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Cuba, March 1999.
December 31, 1958, the National Hotel: the great stone good-time fortress on a rock overlooking Havana's harbour. A new year's party is in full swing. Cuba's upper crust, rich on sugar and spice and all things vice, and the backs of peasant labour, drink their rum cocktails, wear funny hats and throw streamers. The band is preparing to get its maracas round "Should auld acquaintance be forgot" when in walks the man who made all this possible, General Batista, the island's military dictator and president.

Outside, as usual, his outrider tanks have blocked both ends of the street. He takes the microphone, acknowledges the sycophantic applause and makes an announcement. Sadly, the game's up. He's leaving for good, que sera sera. The motorcade streams through the suburbs to a military airport and it's all over. He is followed precipitously by everybody in Cuba who owns anything. Still in dinner jackets and party frocks, the professional class scrambles to hop the 90 miles to Miami. Having lost one Caribbean island, Batista goes on to buy another with money gratefully and unaccountably donated by the feudal Cuban economy.

"My father was a waiter here then," says Carlos, my driver and guide. We are sitting on the National's terrace, one of the most evocative, beautiful bars in the world. He looks out to sea through the colonnade, past the neat palms of formal garden where peacocks strut and fountains splash. "I was seven. I remember my father coming home very excited." And what happened then? Sipping a small espresso that cost the equivalent of two days' pay, he says: "Nobody got any room service." Room service has been problematic ever since.

Next day, Che Guevara rolls into town and proclaims a new socialist republic: happy New Year, muchachos. A week later Castro swings by, and the regime can well and truly start the way it plans to carry on.

Forty years later, Cuba is famous for failed politics, syncopated music, immoral women and cigars, and if an island could be a person, then Cuba would be Bill Clinton. The first thing you notice about Havana is how terribly 1960s it still feels. I remember the 1960s. So this is where it ended up - not the hippie flower power 1960s that gets revived every two years on the catwalk, but the political, righteous, romantic, didactically impressionable 1960s. There's music and mess and clots of policemen and 1950s cars and posters of Che. It's Che that really does it, really reminds you that this is the last un-tidied student bedroom in the world.

But it is difficult to remember that this is a truly bona fide, grown-up communist state. Communist countries are cold, grey, utilitarian and miserable; Cuba is warm, bright, sophisticated and outwardly happy. There are none of those solidly heroic symbols of universally uniting workers, or the international solidarity of metal and dogma bashers that are such a rustily ironic feature of state socialism elsewhere. There are no fraternal statues of Lenin or Marx, just a few walls with Pink Floydish official graffiti. There are statues, though. Havana is stuffed with memorial bronze but it's of the romantic Spanish type - heroic hombres on rearing horses, remembrances of small, hopeless revolts highlighting a municipal truth from all over the world: the more piddling the war, the grander the memorial. Cuba's revolution saw in the decade of left-wing youth and right-on liberation. It is the country that Joni Mitchell, Timothy Leary and Bob Dylan would have designed if anyone had been foolish enough to give them a country to tinker with. It has a fantastic free education system, an enviable free health service, plentiful guilt-free sex and cheap rum. It also has hardly any petrol, food, enterprise, industry or cash.

Although it is the 40th anniversary of the revolution, and communists are generically addicted to anniversary knees-ups, there are no signs of rejoicing, no banners in the streets, no new memorials or exhibitions of international revolutionary art, no callisthenics from schoolchildren. In truth there is little to celebrate. The past 40 years have been tough, the future looks tougher - in fact the future doesn't look like anything at all.

Castro (who is always referred to as Fidel), having been the most famous man in Latin America for so long, having outlasted every Yankee president since Eisenhower, is incapable of confronting his own mortality and appointing a successor. Ask anyone what will happen after Fidel and they just shrug: who knows? The levers of power are kept rigorously in his old but firm grip - anyone in the government who looks even remotely like a contender finds they've been promoted and re-educated in revolutionary lavatory-swabbing.

Havana feels like the town where time stood still. There is an uncanny sense of stasis, as if 1960 had stopped mid-stride, the left foot planted, the right caught in mid-air. The past 40 years in real terms - in human, everyday, quality-of-life terms - have achieved precisely nothing, less than nothing. Cuba just beats time. It nearly wasn't like this. It could have been so different. If Cuba had even been on how-do-you-do terms with its big neighbour, it could so easily have become the Caribbean Switzerland: nonaligned, independent, fat, with sun, salsa and sex instead of snow, yodelling and surface wiping.

Beating time is something Cubans have become very adept at. Music is everywhere. In the hundreds of Hemingway-fell-over-here bars of Old Havana, music syncopates and shimmies across the brindled, crumbly streets, all of it live; it's cheaper to hire the band than buy the CD. Troops of roving musicians stalk public spaces; you're continually mugged and maraca'd by gangs of smiley Desi Amazes chuntering out "Guantanamera", the original 1960s "Birdie Song", and, of course, salsa.

Cubans have salsa instead of lunch. Salsa is country and western music for happy people. They dance continuously. Even when they're not dancing, you know they're dancing inside. There is a sort of pan-national, hip-grinding, buttock-gyrating infection -people dance in queues, they dance pushing wheelbarrows, they dance behind desks. If dancing is a vertical expression of a horizontal desire, then Cuban salsa is sex in Braille.

These are the most libidinously choreographed people in the world. Above and beyond the beauty of this city, its people are beautiful. Beautiful and nubile and erotically confident and deeply COOL Mere is proof that God gives with one hand and takes with the other. The lines of wobbly, pale, plump, clumsy tourists in the ghastly Leisure-wear of sloth look like another species, doughy human mistakes compared with the curvy, coffee-coloured, ice-eyed grace of the Cubans. Cod's joke is that the poor got all the things that the rich so desperately want to buy, and without labouring the point, the Cubans have all the stuff you want in spades. The mixture of Spanish and African blood has produced something close to a middle-aged German's fantasy of perfection. With no money and hand-me-down charity, Cubans still manage to look 100 times more chic and svelte than the rest of us. The look this year, I am happy to say, is Lycra, and Lycra was invented with Cuban bottoms in mind.

The sex, of course, is why most of the tourists come to Havana. Have no doubts about this. They're not here to show solidarity with 40 years of continuous revolution, or to study architecture, and they certainly aren't here for the food. Cuba has a glut of just two things: musical instruments made out of coconuts, and erections, The Teutonic traffic wardens and Nordic civil servants on have-it-away-day hols dribble and ogle like middle-aged Willy Wonkas at a chocolate factory clearance sale. Cuban girls are the Ferraris of prostitution, top-of-the-line Formula One hookers and, boy, are they enthusiastic. But, and this is a big but, a Cuban teenager on the arm of a paunchy, balding pink-eyed Kraut in his holiday socks and sandals says much the same thing about him as his owning a Ferrari would.

In 1492 Havana was invented by Christopher Columbus. Cuba, the island he discovered, was the New World, American before America. The city is built on a natural harbour with commanding torts. Now, it festers in a post-imperial splendour (Spanish colonial is the most elegant of all exported western colonial styles of architecture). The poverty and patina of huggermugger neglect suits Old Havana, the baking balconies decked with pale bleached laundry, the psoriasis stucco and exotic weeds growing out of verandas. There are cool dark patios glimpsed through heavy sun-bleached doors, and a particular washed-out shade called Havana blue.

The grandest dome in the city covers the Museum of the Revolution, full of the cheap tat of desperation and anger, moth-eaten berets and rusty revolvers, and the suit worn by Cuba's only cosmonaut. Weirdly, it appears to be made of denim - perhaps the Russians made him take out the rubbish. On the lawn outside is an installation of decrepit bits of revolutionary kit, skips and bulldozers turned into tanks, a blitzkrieg baker's van and a cabin cruiser incongruously kept in a glass box. This is the Granma, the boat that brought Castro to Cuba from Mexico. He is inordinately sentimental about it, naming the only daily paper after it, and presumably it is kept in a box to stop someone nicking it and making for Florida. Everything else that floats has gone west.

There is also a motor museum - old American cars are a feature of Havana, the tourists love them; Cubans would rather have something with air con and windows that work. Americans like to point out that the fact they're still running is a triumph of Yankee engineering, which begs the question, well, why can't they keep a car on the road in Detroit for more than three years? Rather, these Studebakers, Pontiacs, Chevvies and Thunderbirds are a testament to Cuban ingenuity, make-do and tolerance for inanimate objects.

My favourite car in Havana wasn't a western classic: it was the boxy little 1970s Lada that the Russians exchanged for sugar in the 1980s. The Cuban cabbies stretched them - a stretch Lada, that's class. Despite everything, Havana has bundles of class. The traffic cops outside the National Hotel, for instance, posed all day beside the gleaming Motoguzzi that presumably had an empty tank because it never moved. They'd walk up to change shifts looking the business in Ray-Bans, stretched skintight trousers, gleaming helmets and high boots. I was particularly taken by the spurs.

There is a 17th-century square, shady with old trees, that is a market for second-hand books. As I wandered around the exhausting hagiographies of Che and medical-student manuals, a salesman asked if 1 was looking for anything in particular. "English, ah." He produced two books: Examining Urine, and History will Absolve Me, Fidel's most famous speech, made to a court before it locked him up for an abortive little attack on a barracks. It is his political defence and his agenda for the next 40 years, and quite succinct by Castro's standards, at only 78 pages long. Faking the piss or a Fidel rant - tough choice.

Cuba's revolution wasn't meant to be communist, at least not communist in the Russian sense. Its guiding light was neither Marx nor Engels but a 19th-century journalist called Jose Marti, a political, modernist poet who invaded Cuba after almost a lifetime of exile and got shot a month later in one of the final sad, bitter uprisings against the ruling Spaniards. Marti preached a sort of arcadian equality. He also wrote the words for "Guantanamera", so he has more to answer for than your average social-engineering theorist. Cuba ended up as an outpost of the Warsaw Pact not because it wanted to, but because it didn't want to be American.

The United States always saw this largest of Caribbean islands as part of its rightful sphere of influence. Not only was Cuba extremely profitable, producing at one time a third of the world's sugar but, straddling the Gulf of Mexico, it strategically commands the southern ports of the US and the mouth of the Mississippi. It tried simply to buy Cuba from Spain, lock, stock and indentured labour, the way it had bought Louisiana from the French, but when that failed, the US settled back into the ripe apple theory of colonialism: it would wait until the Spanish empire collapsed with exhaustion and incompetence, and Cuba would fall naturally into US hands.

But in 1898 the US lost patience, invaded and occupied Havana, leaving only after having rewritten the constitution for its own benefit and taking a military base that still exists. One of the most grotesquely grandiose war memorials in Havana was erected by Americans to commemorate Americans who, in a typically American cock-up, had blown themselves up. For the next 60 years Cuba's economy was owned and run almost entirely by the worst sort of American agri-business, and the mafia. The 30-odd years of economic blockade since has been an act of pointless vindictive bullying, the ugly spite of a powerful country that feels cheated because it hasn't got what it wants.

The blockade, more than anything else, has formed Cuba. For the ten years since the collapse of the Soviet bloc it has served no conceivable geopolitical purpose: it is simply there because it has always been there, and to back down would be to admit that it had failed, and the US, as ever, would rather be unjust than unmanned. In the face of all international law, the Helms Burton Act pushed for a mandatory international embargo against Cuba. Recently, $6.7m in legitimate telephone payments owed to Cuba by US companies was sequestered by a Florida judge, in part-payment of compensation awarded to the families of four people shot down by Cuban MiGs in 1996. The island has been forced to cut off its phone lines to the US as a result, sending itself even further to Coventry.

The blockade effectively includes large-scale humanitarian and medical equipment so although Cuba has one of the most impressive and successful research complexes outside the West, and has found the only cure for meningitis in the world, and has an internationally renowned centre for neurological surgery, and an infant mortality rate that is lower than in the US, it does so with virtually no American drugs, equipment or a market outlet to sell its own medicine. So while presidents wink and lap their noses at the embargo on imported cigars, the workers who grew and rolled them are kept in a dreary poverty. And if that sounds like the politics of the playground, it's made all the more infantile because in many ways Cuba has plenty of things that America would dearly love and needs.

In a generation it has become a truly racially harmonious place, wiping away centuries of colour bar. It is virtually drug-free, the crime rate would be envied by a Midwestern suburb, families are important, close-knit and respected, religion is becoming more tolerated and widely practised and everybody eats, although they don't eat well and they don't eat much. The ration is pitiful: a bag of rice a month, a handful of beans, two small pieces of pork or fish and all the sugar you can manage. But the poorest here aren't as poor as the poorest across the water, and they're proud of that.

The blockade has managed, in a predictably contrary US way, to produce exactly the opposite of its desired effect. In sealing Cuba from change, it has made impossible any sort of organic liberalisation or transition. Now cut off from the support of Russia, Cuba is a nation in limbo, it can't move forward and it can't go back, it just sits in the sun, slowly falling to bits. The one incontrovertible effect of the US animus has been to keep Castro in power and Cuba locked into a defunct, meaningless, one-sided confrontation.

The Bay of Pigs is about two hours from Havana. Roads in Cuba are surprisingly good, because they don't get used very much. If you want to get about, you stand at an intersection and wait for a lift from a lorry or an asthmatic Chevrolet. Hitchhiking is the official Cuban integrated transport system and neatly encapsulates everything you need to know about Third World communism. The country is mostly flat and quietly beautiful, spiked with royal palms. The sun bleaches the red earth to a pastel dun. It looks all sweetness and light and that pretty much is what Cuba is. Great swathes of hot sugar cane, stretching away as far as the eye can see. Sugar was always the point of Cuba.

The New World gave Europe something like 30% more new things to chew on, but it was an imported crop that made it worthwhile - sugar brought by the Arabs from India to Spain and then by the Spanish to the new Indies. The world sugar price has always been volatile, boom or bust. To create a market, they invented rum, and sold it to sailors and navvies. Just as an indication of what a serious growth business sugar was in the 19th century, Cuba imported 600,000 slaves between 1800 and 1865. Their descendants still work in ragged lines, hacking their way across the landscape.

You should put cane-cutting right at the top of your list of the worst jobs in the world. They start just after dawn, using a machete that looks like a large Chinese cleaver. There is nothing rhythmic about cane-cutting: it's speed tree-felling. It's clearing a path through dense jungle. They don't sing sad spiritual songs. They don't talk. They just chop and trim and stack at a remarkably unnerving pace until dusk. Two harvests a year. Endless back-breaking piece-rate work. The infant mortality rate may be something to boast of, but death still comes early for Cuban rural workers. Like everything in Cuba, cane-cutting is done by hand. Beside the sugar, oxen tug and buck ploughs over stony earth, men ride high-stepping horses with long stirrups and straw cowboy hats pulled down over their eyes, looking like extras from Hollywood. There are no Russian tractors or pick-ups here to spoil a picturesque scene that has remained unchanged for 150 years.

We stop and watch and listen to the silence and the clopping swish of the machetes and the sighs of the oxen, and suck a cool stalk of sugar and ponder that life-shortening, unremitting poverty and hardship so often have the sharp corollary of a fiercely magnificent aesthetic. Just as long as you're not expected to join in.

On the approach to the Bay of Pigs on the southwest coast, the road becomes dotted with stone slabs, the graves of militia men who defended the way to the heart of their new republic from the CIA-backed invasion by Batista refugees. Incongruously, the bay itself is now a utilitarian holiday resort that looks like a whitewashed, breeze-block RAF station. On the ruggedly ugly beach, ruggedly ugly, red, bare-breasted women from the old East German metal-bashing factories do aerobics classes to tinny Tannoyed pop music, avoiding the empty concrete machine-gun bunkers. It's a surreal vision. The resort's logo is a machine pistol. And there is the inevitable small, unvisited museum, with its obsolete heavy American machine guns and twisted bits of aeroplane. Smudged, cracking photographs of dead martyrs hang above their personal effects, a plastic comb, a cheap fountain pen, a dusty packet of cigarettes, a home-made belt, a mother-sewn badge, "Liberty or Death". It is deeply touching and pathetic. The price of admission is $2.

The average Cuban wage is between 200 and 300 pesos a month (between about £5.50 and £8). Wages are pretty even, this being a communist country. A cabinet minister earns perhaps 400 pesos. The accepted unofficial exchange rate is 20 pesos to $1, but the exchange only works one way. Nobody is foolish enough to buy pesos, not even the banks. A peso is actually worthless. You can't buy anything with it except a banana. The currency might as well be bananas. If a Cuban wants a pair of shoes or an ice cream, then the price is dollars. Get into a cab, and the meter is in dollars. Restaurants and shops only quote in dollars. Small boys only beg for dollars. Officially, Cubans aren't allowed dollars, but the country is desperate for them. The peso economy is bought and paid for like an aged relative, 100% by dollars.

Trying to gain some control on all this to save some face, Castro invented another peso, a super-improved peso, the tourist peso, that has parity. In practice, it's dollar lite. As far as I can see, it is minted entirely in nickels and dimes to be given as change. Convertible currency comes from the depressed sugar market, Cuba's mono-crop.

And, of course, cigars. It is another irony that the most clichéd symbol of paternalistic capitalism should be made in communist factories. They look exactly like a 19th-century set for Carmen. The workers sit at desks in long, Dickensian school rooms listening to novels read aloud from a dais. The women really do spread the leaves over their thighs, and smoke huge hand-rolled splendidos knowingly, and wink at you. A skilled roller makes 50 cents a day for perfectly hand-making 200 of the finest cigars in the world that would cost you $17 each in the official shop. A lot make their way onto the black market, as do even more made out of dried banana. Even though Cuba is replete with cigars, as if to prove everything you ever heard about communism, it's virtually impossible to find a cigar cutter.

To attract dollars to this parched economy, Castro is forced to open the country to tourism. He would prefer the organised visitation of international conferences. In a very 1960s put-the-world-to-rights way, Cuba is still big on conferences, and Castro is not averse to a keynote speech himself, regularly coming out to get-togethers of anaesthetists to show them how the job should be done. Most of the conferences are medical, and you could, if the mood took you, come to attend an international get-together or laboratory animal anaesthetists or laser urologists later this month. But it's commercial tourism, sex tourism, that brings in the big bucks. The largest single group of people to visit Cuba are -and you couldn't make this up - Canadians. Presumably because it's one of the few things they can do that's one up on their North American neighbours. Cuba and Canada are the diametrically opposing poles of possible human variation, and unaccountably they love each other, staring across the immense social, cultural, emotional and physical divide with a mutually amused awe.

Making a virtue of necessity, with its woefully basic infrastructure, there have been allowances for tiny outbreaks of private enterprise like the very successful paladars, or family-owned restaurants. This usually means eating like a character from a Hispanic Pinter play in someone's kitchen. The food is supposed to be better than the official stuff. It's still utterly appalling.

Cubans can't cook, because there isn't anything to practise cooking on. These little businesses are viciously taxed and continually slapped with punitive, arbitrary regulations. They're not allowed more than 12 seats and they're not allowed to serve lobster, which is the only luxury ingredient Cubans have. Cubans are allowed to catch lobsters, but by law they're not allowed to eat them. They must be sold for dollars to tourists. Having never tasted one, they cook them until they resemble fishy Nike inner soles. It's as if Castro, taking a leaf from America's book, wants these small businesses to fail to spite his craggy face. He'd rather be proved right.

Dictators invariably spend the first half of their lives moving and shaking, and the second defending their reputations against the vibrations of current affairs for some brazen posterity - "history will absolve me". Castro is the exception to the rule that no man is an island. He is Cuba. And he's not going to stop being Cuba until they carry him off in a cigar box.

The first officially sanctioned small cracks in revolutionary socialism, the accommodations made for western tourism, point up a truth: capitalism can handle a degree of socially conscious engineering; indeed, it sticks in the throat without it. But communism is wrecked by even the smallest scrape with the free market. Cuba's fragile fabric, based on equitable hardship and a commonly shared isolation, is being ripped apart by dollars. There is a semi-legal, grey middle class emerging - Cubans who have access to tourists: hotel workers, drivers, guides, pimps, prostitutes - and a growing disparity between the rural and urban communities.

Although there are no official crime figures, anecdotal evidence suggests that crime is beginning to rise: lost, gauche, innocent Canadians wandering around in the middle of the night, half-drunk from Hemingway karaokes and with two or three years' wages in their pockets, are a temptation. The frustrations of 40 years of hardship are simmering beneath the smiles and gyrating hips. A pretty girl earns more in one night than a consultant surgeon makes in a month. So periodically the police crack down on bars and nightclubs. But the truth is that Cuba needs the vice to pay for its virtue.

In a late-night club in Havana's suburbs, a salsa group frantically rattles out the atmosphere to a half-empty room. At dark tables, couples drink Cuba Libres - the ironic name given to a socialist rum drowned in Yankee Coca-Cola. The price of entry is $10, an impossible amount for a Cuban. The only locals here have been brought by foreigners, and foreigners would only bring a local for one reason. The prostitutes hang around the neon-lit entrance pouting and hissing in their tiny stretch miniskirts and platform heels. Inside they squirm and cling to their meal tickets. Helmut and Günther are drunk, trying to strike a pose of worldly insouciance. They catch each other's eyes and smile, frightened by their good fortune. For a mere $40 they get to use these two impossibly stunning women, who will be the most perfectly beautiful creatures that ever agree to have sex with them. Having exhausted their meagre shared vocabulary, the girls lick hairy ears and stroke clammy thighs, twitching desperately to escape into the music and dance. Finally pulling the two men to their feet, the girls undulate and slide round them, the men jig spastically, faces slack, impassive, trying not to see themselves looking this foolish. The girls are transported. They swim through the music like dolphins. The men flail and drown. Finally, unable to stop themselves, the girls turn to each other and dance with a fabulous synchronicity. In the strobing lights two men risibly, solitarily, jerk.

We take a young chancer, a ducker, a diver, to dinner, to a smart restaurant where "Guantanamera" stalks every table. We found him in the hotel making a dangerous meagre living, selling bootleg salsa tapes to tourists. He orders an incinerated steak and eats tiny slivers with a deep reverence. He doesn't like salsa. He likes American music. He listened to it on the radio until the radio broke. He loves American things. His running shoes, his T-shirt. His best friend escaped to Miami. Everybody in Havana has friends or family in Florida. They talk about them as if they were dead and Florida were heaven.

In Miami, pizza-delivery boys and valet parkers send easy-street dollars back with stories of the opportunities in that great Mall of the Free. "I should have gone," says Raul. "My friend begged me. He built a raft. When everyone was going, when it was allowed." But Raul didn't go. There was this Canadian girl. "I was going legally, man. I was going to get married. Do you know Toronto?"

You wouldn't like it. He speaks good English, with heavy, inappropriate use of disc jockey slang. He stares at his plate. It was just a holiday fling. But, hey, he brightens. "I know all the states in America. I'm not dissing you, man. And their capitals. I study. New York, Albany, California, Sacramento, Kentucky, Frankfurt."

It's a sad, semi-mythological litany, a prayer of impossibly imagined places. It might as well be constellations and planets. Of all the hardships and restrictions that institutional communism expects of its subjects, the most grating, the most frustrating, is the inability to travel, particularly for the young. Almost anything is bearable if there is the faintest hope of escape, of getting away. The possibility of making plans, of a new, better horizon next year, the year after. And Cuba is a young place, bursting, throbbing, humming with youth. They're missing out on everything. Money, clothes, fun, their lives. And they know it. They don't remember what it was like before Fidel. Will they absolve him, venerate him for giving them dignity and equality, instead of Armani and passports? Probably not. They won't thank him for the hot claustrophobia of being stranded on this island, living in the ashes of a picturesque cul-de-sac decade that the rest of the world left behind a generation ago.

Every evening, young lovers meet on the Malecón, a long promenade that curves round the bay. They lie on the sea wall with bottles of rum and snog ravenously. Sex is Cuba's Prozac. As the sun sets, they stare out across the Atlantic, just over the horizon. Temptingly just over the curve of the earth, 90 miles away, is Florida, and the party that the rest of the world is invited to, but not them. To Cubans, this ocean stretches on, measured not in distance but in time; featureless and flat, and endless, for ever. As it was for Columbus 500 years ago.

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