Photo map of Havana. Click image for interactive map.

For my entire lifespan, Cuba has been an enigma. Less than 100 miles from US soil, but as mysterious as another planet. With obstacles to travel for US citizens both real and rumored, that short trip became daunting. Daunting, but not impossible. Or illegal. Or even ill-advised. Curiosity and access to information are two of the greatest weapons a traveler can wield to turn “I can’t go there” into “I just went there”.

A combination of a long-standing desire to visit Cuba and an opportune moment for wide open flight loads spurred the effort to finally make a trip to Cuba happen. I knew that many of my colleagues had been there legally and without undue drama, so there was no question it could be done. There were just a few more steps involved than for our recent trips to Colombia and Argentina. Since Covid, there are always a few additional steps now, so what were a couple more? Since the first question everyone asks when they found out I went to Cuba is “how did you do it?”, here’s how to do it.

My fact-finding mission began with the basic question of legality. This is a basic matter of choosing one of twelve approved categories for travel to Cuba as a US citizen. Gone are the days of transiting through Mexico or another non-US country; doesn’t matter. You are still a US citizen, and that’s where the rules come in. Strict tourism is forbidden (unless through an approved tour operator), so individuals will generally travel under the “support for the Cuban people” designation. This involves supporting privately owned businesses such as casa particulares for your stay (read: AirBnb), and privately owned restaurants for your meals (most of them). No state-owned hotels. There is an online form for visitors to fill out which generates a QR code, which you will be required to provide at immigration on arrival. You will not be able to check in for the MIA-HAV leg of your flight online, but no worries if you are connecting. There is no need to exit and re-enter security to check in, just find one of the customer service desks located in the concourse. They will check your passport, ask a few simple questions, and get you checked in. Last but not least, a Tourist Card is required (green for US citizens, pink for everyone else). This can be ordered online beforehand, but given the last-minute nature of our air travel, we purchased ours at our departure gate in Miami. They cost $100 each at that point, and a kiosk will be set up at the gate about an hour before departure.

Maybe the most important consideration for a trip to Cuba as a US citizen is CASH. Take the amount you think you will spend during your stay, and then triple it. You will not be able to use credit cards or ATM/debit cards issued by US banks in Cuba. You only have access to the cash you have on you when you leave the US. We exchanged our US cash for Euros before we left Miami, because we were going to Portugal two weeks later and figured we would use it there if not in Cuba. We had heard Euros might be easier to exchange, and many restaurants did accept Euros directly. Our AirBnb host exchanged our Euros for Cuban pesos at a good rate, but believe me when I tell you there will be no shortage of people on the street offering to exchange your money for you every time you go outside. I was actually pretty stressed out toward the end of our trip (not helped by my inability to check flight loads) at the thought of being stuck there longer without enough funds. We were fine (and got seats on the first flight we tried), but more cash would have squashed that anxiety for sure.

So on to the actual trip. It was quick, we got there on Friday night and headed back to the airport Sunday morning. We were picked up at the airport in a fly ‘56 Chevy, so we enjoyed the 45-minute ride to Old Havana in style. We were greeted by our host, Eugenio, who lived in an apartment just across the courtyard from our unit. We hung out with him for a while, and he gave us some information about how things work in Cuba (and a fantastic restaurant recommendation for dinner). We also met his dog, Canela, and his cat, Pitufo (which translates to smurf). Pitufo would spend most of the weekend with us in our apartment, and he was a perfect little ginger gentleman.

We woke up early Saturday morning, and headed out for a little shooting around Plaza Vieja, just a couple of blocks away. We returned for a beautiful breakfast prepared and served by Eugenio’s in-laws. Fed and energized, we hit the streets and headed toward El Capitolio. There were people, cars, and colors everywhere. There were more abundant photographic opportunities in a few blocks than I have had in some entire trips. The sun comes up, everyone goes out into the streets, and they stay there until sundown. Most buildings were rundown, and most of them were still beautiful. A wide-angle lens is an absolute must, as everything is close together and most of the streets are narrow. My Rokinon 14mm AF got a nice workout. Jay was approached constantly, usually for money exchange first, then to sell him cigars. It was not aggressive and neither of us ever felt unsafe, but it was a lot, even though it was absolutely understandable. Real life in Old Havana is not easy, but we were still met with friendly greetings and encouraged repeatedly to “enjoy Cuba!” My favorite interaction on the street was the older gentleman who was walking toward us and yelled “hombre grande!” when he saw Jay.

After the area around the Capitol, we headed over to the Malecón. This gave me a chance to break out my 70-300mm zoom for some shots across the harbor. A fisherman had caught a tiny fish, and we he saw me he clowned with it for the camera. It was a completely spontaneous shot with absolutely no setup or fine-tuning, and it is probably my favorite one of the entire trip. After a lunch break, we headed south through the neighborhood for some architectural shots. We did so much shooting by early afternoon that we had time for some relaxation back at our place before dinner. Jay enjoyed some Cuban cigars in the courtyard with Eugenio, while I read and listened to music under the watchful eye of Pitufo in air-conditioned comfort.

We headed out for dinner, selecting an outdoor table in a cool breeze. Then the breeze turned into a downdraft, followed by an impressive thunderstorm, which drove us inside after appetizers. Ah Caribbean weather, you got us again. We waited the rain out, then enjoyed a leisurely walk back to our place through empty streets, in contrast to the crowds of the day. Most of the next morning was spent sitting on the floor of the Havana airport ticketing area waiting for seats, but our number came up, and we were back in Miami before we knew it. I was curious how customs and immigration would go, considering we were returning from Cuba. It was my first time entering the US since I got Global Entry, and it went like this: (face scan) “Susan?” “Yes.” “Anything to declare?” “No.” “You’re good to go.” So no worries on that end.

Planning and executing this trip to Cuba taught me some lessons and made me a better traveler. I learned not to be intimidated by rumors and hearsay, and to trust the processes that are laid out. Walls fall when we meet each other, and that’s worth the effort.

Boarding Pass: HAV

Boarding Pass: OPO

Boarding Pass: EZE