What to expect on your first trip to Cuba

It was my first time going to Cuba, so we weren’t sure what to expect when we arrived at the Miami airport. ?

I was traveling with June Bradham, CFRE and Earl Bridges ?? who volunteered to scout a trip we are taking with The Post and Courier Travel in March. ?

Academic Travel Abroad put together a condensed itinerary with all the elements of the March trip – music, art, culture, and lots of food. ?

The Cuban embargo remains largely in place, six decades after the revolution, with exceptions in 12 categories for American travelers. ?

We filled out a travel affidavit sent to us by the ATA team, selecting “Educational activities” as the reason for our trip. Then, 48 hours before our flight, we filled out a form sent over by our airline. We were given a QR code, once it was completed, which we printed out and brought to the airport. ?

We flew Delta Air Lines . At the gate, about 20 minutes before our flight, a vendor set up a kiosk. We showed him the QR code and our passports and paid $100 for a pink tourist card. (Pro tip: Keep the tourist card! You’ll show it upon entry, and when you leave the country, they will ask for it again.) ?

The weird and wonderful thing about traveling to Cuba is that it’s only an hour flight from Miami.?

In that time, you can read a chapter in a book. You can eat a bag of SunChips and look out the window at the islands below – outlined by white sand in turquoise water. But just as you start to daydream, the plane banks and you find yourself looking down at the dark red farm fields of Cuba. ?

It’s barely a journey. And so that rite of letting go of yourself that usually happens in the hours of air travel, doesn’t happen before you land. ?

It’s a reminder that Cuba is not just our neighbor, but an estranged part of us. A complicated relationship we’ve been in our entire life. And understanding it better is part of understanding ourselves. ?

It’s as familiar as a childhood memory and just as shocking to see in real life as revisiting a place from your youth. Because we know Cuba as well as any family album we’ve looked through a thousand times. The faded pastels and plaster, the tall wooden doors and marble stoops, the old cars that men care for and love more than any woman. ?

When we arrived, we walked through the streets of El Vedado – that neighborhood of the wealthy now falling into ruin. Wide sidewalks. We saw … A man standing inside his white scrolled iron gate, ready for a conversation with a neighbor. A line of people spilling single file down the stairs of a store, passersby craning their necks to see what is available today. A man sitting at the sewing machine, head down, a pile of shirts and pants to be repaired on the table by his side. Tomato seedlings growing in a garden.?

I think of a line from a short story by Laidi Fernandez de Juan: “The enlightenment of poverty made everyone part of the same family.”?

Laundry drying on every balcony. Chairs on every front porch. Front doors wide open. ?

We piled into a car – a perfectly maintained 1956 Chevrolet Bel Air – and drove to a neighborhood on the outskirts of Havana and knocked on the door of a home. A mother led us up the stairs to the rooftop to listen to a band of college-age musicians - Proyecto Bajareque. ?

The night air. The Afro Cuban jazz with a slight edge of Sun Ra experimentation. Water from a canal reflecting the moon and the palm trees. Cups of strong Cuban coffee with lots of sugar. ?

It was almost too much to realize that my 2:30 p.m. flight put me here on this rooftop at 6 p.m.?

In those first moments, I felt too serious to there. I have no tropicalismo. My clothes are black, brown, blue. ?

Those first moments in Cuba, I realized how much I did not know. I did not know how to move my body, the intuitive way the woman next to me slid her feet front to back. My hips did not move. I felt myself on the chair – pinned there by my brittle rebar spine, ready to shatter and blow away in the tropical breeze. ?

The saxophone player clapped. One, two, one, two, three. But my body was still on some other time signature. ?

The first thing to do in Cuba is reset your metronome and the only way to do that is to stop and listen and really be there. ?

The warmth of the air loosens you up. The easy smiles on the faces of the women sitting in doorways makes you feel comfortable. You slow down. ?

I listened to the keyboard and the drums, the bass and the saxophone. It’s been 76 years since Dizzy Gillespie met Chano Pozo in New York and brought to life this sound. ?

I felt the music – rhythms from Africa traveling through the Americas, passed hand to hand, ear to ear, for all these years, blended and transformed. Listening to that music was the perfect entry point for our journey. It helped me understand where I was in the world and in time. ?

We flew across a bit of ocean to an island. We left our lives behind. We did it to learn something.?

In next week’s newsletter, I’ll tell you more about our trip to Cuba. The short version is that I learned something that shifted my mental map of where I am in relation to other people. It helped me more deeply understand an element of politics of the upcoming presidential election. In moments, my heart broke, in others I laughed so hard that I cried in a wave of optimism about the capacity of human creativity. Most importantly, I haven’t stopped thinking about it the complexity of it all since I left.

The Cuba trip in March is sold out, but we have a waiting list and if enough people want to go, we can create a second trip.?

Enough people signed up for our trip to Rwanda in January 2025 that we were able to buy the gorilla trekking permits to go. There are still a few spots left if you want to see mountain gorillas in the wild - a true once in a lifetime experience - and chimpanzees and the Big 5 in a little visited national park. https://www.postandcourier.com/travel/rwandas-unforgettable-primates-and-wildlife/article_d05ea4b8-5cd1-11ee-ba5b-3f6c3384bcc3.html

As you plan out your 2024 travel, I am taking people to Northern Ireland / Ireland in June, to Morocco in the fall and to Cambodia in early December. And I'll teach you how to use writing as a way to deepen the experience of travel if you are looking for a transformative journey, not just a trip.?

https://www.postandcourier.com/travel/