3 Tips for Traveling to Cuba

#HilaryRowland

How to get there and back without getting fined.

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.

Chatting with a local in Havana
Chatting with a local in Havana
A photo I took of a local entrepreneur
A photo I took of a local entrepreneur and her cat

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.

Shopping for art in the square (although Havana has incredible, and inexpensive, galleries)
Shopping for art in the square (although Havana has incredible, and inexpensive, galleries)

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.”

hilary-art
Street art in Havana

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).

Feeding a street dog (a nursing mother) in Havana. I tried to bring dog food wherever I went.
Feeding a street dog (a nursing mother) in Havana. I tried to bring dog food wherever I went.

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.

Crossing the street, with my dad (in the fedora)
Crossing the street, with my dad (in the fedora)

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.

Joking around with a local (yes, those sunglasses were in style at the time!)
Joking around with a local (yes, those sunglasses were in style at the time!)

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.

Looking very touristy in Havana
Sunburned and looking very touristy in Havana

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.

With my mom in old Havana
With my mom in old Havana

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.

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Hilary Rowland

A writer, artist, and designer since she was young enough to put pencil to paper, Hilary taught herself code and created Urbanette when she was a teenager. Currently, she lives in Monte Carlo, but spent the past decade living in NYC, still considers herself a New Yorker, and visits regularly. She's always traveling, looking for hot new topics, destinations, and life hacks to bring to Urbanette readers.

Reader Discussion: 110 Comments

  1. Does anybody know if as American citizen visiting Cuba are you allowed to purchase food for cooking in Cuba without a problem? What is available to purchase for food? Also what is the departure tax, and what currency do you use to pay it? Thanks! 🙂

    Reply
    • Hiya! The departure tax is payable as you leave Cuba. It is 25 cuc per person and must be paid in cuc and cash only. A good piece of advice that a travel agent gave us a long time ago now, was to set this money aside as soon as you get some money changed that way you will have it and not worry about it. You will be directed at the airport where you need to pay it.

      Reply
  2. We are heading to Cuba in August and I appreciate all this helpful advice. There’s really so much to be aware of when you’re traveling there. But we’re very happy to be going now! Thanks.

    Reply
  3. QUESTION : what about passport stamps for illegal US travelers? Trying to go for this new years and having a difficult time figuring out if it is too risky to go now illegally. Can you really just ask someone not to stamp your passport and they won’t?

    Reply
  4. I love this. Reminded me of my trip to Cuba. It has at its northern coast many beaches that are very belllas as Varadero with its crystal clear water s. The keys have paradisiacal landscapes, in order nauturales an island full of charms. 🙂

    Reply
  5. Enjoyed your blog, Just returned from Cuba. I’ve tried to gather as much information as possible before our trip. The one thing I wasn’t prepared for was the poverty of the people in Cuba. We stayed in Old Havana in a Casa Particular. I purchased items to bring with us on the trip to leave as gifts, like soaps, pens, batteries, reading glasses. The people are so grateful. They want to talk with you and know where your are visiting from. I left with such mixed feelings of sadness for the people of Cuba, and pray that their lives will improve.

    Reply
  6. Great post! my husband is from Cuba and this is my second time to this beautiful country. We just celebrated our wedding ceremony at Hotel Nacional and did a 5 day tour with our group, everything you have mentioned here is by far correct since during my first trip to the country I was not quite prepared and knew the second time around to bring some necessities and definitely learning spanish!

    Reply
  7. great write up, thank you!! we’re planning on going early november and will revisit this post as we get ready for it. was wondering how long would you recommend to stay. we want to be able to really experience / learn the culture without being rushed. any advice helps! thanks again so much!

    Reply
  8. Cuba is a quite stunning country to visit and I really enjoyed seeing your photos. rings back many happy memories from my last trip there in December. I only get to go there once a year but am anxious to get back to Havana (I prefer it to the beach locations actually). Great blog. I have started following your posts recently.

    Reply
  9. The hubby and I too are among the many people who have Cuba in the top 5 of our bucket list. The cars, the architecture, the music, and the food! Such a vibrant country. Hopefully we can make it there sooner than later. Being stationed all the way in the England makes it a little challenging though haha… -We are a navy family.- Thanks for posting this. Love the pics.

    Reply

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