I fell in love with Cuba when I was a teenager. Before I moved to New York City, I went on many trips to Havana with my family. It was one of the few cities that I never got bored visiting. The people are so friendly, the customs are fascinating, the ballet is almost free, and everywhere you look you are overwhelmed by the beauty that surrounds you. I always wanted to go back. But since I’ve been living in NYC (and married to a New Yorker), it’s been impossible. Now, though Cuba’s not quite “vacation-ready” for Americans, we may be heading in that direction.


Since President Obama announced a move to restore diplomatic relations with Cuba and to alleviate certain travel restrictions, American travelers have been anxiously awaiting the opportunity to pay Cuba a visit. This will mark the first time in more than 50 years that Americans have been allowed to travel within the Cuban borders without having permission from the U.S. Treasury’s office. And though many restrictions remain in place, the move still represents a landmark moment for those who want to visit family or who are simply curious about our island neighbor to the south.

That said, we’re still swimming in new waters, so prospective travelers need to educate themselves as much as possible before booking that plane ticket. If you’re considering a trip yourself, here are just few tips to help you stay safe and stay legal when planning a trip to Cuba.
You Still Need a Reason (and some documents)
Traveling to Cuba is not simply a matter of business or pleasure. Although you don’t need expressed permission from the Treasury’s Office of Foreign Assets Control, you do need to have a reason for travelling to Cuba that falls under one of 12 categories permitted by a “general license.” The full list is available here on the Treasury’s website, but you should be aware that one the categories is not “Vacation.”

It’s rare that an American is reprimanded for a trip to Cuba. That said, if the Department of Treasury were to find out that you traveled to Cuba, they are going to want proof that your trip was for an explicit reason. Entry to Cuba is permitted for family visitation, religious ceremony, journalism, humanitarian missions, and even for attending a sporting event. More generally, you can travel there for person-to-person contact and educational or humanitarian reasons (but not for your bachelorette).

If you’re interested in volunteering, there are many organizations you can team up with. Check out this program to help the cats and dogs of Havana, and check this listing to see if any other humanitarian missions interest you. This way you’ll not only get to experience a broadening of your mind — but also of your heart.

Make sure to check this gov website for current details. All travelers to Cuba, including religious workers, should contact the Cuban Embassy (tel: 202-797-8518) in Washington to determine the appropriate type of travel card/visa required for their purpose of travel. Cuba requires visitors to have non-U.S. medical insurance, and sells a temporary policy to those who do not have it. Questions about this insurance requirement should, again, be directed to the Cuban Embassy. Alternatively, you can travel with one of many “Cuba USA” tour operators, and they will arrange all the necessary documents for you. As always, make sure to check reviews (even the “filtered” ones on Yelp, which are usually valid reviews). Here’s a great FAQ article via CNN, and another via the NY Times, that will answer more of your questions.
Protect Yourself Ahead of Time
The general position on traveler safety in Cuba is that it’s just as safe (or unsafe) as being in any other country in the Caribbean, like the Dominican Republic or Puerto Rico. It is a relatively poor country with a low-level criminal element — mostly stealing boxes of cigars from factories and reselling them. Still, as with all travel, the best defense means having a little bit of common sense and taking steps to protect your belongings at all times.

Currently, Havana is a low crime area since there are many police officers scattered around the city, and punishment for any crime against a tourist is extremely steep — an effective deterrent. Still, travelers can be sure that a whole industry of pickpockets and thieves will pop up to take advantage of the sudden influx of American travelers with wallets and purses full of American money.

Before you travel, take the time to read about how to avoid becoming a victim of credit card and identity theft. Protect the personal information on your smartphone by setting a lockscreen passcode. It’s valuable advice whether you’re travelling across the street or across the Gulf.
Have a Contact or Hire a Tour Guide
The move to open the borders with Cuba happened suddenly, so it’s understandable if the country’s infrastructure isn’t yet suited for hundreds of thousands of new travelers. To be sure, Cuba has several incredible resort hotels and tourist attractions to cater to international travelers, but getting around the country can still be very tricky.

Even hailing a taxi can involve a series of negotiations and miscommunications, so do yourself a favor and have a contact or private tour guide who can show you around or make arrangements for you ahead of time. Even if you have to pay extra upfront, you will most likely avoid a lot of anxiety and price gouging. Plus, you’ll have the peace of mind of knowing that you can call someone if your trip starts to go south.



Are there any ATMs in Cuba? When I travel internationally and need cash, I just use my ATM card (my bank reimburses any ATM fees) to get as much cash as I need. This has always gotten me the best “exchange rate” since US banks use the actual exchange rate (with no fees or taxes). I would assume that this would be even better than having euros or pounds to exchange.
This was my question, too but asked before me. Hoping TPG will weigh in on whether or not you can withdraw local currency from ATMs in-country.
Thanks so much for the helpful information! I have a tentative Havana adventure planned for next month. We’re New York natives flying into Cancun and are playing around with our options to get to Cuba as the direct flights into Havana are all booked during our stay. :/ At this point it seems like we’re going to be stuck with at least one layover to get there (and an extra $100+ per person), but it might be worth it if we get a chance to have dinner in Panama. Please keep updating your posts; I’m eagerly awaiting more guidance! Cheers!
Thanks for the great post! Were you able to pay for your visa in the airport with credit cards? Or did you have to bring cash for that part?
Hello Hilary, amazing piece as always. Very useful tips and amazing photos. I admire your work and respect you as a blogger because you’re very brave and good at what you do. Keep up the great work! 🙂
GREAT post! I applaud you!
Canadians and Britons can travel there, but as Americans we can’t. Because somebody in our government doesn’t like somebody else. Yeah, that makes sense.
My suggestion is to go there and decide for yourself if you want to go back, or if you want to recommend it to friends. If you don’t like their government, then don’t go. But my government shouldn’t tell me I can’t go because they don’t like them.
Thanks for posting this. It’s absolutely true.
Cuba has been open to travel to every other country in the world (including the UK, and Western Europe) for decades, and it has not changed the political climate there. It’s incredibly short sighted to believe that opening it up to America will do anything other than boost the regime’s hard currency reserve.
But, again, what’s more important than maximizing credit card points!
Just because a country is ruled by a dictator doesn’t mean it is wrong to travel to that country. If it was, many great and wonderful places would be untraveled. 🙂
Cool tips! And great writing as always. I was in Cuba last summer with my boyfriend. Enjoyed it. But it was a little strange. What I found the most strange about Havana was how safe I felt. It was so hot during the day, so we walked around later at night. We noticed more people were out from midnight to 3am than any other time. We’d walk from our hotel (Hotel Nacional) over to Coppelia. It would be packed with people at all hours. Even walking through the neighborhood to get there in the middle of the night, I was completely comfortable. The police on every other corner helped.
Great tips! I agree with all three of them. 🙂 I was able to visit in 2009. It had the best meal of my life there. I ended up spending nearly a month there and wish I could have stayed longer.
Love your article! I’ve been to Cuba twice. My experience is that Cubans are very educated and curious about foreigners, Europeans and Canadians have never stopped having access to the island. Cubanos randomly approach to ask where you are from, welcome you and then be on their way. A healthy suspicion when they try to take you to a favorite bar or casa is good but you’ll miss some really rich experiences if you avoid personal encounters.