3 Tips for Traveling to Cuba

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.