Last Updated on February 24, 2023
Estimated reading time: 10 minutes
By Jim Ferri
You’ll find many things to do in Havana, Cuba, since it’s the capital of a country caught in a time warp.
There’s no denying that the Havana you visit today is the Havana of 50 years ago. And for that reason, it remains a fantastic place to visit. Moreover, it’s a wonderful experience for travelers, one you’ll find in few other areas worldwide.
It was Prohibition in the U.S. that first brought mass tourism to Havana. Then, at a time when booze was banned in America during the 1920s and early 1930s, Havana flaunted a culture of cocktails and casinos that quickly attracted the rich and famous.
It also attracted the not-so-rich and infamous, and the combination turned the city into the party land of the Caribbean – all just 90 miles off the coast of Key West.
Tourism in Havana and Cuba cooled quickly during the Cold War. And since then, life and culture in Havana have stood still. However, for the past decade or so, Havana, and all of Cuba to a lesser degree, has been seeing its second heyday.
But luring today’s tourists is anything but free-flowing liquor and a clutch of casinos. Instead, many travelers come to experience Havana as it was 50 years ago to experience the warp and see the city before it changes.
If you want to step back in time, head down to Cuba.
A Tour of Cuba
I always wanted to visit Havana and finally reached it on a Grand Circle Foundation tour, which began in eastern Cuba and ended with four days in Havana.
It was not a luxury vacation, but we were comfortable nevertheless, and it was, as promised, culturally rewarding. I highly recommend it.
We did a lot in Havana. One day visiting a dance company. Another learning to play dominoes with a Cuban national champion. We saw a neighborhood in which colorful murals and a self-built community center have transformed the barrio.
Our schedule was full, but we still had plenty of time to wander about independently.
The Race to Transform the City
It’s evident that Havana’s infrastructure is a mess. And obviously, the government is trying to make some repairs to attract tourists.
Some of the most visited tourist areas of Old Havana (part of which is a UNESCO World Heritage Site) are fixed and renovated. Some streets are newly paved, and a few buildings freshly painted.
Just a few blocks away, though, there are streets and sidewalks filled with huge potholes. And dilapidated, crumbling buildings, in which people still live but which would not exist in most western countries.
What’s so incongruous about Havana is that despite their near-horrific living conditions, the majority of Cubans remain very happy people who continue to embrace their culture and music.
A Must-See in Havana: Habana Vieja
One day during a lunch-on-your-own afternoon in Habana Vieja (Old Havana), I explored the Plaza de la Catedral area. The cathedral is one of the most popular attractions in the city and one of its most beautiful squares.
It was a fascinating place, not because the church was no longer in use, but because of the color that ebbed and flowed through the square.
There were vendors all about selling handicrafts and a lively café/restaurant along one side. But the stars of the show were the Cubans walking about the Plaza… women dressed in flamboyant African-Cuban costumes, men in gaudy suits … offering to have their photos taken for the equivalent of a dollar.
Several were chomping on huge foot-long cigars, adding to the circus-like atmosphere.
A Fun Thing to do in Havana: Search for Hemingway’s Haunts
I walked up Calle Empedrado, adjacent to the Plaza, to the nearby La Bodeguita del Medio halfway down the calle. It was one of Hemingway’s favorite bars/restaurants, and when I arrived found a large crowd outside it.
After ferreting my way through the throng, I discovered a larger crowd, a mix of tourists and locals.
Beyond the bar was a series of rooms, all with autographs and photos of famous people covering the walls.
Entering La Bodeguita was taking another step back in time. I later took another step in finding Hemingway’s haunts when we searched for the bar Floridita.
Deeper Into Habana Vieja
La Bodeguita was a lively place where I would have liked to have lunch, but time was short, so I headed back to the far end of the plaza. I watched the show there for a while, intrigued by all the movement, color, and interaction between the locals and tourists.
Then I saw that many Cubans were only crossing the plaza to wander off into another neighborhood. So I joined them as they led me along several different streets.
After walking a few short blocks, I wound up in a lively neighborhood filled with numerous little shops and stores, with music wafting from crowded bars.
There were several little restaurants filled with a mix of tourists and locals wandering the streets. It was a fascinating and colorful couple of hours.
Despite a Dismal Restaurant Scene, a Welcome Surprise
Throughout our time in Havana, we had days to ourselves and wandered all about the city.
Food in Havana, and all over Cuba, isn’t very flavorful due to the land being heavily fertilized for decades to produce sugar for the Soviets. So we stuck to the hotel and larger tourist restaurants where the food was much better.
Many of these “tourist restaurants” were in people’s homes. They are called paladares, private-home restaurants that have been popping up in modern-day Havana.
Later that afternoon, however, our tour guides, one American and the other Cuban, took us across the city to a barrio that had been transformed by the residents. It was a pretty amazing place where neighbors joined to use street art to transform a drab rundown neighborhood and built a community center.
We spent the evening there, listening to music played by local musicians. That was followed by a surprisingly delicious dinner prepared by women in their barrio homes.
It culminated with us all partying up on the roof terrace of the small center as a local combo played the 70s and 80s Rock & Roll with many from the neighborhood and our group dancing along. My wife and I ended the evening doing the Lindy to the local rendition of Little Richard’s Tutti Frutti.
My Search for Hemingway and a Cadillac
We found no lack of things to do in Havana and Cuba, much revolving around Hemingway. One afternoon we visited more of Hemingway’s haunts and searched out the bar Floridita. Some contend it was his favorite bar.
The owners keep the legend alive with a full-size bronze statue of Hemingway at the end of the bar. It’s where it’s said he always sat. And this spot is, supposedly, where Hemingway helped invent the daiquiri.
One afternoon my wife and I jumped on the opportunity and hired a car to take us to Hemingway’s old home outside the city. The author had long lived in Cuba and Havana and had written several of his famous novels in Finca Vigía, a house in the San Francisco de Paula Ward of the city. It’s about a half-hour ride from the old town.
A Must-See in Havana: Hemingway’s House
We spent an enjoyable hour at the Hemingway house, now a museum. No one is allowed inside, and it remains the same as when Hemingway left it in 1960. You can only look through the open doorways and windows to every room. A two-story tower at the rear of the house, which provides a view out over the valley, housed the author’s office.
The land was almost park-like, and we followed a path back to a large empty swimming pool. Alongside it is a small pet cemetery containing the remains of four of Hemingway’s favorite dogs. It’s pretty incongruous since he has a cat cemetery at his Key West home.
But the real star beyond the pool was the Pilar, Hemingway’s impressive fishing boat on which he not only went deep-sea fishing but also used to watch for German U-boats during World War II, providing his intelligence to U.S. officials.
My Dream Fulfilled
That night our group had a delicious dinner at a paladares. It was our farewell dinner, which we were all enjoying until our tour guides announced that the bus that had brought us had broken down.
The only alternative, said our guides, is a 20-minute walk back to our hotel since taxis were not running at the time.
We were not thrilled with the idea, but we had been warned beforehand that flexibility was key in dealing with the aging Cuban infrastructure. So after a few moans and groans, we decided to get on and set out from the restaurant.
We all walked down the street in the dark, there not being an abundance of streetlights in Havana until we got to the far corner, at which time our tour leader shouted: “Here we are – there’s no more walking!” Lined up on the side of the road was a line of vintage Chevys, Buicks, and, most gratifying to me, a 1952 Cadillac convertible.
We bolted to our Cadillac time capsule with my wife and another couple and joined the other vintage cars in a conga line that sped down the street. Horns were blaring, and several of us yelled and screamed like kids after winning a high-school football championship.
It took us about 10 minutes to get to the hotel, 10 minutes none of us will forget. Nevertheless, it was a perfect ending to four fascinating days in Havana.
If you want to enter the time warp, now may be the time to go.
If You Go:
Grand Circle Foundation
347 Congress Street
Boston, MA 02210
Tel: (800) 859-0852