With pristine beaches, world-class resorts, and seamless luxury experiences, the Caribbean offers no shortage of easier, more comfortable travel destinations. So why would anyone choose Cuba – a country with frequent power outages, a crumbling economy, and a government that has earned international pariah status? finews.asia traveled to Havana to find out.

As finews.asia arrived in Havana for the XXV Festival del Habano, the 25th iteration of an annual cigar fair, the grandeur of the gala evening stood in stark contrast to the darkened streets just beyond its doors.

At the same time collectors were bidding millions for rare humidors, entire neighborhoods were plunged into darkness—a consequence of Cuba’s crumbling energy infrastructure. finews.asia set out to decode the world’s most unique travel experience: where to stay, where to eat, how to get from A to B, and most importantly, how to navigate Havana as a sophisticated traveler caught between postcard charm and economic despair.

Why Travel to Cuba?

The spotlights in Havana’s Pabexpo convention center hammered in the golden glow of the ever-growing global cult surrounding Cuban cigars. Smoke curled through the air, scented with the world’s most coveted smokes, as the reflections of fine rum shimmered across the glasses of nearly 2,000 guests.

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A symbol of old-world glamour: Hotel Nacional de Cuba. (Image: Courtesy)

It was the grand gala of the XXV Festival del Habano, the pinnacle of Cuban luxury, where industry moguls and select high-net-worth aficionados gathered under the watchful eyes of the country’s leadership. Even President Miguel Díaz-Canel Bermúdez, successor to Fidel and Raúl Castro, graced the evening, observing as a Behike humidor—filled with the rarest Cuban cigars—fetched an astonishing 4.6 million euros at auction.

Opulence of the Festival del Habano

But step outside the opulence of the festival, past the stunningly attractive hostesses, and another reality unfolds.

Just a few blocks away, entire neighborhoods are left in darkness. The city's antiquated, Soviet-era power plants, struggling with crude oil shortages, cannot meet demand. Power outages are a part of daily life for Habaneros, a stark contrast to the cigar-fueled grandeur that lights up the capital for just one week a year.

The Last Gasps of Communism

For aficionados of Cuban cigars or rum, Havana is a must-visit—a place where these crafts can be experienced in their purest form, rolled by the island’s finest torcedores, aged in its humid Caribbean air, and paired with the terroir that shaped them.

For those fascinated by the last vestiges of communism, Cuba offers a firsthand look at a nation where ideology still dictates daily life. It is a country frozen in time, where classic cars from the 1950s rattle over pothole-ridden streets lined with crumbling colonial mansions. Here, state control, black markets, and human adaptability have merged into a surreal coexistence.

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Havana’s finest restaurant: The terrace of La Guarida. (Image: Courtesy)

A Fragile Economy

And for those simply drawn to the romance of a place that refuses to conform, Cuba rewards with unforgettable moments: A son Cubano melody drifting through a side street, the scent of a freshly rolled Habano in the warm night air, the unshakable warmth of people who have learned to find joy despite everything.

Yet beneath the colonial facades and vintage-car nostalgia, the country’s economic hardship is starkly visible. Often romanticized, Cuba remains one of Latin America’s least developed nations in terms of infrastructure. Travel beyond Havana and Varadero, and the island’s fragile reality quickly becomes apparent.

Where to Stay?

For travelers with refined tastes, Havana still holds its allure—if one knows where to look. The legendary Hotel Nacional de Cuba, with its sprawling gardens and storied past, remains a symbol of old-world charm.

For those seeking modern luxury, the Gran Hotel Manzana Kempinski offers Havana’s closest equivalent—at a price that may be justified in a Western five-star hotel... but five stars in Cuba are, in reality, more like four.

For the true connoisseur, casas particulares offer authentic Cuban hospitality, ranging from intimate bed-and-breakfasts to grand, luxurious villas—though with the ever-present risk of sudden power outages.

A Cash Economy

Havana’s financial system follows its own rules. The official exchange rate is 120 pesos per dollar or euro, yet the black-market rate fluctuates between 320 and 340. Due to U.S. sanctions, most international credit cards are useless, making cash king.

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Contrasts: A luxury gala evening at the Festival del Habano. (Image: Courtesy)

Experienced travelers rely on trusted local contacts to secure fair exchange rates and access premium services, including transport—a necessity in sprawling Havana. Tourists typically pay between $8 and $15 per ride, though locals using the Cuban ride-hailing app La Nave enjoy a fraction of that price. The catch? It only works with a Cuban phone number.

Where to Eat?

Cuba’s economic scarcity affects its cuisine. High-quality beef, fresh seafood, and vegetables remain hard to come by.

Nevertheless, there are culinary gems: La Guarida serves gourmet cuisine in a magnificent colonial mansion, El del Frente offers rooftop cocktails, and Santy Pescador boasts Havana’s finest seafood. For those tiring of the omnipresent rice-and-beans staples, Marechiaro provides a welcome Italian escape.

Indulging in Cuba’s True Luxuries

No visit to Havana is complete without cigars, rum, and classic cars. Official Casas del Habano guarantee authenticity, but their selection pales in comparison to Europe’s well-stocked cigar merchants.

For connoisseurs, Vuelta Abajo is a must. Here, legends like Hector Luis Prieto and Hirochi Robaina cultivate the world’s finest tobacco.

A Nation on the Brink

Tourists witness a country stretched to its breaking point. Much of the carefree joy that once defined Havana’s charm has faded under the weight of daily survival. Long queues at the few functioning gas stations last hours, sometimes days, as sporadic fuel deliveries arrive.

A sense of hopelessness lingers in the air, exacerbated by the near-total closure of the Mexico-U.S. border, which until recently offered many Cubans a last glimmer of escape and opportunity.

Within Cuba, as international tourism dwindles—Edelweiss recently canceled its direct flights from Zurich to Havana—locals greet the few remaining visitors with a kind of desperate openness. The resilient hospitality that once defined Cuban warmth has, for many, been replaced by growing despair.

How long can it last?

The room for personal agency is shrinking. Those without financial support from family abroad are left entirely at the mercy of the country’s harsh realities.

Against this backdrop, the glitz and glamour of the Festival del Habano are approaching the point of absurdity. Each year, the contrast between staged opulence and stark reality becomes sharper, moving inexorably toward an inevitable rupture. The only question that remains: How much longer can it last?