Bespoke Cuban Holidays for the Discerning Traveller

Bespoke 1950’s Style Havana Holiday

While the louche entertainment world of 1950s Havana disappeared when Fidel Castro and his bearded acolytes marched into the capital in January 1959, alluring remnants of the cabaret, casino and cocktail world remain.

1950s fantasists, retro lovers and architectural fans will find plenty in a nostalgic trip down memory lane to Mob-ruled casinos, bars and clubs that thrived during US Prohibition, and gangster-funded hotels preserved by half a century of neglect.

Prohibition in 1920s America drove holidaying Americans on low-cost flights and ferries to the bars of Cuba’s capital. Punters propped up the bar at Dos Hermanos by the port, and Sloppy Joe’s near the Hotel Sevilla. Until recently Bar Dos Hermanos was a classic down-at-heel port side bar; its seediness has now been lost to gentrification. The colonial building that housed the infamous Sloppy Joe’s bar in Old Havana, and featured in the movie of Graham Greene’s Our Man in Havana, is under restoration. While cocktail connoisseurs await the reopening of this Havana landmark, a stop at Floridita is de rigueur. Mixologist Constantino Ribalaigua served up the classic daiquiri in this Old Havana haunt until the early 50s. After a cocktail in the ‘cradle of the daiquiri’, favoured by writer Ernest Hemingway, wander the bar-lined streets of the old town to another Hemingway haunt, La Bodeguita del Medio. This small drinking hole, close to the cathedral, opened its doors to the drinking public in 1951, and it’s where the author would drink his mojitos.

It was Cuba’s double dose dictator Fulgencio Batista who permitted the floodgates of hotel and casino development, through a 1955 law, that saw the capital flushed with money and Havana become the world’s en vogue city of the night.

While the bawdiest burlesque show in Havana at the Shanghai Theater no longer exists, the capital’s nocturnal entertainment is still a seductive offering. Havana’s most famous cabaret, the Tropicana, acquired greater fame in the 1950s through the building of the Arcos de Cristal and casino development. Today, this starry spectacle of sequins and sparkle is a highlight of any visit to the city.

Cuba’s favourite music maestro Beny Moré would play at the Alí Bar on the city outskirts in the 50s; today it’s still a feature on the bolero nights’ circuit.

Mobster Santo Trafficante Jr built the Hotel Capri and casino close to the Hotel Nacional in 1956. The 19-story building and rooftop pool that features in the opening scenes of the iconic movie Soy Cuba, is under renovation. Its Salon Rojo is a hot favourite for nighttime acts.

In 1957, mobster king Meyer Lansky built the Hotel Riviera, a glorious monument to 1950s architecture and interior design, that is remarkably preserved on the Vedado Malecón. Its coffin-shaped pool and diving board are the epitome of retro glamour. Its casino filled the Copa Room, in use today for musical acts.

The last in the trio of big bucks hotels to be opened in the late 50s was the Habana Hilton whose casino was run by Meyer Lansky’s brother, Jake. Its trademark Trader Vic’s tiki restaurant is today El Polinesio. Conrad Hilton’s 1958 landmark hotel became the de facto headquarters of Fidel’s band of rebels in January 1959. Renamed the Hotel Tryp Habana Libre, it still dominates the popular La Rampa in Vedado, its vast horizontal Amelia Peláez black, blue and white mosaic mural sparkling in the Caribbean sun.

As soon as visitors step off the plane in Cuba, an antique Chevvy, Dodge, or Buick with original, if decrepit interiors, will collect them before lumbering along the highway, devoid of commercial advertising, to deliver them to the front door of a 1950s-era masterpiece for retro pleasure not possible in any other part of the world.



  • Day 1 Stay overnight at the Hotel Riviera and enjoy the entertainment in the hotel’s Copa Room.
  • Day 2 Stay overnight at the Hotel Riviera. Visit the Tropicana Cabaret
  • Day 3 Stay overnight at the Hotel Riviera. Visit the Bar Dos Hermanos
  • Day 4 Stay overnight at the Habana Libre and dine at the iconic El Polinesio restaurant
  • Day 5 Stay overnight at the Habana Libre and bar crawl from El Floridita to La Bodeguita del Medio.
  • Day 6 Stay overnight at the Habana Libre and dine at El Polinesio
  • Day 7 Stay overnight at the Habana Libre and spend the day cruising the capital in an old American car before dining at the Hotel Nacional.


If you are interested in more luxury experiences, take one of our art tours in Cuba. We offer everything from a half-day tour to a full 2 week tour across the island.

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