benefits to this method of travel — I didn’t have to research or plan anything and all I had to do was show up, everything was pre-paid, it’s so convenient — but I think my favorite part is having a local guide.

Antonio, our guide for the week, was funny, friendly and incredibly knowledgable. I learned so much from him that I could never have learned from a book or movie, which really brings the destination to life! He provided a local’s perspective on issues and had little anecdotes to share with us about life in Cuba. I feel as though I learned a lot more during my 9 short days there than I would have if I traveled on my own.

I certainly don’t regret my organized tour, since it was so easy & convenient, but it was expensive and there were some limitations in terms of flexibility. You do have to follow the group’s agenda and don’t get a ton of alone time, but it’s fun meeting new people and reflecting on your shared experience.

I ultimately decided to go with Intrepid Travel, because I was familiar with them from my Jordan & Egypt tour and already had a good understanding of their business practices, but I also liked their itinerary and variety of cultural activities. While I was doing my research, I found several other great options besides Intrepid which I’m sharing below for anyone who hopes to plan their trip there!

Build Your Own Tour

  • Pros: Legal, less expensive
  • Cons: Time-consuming, difficult to research, lack of local support

If you’re not someone who enjoys group trips and prefers the customizability of designing your own abroad experience, then building your own itinerary is the way to go. This process is much more time-consuming than the above option, but gives you plenty of flexibility to do what you like with your money & time while in Cuba.

For the People-to-People visa (the easiest visa to acquire), the US government requires that you have 3 cultural activities per day in order to “better understand the culture and help bridge the divide with the Cuban people”. Cultural activities can count as anything — museum visit, staying with a host family, taking a salsa lesson — so the options for building a trip that fits your interests are endless.

Note: other visa categories that you could choose from include volunteer visa, student visa or cultural exchange visa, all of which fall under the 12 categories of options.

Because Cuba is only now opening to mass tourism from the US, finding up-to-date, relevant English-language resources to help plan your trip can be little challenging but not impossible. I found the Cuba Lonely Planet book to have lots of good suggestions, but I liked looking over these online resources as well:

Regardless of what type of trip you do (organized or not), the US-based flight agent will ask you during the check in process “what is your purpose of travel”. This is when you will say for People to People purposes or to help the Cuban people with volunteer work or whatever category you plan on traveling on. Aside from this verbal confirmation, I wasn’t required to turn over any paperwork or itinerary during this step.

From my personal experience, that was the only time that I had anyone ask me about my purpose of travel. Once I was actually in Cuba, nobody checked my itinerary or ensured that I followed the activities that I was supposed to be doing. With this said, there are some horror stories of people who are caught by American officials not following an itinerary who’ve faced steep fines or even jail time so I would probably recommend being cautious here just in case. At the least, have a printed itinerary that you plan to roughly follow in case you get stopped at the border or by local authorities. You don’t necessarily need to have every activity booked, a general itinerary or idea of what you plan to do will help you avoid any issues at the border.

The enforcement of the itinerary thing seems to be a lot less intense than it was made out to be online and it seems much more do-able to me now in hindsight. Prior to going, I was feeling intimidated about it because I had to sign an affidavit and provide all this paperwork — it just all seemed like a lot of official things to do. If you’re up for the adventure, I think building your own itinerary would be a good way to make the most of your time in Cuba while also keeping it within a more reasonable budget. But if you’re not up for planning & researching prior to arrival or aren’t open-minded to changes or deviations, then a group trip is probably better for you.

Cruise

  • Pros: Easy, convenient, legal
  • Cons: Crowded, fixed itinerary, short visit

With the lessening of travel restrictions to Cuba, cruise lines are getting in on the travel boom to the Caribbean’s largest island! There are several cruise lines offering weekly service to Cuba and I even saw some of them in Havana’s port while I was there.

I’m personally I think the cruise industry is an environmentally degrading, non-experiential and culturally damaging means of tourism, which is why I probably wouldn’t choose this method of travel to Cuba. But I understand the appeal for certain travelers, and with expanded service to Cuba, assuredly people will be signing up in droves.

The following cruise lines are some of the lines currently offering services to Cuba:

Flying through an International Destination

  • Pros: People have been doing it for years
  • Cons: Not legal, punishable, uncertain

With the ease of planning your own itinerary or signing up for a pre-planned itinerary nowadays, I don’t really understand why anyone would opt to fly to Cuba illegally through an international destination such as Canada or Mexico. It’s easy enough to to do it legally. I suppose the argument is typically frugality? Regardless, this is a fourth option for traveling to Cuba.

Essentially, you can fly to a place like Cancun or Toronto and connect to Havana (or another Cuban city) by flying on a non-American airlines. The border agents are familiar with this method of traveling, since thousands of people have been doing it for years, so they will not stamp your passport with a Cuba stamp, but instead will stamp your boarding pass and visa. Then you will travel onwards to Cuba, and return to the US back through the same international destination.

The issue with this is if agents look closely at your passport, they will notice two sets of exit stamps from Mexico (or Canada) but no other entry stamps. How could you leave Mexico but not go anywhere? See the problem here? Furthermore, US law stipulates that you cannot spend money in Cuba without a proper visa because of the embargo so it makes traveling there quite suspect. How can you go somewhere and spend no money? It’s a Catch 22.

With this method, there are lots of unknown variables and even if you do this, you could still get denied at the border by patrol agents. With so many other options to choose from now, I don’t think option 4 should be your top choice for visiting Cuba.

Conclusion

Based on my personal experience, I would be most likely to recommend either option 1) Organized Tour or 2) Self-Created Itinerary for adventurous travelers hoping to plan an upcoming trip to Cuba. At the beginning of the research process, don’t get turned off by the intimidating language and high prices. It isn’t nearly as they make it seem, and thankfully, the trip itself can be incredibly rewarding.

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Author: Megan Arz

I am a travel and food obsessed Midwesterner living in Chicago and dreaming of the world. I work as a full-time program manager for Greenheart Travel, but I am also committed to integrating the travel lifestyle into my every day routines. I am passionate about ethical travel, meeting new people, creating unique memories and eating local cuisine!

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