After a busy day exploring Havana’s historic sites, there is little more relaxing than enjoying a mojito on the expansive colonnaded veranda and the well-kept lawn terrace of Hotel Nacional. Palm trees bring welcome shade for your ringside view of the Malecon – the Cuban capital’s 9km open air promenade along the ocean – and the blockbuster sites of the old town in the distance.

The iconic Hotel Nacional

Built in 1930, the Nacional remains the country’s most famous hotel and a popular tourist attraction in its own right. During its illustrious history it has welcomed numerous famous guests such as Winston Churchill, Frank Sinatra and John Wayne.

Entering the lobby you feel as if you have arrived at an Arabian Palace, with fantastic decorative Moorish-style floor tiles and a wooden beamed ceiling. Outside there’s a great pool for residents to plunge into, plus a number of cafes and restaurants. The institution is run by the Cuban state and there are frequent complaints about the food and service, but that’s not what the hotel is famous for – it’s the wonderful setting that provides the biggest selling point here.

Historic lift at Hotel Nacional

The Nacional also stands as a symbol of Havana’s wider history, in that it was a later part of a move west by the city’s elite – that began in the 1860s – who were fed up with living in the cramped conditions of Habana Vieja. Called Vedado, this area is often referred to as the cultural heart of the city, given its galleries, theatre and university buildings set in and around a grid system of Parisian-style streets.

The district came of age in 1950s as a place for American tourists who enjoyed gambling and mobsters who partook in all-night parties. The American Mafia paid for many luxurious hotels to be built with casinos – which benefitted from lax gambling rules introduced by Cuban president Fulgencio Batista in 1955 – and nightclubs attached. Thanks to promises of generous tax incentives and government investment, the Mob grew a large property portfolio in Havana (which included the Nacional and Sevilla, as well as the new Havana Hilton).

For Graham Greene who wrote the 1958 novel Our Man In Havana, which poked fun at Batista’s regime and the British Secret Service, the city at the time was absorbing. As well as enjoying the Floridita restaurant (immortalised by Ernest Hemmingway for its daiquiris), Havana provided the perfect backdrop for the book given“…brothel life, the roulette in every hotel, the fruit machines spilling out jackpots of silver dollars, the Shanghai Theatre, where for one dollar and twenty-five cents one could see a nude cabaret of extreme obscenity with the bluest of films in the interval. (There was a pornographic bookshop in the foyer for young Cubans who were bored by the cabaret). Suddenly it struck me that here in this extraordinary city, where every vice is permissible and every trade possible, lay the true background for my comedy.”

One of the most insightful contemporary accounts of Havana during Batista’s rule was that written by attorney Frank Ragana – with New York Times Crime reporter Selwyn Raab – who was guided around the city by the mob. He was taken to everything from the capital’s infamous los exhibiciones (its sex shows) to big impressive nightclubs and concluded that “Havana was the most fantastic city in the world.” He added: “It had everything – glamour, a great climate, excellent food, and an incredible nightlife.” Havana drew in a certain kind of tourist:

“Sex was a big draw for the tourists and some motels in Havana rented rooms for fifteen minutes or half an hour – a practice that would come to America two decades later. The Cubans new that some couples did not need an entire night to enjoy themselves. To ensure privacy, high walls were built around the motels so cars could park unseen.”

During the 1930s when Batista was first in power, gangster Meyer Lanksy described him as “the best thing that ever happened to us,” adding: “I’ve got him in my pocket, whether he’s president or whether he puts someone else in, no matter what happens. He belongs to us (the Mafia). I handle all his money – every dollar, every peso he takes, I’m handling the transfer to his account in Switzerland.”

It was this sort of corruption and vice amongst Fulgencio Batista and his cronies in the Mafia that drove Fidel Castro and his comrades to Revolution. When the new regime took over, they put a stop to the casinos, sent the Mob back to Miami and closed down brothels. Many of the glittering hotels were divided up and given to the rural poor as homes.

The US built a new Embassy building in Vedado on a prominent position on the Malecon in 1953 (today the US Interests Section organisation, although initial talks were underway when I was in Cuba that could lead to it regaining its original status). Since the two nations severed diplomatic relations in 1961 there has been an ongoing tussle here, with the construction of the Plaza Anti-Imperialist in 2000 as a place for Cubans to protest against the US. And in January 2006 US diplomats installed a Time Square-style ticker tape where they displayed messages about human rights, which the Cuban responded to by erecting 138 black flags to shade the screen.

Empty flag poles at US Interests Section organisation building in Havana

The flag poles may today be empty and the message board gone (the latter went in 2009), but security remains tight here. When I visited the area, overzealous guards whistled at joggers getting near to the ugly concrete building and compound, ushering them to cross to the pavement nearest the ocean.

Today, the hotels in this area are once again popular with tourists, but they are fading splendours that are showing their age. And not far from the pool terraces – raised above the hustle and bustle of the busy streets below – some (but by certainly no means all) of the residential and commercial buildings on leafy streets are crumbling due to years of neglect.

The area between Vedado and the Habana Vieux (known locally as Centro Habana) is particularly bad in terms of urban decay. In the 1950s however the streets around here – concentrated around the spot where San Rafael meets Avenue de Italia – contained the most fashionable shops in the city. El Encanta was a renowned department store that attracted Hollywood stars such as John Wayne.

While the lovely iconic pink and yellow building remains, the store inside is anything but attractive with baskets of tat that makes Primark look upmarket. Outside, the square was lined with scruffily dressed young and old men drinking cans of beer in the afternoon sun; some had clearly had too and had collapsed onto the pavement. Having spent a night in a hostal in this district (which was extremely pleasant inside) nearby, I know how noisy this area remains 24 hours a day.

Formerly the famous El Encanta store

For a much more pleasant walk to the old city, it worth taking the Malecon, particularly in the evening as the sun goes down on and musicians provide atmospheric entertainment. When I strolled along here the crashing waves were splashing water onto the walkway – constructed in stages between 1901 and 1950 – yet few seemed deterred on missing out on the panoramic views it offers.

Urban decay in Centro Habana

The Malecon in Havana

Before moving on from Vedado, I took a short ride in a 1950s American car (extremely common on the roads here given the US embargo) to Plaza de la Revolucion. Passing along tree lined avenues, it was a fitting place to take stock of life before the Revolution.

The huge open air concrete complex was renamed from Plaza Civica in 1959, just after the vast marble statue and memorial of Jose Marti – the centre piece – was installed. Since the Revolution this space has been used for large government rallies and speeches (Fidel Castro has on occasions spoken for hours here).

And on ugly concrete office blocks along one side of the plaza, there are large murals of Revolution heroes Camilo Cienfuegos and Che Guevara. The latter depiction is particularly famous given it is seen as a symbol of the Revolution and is based on a photo by Alberto Korda. In contrast to the American inspired hotels just a short ride away, these images are a powerful symbol of life after Batista’s fall.

 Tomorrow: Visiting Batista’s palace and discovering about the Revolution in Fidel’s words.

Che Guevara in Plaza de Revolucion