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Andreana Bitsis / Alamy Stock Photo
Andreana Bitsis / Alamy Stock Photo

Havana is a throwback to times past. Little has changed here since the Cuban revolution in 1958, and the city looks much like it did in the Fifties when the American mafia had turned it into party central. This all makes for a truly authentic experience today.

Back to the 50s
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Day 1

Pirates, mafia and cocktails

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Keepers of the colonial loot

Morro Castle on the bay is well worth a visit. Built in 1589 when Havana was the main city of the Spanish colonial empire, it served as a bastion for Spanish treasures. Walk through the vast corridors and check out the exhibition on the pirates who preyed on colonial booty. From the platform with the cannons, you can look out over the sea and imagine how pirate Piet Hein captured the Spanish silver fleet ninety kilometres away in 1628.

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Ts Havana 03 Bg Half Cannon

A classic Cuban lunch

Enjoy a delicious lunch with fish or shellfish in La Divina Pastora, a traditional Cuban restaurant on Havana Bay with a view of the old town. Sip a cocktail while musicians play a Cuban son or bolero for you. After lunch, take a walk to La Cabaña. This 18th-century fortress formed, together with El Morro Castle, the most important defensive structure in the city. It’s located on a sixty-metre rock and is the third largest Spanish colonial fort in the New World.

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Inspired By Maps

Photos from that time of celebrities like Frank Sinatra and Rita Hayworth still hang on the wall. The beautiful garden is an ideal spot to sip a piña colada or other cocktail.

Celebrities and cocktails

Situated on a rock, the stately Hotel Nacional from 1950 looks out over the Malecón, a wide boulevard where Cubans play guitar with a bottle of rum within easy reach. In the Fifties, the hotel was owned by the mafia group of Meyer Lansky and Lucky Luciano, who ran the city together with dictator Batista.

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Day 2

Revolution, heroes and legendary cocktails

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Resting place of Cuban heroes

The spectacular Cementerio de Cristóbal Colón is a majestic burial site. Named after Christopher Columbus, it is known for its many superb sculpted monuments. The country's most famous politicians, writers, artists and politicians are buried here, including Rubén González, the pianist of the Buena Vista Social Club. The crowded cementerio covers half a square kilometre in the Vedado district.

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Jeremy Woodhouse
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Ts Havana 09 Square

Where Fidel made his speeches

The immense Plaza de la Revolución houses the monument to José Martí, father of the nation and one of the leading figures in the struggle for independence. The monument is over one hundred metres tall and can be visited: take the lift to the top for a magnificent view of the city. This is the site were Fidel Castro used to give his famous hours-long speeches, while up to a million Cubans would gather in the square. The area also contains the main government buildings.

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Back to the Fifties

Habana Vieja, the old city, is without doubt the most beautiful part of Havana. This lovely district was placed on the UNESCO World Heritage List in 1982. Walk through the bustling street Obispo to the Cathedral and the Plaza de Armas, where a book market is held every day.

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Julian Peters Photography
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Around the corner is La Bodeguita del Medio, Cuba’s most famous restaurant, where the mojito – the popular cocktail with rum, mint leaves and lime juice – was invented. When the writer Ernest Hemingway lived in Havana, he came here almost every day.

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Ts Havana 12 Dag3 Intro

Day 3

Batista’s opulence, cigars and Chinese

Batista’s decadent palace

After Fidel Castro and his revolutionary comrades celebrated their triumph on 1 January 1959, the presidential palace was turned into a museum. Here you can get a good idea of the background to the revolution and the decadence in which the dictator Batista lived – his golden phone is still there.

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Federico Julien / Alamy Stock Photo

After a visit, have a drink around the corner at the world famous bar Sloppy Joe's. Many celebrities came here in Batista's heyday, including the writer Graham Greene. His Our Man in Havana, starring Alec Guinness in the lead role, was filmed there.

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The best cigars in the world

Cuban cigars are world famous. While the best tobacco leaves grow in the western province of Pinar del Río, the most famous cigar factory, Real Fábrica de Tabacos Partagás, is in Havana. In the factory you can see how the cigars are still made by hand, and you can smell the sweet smell of fresh tobacco.

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During the tour a cigar roller reads out loud the official state newspaper. This is one of the ways the state has attempted to educate workers since the Cuban Revolution.

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Jeremy Woodhouse/Holly Wilmeth

Cuban Chinatown

Next to the tobacco factory is the huge Chinese gate where Chinatown begins. After the abolition of slavery, hundreds of thousands of Chinese indentured labourers were brought to Cuba to work on sugar cane plantations.

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Rosita So Image

Many of their descendants live in this Chinese district around calle Zanja. This area is home to dozens of Chinese eateries, which are also very popular among the rest of the Cubans. One of the best restaurants is Flor de Loto at calle Salud 313.

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