My voice wobbled and my hands shook as I faced my boss, Alan Rusbridger, editor of the Guardian, across his office table and resigned. Not to work for another paper, nor for a bit more money, but to go to a foreign country where I didn't speak the language or know anyone, to try to arrange a world heavyweight title fight between Felix Savon and Mike Tyson.

Don King had failed to do it with a $25 million contract in his pocket at the Cuban training camp before the Mexico Olympics. I had a credit limit (recently raised to £2,500) and £2,000 in travellers' cheques. At least Don Quixote had Sancho Panza to talk to on his trip.

I didn't even have an obsession with the country, or with Cuban boxing, or with any particular Cuban boxer. I wish I could say that I had dedicated my spare time to clipping out articles about Savon or Teofilo Stevenson, but my only scrapbook contains Everton's full results, teams and match reports between 1978 and 1981, perhaps the least interesting and most unsuccessful era in the club's post-war history.

Communism leaves me cold, though I did have that red-and-black Che Guevara poster above my bed when I was in the Harrogate branch of the Workers' Socialist League back in the early Eighties. No, if I take the chain of events back before that Monday morning, I ended up spending a year in Cuba because I needed some serious time off work.

It all started when I went on holiday for the first time in two years. January 1996 was freezing, that damp, in-your-nose sort of cold London specialises in. The Northern Line wasn't working, the coffee machine at work was empty, my love life was in a coma, I was having a bad day and I decided I needed a holiday.

Why Cuba? Well, like all decisions that change your life, I can't claim that I thought very hard about it at the time. Guilt maybe? Two years earlier I had split up with my Spanish girlfriend, Beatriz. I told her, crassly, I needed to be with someone who understood the subtleties of the English language. When I decided to go to Cuba for a holiday, that remark kept banging around my head. I had to make some amends to Beatriz.

But it was just a holiday, it wasn't a life- changing decision, or so I thought at the time. It was a butterfly flapping its wings in one corner of my life.

I landed in Havana on 20 February, 1996. My nine-hour journey had lasted 36 hours because of a punctured tyre on the plane. Cubana, the national airline, had to put me and the other 167 passengers up in the Stansted Hilton because no one at the air port would allow it any credit or lend it a tyre. Stepping off the jet in Cuba felt like walking into a badly ventilated laundrette.

I stayed with a Cuban family, who were well-to-do and terrified of everything. Allergic to any activity other than staying at home and watching television, they kept their son off school (about 300 yards away) if it was raining. Every time I asked them how I could arrange to do something, Miguel, the head of the house, would shake his head in awe at my stupidity. 'Let me explain you something about Cuba ...' he would say, and a sad diatribe about the inadvisability of leaving the house would follow.

I asked him once if I could get a ticket for a baseball match. 'Let me explain you,' he said. 'Now is very bad time, with planes being shot down, and the atmosphere is very, very tense. The crowd will be bad. Everyone is very nervous, and you will probably not get a ticket, and transport here in Cuba is very, very difficult. Why not watch it on the TV?'

Miguel was scared because the Cubans had just shot down two planes flown over Havana by the Brothers to the Rescue, anti-Castro dissidents from Miami. Miguel was afraid the police would be jumpy and bombs might be planted in reprisal. Fortunately, for a Brit like me, the politics of Northern Ireland make you fairly sanguine.

I went to the baseball anyway, figuring that I could cope with a bit of bad 'atmosphere' in Havana. And I could get a ticket from a tout. I knew what Miguel did not want to admit: that you can buy anything for dollars in Havana. When I got to the Estadio Latinoamericano, there were no touts for the simple reason that the entry cost three pesos (about 8p).

The atmosphere in the 40,000-seat stadium was considerably less tense than bingo night at Walton Women's Institute because there were, at most, 900 people there. And transport home was a cakewalk. I stood looking confused at a road junction for a second and a bloke stopped and gave me a lift for the price of a one-zone London bus ride.

On top of the baseball I discovered the Bulería, a small nightclub in which women, most of them prostitutes, paw you as you walk to the bar. It was not something that had happened to me before. I found the Care Cantante, a higher-class club. I found respite from the attentions of prostitutes in the Sunday-afternoon, Cubans-only disco at the otherwise hooker-infested Hotel Commodoro, and I found a soccer team to play with.

I travelled in old American cars; was hassled by men and women alike ('Hey, you, my friend, where you from!'); had the worst steak and chips of my life in the best surroundings, at the top of a tower in central Havana; drank too much rum; smoked too many filterless black-tobacco Populars (less of a cigarette, more a state-assisted suicide scheme); walked for miles around the city, awed by its beaten-up buildings and bleached beauty, and at the range of women, from supermodel drop-dead gorgeous to the overweight with an inexplicable fondness for lurid Lycra catsuits, the most popular of which was crafted fraternally of the Stars and Stripes.

It was a fantastic time and I fell in love with Havana. I even started to be understood in Spanish. I began to wonder what it would be like to live there. So I decided to go back only two months later, in April, with what I thought would be a more critical eye.

On this occasion the plane left on time. And I arrived on schedule in Havana airport's Terminal Two. There were only about 15 flights a day from the José Martí International, but they reckoned they needed three terminals (one international, one Caribbean, one internal).

Everyone piled off the plane and walked to a well-appointed Soviet-style concrete shed which housed Immigration, a row of booths in front of which you queue. They are chest-high, flimsy wooden constructions, with a glass pane from waist to head height and a wooden shelf on the inside so you can't see what the man behind the counter is doing with his hands. Next to each booth is a chest-high wooden door, which swings open once you are deemed worthy of entry. There were 12 of them, each staffed by a uniformed officer, with Ministerio del Interior sewn untidily on to his bright green, crumpled combat shirt.

Imagine the least 'customer-oriented' dole officer you have ever signed on for, the one who looks at you as though the only thing he hates more than his job is you. Add the sort of nightclub bouncer who you sense would rather be at home dismembering small woodland creatures, slowly, with a blunt knife, than assisting in your enjoyment of the evening. Then multiply by the most authoritarian, cane-happy PE and geography teacher and throw in a doctor's waiting room full of traffic wardens and park attendants. Stick on a black moustache. That's him.

His is the first face seen by visitors to Cuba, who are a generally affable lot, oozing with goodwill towards the slightly risqué holiday destination they have chosen, but jolly happy to be here (and at least there won't be any Americans). Above all, you are left with the impression, once you have been stamped and approved and the wooden door swings open, that you are entering a country which considers you an enemy.

The flat I was staying in was pleasant enough: hottish water, clean, but penned in by other blocks. Next door was so close that it would have been easier to ask my new neighbour for the salt than go to my own kitchen. And I discovered one of the negative sides of Cuba, that the invention of volume control has totally passed the nation by. A Cuban TV set is either on or off, and the same principle applies to the volume: with no carpets and the windows open, if the programme can't be heard in the next postcode the set needs adjusting.

Cuban friends say the top-volume trick is a habit from the more paranoid days of the revolution when people wanted to talk politics and didn't want the neighbours to hear. But Cubans are noisy in pretty much everything that they do. There is a gaggle of men in the Parque Central every day, shouting at each other as though they have all just discovered that everyone else in the group has slept with his wife. All they are in fact doing is discussing baseball, the supposed national obsession which so few people in Havana bother to go to watch. It says something about Cubans that they consider it more fun to shout and argue with each other than actually do anything. It may even explain why the government survives.

There are three things which everybody thinks they know about Cuba. The first is that the island produces excellent cigars rolled on the thighs of beautiful maidens. They are indeed excellent. Having been around a few cigar factories, I now know that they are rolled on a wooden table by hand, and the people who roll them are men and women of widely varying ages and degrees of desirability. They're about as romantic as fish-processing plants in Grimsby, only with more sunshine.

The second is that Cuba is the last bastion of communism, the embers of the greatest social experiment in human history, but one which still has great education and health systems. In Latin American terms, the education's not bad at all, compulsory, well organised and free. There is no child labour in Cuba. But its quality has been ravaged by a lack of resources, teachers and textbooks.

Despite that, literacy levels are high and everyone has a chance to go to university for free, provided they can put up with the pre-university requirements that they work for a period of time in the countryside and pass a course in Marxism-Leninism.

The hospitals are there, in greater numbers than in many Latin countries. The doctors are well trained and of high calibre and their services are free. But there is little modern equipment and only the doctors' diagnostic skills prevent the system from collapsing completely.

But to talk about communism is to talk about Fidel Castro. Everything about him seems mythical, and this aura is fed by the myriad failures to kill or replace him. The stories about the CIA's attempts to topple him are endless: how they concocted a boot polish which they thought would make his beard fall out, removing his magical hold over the population. The attempt to slip him an exploding cigar is celebrated, along with the rest of these pitiful schemes in the Interior Ministry's museum in Miramar, where the cigar in question, successfully defused, now resides.

It is said the CIA discovered a weakness in his elaborate security procedures: he visited the same ice-cream stall every day at the same time. They paid the woman who worked there to poison him. When Castro turned up, the woman took the phial of poison out of the fridge only for her to shake so violently that she dropped it on the floor, where it smashed. These stories, and his longevity, add to the sense on the streets of Havana, as much as in Washington, that Castro has a pact with the Devil.

The third thing people 'know' is that Cuba is good at sport: baseball, athletics and, of course, boxing. Cuba has produced some great boxers. Kid Chocolate, the little fighter in the Twenties who could stop traffic in Broadway. World champions such as Ultiminio Ramos, who tragically killed two men in the ring; José Mantequilla Napoles, who left after the revolution and fought out of Mexico to become a longstanding World Boxing Council middleweight champion; Luis Rodríguez, another boxer who left after the revolution, and had the misfortune to be on a plane which was hijacked and flown to Havana, while he was allegedly on a Cuban death list. Rodríguez survived and died a couple of years ago. Then there was Kid Gavilan, whose world championship welterweight bouts in the Fifties were massive events; Adolfo Horta, Angel Espinosa - and the heavyweight everyone was talking about now, Felix Savon.

All this was in my mind when I came to think about how I could make a life in Cuba pay. I had considered starting a cultural centre, organising events to encourage friendly relations with Britain, teaching English cheaply, holding an annual festival maybe, a Beatles exhibition (the Beatles were banned in the Sixties, and Cubans are just catching up on them). But I didn't know anything about organising exhibitions or teaching English and, anyway, all of that would have relied on the generosity and desire for self-promotion of British companies, which were sensibly keeping their heads down as the United States sought to tighten the noose around Cuba. Maybe a bike race, a football match, a boxing match. Rubbish, really. Strictly beer-mat stuff. Except for the last. That might actually have some mileage in it.

And when I got home this was the idea I chose to look at more closely. I spoke to the chief sports writer and boxing correspondent of The Observer, Kevin Mitchell. We went to the local pub, the Coach and Horses, and sank a few Guinesses. Our enthusiasm got stronger with every passing pint. He told me more about Felix Savon, the Olympic heavyweight champion in 1992 and unbeatable, according to those who claim to know about these things. I knew the name from the last Olympics, but not much more.

Kevin told me about Teofilo Stevenson, in the Seventies, who was so frightening that opponents sometimes didn't turn up for Olympic finals, so assured were they of a bad beating. Savon was his heir, said Kevin. And there would be big money on the table for a fight between Savon and Mike Tyson, then re-establishing himself as the king of the heavyweight division after he was locked up for a stint for rape.

The thinking then was that, once Tyson had reunified the divided bodies running boxing, it would become as dull as ditchwater within a year, as the bum-a-month club lined up to give Tyson a yawn, a stretch and a few million dollars in ever-decreasing amounts as the fights became less and less interesting and pay-per-viewable. Something fresh would be needed. By the end of the conversation, Kevin and I had decided we were the men to save heavyweight boxing. And then the minicab came ...

• To order a copy of 'In the Red Corner' by John Duncan for £9 plus 99p UK p&p (rrp £12) freephone 0800 3168 171, or send your order with a UK cheque payable to The Observer CultureShop, to 250 Western Avenue, London, W3 6EE.

Cuba facts

Currency: Cuban peso and US dollars. Many credit cards and travellers' cheques are useless in Cuba.

Visas: A Cuban visa or Tourist Card is required - available from travel agencies, tour operators or a Cuban Consulate and valid for a stay of one month.

Climate: Sub-tropical, with gentle north-easterly trade winds. May to October is the rainy season.

Getting there: Cubana, the national airline (020 7734 1165) flies to Havana three times a week from Gatwick, and once a week from Manchester. Regent Holidays (0117 921 1711) tailor-makes packages - a six-night tour from £760 including Air France flights, accommodation and meals. First Choice (0870 750 0001) is offering a 14-night package from £749.

Further information from the Cuban Tourist Board on 020 7240 6655.