Cuba’s capital is stuck in a curious and appealing time warp, but with real hope that the 50-year-old US embargo will finally be lifted, the city’s endearing character is under threat

despite reading about Havana for decades, when I finally arrived at modest José Martí Airport on the eve of the 50th anniversary of the city’s conquest by Fidel Castro’s communist revolutionaries, the sheer physical voluptuousness of the city was a revelation.

Virtually all the accounts I had read about the city had been ferociously focused on the its perennial economic problems and murky political moods; the writers seemed never to mention the unique beauty and charm of Havana. The city sits on the edge of the Caribbean – not the shallow aquamarine sea that most people imagine, but a deep, dark, inky blue ocean, complete with big rolling waves that splash up hard against the massive seawall that protects the sweeping, 8km long promenade called the Malecón.

The Malecón is an enduring Havana icon. All day it draws optimistic fishermen and Havana families, who have nothing in abundance save for time and a love of the breeze. But the best time to come here is late in the day, when the mellow afternoon sun turns the city a lovely sepia tone and young lovers appear as backlit silhouettes.

In the beguiling, faded colonial grandeur of Old Havana, or La Habana Vieja, walkers risk death by ecstasy. The architectural eye-candy is astonishing. There are kilometers upon kilometers of cobblestone streets (the stones carried over as ballast in Spanish galleons), Spanish churches, plazas, courtyards – complete with cool marble benches and graceful gas lamps – and hundreds of flamboyant old buildings festooned with Corinthian columns and elaborate ironworks, their huge and often crumbing stone balconies bedecked with regal marble flower pots and topped with reams of colorful laundry.

In 1982, UNESCO declared this 7.75sq km area of nearly 1,000 colonial buildings a World Heritage Site. But this is not some dusty historical morgue. Tucked between buildings of great majesty, you find bars and art galleries, newly renovated boutique hotels, libraries, shops, bookstores, museums, cafes and restaurants. The Cuban government hopes that, someday, much of this sumptuous open-air museum can be eventually repaired and restored. Already, a number of blocks are being painstakingly repaired and preserved but, of course, there is no simply no money to complete the work.

Some travelers say that cities are either male or female and I subscribe to that illogical conviction. Paris is definitely a female city, while London is just as assuredly a male metropolis. Havana is truly a female municipality in the softness of her physical beauty and the coy, flirtatious charm of her people.

intriguingly, at one time, there were 200,000 Chinese living in Cuba, many having made their way from Guangzhou to Cuba in 1949, when Mao Zedong’s communists took power. But when, just 10 years on, Castro proclaimed his own socialist victory, the Chinese fled to Miami, New York, Chicago and New Orleans.

Today, the sharp-eyed visitor may still catch sight of a few Cuban-Chinese, the children or grandchildren of those who decided to stay in Cuba. Most live in and around tiny Barrio Chino, which boasts a traditional arch – financed by the embassy of the People’s Republic of China – as well as a handful of Chinese restaurants offering Cantonese fare prepared by Cuban cooks.

After Old Havana, my favorite place is Vedado, the so-called “new” Havana, but where everything seems framed in another time, around December 31, 1959, to be exact. Whole neighborhoods stand exactly as they were then and you almost expect to see Frank Sinatra and his Rat Pack popping out of the lobby of the old Hilton Hotel (now the Habana Libre) to hail a mob pal in a passing 1956 candy-apple colored Cadillac convertible. The Rat Pack and the mobster are fantasy, but the Cadillac actually passes me by.

The American Mafia held a special affection for the nearby Hotel Nacional de Cuba. Then, as now, its large suites provided sweeping vistas of the Malecón. In 1946, the mob held a summit in the hotel hosted by Meyer Lansky and attended by such crime boss colleagues as Santo Trafficante, Albert Anastasia, Vito Genovese and Lucky Luciano (who owned the hotel’s casino). This meeting was depicted by Francis Ford Coppola’s in The Godfather Part II.

The Hotel Nacional perhaps best captures the weird but not unpleasant sensation of a time warp. It was a favorite of such 1940s and 1950s film stars as Johnny Weissmuller, Tyrone Power, Errol Flynn and Marlon Brando. More recently, such Hollywood heavies as Jack Nicholson and Steven Spielberg have stayed there, having been invited to attend Havana film festivals. Other worthies who rested their heads there included Winston Churchill and the Duke and Duchess of Windsor.

At its peak, the Nacional marked a period when both Yanqui dollars and depravity were in great abundance in Havana. In the mid-1950s, while Castro was still fighting in the mountains, Cubana Airlines offered special flights that would whisk VIPs from Miami to Havana, provide transport to the famed Tropicana Nightclub, and then return them to back to Miami by 6am the following morning. However, when the American-backed dictator Fulgencio Batista fled Havana on January 1, 1960, the Tropicana’s owners booked a one-way flight to Miami for themselves.

An amazing sight is the hundreds of big-finned old American Fords, Chevys and Buicks rumbling along the potholed roads of the city. On my first sun-dappled winter morning in Havana, I stood in the street slack-jawed, gawking at these vintage beauties (and very nearly got hit by one), before realizing that they were everywhere. Checking, I found that a few still held their original and rusting engine blocs, but most had old Soviet-era Lada engines or newer Japanese motors; like elderly men who had been given a younger new heart and thus can still get around, even in Havana’s heat.

Aside from the great old chrome ghosts of Detroit, another specter haunts the streets of Havana. Revolutionary hero Che Guevara has been dead for 41 years, but his handsome visage appears everywhere in the city – on the sides of buildings, on billboards and posters, on T-shirts and in Old Havana souvenir shops. Biographies of Che are still in big demand from the outdoor booksellers in Plaza de Armas – Havana’s oldest and most elegant square.

fidel castro will be 83 in August, and can no more give speeches longer than most feature-length films in the drab Plaza de la Revolucion. In one such chat, given at the 1986 Communist Party Conference held in Havana, he waffled on for a staggering seven hours and 10 minutes.

Castro has survived the Cold War, nine American presidents and a claimed 600 assassination attempts. Following a fall two years ago, he has become increasingly frail and has traded in his traditional army fatigues for more comfortable track suits. In February 2008, he handed power to his younger brother Raul – a mere 77 – after having absolute control over more than 11 million Cubans for 47 years.

In the rural and remote countryside, Castro is still largely viewed with respectful awe. But among Havana’s 2.5 million residents, many have a quiet – if not silent – contempt for the old dictator. Speaking out is still dangerous, but whispered criticisms of Fidel and the government are common, despite the presence of the CDR (Committee for the Defense of the Revolution): well-organized cells of government informers that have a presence in every neighborhood in the city.

A lovely 25-year-old student named Maliuska told me: “We Cubans are a very smart people with a high level of culture. But right now we are going through one of the most difficult moments since Castro’s 50 years of revolution. We know political and economic change is imminent. Many young people like me want the embargo to be eliminated, because it is no longer justified. The biggest problems now are the [lack of] human rights, the [lack of] freedom of speech, intellectual and personal development, and the economy. That’s why many people still leave their homeland in order to forge a future that is impossible here in Cuba.”

Despite pervasive poverty (which Castro has blamed on 50 years of embargo), Cuba’s healthcare standards are claimed to be exceptional. The average life expectancy, around 76 years, would seem to bear some of this out. Doctors are well trained and committed, but most must work with outdated equipment and limited access to the kind of pharmaceuticals that Western doctors take for granted. Free universal education is also one of Castro’s few enduring achievements.

Speaking to scores of Cubans, from taxi drivers and store clerks, to a doctor and a professor of English at the 300-year-old Universidad de La Habana, all were eagerly waiting for US President Barack Obama (“mui intelligente”) to lift the embargo, which Cubans refer to as “the blockade” – a leftover term from 1960, when President John F Kennedy ordered the US Navy to block any Soviet ships attempting to berth in Cuba, suspecting them of carrying missiles.

the rest of the Caribbean is worried that the Cuban embargo will end. Tourism is the main employer for the people in the Caribbean and the US is their key market. Tourism ministers of some Caribbean nations fear once Cuba opens up to 300 million Americans, it will suck the oxygen out of their local tourism industries, as Americans will be keen to explore a country that they have been barred from entering (officially at least) for the last 50 years.

The American Association of Travel Agents has issued a formal request to President Obama to allow US citizens and airlines into Cuba. Obama has already indicated that he will soon move on this issue, probably in staggered stages. The political risk in doing so is considerable less than previously. The hardcore anti-Castro Cuban-American lobby in south Florida, which for so long ruthlessly bullied so many American presidents on this issue, has now lost most of its influence.

I wanted to visit Havana and Cuba before the travel ban is lifted. I had been in Beijing, Moscow and Saigon before these cities were fully opened to the West. So I can guess what is in store for Havana once the inevitable wave of Western investment pours in. But for the vast majority of Cubans it will be a good thing, although it will almost certainly cost them something very dear. As ever-increasing numbers of foreigners arrive, especially in the form of mass tourism, Havana runs the big risk of losing its unique character.

on my last day in Havana I sit and sip a mojito on the wide green lawn that spreads out in front of the Hotel Nacional. High on a hill above the sweeping Malecón, I watch as the late afternoon sun turns the ocean into a vast sheet of liquid silver. It seems almost impossible not to be buoyant about life in Havana. However, I also sense a real sadness at the millions of missed opportunities, countless crushed lives and two generations lost to the lead hand of Communism.
On the outskirts of Havana – as in Moscow of the Soviet era, and pre-1990s Beijing – I see squalid, poorly made Soviet-style apartment blocs, with their stairways scarred, littered and unpainted, fronted by crumbling sidewalks and the bleak sight of empty shelves in food markets. Adding insult to this injury are the over-sized, vividly painted political billboards with those sacred but worthless socialist promises and the hollow, now meaningless, exhortations to strive for greatness. Attached to every billboard in Spanish reading “Celebrating Fifty Years of Revolution” is the slogan “y 50 más!” (“and 50 more!”).

All this heaviness of history merely adds a sense of bitter sweetness to seeing Havana now, in this crucial moment in her long history – before the tidal wave of change washes over her.