Havana Holidays

vintage coke ad 1950s illustration people on the beach in Cuba

Right now sipping a rum and coke on glistening white sand basking in warm Caribbean sun sounds about right. Vintage illustration Coca Cola ad 1958 “Enjoying a Coke on Cuba’s famous Varadero Beach,” a 13 mile long peninsula with powder soft sands.

Bracing for yet another bone chilling winter storm, dreams of languishing on a white sandy beach soaking up the warm Caribbean sun are never far from my winter-weary mind.

And now a new dream vacation spot may open up… and its no dream.

Let’s raise a Cuba Libre in praise of normalizing relations between Cuba and the US.

Over half a century of waiting, my long-delayed Havana holiday might actually happen.

Despite the all too predictable political backlash  and initial outrage by some Republicans about this development which now feels overblown and as wildly outdated as the vintage Chevy’s that fill Havanas streets, the first commercial U.S. flight to Cuba since 1961 has just taken off.

Cuba  Where Yesterday Meets Tomorrow

vintage travel advertisement cuba

Vintage tourism ad that touted “Havana Where Yesterday Meets Tomorrow” has never rung truer.

The frozen-in-time feeling in Cuba fits perfectly with childhood memories of stories shared by my parents of their mid-century Havana holidays.

Dinner time in the suburbs sometimes took on a fiesta feeling when my parents wanted to reminisce about their travels.

Over a festive dinner of arroz con pollo – a dish first enjoyed by Mom in Havana and now in the suburbs  made the authentic Ladies Home Journal way with a can of Hunt’s tomato sauce and EZ Minute Rice – Mom and Dad would regale us with their adventures in Cuba, casting a spell as intoxicating as the island itself.

The glitter and glamor of pre-revolution Cuba, that tropical Technicolor paradise of palm fronds and turquoise water, a sultry cocktail of casinos, corruption and the Caribbean Sea would fill their Kodacolor memories for decades …and fuel mine.


Travel Cuba Vacation Castro

On the triumph of the Cuban Revolution on January 1, 1959 the representatives of American company’s that operated the Havanas world-renowned Hotel National de Cuba departed. The glamorous hotel was the setting for the formation of the 26th July Movement revolutionary cell led by Castro. (L) Vintage travel ad Hotel Nacional de Cuba 1955 (R) Vintage Life Magazine cover Fidel Castro 1961

But New Years 1959 shattered any hopes of my own Cuban getaway. Along with ringing in the New Year with Guy Lombardo, Fidel Castro took over Cuba forever shuttering this Garden of Eden to American revelers.

Any dreams of rum-soaked nights dancing the rumba till dawn would have to marinate for well over 50 years.

For the  balance of my childhood, Cuba remained a mysterious and forbidden place; the romance and allure of pre-Castro Cuba now melded with a menacing bearded man, the specter of Communism looming so close to our borders  became a hot button issue in the cold war.

Honeymoon in Havana

vintage photo couple on Caribbean beach

My Havana honeymoon parents catch the rays on the Playa del Este a string of white beaches and brilliant aquamarine waters 12 miles west of Havana 1950

My parents had a romanticized sense of Cuba, and for good reason. It was after all where they had honeymooned in 1950.

As the years passed, the paradise would almost grow lusher, conjured by an imagination infused with nostalgia.

Did my PTA Mom and Republican Dad really linger an entire afternoon at La Floridita nursing daiquiris poured by highly skilled cantineros in the hopes of catching a glimpse of Ernest Hemingway at his favorite watering hole, which in their multiple tellings they had.

Hotel Nacional de Cuba

vintage illustration ad featuring diners at Hotel Nacional Cuba

“In Havana at the famed Hotel Nacional de Cuba Roma Sherry precedes a happy dinner party.” Vintage illustration from 1947 ad for Roma Sherry

Like so many they were drawn to the fiesta that was Havana, the most exciting city in the Western hemisphere, the Caribbean playground to American socialites, politicians and movie stars.

Of course  the Honeymooners stayed at the world-renowned Hotel Nacional de Cuba , the iconic hotel filled with flowering gardens, sumptuous sun clubs and swimming pools where these newlyweds from NY could rendezvous with the smart Cosmopolitan set.

Tropical Adventure Awaits You in Sunny Havana

vintage ad travel cuba nacional de Cuba

Gay Days in the Cuban Sun .The iconic hotel with its eclectic architectural style blending Art deco, Moorish with Spanish colonial was built in 1930 through an agreement with Cuba and US backed banks. Vintage ad Hotel de National Cuba 1947

This was the very same hotel that only 4 years earlier had turned my father away, during a winter school break.

It seems Lucky Luciano beat him to it, booking the entire hotel that Christmas week of 1946 for a big mafia summit at which the carving up of Havana among the crime families was on the agenda.

Undeterred, Dad found refuge in a little hotel on Obispo Street The Ambos Mundos Hotel, a place that Hemingway himself had stayed in during the 1930s

For a war-weary soldier 6 months out of the service and a few months into law school, Cuba with its tropical beauty and tropical beauties beckoned him.

It was a post war paradise

travel- cuba -1950

The streets of Old Havana, pulsating with African and Caribbean rhythms, were lined with architectural marvels of Spanish colonial architecture evoking tales of Cuba’s colonial past

A tourism magazine had described Havana as, “a mistress of pleasure, the lush and opulent goddess of delights.” It didn’t disappoint.

Havana was a paradise living up to its reputation as a tropical playground, a blend of glittering nightclubs, outrageous cabarets, all night bars with exotic drinks and backstreet brothels.

This young man from Astoria Queens was livin’ la vida loca!

Mama Loves to Mambo But Papa Likes to Cha Cha Cha

travel cuba tropicana SWScan00478

But the best stories were about the mythic Tropicana nightclub, the brightest jewel in Cuban nightlife.

“Havana’s glamorous Tropicana,” Dad never failed to point out between bites of Mom’s take-a-can-and-take it-easy arroz con pollo, “bore no resemblance to the one portrayed on TV!”

As much as Mom loved Lucy she would always smirk at the fictional Tropicana Club run by Lucy’s bandleader husband Ricky Ricardo ( famously played by Cuban Desi Arnez) a sanitized version of the sizzling club in Havana.

Billed as “a world of pleasure within a paradise of Magic,” the Tropicana, set in bucolic surroundings was a lush paradise of rumba and roulette, dazzling lights and equally dazzling “goddesses of the flesh” as the scantily clad showgirls were called, who pranced on catwalks set among tall royal palms rising above the tables through the roof.

Tropicana in the Sky

vintage ad tropicana Special flight 1957

Taking off every Thursday from Miami International Airport , the flying party sets its happier patrons down in the balmy air of the land of daiquiris and sex at Havana’s Aeropuerto Jose Martin an hour later In between you are treated to excellent drinks, top-notch Latin Music and a floor show. Brainchild of Antonio Mintero, the promotional manager of Cubana Airlines, the flying saloon took 2 months to prepare before it was unveiled in 1956. Operated in a package deal with the fabulous Tropicana night club, revelers who want to try the thrills of a night spot in the air pay $68 for a ticket. Vintage ad 1957

Heralded as a “paradise under the stars” my parents took the nightclub’s slogan literally.

In 1958 they booked a flight on the famous Tropicana Special the first flight in the world with a live show aboard.

Offered by Cubana Airlines, the extravaganza was billed as The Greatest Show on Air!

“Treat yourself to an evening beyond your fanciest dreams Havanas Tropicana “The Monte Carlo of the Americas. Flying from Miami to Havana the 1 hour flight had a live show featuring Mambo, Rhumba, Cha Cha Cha and drinks on top of the clouds.”

Why wait until you got to sunny Havana to start the fiesta?

Whisking patrons 10,000 feet into the air, plying them with unlimited pink daiquiris and vibrating music  it wasn’t long before Conga lines of passengers and performers would be snaking down the aisles in the plane,  as the diamond chain of lights that were the Florida Keys move slowly behind.

Vintage Rum Advertisement

Complete with miniature stage installed at the front of the cabin, decorated with a glowing arch like that at the Tropicana night club, musicians decked out in fiesta outfits played sizzling music on the piano trumpet, maracas and bongos.
Cha cha Cha’ing up and down the aisles were 2 saucy performers from the club, Gloria and Rolando encouraging passenger to sing along supplying them with Spanish lyrics printed on a card.

”As the torrid Cuban music poured over you would lose consciousness of the plane and its 4 huge engines and that 1 hour flight would fly by literally!” Dad would remember.

Of course lubricated by unlimited pink daiquiris didn’t hurt.

Breezing through the airport  in Havana  since Americans didn’t have to bother with customs thanks to a special arrangement through the airline and the Tropicana,  they were whisked to the real Tropicana Night Club, put up at the Hotel de Nacional for a few winks and flown back to Miami the next day with a complementary champagne toast.

vintage airline Travel ads cuba florida

Only 4/1/2 hours non stop from NY by air from Miami, American tourists flocked to Cuba in the winter. With the advent of cheap flights and hotels deals, the once exclusive hotspot became accessible to American masses.”Blend the glitter of Miami Beach with the romance and chance of the Riviera, spice of the West Indies and the rhythm of Havana.” vintage travel ads National Airlines

The best part was, this paradise was only 90 miles from Miami, my parents would remember wistfully.

For Whom the Bell Tolls

collage vintage travel ads Miami and Cuba and Missiles in Cuba

The proximity of Cuba being so close to Florida would take on a very different meaning especially in October 1962 with the Cuban Missile Crisis .

But while tourists eagerly spun the roulette wheel in sexy Havana, a revolution brewed in the less glamorous countryside.

This playground to American’s was abruptly shut down when Fidel Castro took over. The Tropicana that had opened to such fanfare on New Years Eve 1939, would close on another New Years Eve twenty years later, one which would ring the death knell of Cuba. Cuban revolution brought the curtain down on that era.

Soon the proximity of Cuba being so close to Florida would take on a very different meaning to me especially in October 1962 when Armageddon was narrowly avoided.

After that it was as if Moms famous arroz con pollo was seasoned with communism and its Spanish origins were emphasized as the chilly cold war came closer to home.

© Sally Edelstein and Envisioning The American Dream, 2015. Unauthorized use and/or duplication of this material without express and written permission from this blog’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Sally Edelstein and Envisioning The American Dream with appropriate and specific direction to the original content.


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  1. You have to see “The Mambo Kings”. Awesome movie. https://www.youtube.com/watch?v=GadbFPUKx6A

    Liked by 1 person

  2. dirk

    Cuba was rulled by the maffia and a corrupt goverment,there nothing sunny for the people of Cuba,that was the reason of the revolution.


  3. Marcos Roman

    RULED !! . Yes the mafia was profiting from the turism and the casinos and so what? like many other business the mafia have, See if the mafia is interested in Haiti.
    Cuba was on first, second, or third place on ANY index you want to look at for the latinamerican countries, Cuba was country where people from every corner of the world could found a new home, From 1900 to 1959 were a total of 2,2 million of immigrant in a country of 6 million of inhabitants in 1959.
    And true Bastista overthrown the constitutional government 6 month before an election but I would prefered him than the Castro brothers that has hijacked a whole country for 55 years turning it his private farm.


  4. John Anderson

    I always enjoy your posts. They’re not just entertaining, they’re educational too. I’ve never been to Cuba before, and now I’m not sure how things will turn out. I do feel this change in policy with regard to Cuba is a step in the right direction – and long over due.


  5. Marcos Roman

    Dirk, Yes, to solved a small problem Cuba got into a big problem, you know that >80% of the people that fought for the “Involution” ended in jail or escape the country, in fact Fidel said so many lies while he consolidated the absolute power, he betrayed those who were willing to give their life for a better Cuba.

    Liked by 1 person

  6. Growing up in Florida, I have heard so many tales of what it was like growing up in Cuba by those who fled and those who had the opportunity to vacation there before the Castro Regime took over. Everyone speaks of Cuba as this mythical place for beauty, entertainment and making dreams come true. I am with you, that I would love to vacation in Cuba and see what people are talking about since from what I have heard, in just beauty alone, Cuba has not changed in 50 years.


  7. Alejandro

    I was born and grew up in Cuba until age 16. Came to the U.S. In 1980 on the Mariel boat lift. I am sure my parents suffered a lot under the Castro government. Yet..I had a lot of fun and happy experiences there as a chid and teenager and I would love for my U.S. friends to have those experiences too. An early morning ocean swim at the beach there is priceless. I welcome the new re-opening between the U.S. and my old country. It is about time all suffering and all resentments came to and end and everyone can enjoy the beauty of the island again. Even though I am an American now, I am nostalgic for my morning swims and miss them a lot…


  8. Jorge

    see you in the Malecon sally


  9. Does anyone have a link to those great vintage photos of the open air sit on top plane flights to Cuba?

    Also of the in cabin dance lines?

    Thanks in advance!


  10. I need a time machine… this place looked fabulous…


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