I’ve always wanted to travel to Cuba, the forbidden fruit of the American traveler, to see a place that time and technology forgot…and finally did. Here’s how:
Booking Your Trip
Traveling to Cuba no longer requires the casual American traveler to book through a complicated application process, or via some clandestine travel itinerary through Canada or Mexico. I kept hearing that it was still difficult to get to Cuba so I, along with a few brave others, took the Cuban travel challenge to the test.
After asking many people about the logistics, and getting many opinions, I found a Naples, FL based travel agency named 3E & D Travel and Tours Service that seemed quite confident about their answers. I spoke with one of their agents, Daysel, and was a bit skeptical after our conversation since her overly simplistic answers seemed too good to be true. How could one just book a direct flight from Miami International Airport to Havana International, armed with nothing more than a passport and a $90 Cuban Visa? Could it be that easy?
Our travel group was initially five; however, two of them got cold feet just weeks before the trip due to the complicated language found on the US Office of Foreign Assets Control, which regulates travel to Cuba for Americans. Officially, Americans can only travel to Cuba under 12 specific categories. Then there’s the fact that there isn’t a US Embassy there and we wouldn’t be able to use our cell phones, which had them retreating.
We proceeded to book our flights, and our visa, with 3E & D Travel. We had a few flight options from Miami: one was American Airlines and the other was Vision Airlines. Both fares were comparable at roughly $450. The price seemed a bit steep considering a flight duration of only 45 minutes. We went ahead and booked the flight, and paid an additional $90 for the visa. We asked Daysel what we should say as the reason for our trip. She asked, “Why are you going?” I answered, “To learn about Cuba.” She replied, “then say that. As long as you’re going to learn about the country and not for tourism, you are completely fine.”
Under no circumstances is traveling to Cuba allowed for Americans traveling as tourists. That means no fun visits to lounge on the beach, no bachelor/bachelorette parties, no honeymoons, etc… I was prepared to let the immigration officials know that I was traveling as a freelance journalist for this piece if needed to. My travel partners are both educators and they were prepared to talk about what they learned on the trip to enhance their educational careers. It turns out we did not need to worry. When we left, there were no questions asked. At the Cuban airport, a plain-clothed Cuban official stopped us at the airport before we went through Cuban customs. He asked why we were there and we simply told him we were there to learn about Cuba. He asked, “Learn what about Cuba?” We told him we were there to learn about the culture, the food, and the people. That answer must have been sufficient because he left us alone after that.
Returning to the US
Since we left the US without incident, the next concern was the return. After all, that was the scariest part due to Cuba officially being the forbidden fruit of American travel, right behind North Korea. We prepped for an interrogation by familiarizing ourselves with the OFAC questions and even did mock interviews with each other in anticipation. It turns out that when we arrived in Miami, we were not asked a single question. In fact, we did not even talk to a live person. I entered using my Global Entry credentials, which allowed me to go through customs via a short, expedited line. It was completely automated and required no human interaction. My travel partners used the “US Citizens” line through customs, and they, too, went through the airport with no human interaction since US Passport holders now simply scan them at the kiosks.
We had zero problems, nor did we even have to worry about the 12 categories. Of course, there is no guarantee that your trip will be as seamless, so I still recommend that you have a category in mind when planning your trip to Cuba. The prepping you do may just be for your peace of mind only, which may be worth it in the end.
And whatever you do, do not use the word “tourists” or “tourism” at any point unless you feel like flirting with a hefty fine.
Travel Agency I used for booking: 3E & D Travel and Tours Service – (786) 210-8708
Continue Reading A Traveler’s Survival Guide to Cuba: Cuba 101