Certain images recur irritatingly in writing on Cuba. It's rare to find any descriptions of the country which avoid mention of cigars, Chevrolets or colonial decay in the first couple of paragraphs. These same impressions, etched in the memories of every visitor, make Cuba the ever-popular subject for coffee-table photography books. Yet these are essentially images of Havana, the capital which has a particular life all of its own, and their ubiquity conceals the national complexities and tensions that give Cuba its strange momentum, its contagious energy, the glint in its eye.

Fair enough. It's hard not to get intoxicated by Havana's cocktail of faded glamour and sprightly kitsch, with its tinpot American junkmobiles and dilapidated edifices (described by Theodore Dalrymple as "a great set of Bach variations on the theme of urban decay"). But still, the pleasure you derive from using those ancient chariots as taxis is only half the story – to learn the rest, count the number of times the car breaks down during the journey, forcing the weary driver under the bonnet again. And those colonial facades, whose beauty is increasingly obliterated by neglect and the pitiless passing of time, act not only as magnets to the eyes but also as houses – in Havana, a building only becomes uninhabitable when it falls down.

President Fidel Castro (or El Caballo, or el Jefe Máximo, or a multitude of other monikers) is the longest-serving head of government in the world. He's also on his last legs, as became embarrassingly clear last year when he collapsed in front of thousands in the middle of one of the four-hour-long speeches for which he's renowned. Doubtless this wasn't lost on the Habaneros but they seemed to have other things on their mind when I visited. I talked politics with Ronaldo, a young guy I met on the evening of my arrival who was taking advantage of the confusing blackout (a consequence of the recent visit of Hurricane Michelle) to hustle a few dollars out of me. "I work in the cigar factory. But I want to get out of this shit country when I can, go on and make some money in America or somewhere," he said in between attempts to sell me boxes of fake Montecristos. Then there was 31 year-old Jésus, who struggles to support his young family by combining his workaday hustling with a job in a local casa particular. He described Castro as a "motherfucker" and told me he wanted to leave Cuba as soon as possible. Do most Cubans feel the same? "They don't care as long as they're having a good time. They can't see beyond fiesta, fiesta, fiesta." "What will happen when Castro dies?" "Don't know. Riots, probably."

The Habaneros meet their aggressive poverty with an equally aggressive determination to squeeze every possible drop of pleasure from life. A Cuban man, we were repeatedly told, will feed his family on bread and water so that he's got enough money to drink and dance all night. Sometimes he'll do this with shame, more often with an irrepressible pride. The city buzzes all day, all night: you can hear it in a living room where a salsa troupe is polishing their repertoire; you can smell it on an impromptu tour of the city's fast food establishments; and you can watch it in Parque Central, which daily plays host to heated discussions on last night's baseball. And yet it's hard to suppress the nagging feeling that there's a certain hopelessness behind this vigour – that the Habaneros, like any alcoholics, are drinking to forget; that their lively street chit-chat is merely a symptom of an unhappy inability to see beyond the end of their noses, to work for the future, to get out of the moment. Havana is, undoubtedly, a city of fiestas ­ and what fiestas – but it never seems to get over its hangovers.

Bright, brassy, and in-your-face – such is Havana, not to be confused with Cuba. In fact, Santiago, Cuba's second city, contrasts so sharply with its screaming neighbour that it's hard to believe that they inhabit the same island.

On arriving in Santiago the morning after taking the overnight train from Havana, you're reminded that you're in the Caribbean: the moist heat, the lush greenery poking through gaps in fences, the noticeably higher black – and particularly Rastafarian – population, a distinctly calmer pace of life. Jamaica is only 90 miles to the south. Wander the streets by day, with 'Buffalo Soldier' or 'Could You Be Loved?' pumping from every first floor window or ramshackle café, and you'll begin to wonder if the government has issued every Santiagero with a copy of Ché stare confidently from every wall. Well-disciplined rows of schoolchildren, all decked out in identical uniforms of red and white – the colours of Cuba's flag – march through the streets like mini footsoldiers of revolution. People speak of Fidel in hushed tones at best, preferring to mime a beard with their hands when making reference to El Jefe. The anachronistically named Committees for the Defence of the Revolution – armies of net-twitching Cuban grannies looking out for "un-revolutionary" activities – are at their strongest here.

In Santiago, you'll find only rumblings of discontent. Street musicians, their minds only mildly addled by the bottles of Havana Club invariably making their way round, cast a wary eye for eavesdropping police and then slag off Fidel in song, following the best traditions of nueva trova. The more upwardly-mobile Rastas, toiling under the racism they suffer at the hands of a bored police force, take evening classes in English to improve their chances of finding jobs that might offer some way out of the country. Students at the city's biggest university tell me of young Cubans' optimism for the future, only for a Haitian among their number to reveal afterwards that his classmates' optimism was merely a safeguard used to convince foreign visitors, presumed hostile, that Cuba's not so bad after all.

The garish propaganda posters, exhorting citizens to live up to the hefty revolutionary ideals of Ché, José Marti, or whoever, are thickest on the ground here, giving rise to the interesting question of whether this is preferable to the visual drone of advertising back home. To be sure, the psychological space opened up by the lack of explicit calls to consumption is soon enough filled by a tiring sense of reforming zeal gone awry. But in Santiago, people still believe that Cubans have the power to shape their own future collectively, according to their own needs and wants. Meanwhile, back in Havana, those who can't take it any more jump over the sea wall into rafts bound for Florida, their heads full of Miami dreams.

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Tom Nuttall is the assistant editor of Prospect. His writing has appeared in The Guardian, Venue and Flux magazines and on a number of websites. He lives in London.

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