How to Travel to Cuba for Americans: A Guide

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Traveling Cuba Guide

Be sure to check out Jenn’s article on the Huffington Post, ‘8 Things to Expect When Visiting Cuba

Cuba is the hot spot for travelers for 2017. With recently relaxed political relations, an uncertain future, and a rich history, plenty of adventurous travelers are putting this Caribbean nation on their must list. But a DIY trip to Cuba isn’t the easiest thing to organize. Tourism is still catching on, internet access is limited, and getting off the beaten track can be tough. So how to plan an authentic Cuban travel experience? Read on for all the tips and tricks.

The Beginner’s Guide to Traveling Cuba

A Beginner's Guide to Cuba on JetsetterJenn (dot) com! #Travel

The Visa Sitch

Technically, US citizens are prohibited from visiting Cuba for tourism purposes. But a recent redefinition of the approved visa classes means almost anyone can visit Cuba without catching flack from US immigration upon their return.

There are two travel licenses for American citizens: A Specific license, or a General license. Nearly every casual traveler will fall into the General category, which does not require advanced approval from the US Government.

The General License

Within the General License, there are 12 reasons for travel that are acceptable to the US Government. They are:

  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
  12. Certain authorized export transactions

Which Visa to Choose

Within these 12 categories, the easiest to qualify/explain upon re-entry is Educational Activities. If you take any kind of organized tour, stay in casa particulares, or generally have close contact with the Cuban people, you could say that you took a self-organized people-to-people tour. If you go this route, keep a record of your daily activities. On the (very rare) chance than an immigration officer asks you to prove your educational experience, you’ll have a handy list of all the things you did to better understand the Cuban culture.

If you are also a blogger, you could make a case for Journalistic Activity. A list of articles you plan to write and your URL should be enough to prove that you are a self-employed journalist. If you happen to be asked for the purpose of your visit at the Cuban border when you enter, don’t disclose that you’re a journalist. We’ve heard that it could cause issues, so simply saying ‘tourism’ will work fine there — though I’d be surprised if they even ask!

How do you choose a visa category? When you book your flight from a US city with a US passport, you will be asked for the reason for your trip. Select from a drop-down when you book your flight. That’s all it takes!

Traveling Cuba
You’ll be Cuba bound in no time!

If You Don’t Want to Bother With This Visa Business

Simply book your flight from another country other than US. This is how Americans were making their way to Cuba before sanctions were relaxed. It used to be required to fly to Cuba via Mexico, Panama, Canada, etc. Instead of stamping your passport, Cuban immigration would stamp the paper visa card they issue you upon entry, so no incriminating evidence would be in your passport.

Here’s what I did:

  1. Booked a round-trip flight between Los Angeles and Cancun
  2. Booked a separate round-trip flight between Cancun and Havana
  3. Got my passport stamped by immigration upon entry/exit of Cuba
  4. Filled out my immigration form with Mexcio as the only country I visited upon my return to LA

Immigration didn’t bat an eye when I came through. Of course, I’d never advocate dishonesty to a government authority. I’m just relating my personal experience!

Health Insurance

Cuban authorities request that you have your own health insurance for the duration of your stay. Whether or not they actually ask you for it is another matter entirely. When I arrived in Havana, there was a table set up with what looked like medical professionals as you exited immigration and made your way to baggage claim. They asked if we were tourists, and when we said “yes” they waved us through.

We had already purchased travel insurance from World Nomads anyway, and had our policies printed out in case we were asked. Even if you don’t do this, sources say you can purchase health insurance at the airport for a pretty small fee.

Get There

Havana Traveling Cuba
Havana at Night

For Americans, getting to Cuba used to involve some airport gymnastics and trickery at immigration. Thanks to the most recent political administration, this has changed a lot in the past year. Without knowing what 2017 will bring for US-Cuban relations, it’s important to know all the ways to get in and out of Cuba, just in case things turn around.

Fly Direct

US Airlines are adding more and more routes to major Cuban cities every week. Jetblue, Alaska Airlines, and Southwest are just a few who are joining ranks with major carriers like American Airlines and United to connect the two countries. With more competition on these routes, you can bet that fares will be reasonable. Win!

Tourists who go this route need to qualify within one of the 12 visa classifications for a trip to Cuba. In general, the Educational Activities category is a catchall that doesn’t require a ton of evidence to prove. There are always exceptions and things could change at any time, so do your research before you go!

Fly Via Mexico, Canada, or Central America

If you don’t want to run the (pretty small) risk of getting into trouble with US Immigration upon your return home from Cuba, you can book a flight to another country first. One of the most popular spots is Cancun, a short 1-hour hop away from Havana. Another popular departure point is Panama. Any flight from Canada or Europe should also help you skirt the visa restrictions. If you do this, it’s best to book your return flight through the same city, just to keep US immigration from raising any eyebrows.

Take a Cruise

If all-inclusive luxury and no red tape is more your bag, a cruise is where it’s at. There are cruises that depart from Florida that stop in Cuba, with no visa required — the cruise line takes care of everything.

Where to Stay

Accommodation in Cuba ranges from the most humble homestay to the glitziest all-inclusive resort. There is no bad choice; it all depends on the kind of trip you want to have.

Resorts and Hotels

Resorts Traveling Cuba
Plenty of luxury in Cuba

Luxury travelers, rejoice! If all  you want to do is kick back and have every need catered to, this is your jam. Many of the beach destinations in Cuba are chock-full of all-inclusive resorts. Seasoned luxury travelers say that some of these resorts don’t quite measure up to other destinations. My experience at Melia Las Americas in Varadero was on par with other beautiful resorts I’ve stayed at. The only thing lacking perhaps was the food, but this is a consistent issue across Cuba.

If you go the hotel route, be prepared to pony up some serious cash, and book ahead. A standard hotel in Havana is a minimum of $300/night, and they can be booked months in advance.

Casa Particulares

These are the Cuban equivalent of a bed & breakfast — it is usually a spare apartment or rooms within an apartment owned by a local Cuban. They are registered and regulated by the Cuban government, and they are usually never more than $25/night. We have seen some prices quoted higher in places of high demand (Habana Vieja in Havana, for example), or when availability is tight. Since the extra cash most likely goes straight to your host family, ponying up an extra $10/night isn’t the worst thing in the world. Casas are clearly marked on the street with this sign:

Casa Particular Traveling Cuba


Some casas are called hostals — I’m not 100% clear on the difference, but they appear to offer more rooms per property, and the prices can fluctuate wildly. In one the going rate for a room was $70/night! They are marked with the same symbol as the casa particulares, and I assume they are regulated by the government as well, but perhaps not as strictly.

Get Around


There are plenty of buses that can take you from city to city. The primary operator is Viazul, a government-operated company. Prices are reasonable, but the bus stations can occasionally be inconveniently located. If you don’t mind schlepping your bags from the station to your accommodation, this is the most cost-effective route for solo travelers.

Colectivo/Share Taxi

There are a set number of share taxis that can be booked through the InfoTur offices in the major Cuban cities. Usually for about the same price or a little more ($5 – $10) you’ll get door-to-door service from Point A to Point B. Cars can be cramped and may or may not have A/C, but it can be a fun way to meet fellow travelers!

Official Taxi

These are the government-sanctioned taxis that you’ll see around any major city. While they can be hired to take you from town to town, it would be ridiculously expensive in comparison to the other options listed here. I wouldn’t recommend it.

Private Car

Traveling Cuba Private Car
A quick pit stop with our driver to get some fresh sugar cane

If you’re traveling with a group or can stitch together at least four people, then you can create your own collectivo! Many enterprising Cubans rent cars long-term and troll the streets looking for people to drive around. I preferred this option because it felt like the route that gave the most cash directly to the person driving me, not the government. Prices are negotiated directly with the driver, and they’re usually competitive with ‘official’ collectivos.

There it is! The basics for getting to and exploring Cuba to the best of your ability. Did I miss anything? Let me know in the comments!


  1. This is such great info! I´m thinking about heading to Cuba in April, and will definitely be saving this for future reference. Did you find there was hoards of other tourists as well or were they far few and in between? I´d imagine since the embargo was lifted that tourism has picked up quite a bit.
    1. DEFINITELY GO! Yes, it gets a little crowded, especially in Havana (I was there in early November right before the major tourism season), but there are unlimited opportunities to get away from it. Definitely check out Vinales, so gorgeous!
  2. Great tips! I went this fall on a cruise with Fathom and luckily they did all the thinking for me. I think I'm ready go to back on a land trip now. Loved your photos.
    1. It's a great place to DIY -- challenging but so worth it. The people are the BEST part of Cuba. I heard about that Fathom cruise, it sounds like it was fun!
  3. I absolutely love Cuba - I've been about four times now. This was way before I had a travel blog so I can't remember too much of what I saw and did but I absolutely loved Varadero, Cayo Coco and taking a day trip to Havana and seeing Old Havana. The old style cars are just so neat! I can't wait to go back to one of my fave countries in the world!
    1. Ahh so lucky! I loved it too and I definitely want to explore more... you don't realize how big the country is until you're there. I'll need a return trip (or two) to make sure I check everything off my list. Thanks for reading!
  4. I definitely want to get to Cuba soon, so I'm eating up all these Cuba posts. Yours is full of great tips and hints, my favorite kind. Thanks.
  5. This is a super useful post! There's not a ton of information for Americans about traveling to Cuba. I know I looked into it late last year, and just couldn't find much about transportation or lodging, so I decided not to book the trip! Now that I've read this, I feel way more confident about a Cuba trip!
    1. I'm so glad you found it useful! Traveling in Cuba isn't as easy as, say, Thailand, but it's SO worth navigating it. Amazing people and such natural beauty. Book that trip! :-)
  6. Great post, and it's hard to imagine how big a change US tourism will make to Cuba. But it's such a beautiful country worth visiting. And I found getting around surprisingly easy when I was there. Loved the collectivos!
    1. I know! Hopefully it retains it's authenticity as more people come in -- I absolutely loved it!
  7. These are great tips!! I visited Cuba last month, and I am so glad I conducted research prior to my trip. This article will def help those planning a trip to Cuba.
    1. Ah too bad I couldn't get this one out before you went! Where did you go in Cuba? I really loved Trinidad -- such a pretty and relaxed little town.
  8. Great info! I didn't know much about visiting Cuba as an American. It's crazy some of the hoops we have to jump through to visit. But I hope to make it there someday! And I'd love to stay in casa particulares; I'm a big fan of B&B's.
    1. It's easier than ever before, and if you just get on a plane and go you'll probably be fine. But it definitely used to be much more difficult. Thank goodness it's easier to visit now -- so worth it!
  9. Fantastic guide. I haven't been to Cuba yet but so want to get there before it changes big time (and I think it will). Love the photos.

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