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48 Hours in Havana Cuba

Updated: May 24, 2023

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Updated January 29, 2023

When my husband and I first started dating, we talked about travel a lot—Cuba in particular. Cuba's history is closely tied with that U.S., from Earnest Hemingway's 30-year affinity for Cuba to the Cuban Missile Crisis. Like many, we were captivated by the music, the cars, the time-capsule-like promise of Cuba.

The Obama administration re-opened travel to Cuba in 2016, but when we heard rumblings that the Trump administration would soon close travel again, we booked a five-day cruise out of Tampa in May of 2018 with my sister and her wife.

A bit about cruises

When we travel, we prefer to be our own tour guides, so we were nervous about the confined setting and set schedule of the ship. To boot, we sailed through heavy storms that kept us from hanging out in the sun on the deck. Still, we managed to stay occupied by playing cards and people-watching. Cruises always have something going on, from movie screenings to a "sexiest cruise member" competition. I think one more day on the ship would have been too much for us.

Additionally, all activities in Havana were accessed and arranged through the cruise. We picked our walking tour and bus tour from a list of "excursions" on the Royal Caribbean website. Maybe other destinations allow for more freedom, but the U.S. Government really didn't want us striking out on our own in Cuba.

Walking Old Havana with Hemingway

Our first morning in Cuba started with a walking tour starting at Ernest Hemingway's favorite watering hole, the El Floridita, where we enjoyed a complimentary daiquiri while a local band played raucously. We saw several cathedrals, squares, and former military parade parks. The armed military presence and history were subtle, yet constant. Armed soldiers with firearms and dogs stood sentry at major locations. Almost everywhere we looked, we saw a former barracks or fort among the lush greenery. At the conclusion of our tour, we were allowed an hour or so to roam more or less freely. My husband bought a few cigars and a few bottles of rum for the ship, and we wound our way through the squares and alleys, taking in the sights and the people and popping into random places for a mojito.

A Few Things About Travel to Cuba

There isn't really any shopping to be done. Because the government controls commerce in Cuba, there isn't much to choose from, especially brick-and-mortar shops. For instance, Havana Club was the only brand of rum we saw. They had a regular bottle, a mid-shelf bottle for a few dollars more, and a top-shelf bottle that was even more expensive (which wasn't very much). A few Cubans had stands where they sold used books and records, even old Soviet enamel pins, remains of Cuba's alliance with the Soviet Union. Cubans selling items in the street can be pretty in-your-face. One popular thing there is for a Cuban to follow you and sketch your portrait on a piece of paper, then try to sell it to you. These aren't artists, they're usually just trying to make a buck, which is fine. We bought our portrait, and my husband and I still chuckle about it occasionally. There are definitely a few tourist scams to look out for, and you should educate yourself before you go.

Restaurants can be complicated. If a restaurant looks like a regular restaurant, it's run by the state. We weren't supposed to eat at these places, but we unwittingly had a questionable hamburger and salad that weren't that great. Cubans run private restaurants out of their homes, and we wish we'd tried one of those. The only other meal we had was at a Swedish expat's restaurant, so the fare was a blend of Swiss and Cuban. It was delicious! Odd, though, being an American, eating a Swedish meatball in Havana, Cuba.

Cuba is far from pristine. It was jarring how one moment you could be in this beautiful cathedral square, then turn the corner to an alley of half-demolished buildings and raw trash piled several feet high on a street corner. From what I've read, it seems like the maze-like bureaucracy of Cuba's government makes it hard to provide infrastructure services around water, sanitation, and so forth. The long-standing U.S. embargo against Cuba that limits trade with Cuba also cuts off significant income from the country. The austerity and the rubble of Havana represents what makes Cuba so fascinating in the first place. For example, Cuba's famous old American cars make for a colorful part of the landscape, yet the reason they exist is because of the U.S. embargo—Cuba hasn't been able to import new cars, nor spare parts to maintain them. But they've made do with what they have, and made something beautiful out of it. I would describe that as the Cuban spirit.

The language barrier is real. In other countries more accessible to tourists, residents and workers tend to know a bit more English. Cab drivers, bartenders and others can be hard to communicate with if you don't know Spanish. However, it would be easy to learn enough Spanish in advance of your trip to get around just fine.

Havana by Bus

After our sketchy lunch, we boarded a charter bus, which let us out for a few minutes at a time at Havana's most significant places. The highlight for me was Fusterlandia, a whole neighborhood designed by Cuban artist Jose Fuster in the 70's. Buildings, benches, retaining walls, and more are completely tiled by the mosaic artist. It's quite a rare and powerful sight to see, such a whimsical imagination allowed to run completely wild. Today, the area is an artist's haven and still a working neighborhood. Riley enjoyed Revolution Square, aka La Plaza de la Revolucion, where the faces of Che Guevara and Camilo Cienfuegos stare down from the Ministry of Interior and Telecommunications buildings, across from the towering Jose Marti Memorial, the National Library, and other government complexes. It's an eerie feeling. The big gray concrete buildings feel cold and intimidating, but the guards in the parking lots, the cab drivers whizzing by, have smiles on their faces.

We finished our tour at Casa Miglis, the aforementioned Swedish restaurant. Its owner, Michel Miglis, fell in love with Cuba when he came there in the 90's to make a film. He fell so in love that he never went back. He sold his house and belongings without ever returning to Sweden. After our tour bus dropped us off near the port, we wandered around for an hour or so. We bought a few posters from a large maker's market, but at least half the booths were all selling the same touristy trinkets.

An Unexpected Extension

Originally, our cruise was scheduled to stay just one day in Havana before heading to Cozumel, but Tropical Storm Andrew kept us docked in Havana, and we were allowed to book an excursion at La Zorra y el Cuervo. What a night! La Zorra y el Cuervo is one of Havana's most famous Cuban jazz clubs, and it did not disappoint. We sat front row for hours of lively performances that perfectly capped off our trip.

Who is This Trip for?

If you're looking to kick back on a beach, wine and dine, and take cute walks through cute neighborhoods, Havana probably isn't for you. The political and historical legacy of Cuba is present at all times, and to navigate its infrastructure is to engage with that legacy. That said, if you want to see a completely different way of life and observe a lively, colorful culture completely different from that of America, you'll have a great time. Honestly, all the research we did in the months leading up to our trip made us fall in love with Cuba even more.

Before You Go

We read a few books and watched a few documentaries before we went that really helped us understand the context of our experiences in Cuba. Cuba and the Cameraman (Jon Alpert, 2017) – In this documentary, Jon Alpert visits Cuba in three- to five-year increments for a span of 45 years. Each visit, he tracks down the same residents he met on his first trip to check in on how their life is going. He even gets some facetime with Castro himself. As of this writing, you can catch this one on Netflix. Before Night Falls: A Memoir (Reinaldo Arenas)* – Cuban author Reinaldo Arenas tells his story of growing up impoverished in the Cuban countryside and the oppression he endured as a gay man and an artist through Castro's revolution. Many parts of his memoir are exaggerated (full disclosure, tons of explicit sex content in this book), but these exaggerations are meant to spit in the face of the regime. Bacardi and the Long Fight for Cuba: The Biography of a Cause (Tom Gjelten)* – This book is quite a long one, but it's a fascinating look at the Bacardi family and the rum empire that is integrally tied to Cuba's history. The Cuba Libre Story (Netflix, 2015) – An eight-part series, the Cuba Libre Story explores Cuba's history from its time as a Spanish colony through the fall of the Soviet empire.

To read more about Cuba, check out the Cuban Stories book list on The Ever Curious’ Bookshop*.

Want to Plan a Trip to Cuba?

For U.S. passport holders, travel to Cuba is possible but highly regulated and restrictive. For the best experience, you want to work with a travel professional (like me!) to build your itinerary and ensure it meets U.S. regulations. As a travel advisor, I have trusted partners in Cuba that can help do just that!

Reach out to me at or fill out a travel planning questionnaire to get started.

*Disclosure: The Ever Curious is an affiliate of, and we will earn a commission if you click through and make a purchase.


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