Exploring the Magic of Havana

The last big trip I took before the world shut down was a weekend in Havana. Looking back over a year later has shifted my perspective.

Cuba has a fabled allure because time seems to have stood still on this small island nation. As the entire world has paused for a year now, how different are we really? What have we learned to appreciate? Maybe that human connection matters most. Travel allows us to understand ourselves as much as the world around us.

My trip in November 2019 coincided with the 500th anniversary of Havana. Few Western capitals have reached this milestone. Over 48 hours, I saw why Cuba is far more than classic cars, Cohibas, and the perfect mojito. For starters, its creative scene is on fire.

Physically getting there from NYC was easy. I boarded a full JetBlue flight from JFK to Havana one early Friday morning. I was taking a group of five US travel journalists to Havana to experience Cuba’s exciting evolution in arts and culture. Our host Cultural Cuba organized the entire trip. They specialize in custom, private travel under the “support for the Cuban people” legal guidelines, which means their immersive trips directly aid everyday Cubans. Founder David Lee met us on the ground along with Alain Rubio, the company’s dynamic local guide. 

Within the first few hours, we saw how education and the arts go hand in hand. At a brief visit to the Head Start Pre-School for Disadvantaged Students, Sister Teresa explained that education is free from pre-school through university. It is also mandatory through 9th grade.

Next, we were invited to Amos, the renowned photography studio of Ramses Batista and Alex Castro, son of Fidel Castro. Over a rum toast and surrounded by their work, the two photographers shared how they teamed up to mentor aspiring photographers through youth workshops. I studied Alex’s gritty ballerina photos and asked him about his inspiration. He explained how his mother took him to the ballet as a child, where he fell in love with the art. 

Our Friday night GPS was the Fabrica de Arte Cubano or FAC. Am I in Bushwick or Havana? This converted peanut oil factory is the country’s most celebrated arts center. $2US gains entry to the factory of cool. A head-turning labyrinth connects a contemporary art gallery, dance club, cinema, live music venue, and VIP dining at Paladar Tierra. 

We slipped into the restaurant for an early dinner, but the real fun was getting lost in the art and music. While admiring the racy photo exhibit of Enrique Rottenberg, a local artist who tackles controversial themes of inequality, we looked up to see him cheekily mingling with the crowd. 

Our hotel, the Gran Hotel Manzana Kempinski La Habana, is the most glamorous place to stay on the island. The historic whitewashed building spans a full city block at the edge of old and new Havana. In the early 1920s, fashionable Cubanos shopped here when it was the country’s first European-style department store. Today, its airy chic interiors and lovely staff welcome international guests. The rooftop pool is one of the most coveted spots in town.

Across the street, the legendary bar El Floridita beckons. After 200 years, it is still Cuba’s most famous cocktail bar. Sure, it’s touristy, but fun to pay pilgrimage to Hemingway’s favorite watering hole and the birthplace of the daiquiri.

Early morning was my favorite time. The magic hour. At dawn, I quickly brewed an espresso, grabbed my camera, and headed out. The elevator opened directly onto the rooftop pool and breathtaking skyline. The gold Capital dome glowed. In the distance, gritty buildings were falling apart. In the soft light, decay is replaced by the pastel-hued romance of a capital whose complex history speaks through magnificent architecture – colonial, Baroque, and Art Deco. I felt deep gratitude for witnessing this moment.

The streets of Old Havana are impossibly picturesque. Yes, a step back in time. You can spend hours wandering the crumbling side streets, poking your head into colonial doorways to uncover poetic relics of the past. But a word of caution: Later in the day we would meet Havana’s renowned urban planner Miguel Coyuela. He is an expert on the history and preservation of the city of 2.2 million people. His most powerful words were: “Cuba is not a museum.” It was an important reminder to look to the future. 

A rising generation of female Cuban creatives is stepping onto the world stage. In the afternoon, we met one young fashion designer named Lauren Fajardo at her upscale boutique Dador. Lauren opened Dador, which sells handmade fashions and artwork, with two other female entrepreneurs. The shop would be at home in Soho or Le Marais. In Havana, it is a rarity. Before 2012, private businesses were not even allowed. 

“Dador means giver,” explains Fajardo. “I want to give back.” Her store is remarkable not only because it exists but because the owners are women: “We are part of the New Cuba. We are changing the mentality of what a Cuban woman is today.”

Cuban cuisine is having a renaissance with the rise of the paladar. Paladars are private, family-run restaurants, which is a concept that only started in 1993. After our walking tour of Old Havana, including a stop at Taller Experimental de Grafica, Cuba’s oldest printmaking studio, we entered 5 Sentidos for lunch. This airy restaurant is the current darling of the paladar scene. Course after course of inventive seafood dishes showed us why its fan base keeps growing.

After lunch, it was time to experience Cuba’s most famous exports – rum and cigars. At Havana Club Rum, charming brand ambassador and sommelier Damian Dominguez Perez led us to a secret tasting room. We spent the next few hours learning the finer points of rum and cigar pairings. It was so much fun that that we missed our private salsa lessons! Next time.

Saturday night was full of more exciting surprises that began with cocktails and elegant canapes in the hotel’s bar. Just before sunset, David and his talented photographer Natasha Forcade Goméz led us to the lobby. Outside a pair of candy-colored classic convertibles was waiting. We carefully climbed in like giddy kids. Natasha jumped in a nearby van aiming her camera at us.

Within minutes we were cruising down the Malecon, watching the sun fade over the scenic harbor. Natasha’s van raced alongside us capturing every beaming smile. We felt like 1950s celebrities trailed by paparazzi. Thankfully, I’ll always have the pictures to prove it.

The sunset drive built up our appetites. We pulled up to La Guarida (“the hideout”), Havana’s most iconic restaurant. Many celebrities have climbed the magnificent marble staircase, immortalized in movies, to its intimate dining room. La Guarida was one of the first private restaurants and continues to be a coveted reservation for its Cuban-inspired international dishes and views of Old Havana.

After dinner, David had one more pinch-me moment lined up as he ushered us to the restaurant’s rooftop terrace bar. Outside three stylish young musicians – known as the William Roblejo Cuban Jazz – sweetly greeted us. Over the next hour, their sultry rhythms filled the night sky. We swayed in silence, enchanted by this magical private concert under the stars.

Before heading to the airport on Sunday, we were treated to a final private performance by the dance school of Habana Compas, a troupe of high-energy Afro Caribbean rhythmic dancer-musicians. The teens infused passion into every move. Some traveled hours to get there that morning. They’ve performed around the world in South Korea, Mexico, and Turkey. I can’t wait to see them in the US one day.

I traveled with Cultural Cuba, a US-based luxury destination management company that specializes in custom private travel to Cuba. All experiences were curated for us. Cultural Cuba operates under the Support for the Cuban People guidelines. They will plan a seamless trip including securing required US visas. Note US credit and debit cards are not accepted in Cuba. WiFi is limited to hotels.