Growing up in a traveling family, I always dreamed of exploring the world, of discovering new cultures, cities, and societies. There were only a few places marked as off-limits in my mind. Cuba was one of them; like Iran and North Korea, it was insular, insulated, and utterly inaccessible.

This propaganda in Havana reads “Blockade: the longest genocide in history.” Image courtesy of

Though only 90 miles of the Gulf of Mexico lay between the shores of our two nations, we were separated by a much stronger force than the ocean’s currents: a mutual unwillingness to let go of the past.

Now, for the first time in more than half a century, relations between Cuba and the United States are rapidly improving. The American and Cuban embassies reopened days after charter flights started between Havana and Houston. When we went in the summer, there was still (technically) a ban on tourism. Since we went through Mexico, however, getting a Cuban visa was painless. From the modern resort town of Cancún, it was 20 dollars and 90 minutes until we touched down in 1957.

Cars from the 50s are a common sight in Cuba — there are over 10 thousand in Havana alone

There’s no experience quite like riding through the Cuban capital in a 1950s taxi. As we race through the blurred tropical countryside, plunging headfirst into the urban wild, I get the sense that this is not like other cities I have seen. Going to Havana is like opening an old classic, the pages tattered and torn but the words nonetheless as inspiring as the day they were written.

The taxi comes to a stop in front of the casa particular where we’ll be staying for the next week. Casas particulares are essentially Cuban B&Bs — intimate family-run places occupying a house or a single floor of an apartment building.

Our family picked Casa Deysi y Adiel, a guesthouse in the middle of Centro, Havana’s bustling downtown district. At just $42 a night for a family of 3, it was a cheap and authentic way of experiencing Havana life. For just a couple more dollars a day, Deysi served us a fresh breakfast of Spanish tortilla, fresh guava juice, and rich homemade coffee.

The family was always eager to offer us local knowledge of their hometown. Late at night after we came home, we sat in the living room sipping coffee (consumed in Cuba 24 hours a day), sharing our impressions of the places they’d recommended and answering their questions about life in the States.

The view down Calle Concordia

Casa Deysi y Adiel lies on Calle Concordia, just a block over from Calle Neptuno, the bustling main artery of Centro. During the morning rush, Habaneros crowd Neptuno and the surrounding area. At night, they hang around the “window cafes” — little restaurants operated out of people’s homes — drinking orange juice mix and eating delicious 10 CUP (40¢) pizzas.


Next door, near the somewhat overgrown Parque Central, taxi drivers wait eagerly to take tourists around town in restored old convertibles.

Fancy a trip, anyone?

Of course, Cuba is known for its gorgeous mid-century cars — there are as many as 30,000 in the country — but, like almost everything in this city, their beauty is only incidental. Cubans drive 70-year-old cars not out of choice, but because they have nothing else to drive. Their mechanics are among the best in the world because they have to be.

That’s what strikes me most about Havana — not the incredible colonial architecture, not the historical cars, but the sense of perseverance felt throughout the city and its people. Cuba has taken a beating from the wind, the sea, and the West, and it’s endured. Not without getting a few scars in the process, but it’s endured.


Tune in next time as I explore Vedado, the neighborhood in the west of Havana.

The title image of the Capitolio Nacional (by Kofi Lee-Berman) was originally featured in “10 Photos: Time Travel to Havana,” The Points Guy, 2015


2 thoughts on “Havana: Touching Down in 1957

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