Sunny days, sultry nights, and icy daiquiris to cool things off -- a long weekend in Havana is everything and nothing like you think it will be.
As the sun dropped low on the horizon, our caravan of 1950s American convertibles motored along Havana’s famed esplanade, the Malecón, where residents strolled the waterfront and fishermen cast lines into the surf crashing against the seawall. Passing the faded, crumbling facades of once-grand architectural buildings, my friends and I should have been reflecting on the paradoxical paradise that is Cuba. But caught up in the carefree moment, we were grinning unabashedly, snapping selfies, and relishing every mile of the sunset drive. While jaded globe-trotters pride themselves on avoiding touristy clichés, some clichés transcend themselves to become quintessential experiences – and a classic car ride in Cuba definitely qualifies.
We were there to celebrate my (ahem) 50th birthday. Milestones are funny things: I’d toggled between pushing the occasion to the furthest corner of my mind in a wishful attempt to forget it and pondering unforgettable ways to welcome it. If I was going to go somewhere, I wanted bucket-list big, but doable in a long weekend – nixing long-haul flights and lengthy itineraries. Narrowing the search to North America, I sought sophisticated but not sleepy (next time, Napa) and fun but not frenzied (been there, done Vegas). Most of all, I wanted to leave the planning to a pro so I could actually enjoy myself. When my mental globe-spinning landed on Cuba, I knew just who to call: Orlando-based Virtuoso travel advisor David Lee, who has built a business specializing in the destination.
“Havana is the heart and soul of Cuba, and three to four nights is ideal,” he assured me. “In fact, it’s recommended, especially for a private group, to make it easier for more couples to go.”
After the U.S. briefly restored diplomatic relations with the country in 2015, following a five-decade standstill, the Communist Caribbean republic became the darling of the travel world, thanks to eased restrictions for U.S. visitors. Even with President Donald Trump’s recent rollback of that short-lived Obama-era “Cuban thaw,” Americans can still visit today – but it’s not really a plan-it-yourself destination.
“U.S. citizens must travel under one of the U.S. Treasury Department’s Office of Foreign Assets Control-approved categories on an approved itinerary,” Lee explains. “That doesn’t mean big bus tours with large groups of strangers are the only option.” Instead, he can customize private itineraries for groups of any size. “Cultural interactions with Cuban historians, architects, musicians, and artists will be the most memorable and rewarding experiences of your visit,” he says. Independent types may bristle at the notion of an “approved” itinerary, but it makes the most of your visit – and you’ll still have plenty of time for soaking in your surroundings with a mojito in one hand and a cigar in the other.
Our party of ten couples included friends from the travel industry – several of them agency owners and advisors – but surprisingly, no one had yet checked Cuba off their list. Studies show that looking forward to a trip can bring as much enjoyment as actually taking it – and collectively our anticipation was off the charts. Indeed, there’s nothing like political espionage, governmental chess moves, and an overactive hurricane season to add to the excitement. As our departure date drew near, news of American diplomats in Cuba suffering mysterious symptoms, threats of a U.S. embassy closure, and yet another looming hurricane only added to the drama befitting such an evocative, complex destination. Lee calmed any concerns, and the trip was on as planned.
We rendezvoused in Miami
for a 45-minute American Airlines 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 ridiculously 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. You can’t help but marvel at and mourn what Havana once was, what’s been lost, what it could’ve been, and what it still could be. The people and the politics and the U.S.’s intertwinement with it all imbue even a breezy weekend getaway with a tangle of mixed emotions. Travel can be a force for good, helping to connect cultures, break down barriers, and benefit the local economy, but knowing your tourism dollars may support an oppressive government is unsettling, which is part of what makes Cuba so perplexing.
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.
Lee can book 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 am presentation by Havana’s lead city planner” on the itinerary. “My friends aren’t going to want to sit through a lecture on their first morning!” I whined, but Lee assured me it would be a crowd-pleaser. He was right; 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 openly 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. The majority of Havana’s buildings were constructed before 1959; on average, he said, three collapse every day. The disrepair continues, he pointed out, because paint alone eats up a huge percentage of the $25 monthly salary the average citizen earns.
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.
Like the rest of the world, they’re unsure of what the future holds as the Castro era ends after 59 years of rule (Miguel Díaz-Canel recently became president, replacing Fidel Castro’s brother Raúl) – but they persevere.
One afternoon we wandered the picturesque squares of Old Havana, with a photographer arranged by Lee 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.
Orlando-based David Lee specializes in cultural tours of Cuba and can work with your travel advisor to customize a trip based on your interests. He can also arrange shore excursions. Our itinerary was all-inclusive of accommodations, a dedicated guide and driver, tours and activities, most meals, and even a few drinks. Lee and his team handle everything, including all required documentation.
Shop a farmers’ market, visit a food ration shop, and learn the secrets of arroz con pollo and ropa vieja at top paladares on Access Culinary Trips’ five-day Havana itinerary. Raise a glass to happy hour at a private home, where you’ll mix cocktails with a retired barman from El Floridita.
Highlights of Rico Tours’ four-day Havana itinerary include a possible visit to a mechanic’s shop to see what goes into keeping those iconic cars running smoothly.
Overnight in Havana on Azamara’s five-day round-trip Miami sailing aboard the 690-passenger Journey. After a day exploring the city, take in a high-kicking show at the famed Tropicana Cabaret. This sailing also spends a day in Key West, where you can follow Hemingway’s footsteps.
Cruise along the Malecón and through stately Miramar in a classic car with ShoreTrips’ half-day guided ride, which goes into neighborhoods such as Vedado to visit Cristóbal Colón Cemetery.