Cuba is an amazing country with an amazing history of music, wonderful people, and beautiful beaches and cities. It is unfortunate Americans can’t travel there easily. This is a guide on how to travel there without a visa issued by the United States (which is what I did). Of course there are ways to do it legally but it takes more time, money, and resources to make that happen. We can only hope this administration will open up travel to Cuba but until then it is a great adventure to travel there “illegally.”

A Little Background about Cuba

It is legal to travel to Cuba but it is illegal to spend money there which is due to the trade embargo. The US State Department will allow anyone to travel there legally but you will need to fall into certain categories such as a journalists or education to name a couple. This means you will need to apply for a license and be pre-approved for travel to Cuba. Most of us wouldn’t qualify for this which is why thousands of people every year travel to Cuba illegally from the US.

More of my Favorite Travel Photos from Cuba

More of my Favorite Travel Photos from Cuba

People-to-people tours are becoming very popular and basically allow you to skirt around the travel laws. They are tour companies that get you into Cuba for an organized tour with an agenda. There are a few set things and they arrange the flights and hotel. This allows anyone to side step the embargo. There are plenty of these companies online and they are not cheap. This guide will teach you how to do it without a visa issued by the US.

How to Travel to Cuba from the US Without a License

1. Fly through another country such as Canada or Mexico. I recommend Mexico since flights from Cancun are cheaper and quick. You could also fly from any other Central American country or somewhere else in the Caribbean. Some people have reported being questioned upon reentry through Canada as an American citizen. Those chances are low and Mexico was a cheaper and more direct option for my travel. Others use Panama City, Panama as the third party entry point but just do whatever works best for your itinerary.

2. Purchase a flight to Havana from the US. Keep in mind sites such as Kayak and Orbitz will NOT have flights to Cuba. Many airlines will fly there such as AeroMexico and Cubana Air. There is no possible way to book a commercial flight to Cuba at this time with online booking agents in the United States. All flights through organized tours are arranged through third party tour operators. Even if you have a legal visa for travel, Kayak will still now show you results for flights to Cuba.

Travel Hacking Tips

I flew the first leg of my trip to Cuba for free using miles. I flew into Cancun before departing to Cuba a few hours later.

Here are some great ways to earn miles:

• Travel Hacking Without Credit Cards
• How to Earn Miles at Hotels
• Best Travel Hacking Credit Cards
• Learn How to Hack a Flight with No Miles at All
• All My Travel Hacking Resources

However, you can book a flight online with non-US airlines.

CubaJet.com is a great place to start looking for flights. They booked me on Cubana and the customer service was great even when my flight was rescheduled.

 

Flights range from $275-375 roundtrip from Cancun. Not cheap for a 1 hour flight but it’s worth it, trust me.

3. Before you leave the airport pre-purchase your Cuban visa. This ran me $25 at the Cancun airport and was easy to setup. Give yourself an extra 30 minutes to get this on arrival or between flights. There is a counter at most airports where these can be purchased before you head to Cuba.

4. Prebook your accommodation for Cuba. Some immigration officers in Cuba will ask where you are staying and you will have to fill it out on your customs sheet anyway so book ahead of time. If you want to save some money and have a more authentic stay book with a Casa Particular. They are private rooms in Cuban families homes and will run you $25-35/night.

Many forums will say Casas are not acceptable housing for visitors but this is not the case. I did not pre-book a hotel and had no issues at immigration. Just be honest with the officer. They want Americans to come and there is no need to hide it. They are going to see your passport anyway

See my guide for where to stay and how to book a casa particular.

Note: Some Casas will arrange an airport pickup if you ask. This makes life easier on arrival and will run you $20-25 USD to get downtown Havana.

 

 

 

 

 

 

 

 

 

 

 

 

5. Cuban Immigration and customs is pretty straight forward. They may ask where you are staying, how long, and why. They are happy to welcome Americans so no need to lie. They will NOT stamp your passport so don’t worry. They will stamp your visa so don’t lose the other half they give to you for your exit.

They actually did not stamp mine correctly on the way in and when I departed it took about 30 extra minutes for them to sort it out. There were no issues of course and honesty is key here.

6. Bring a lot of cash. Your credit cards will not work anywhere in Cuba. If you run out of money it will not be an enjoyable experience. Plan your expenses well and then bring more on top of that. You want to be prepared. There are two currencies in Cuba, the Cuban convertible peso, for tourists, and the peso, for the Cubans. You will use the convertible (CUC) everywhere in Cuba so no need to exchange money for the Cuban peso unless you want to collect some unique currency (which I did to bring home).

It is very easy to exchange your cash but don’t expect a good rate. Basically the Cuban convertible is about 1:1 with the USD but there are fees to exchange it on top of the exchange fee. A nice hotel in town is an easy place to convert the cash just don’t expect a great rate. Some people recommend exchanging your USD to Euros before you leave to get a better rate. That is up to you but was not a concern for me.

7. Leaving Cuba. Don’t forget the other half of your visa when you return to the airport. Just keep in in the pages of your passport for safe keeping. They will stamp it and take it on the way out of the country.

It is just like any other international flight so no need to worry. Two hours prior to take off is plenty of time. They forced me to check my carry-on but was able to bring my backpack on the plane. Just be sure to take all valuables out of your luggage if you are forced to check your bag.

8. Reentering the US. Remember you are not the first or the last person to travel to Cuba without a license. Thousands of people do it every year. Do NOT list Cuba on the “countries I have visited” part of the immigration form in the US. And when the immigration officer asks just say Mexico or whichever country you just came from.

Now, I do not recommend lying here but when they ask, “where have you been?” you can honestly say Mexico. Do not include Cuba. Some people have reported on forums they mentioned Cuba and had no issues but I do not recommend this. It is possible to still be fined heavily for traveling there and there may be additional questioning if you mention your trip to Cuba.

This was a much more straight forward process than I imagined and 100% worth it. I will return again some day with or without a license from the US.

Other Notes

The Mexican Death Stamp

If you read enough on the forums you may hear about the “Mexican death stamp.” This applies to any third party country but was named for Mexico since it is a common departure country for Cuba. This process can make anyone a bit nervous until you realize you have nothing to worry about.

Here is how it works:

When you fly into Mexico you receive an entry stamp in your passport as you would in most countries. You then proceed to Cuba where you get no stamps at all. You then fly back to Mexico and receive another entry stamp. This means you now have two entry stamps into one country(Mexico) with no exit/entries to any other country. If you were to line up the dates of the stamps in your passport it would be clear you were somewhere for a period of time with no record of it. A curious US immigration officer may notice this or question it but most likely will not care at all. Seems like this could be a problem right?

My Experience:

I read on most of the forums when I was doing research that this was a non-issue but just based on the name of the it I was slightly concerned. Some suggested bribing the Mexican officer with a $20 and politely asking for no stamp but I didn’t take that route.

When I first entered Mexico I asked in Spanish for the officer not to stamp my passport at all and failed. My Spanish is ok but the officer could not have cared less and stamped where he pleased.

I then tried again when I entered the second time. This time he responded in English that he has to stamp it by law. Of course I knew this, but so many border officials around the world will look the other way and have for me in the past. I then asked if he could please stamp a different page from the first stamp to separate the two. The officer nodded (what seemed like a yes) but put the stamp right next to the first one (just doing his job I guess).

My passport was 100% full with new pages sewn in. I was hoping a couple stamps mixed in with all the other stamps would be hard to notice. He found one of my brand new pages I just put in and put them side by side.

At US immigration in Atlanta I didn’t mention Cuba or write it on my form at all. The officer looked at the stamps and said welcome back. There you go. Don’t worry about it. It was like any other return home. Where did you go? How long were you there? Thank you, stamp, move on.

A way around the US checkpoint

The US is rolling out the Trusted Traveler Program to more US cities this year. In Atlanta, had I applied for this, I could’ve bypassed some of this interaction all together. This will cost you $100 to sign-up and you must pass a screening process but if this is something you plan to apply for anyway it is great for return travel from Cuba. Just be sure to make your connection that has Trusted Traveler.

What can you bring home from Cuba?

If you go down as part of a people-to-people tour or any other legal way you are permitted to bring home art, music, and anything along those lines. You cannot bring back Havana Club Rum and Cigars. Chances of getting searched are low when you get back to the US but if you are trying to bury the evidence don’t bring back anything at all. This means currency, paperwork, ticket stubs, maps, guide books, or anything else that proves you went there.

However, I brought a few things with the help from some friends in Mexico. I always bring home currency and since Cuba has two currencies I couldn’t leave it behind. Along with some cigars and some artwork I picked up in town. All small enough to not raise any alarm entering the US but the risk is up to you. I don’t recommend it.

What to Remember For Your First Trip

Relax. Thousands of people travel to Cuba every year illegally and have no issues at all. There are reports of people being fined up to $10,000 or more or lesser fines of $2,500. This is rare and I wouldn’t worry about a fine. Also, if you don’t speak Spanish make sure your Casa Particular owner speaks English or you may find life difficult in Cuba. All of the major hotels will speak English but be sure to establish communication in English with your Casa before you leave. This way when you arrive you won’t have any communication problems. My casa owner spoke 100% Spanish but that just made it more fun and allowed me to practice my Spanish.

Legal Travel to Cuba

There is a lot more information about this readily available online. Essentially you need a “people-to-people” license issued from the US. You can go with tour companies or in groups depending on what your travel is for. Journalism, educational and religions purposes are just a few of the ways you can gain entry through application. The benefit of this is you can leave on a chartered jet from a few different US airports. These flights are off limits to ordinary people who don’t have a license.

The negative side of these tour groups is they are usually more expensive and a lot more structured.

Go to Cuba before the US invades (with tourists) and have fun! Drink where Hemingway sat, watch a Cuban béisbol game, and smoke cigars on the Malecón! It is a beautiful country and now one of my favorites. It is not to be missed!

Do you want to learn how to travel to a place like Cuba for free? Sign-up for my Newsletter below. Learn how to start travel hacking and see more of the world for less!

 

Other Resources

Triphackr Travel Hacking Resources

My Huffington Post on Cuba

My Guide to Havana

Triphackr Travel Photos