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Craving an Immersive Cruise to Cuba? Come Along With Us

Laura Bly

Last updated
Oct 10, 2019

Sponsored by Azamara

Editor's Note: Effective June 5, 2019, Americans are no longer permitted to travel to Cuba by cruise ship due to U.S. government policy changes.

Off limits to most Americans since Fidel Castro took communist control six decades ago, Cuba is back on the radar, particularly among cruise travelers, who accounted for a nearly 50 percent surge in arrivals last year.

Under the continuing U.S. trade embargo, Americans are officially outlawed from a tourist schedule spent swilling mojitos and lolling on powdery beaches -- in contrast to Canadian and European sun-seekers, who've been doing just that for years.

Still, thanks to a thaw in U.S.–Cuban relations initiated under President Obama, planning a trip to the Caribbean’s former “isla non grata” is easier now than it was for my first visit in 1994 (a "special period" of economic hardship that followed the collapse of Cuba's benefactor, the former Soviet Union) and my last in 2012, when U.S.-licensed travel programs required that participants adhere to tightly scripted, educationally focused schedules.

In April, as part of an effort to stifle the struggling Cuban economy and eliminate the country’s support for Venezuela’s embattled government, President Trump’s national security advisor vowed a crackdown on “veiled tourism” with plans to further regulate non-family visits to Cuba. The Trump Administration had already nixed individual "people to people" visits by Americans and prohibited "direct financial transactions" with nearly 200 hotels, stores and other companies controlled by Cuba's military.

There's good news, though: Cruise lines still meet current Treasury Department requirements because their Cuban shore excursions qualify under the existing group "people to people" license, and cruises are continuing normally in the absence of concrete new U.S. sanctions.

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The current administration rolled back some of Obama's travel reforms in 2017, nixing individual "people to people" visits and prohibiting "direct financial transactions" with nearly 200 hotels, stores and other companies controlled by Cuba's military. There's good news though: Cruise lines still meet Treasury Department requirements because their Cuban shore excursions qualify under the group "people to people" license.

On this, my third trip to Cuba and my first cruise visit, I’m curious to see how Cuba’s recent tourism boom has changed Havana’s “frozen in amber” nature (thankfully, no Starbucks or Colombian Emeralds outlets here yet), and look forward to admiring the Spandex-clad hips of grandmothers as they sway to the live music that pours from open doorways all over town. And I’m particularly eager to experience the country beyond the chaotic confines of its capital.

Our nine-day "Cuba Intensive" trip launches with two nights and three days in Havana as the capital preps for this year's 500th anniversary of its Spanish founding. From there, the ship will take us around an island that's roughly the size of Florida. We'll stop for a full day in Cienfuegos (with a side trip to the exquisitely restored colonial town of Trinidad) and spend a night in Cuba's second-largest city, Santiago de Cuba.

So put on those dancing shoes, crank up that Buena Vista Social Club CD and come along for the ride as we share day-by-day impressions of the journey.


Day One: Departure from Miami

Azamara Journey was heading down Miami's Government Cut shortly after 5 p.m. and would arrive in Havana by 9:30 the following morning -- about the same time it used to take the S.S. Florida on its three-days-a-week sailings during the 1950s.

Located just 90 nautical miles south of Key West, Cuba is a tantalizing enigma.

And a cruise visit, particularly an island circumnavigation like ours, offers several advantages over land-based alternatives.

Long distances, mountainous terrain and sometimes sketchy road conditions are major factors; it's roughly 550 miles and a long day's drive between Havana in the north and Santiago de Cuba on the south coast.

Comfort is a big consideration, as well. Like us, many of our fellow cruisers are first-time passengers drawn to Azamara Journey specifically for its Cuba itinerary, which includes more time in port than other ships. Dozens more are globe-trotting repeaters who clearly feel "at home" on the ship, and it's easy to see why. With fewer than 700 passengers and only five public decks, orientation was a breeze, and a cozy, all-inclusive vibe (both gratuities and house wines/spirits are part of the cruise fare) took hold from the first glass of gangway bubbly.

Discovery of the Day: Added during a major refurbishment in 2016, the Azamara Journey's Living Room lived up to its name. It proved to be an ideal vantage point for watching waves (and fellow passengers). With its cushy armchairs, neutral colors, floor-to-ceiling windows and a prime forward location on Deck 10, the lounge attracted everyone from early-morning yoga enthusiasts to late-night dancers, when a DJ cranked up hits from Motown and ABBA.

Day Two: Arriving in Havana, Hemingway & An AzAmazing Evening

Arriving in Havana by ship in 1895, Winston Churchill observed that "here was a place where real things were going on … a place where anything might happen."

We felt the same way as Azamara Journey pulled into its berth at the Terminal Sierra Maestra, a cigar's throw from the 16th-century Plaza de San Francisco in the heart of Old Havana.

To our left was a rotting, roofless hulk that only dimly recalled its robust maritime past. But in the air-conditioned terminal on our right, we sailed through customs and security surrounded by travel posters and souvenir stands selling Havana Club rum and Che Guevara T-shirts. Our welcoming party: a cadre of smiling young officials, most of them clad in skin-tight uniforms and lacy black stockings.

Azamara offers a choice of 19 shore excursions in Havana, from an exploration of the city's rich Jewish heritage to an evening at Cafe Taberna, an Old Havana bar that plays tribute to onetime resident mambo king Benny More.

Our first-day pick was a passenger favorite, Hemingway's Havana, which includes stops at several of the haunts the American writer frequented during his longtime love affair with the island. He spent more than a third of his life here and donated the medal from his 1954 Nobel Prize in Literature to the Cuban people.

I could have skipped the assembly line mojitos and scrum of tourists at Old Havana's La Bodeguita del Medio, a watering hole where Hemingway may -- or may not -- have scribbled the framed tribute, "My mojito in La Bodeguita, my daiquiri in La Floridita." (In the confines of that nearby and equally popular bar, legend has it Papa would down up to a dozen daiquiris in a single session.)

But a half-hour drive east of town, at his beloved hillside estate Finca Vigia (Lookout Farm), Hemingway's legacy is more potent than any of his cocktails. Finca Vigia is now a national monument, and visitors can prowl the grounds (including the now-empty swimming pool where houseguest Ava Gardner once paddled in the buff) and peer through the open windows of the low-slung house whose contents look exactly as they did when Papa left in 1960, a year before his suicide in Idaho.

And as Azamara Journey passengers, we were lucky to be accompanied by Hemingway scholar and onboard lecturer Nancy Sindelar, who pointed out everything from the bedroom where he wrote standing up at a Royal typewriter to the bathroom where the burly author obsessively scribbled his weight measurements on the wall.

Discovery of the Day: Azamara's complimentary AzAmazing Evenings are designed to give passengers an insider's view through an event unique to, or particularly reflective of, a ship's destination. And it's tough to imagine a better introduction to Cuba and its legendary nightlife than the performance we attended by Havana's Lizt Alfonso dance company.

What one New York Times critic described as "dancing with precise abandon," the show was an intoxicating fusion of ballet, flamenco, cha-cha, rumba, bolero and salsa. A bonus: It took place at the neoclassical Teatro Marti, which opened in central Havana in 1884 and was restored to its original glamour in 2014.

Day Three: Rambling Around Havana & the Culinary Scene

After sharing dinner with a well-traveled couple taking their 11th Azamara cruise, we joined them today for a jaunt that combined a ramble through Old Havana with a spin in a mint green, mint condition 1953 Chevy, one of the Eisenhower-era sedans that still cruise the streets of Havana and other Cuban cities. While many are weathered relics held together with spit and baling wire, the restored versions have become obligatory photo ops -- and a welcome source of income for their drivers.

At a quick stop to buy some fresh produce in an Old Havana farmers market, our guide Lauren noted that despite monthly government food rations and access to costlier free enterprise options like this one, shortages and long lines (during our stay, for flour and bread) remain a part of daily Cuban life.

At the same time, tourism has helped finance renovation of the city's crumbling colonial ruins -- an effort now on overdrive for the 500th anniversary -- and construction of new hotels such as the five-star Gran Hotel Manzana Kempinski.

When I asked about taking a peek at the Kempinski's gleaming lobby, Lauren demurred. Only registered guests or those willing to pay for a drink on the rooftop terrace were allowed inside, she told us -- a seeming clash of capitalism and socialism.

The three greatest legacies of Castro's revolution, according to a popular Cuban joke: education, medical care and sports. The worst: breakfast, lunch and dinner.

That was certainly the case during my previous trips, when most meals were drab affairs at government-run establishments. Privately owned restaurants called "paladares" were still in their infancy, and at a Havana paladar I visited in 1994, which consisted of the dining table in a cramped, dimly lit apartment, I paid $5 for a plate of beans and gristly pork.

By contrast, our stop at TocaMadera (knock on wood), a paladar tucked into a side street in the city's embassy-filled Miramar neighborhood, was exemplary proof that the joke is sorely outdated.

Chef Enrique Suarez, who wound up joining us for lunch, touts TocaMadera as Cuba's first gastropub. The chalkboard choices change daily, with many ingredients sourced from a nearby organic farm. Surrounded by a bohemian jumble of vintage cameras and typewriters, we savored casabe con ropa vieja (cassava flatbread topped with shredded beef) as we listened to Suarez' thoughts on Cuba's future. The most radical changes may be still be happening underground, he told us, "but they are happening."

Discovery of the Day: In 1975, artist Jose Fuster transformed his home in the western outskirts of Havana into a whimsical kaleidoscope of eye-popping mosaics and sculpture. Today, Fusterlandia encompasses the entire surrounding neighborhood -- from more than 80 houses to bus shelters and a chess park -- and helps support a new generation of artists and entrepreneurs who sell their wares on the nearby streets. It's about a half-hour ride from Old Havana and is included as a stop on Azamara Journey's "Havana Bucket List" excursion.

Day Four: Havana's Living Room & Other Famous Landmarks

With a fresh breeze and welcome peeks of sunshine in the forecast, we spent a few of our final hours in Havana catching up on some must-see attractions.

Just outside the cruise terminal, we had no trouble hailing an aptly named CocoTaxi. A big hit with tourists, the blindingly yellow contraptions are three-wheeled scooters outfitted with plastic seats and a coconut-shaped fiberglass shell. Our 10-minute ride included nonstop commentary from our animated driver, and the only nail-biting moment came when he couldn't wait for a traffic stop to pull out snapshots of his family in Seattle.

Our destination, the Hotel Nacional de Cuba, ranks among the city's most famous landmarks. Perched dramatically on a cliff overlooking the Atlantic, it opened in 1930 and has hosted an impressive line-up of Mafia kingpins, Hollywood celebs and world politicians.

According to the U.S. government, one of several mysterious, still-unsolved "sonic attacks" that caused American diplomats to fall ill in 2016 and 2017 took place here. As a result, a current State Department advisory recommends U.S. travelers avoid the hotel, but we saw plenty of other Yanks sipping daiquiris on the ocean-view terrace. And the Nacional's iconic Cabaret Parisien is a popular evening excursion for Azamara Journey passengers.

This year marks the 60th anniversary of Castro's overthrow of U.S.-backed dictator Fulgencio Batista, and the Museum of the Revolution gives an unabashedly one-sided view of 20th-century Cuba from what was once the Presidential Palace (still riddled with bullet holes from an unsuccessful coup attempt in 1957).

We clambered up a courtyard stairway to ogle the Granma, a 60-foot cabin cruiser that carried Castro, Che Guevara and 80 other rebels from Mexico to Cuba to launch the revolution. But the museum's Versailles-like Salon de los Espejos (Hall of Mirrors) was blocked off and swaddled in scaffolding -- yet another example of the city's ongoing efforts to shore up and showcase its 500-year history.

Discovery of the Day: Havana's seaside wall and promenade, the Malecon, has been nicknamed the world's biggest outdoor sofa because it's a favorite gathering place for throngs of Habaneros (someone born in Havana). It extends for 5 miles through three neighborhoods and starts less than a mile from the cruise terminal.

And since Azamara Journey didn't sail for Cienfuegos until sunset, we had time before a rain squall moved in to chat with a passing Sunday parade of families flying kites, teenagers preening for selfies and grizzled fishermen using worms and weighted hand lines to try their luck for bonito and snapper.

Day 5: A Day Off At Sea

After a night of rocking and rolling through 15-foot swells and wind gusts of up to 70 knots, we awoke to gratifyingly calmer seas. But during an early morning stint in the Journey's well-equipped fitness room, a fellow passenger relayed some troubling news: Just a few hours after our sunset departure from Havana, the city had been slammed by a powerful (and rare) tornado that killed at least four people.

Grateful for both our good timing in leaving Havana and our captain's skillful passage through the storm, we were happy to relax by sampling some of the Journey's varied shipboard diversions -- most of which are gratis.

Staff photographer Paula Machado garnered a big crowd for a session on how to take better smartphone pictures, and her snappy, informative slideshow covered everything from an often-overlooked basic (always start by wiping off the phone lens) to tips that even this experienced iphonographer found helpful. Among them: To capture a vertical panorama (particularly useful if you're photographing trees, cathedrals or any spaces taller than what's included in the normal range), simply set the camera to "pano" mode, put the phone in a landscape (horizontal) position and shoot from top to bottom.

During an earlier stroll through Old Havana, I'd been captivated by a sidewalk round of Cuban dominoes. Played at a wooden table by men who were far more intent on their fortunes (or lack of them) than by a curious American tourist, the contest inspired me to check out a demonstration in the Azamara Journey's card room. I learned the game uses one double-nine domino set, played by four people in two partnerships.

We opted for dinner that evening at Aqualina, one of the ship's two specialty restaurants. Our timing, with reservations shortly after the 6 p.m. opening, was perfect: The floor-to-ceiling windows at the aft of the ship's top deck provided great views of the sunset afterglow. But with glasses of complimentary Chianti in hand, we quickly focused our attention on the four-course Italian menu, which ranged from a refreshing watermelon, tomato and basil salad to a decadent flourless chocolate torte. And knowing we'd be working off some of the lobster bisque and duck confit risotto at a dance party later that evening, we didn't even feel guilty.

Discovery of the Day: As part of Azamara's partnership with the New York cabaret club Feinstein's/54 Below, the performance by jazz violinist Douglas Cameron and his band in the Cabaret Lounge ran an engaging musical gamut from Coldplay to "Fiddler on the Roof." Cameron's Cuban selections were the best -- including a cover of the Buena Vista Social Club's "Chan Chan," with Spanish lyrics displayed for an audience sing-along.

Day Six: Power Touring in Cienfuegos and Trinidad

Azamara Journey's final approach into Cienfuegos, following a pre-dawn glide through an expansive, mangrove-lined bay, was a surprise.

I knew the city on Cuba's south central coast had been founded by French emigres. Dubbed the "Pearl of the South," it was gearing up to celebrate its 200th anniversary this year.

But I wasn't expecting the sleek sailing yacht anchored off our starboard side, next to a peninsula with a conga line of neoclassical, Art Nouveau and Moorish gems whose ornate towers stood in sharp relief against the sunrise above the Sierra de Escambray.

Like Cienfuegos, the somewhat nearby town of Trinidad -- about an hour-and-a-half drive to the south along a two-lane highway more frequented by horse-drawn carts and rusting bicycles than cars -- owes its architectural fortunes to sugar barons and the slave trade they profited from.

During its heyday in the mid-19th century, Trinidad and the surrounding Valle de los Ingenios was the epicenter of Cuba's sugar production. Today, according to our tour guide, most of the candy-colored buildings in its historical core are privately owned -- from a growing roster of paladares and casa particulares (guest houses) to art galleries and shops selling hand-embroidered lace.

Discovery of the Day: Our daylong Trinidad excursion ended with a stop at Cienfuegos' Palacio de Valle, a Moorish-inspired edifice on the city's Punta Gorda peninsula. Built by an Italian architect as a private home in 1917, it was slated to become a casino in the late 1950s before the Cuban Revolution intervened. We admired the view of sparkling Cienfuegos Bay from an expansive ground-floor terrace, where jousting knights were splayed across a tiled floor. We climbed a marble staircase for an even better vista -- after squeezing past a contingent of workers doing meticulous restoration on what is now a government-run restaurant and small hotel.

Days Seven and Eight: Santiago de Cuba

We arrived midafternoon at Cuba's second-largest city to some welcome news about our final port of call. Instead of anchoring in the Bahia de Santiago de Cuba and tendering 20 minutes into town, we'd been cleared to tuck in next to a docked Panamanian freighter. From there, it would be a short -- albeit steep -- clamber up to the main plaza, Parque Cespedes.

By the time we started our trip back to Miami almost 24 hours later, we'd have a solid overview of Santiago's complex and convulsive history, from Teddy Roosevelt's Rough Riders assault on San Juan Hill during the Spanish–American War to the city's star turn in Castro's launch of the 1959 revolution. El Comandante was born nearby and went to school here; his ashes are buried in the Cementerio Santa Ifigenia, where every half-hour, Cuban soldiers perform a changing of the guard ceremony in front of the simple granite boulder that serves as his tomb.

But that first evening, after a waiting tour bus gave us a welcome lift through the hilly streets, we got a chance to sample a blend of African, Spanish and Caribbean musical influences at Casa de la Trova, a Santiago de Cuba favorite since the 1950s. (Among the club's fans: The Beatles' Paul McCartney, who stopped by almost two decades ago and reportedly wowed the locals by trying his hand at the clave, a traditional Cuban percussion instrument.)

Though the wooden tables in the breezy, second-floor performance space were packed with fellow passengers instead of Santiagueros, we were still swept into the spirit -- and swept off our feet onto the dance floor, with a little help from a sultry duo whose sizzling moves managed to make even the couch potatoes among us look smooth.

Discovery of the Day: Peripatetic author Graham Greene wrote part of his novel "Our Man in Havana" while ensconced at the Casa Granda, which opened in 1914 and was renovated a century later. The rooftop bar, where we stopped off for a nightcap after our excursion to Casa de la Trova, commands an impressive vista of Parque Cespedes -- and, its deck lights twinkling, of our home away from home.

Day 9: Heading Home

The last day of a cruise is always bittersweet, and ours on Azamara Journey was no exception.

It was a time for thanking the perpetually affable crew members who'd managed to remember not only our names but also our favorite table (in a sheltered corner of the outdoor deck just outside Windows Cafe).

It was a time for indulging in one more over-the-top buffet -- a traditional German fruhschoppen, including five varieties of grilled sausages -- and realizing, too late, that a few shipboard gym sessions and an introductory salsa class wouldn't begin to compensate for the extra calories.

And as we grabbed cellphones to capture a rainbow framing our path back to Miami, it was a time to remember an encounter that symbolized the hopes, fears and determination of a country on the cusp of an uncertain future. **

Jorge, our guide during the previous day's panoramic bus tour of Santiago de Cuba, had been a pro at weaving favorable statistics (the island boasts one doctor for every 130 Cubans, who have a life expectancy of 78 years) with tailored-to-his-audience jokes. Last year, he told us, the U.S. became a top tourism market in Cuba, second to Canada -- "and we are crossing our fingers," he added, "that someone doesn't use a Trump card to change that."

But Jorge shared his most poignant observation as our Chinese-manufactured tour bus headed for the Castillo del Morro, a massive 17th-century fortress that looms over the entrance to the city's harbor.

Our route took us along a four-lane, nearly empty highway, its median strip lined with meticulously trimmed, riotously blooming bougainvillea. We'd encountered the flowering plant nearly everywhere we stopped -- with apparent good reason.

Jorge explained that the hardy bush takes whatever nature throws its way, from drought to floods, and manages to survive: "Just like Cuba itself."

Discovery of the Day: It was our final night onboard, and although I'd already paid about $10 apiece for five Cohiba cigars (Castro's favorite) in Santiago de Cuba, I knew I couldn't deliver my souvenirs without instructions on how to appreciate them.

My solution: a $15.99 "Azamara Cuban Experience" that included a shot of seven-year-old Havana Club rum, two chocolate truffles, a demitasse of Cuban coffee and a No. 2 Romeo y Julieta, a popular brand famed for its mildness.

Truth be told, I don't think my waiter at the Patio Bar was certain whether I should puff, sip or nibble first -- and neither were the handful of cigarette smokers the next table over. But as we compared notes about our experiences before heading back for some last-minute packing, there was one thing on which we could all agree: the open warmth of the Cuban people and the value of a trip like this one to keep the dialogue between neighbors going.

Find your cruise on Azamara!

Award-winning veteran travel reporter and photographer Laura Bly has visited more than 100 countries on seven continents. Following stints at USA Today, the Los Angeles Times and the Orange County Register, she and her husband are now based in the UNESCO World Heritage city of San Miguel de Allende, Mexico. Her favorite place: a window seat or cruise ship balcony, headed somewhere she’s never been.

Publish date October 10, 2019
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