Make Unforgettable Vacation Memories in Colorful, Captivating Cuba

From salsa to Sinatra, cigars to classic cars, Cuba is imprinted on the American imagination. The good news is that Cuba is open, and its rich heritage and relaxed pace are a short plane ride away. Travelers looking for a superb cultural destination without a lengthy flight should put it at the top of their list.

Cuba no longer requires proof of vaccination or a negative PCR test to enter the country. What do you need to visit? A valid passport, a Cuban Tourist Visa, and an approved itinerary meet the requirements. Cuba is not a DIY destination, however; you should work with a travel pro for this vacation.

Cuba is largely an unexplored gem for American travelers. For now, it's also refreshingly uncrowded. Picture the Eiffel Tower minus the frustrating wait time or the Louvre on a springtime Saturday without throngs of tourists. What would it be like to set your own pace without the pressure of keeping the line moving? That is Havana right now.

It's close enough for a long weekend and a great destination for a group, as one traveler learned when celebrating a milestone birthday in Havana with friends:

We rendezvoused in Miami for a 45-minute flight to Havana’s José Martí International Airport. Though the flight was short – Havana lies just 100 miles southwest of Key West – we landed a world away. After a long wait for the suitcase of one friend who shall remain nameless (we’d been advised to travel with just a carry-on), we met our guide and driver, boarded our luxury coach, and were off on our three-night adventure.

Situated on Cuba’s northwest coast, the once-walled city of Havana, settled by the Spanish in the 1500s, is now a UNESCO World Heritage site with a population of 2 million.

Our first stop was Revolution Square, a monumental public space where former president Fidel Castro delivered many political addresses before we headed to the iconic Hotel Nacional for an alfresco lunch and a rum tasting with Havana Club’s head sommelier. Later, we toured the world’s oldest cigar factory – home to Cohiba, Partagás, and Romeo y Julieta, among others – and even tried our hands at rolling our own.

Travel advisors can book their clients in casas particulares (private homes), boutique hotels, and classic celeb favorites such as Hotel Saratoga, but we were able to stay at the city’s newest and most luxurious property, the 246-room Gran Hotel Manzana Kempinski.

We settled into our suites (complete with high ceilings, marble bathrooms, and balconies overlooking the Capitol building) and reconvened for poolside cocktails on the rooftop, where we took in a lively performance by the Habana Compás Dance troupe.

After dinner at an intimate paladar (a small family-run restaurant, usually in a private home), we stopped for a nightcap and live music at former Hemingway hangout El Floridita.

The 200-year-old establishment proclaims itself “the cradle of the daiquiri,” with a richly lacquered bar that runs the length of one wall, where seasoned bartenders sporting red tuxedo jackets ceremoniously whirl blender drinks for a constant crowd. Touristy? Sure. Essential? Absolutely – and a perfect way to end an exhilarating first day.

I’d groaned when I first read “10 a.m. presentation by Havana’s lead city planner” on the itinerary, thinking my friends wouldn't want to sit through a lecture on their first morning. Turns out, it was a crowd-pleaser!

Our group peppered architect Miguel Coyula with questions far beyond the allotted time. Cuba is a little piece of Europe in the Caribbean, he explained, while describing how its mix of colonial, baroque, and neoclassical styles came to be. Weaving together politics, architecture, and culture, Coyula discussed the country’s history, from its Spanish colonial roots to the glitzy, Mafia-fueled casino and hotel spree in the 1950s and the austerity of its post-revolution socialist principles.

He exemplified the Habaneros we met – including Alain, our dedicated, knowledgeable guide – who were all welcoming, open, and articulate (thanks to state-subsidized education, Cuba has a literacy rate topping 98 percent, one of the highest in the world).

They’re also resilient and resourceful since generations have endured long queues for limited government rations and repurpose and repair material goods to make them last (those vintage cars, for example). They shrug at the dichotomy of their predicament, and though they acknowledge governmental shortcomings, patriotism prevails.

One afternoon we wandered the picturesque squares of Old Havana, with a photographer documenting our day as we navigated narrow cobblestoned streets, peeking at courtyards and balconies for a glimpse of everyday life. A deluge forced us to duck into a covered café patio on a sixteenth-century plaza and wait out the rain with rounds of mojitos, Cristal beer, and daiquiris while a live band played traditional Cuban music – setting the mood for private salsa lessons later that day.

We ate and drank well the entire trip. Though Havana’s culinary scene is evolving, practically every menu included Moros y Cristianos (black beans and rice), and most meals weren’t as memorable as the settings themselves. Eschewing state-run restaurants, we dined exclusively at privately owned paladares.

La Guarida is the most famous one in Havana, located in a former colonial-mansion-turned-tenement, with ornately carved stone columns, a sweeping staircase, and an aging mural that pays homage to Fidel Castro. (The building was also the setting for Strawberry and Chocolate, Cuba’s only Oscar-nominated film.)

Statement-making art covered the walls of the second-story dining room, and a warm breeze wafted through the open balcony doors as we dined on tuna tiradito, smoked duck with Brie, and beef tenderloin with pepper sauce. The whole experience was a collision of trendy and historic, then and now, high and low.

Those walls gave us a taste for Cuba’s flourishing art scene, which we explored more in depth with private appointments at galleries showcasing emerging artists. We even met Fidel Castro’s photographer son, Alex, and his business partner, Ramses Batista, at their studio.

Art and entertainment merge at the Cuban Art Factory, a former peanut oil factory that’s been transformed into a sophisticated contemporary nightclub and gallery space, attracting a bustling late-night crowd with rotating exhibits, video installations, and a concert venue.

Our final night, we took in a show by the Buena Vista Social Club, the acclaimed ensemble known for their romantic, old-fashioned ballads. As we danced onstage with the band (hey, it was my birthday), I was warmed by a “life is good” feeling of gratitude for my life, my friends, and my terrific fortune to be there.

Even though I probably picked Cuba initially for the buzz factor, it turned out to be so much more than a passport stamp, impacting me – and my friends – far beyond the usual birthday bash.

I’ve been lucky enough to travel the world, but Havana stands out as a place that demands you pay attention, where every interaction makes you hyperaware of the past, present, and future. It’s much like the introspection a milestone birthday begets: Learn from yesterday’s mistakes, celebrate the moment, and be hopeful about what tomorrow holds.

Are you interested in an enlivening, enriching travel experience in Cuba?

Contact me to start planning.

Excerpt adapted from virtuoso.com article by Elaine Srnka. Read the entire article here.