After posting pictures the other day, I had a lot of people contact me privately asking the same thing: “Isn’t it illegal to go to Cuba? And if so, how did you get there?”


First of all, it’s only a question for Americans. Virtually everyone else can travel to Cuba, spend money there and even bring home Cuban goods without repercussions.

For Americans it’s a different story. Because of the trade embargo, it’s technically legal to travel there, but illegal to spend money. (A nice catch-22.) But here is where it gets murky… the state department says that if you want to go, you need a special permit that they will issue for exceptions. For example, if you are a journalist or for educational purposes. But you don’t need to apply for the permit, you just need to qualify for one. (Others say you do need to apply). It’s a big mess. If you look at 20 different sites, there will be 20 different explanations of the laws. If you ask the State Department, they will say, “Don’t go.”

One thing to understand, is that this is only on the American side. The Cuban government has no restrictions on Americans traveling in Cuba and don’t check to see if you have some American issued “permit”.

So is it illegal for me to be in Cuba? I have no idea. Perhaps, because I’m writing this blog, I qualify as a journalist. This is also the intent of my trip, so it falls within the guidelines. But I traveled the same way that thousands of other Americans travel to Cuba every year– under the radar.

Here’s how you do it:

1. Fly to a third country. I like Mexico because flights are cheap. But you can fly into Cuba from all over Central America and the Caribbean. (Also Canada, but I’m not sure how that works).

2. Purchase a flight to Havana through a local travel agent using cash (no paper trail). I used Cubano Air, because I heard rumors that some airlines turn over their flight registry to US officials. From Cancun, my flight was $277 round trip.

3. Arrange with your travel agent to secure a Cuban visa. These are $18 and allow you entry into the country. It took my agent 1 business day to get mine.

4. If you’re not sure where to stay, you can book a package deal with your agent that includes housing. I didn’t go this route. Instead I booked a Casa Particular, a room in a private house that is much cheaper than a hotel. Mine has a double bed, private bath and cost $30 a night. Most run from $25 – $50 with hotels being more expensive.

5. You’ve got your flight, your visa, and your American passport. Make sure you have lots of cash on hand (American dollars or Mexican Pesos or whatever, you can change it to Convertible Pesos (CUC) when you arrive). You won’t be able to use your credit card or ATM card, so take a bit extra. Turn off your cell phone. It probably won’t work, but no need to leave proof of where you were.

6. Ok fly to Cuba. If you’re taking Cubano, you’ll love the Russian aircraft with it’s noisy engines and strange seats that fold all the way forward. From Cancun it was about a two hour flight.

re7. At the immigration desk in Cuba, they will take your visa and passport. The visa tears into two parts, one page that they keep and the other that they stamp and put into your passport. They don’t stamp your passport for obvious reasons.

8. You can change your money in the airport, but your taxi driver will probably take American dollars if needed. (Mine couldn’t break the $40 I gave for the fare so I paid $5 of it with dollars).

9. There will be a queue of taxis waiting for you and a ride from the airport to Downtown Havana or Vedado should be about 20-25 CUC.

10. When you check into your hotel, they will likely ask to see your visa, so they can fill out their paper work. Make sure you get it back.

11. When you leave, the immigration desk will take the other half of the visa. Again, no passport stamping will happen.

12. Eventually when you go back into the States, you will need to list the places you had traveled to. Don’t list Cuba. How will they know you went? The answer, they won’t. Besides, you totally forgot about Cuba. Cuba? Huh? Oh right, I forgot. (I did read one report where the person listed Cuba, but didn’t get fined, just hassled.)

Ok all the obvious caveats. This is informational only, and I’m not suggesting that anyone do anything illegal, I’m just describing how it could and is done by some travelers.

What happens if I get caught?

I’ve heard that the fine can be up to $10,000, but more likely $2500. I’ve heard that no American has been fined for merely traveling to Cuba. The people getting fine are doing things way outside the scope of spending a week on a beach and drinking mojitos. I’ve also heard that people don’t get fined, they get “Letters of Intent to Fine” which is basically like a big warning. And I’ve heard that this hasn’t been tested in court, seeing as Americans we have a right to travel where ever we want, and I’m sure the ACLU would have a field day if they actually got serious about fining people. For now the threat of action has been enough to keep most Americans away from Cuba, which was the desired result.

The bottom line: I couldn’t find a single confirmed story of someone getting caught, it’s all rumor and intrigue. I’m sure there are exceptions, but really the only person that knows for sure you traveled there is the airline and Cuba.

Medical and Other Emergencies

Your US health insurance won’t be accepted, but you can pay for treatment with cash.  There isn’t a US Embassy but there is a US office supported by the Switzerland Embassy, if you really needed it.

Why should you go?

Go for the culture, the beach, the rum, the dancing, the art, the people. Go because you think it’s ridiculous that the US Embargo has lasted this long, and anything that can be given for a reason can be said about China times a thousand. Go because as an American you think you should have the right to travel anywhere where they will have you. Go because you want to see Cuba for yourself. Go because you can.


There isn’t a ton, but if you have any outside of this list, please post in the comments.

Illegal Travel to Cuba from Bootsnall

National Geographic Cuba Guide

CNN’s report on Travel to Cuba

Yahoo! Answers: Is traveling to Cuba Legal?

Business Week: Traveling to Cuba

Why Obama Should Lift the Travel Restriction and Embargo (VERY GOOD)