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Fidel Castro was sitting on a bollard in Parque Santa Catalina, taking in the world from behind implacable shades. His beard flowed like a frozen waterfall, and from the rear of his trademark forage cap a radio antenna pointed straight up at the sky. A group of oriental fisherman passed behind him, sniggered, and disappeared into duty free bazaar run by an Indian who could manage a few words of Russian when he had to.

As I loitered momentarily to satisfy myself that this doppelganger wasn't the real thing on a decadent capitalist week away, it occurred to me that he wasn't as completely adrift from reality as the oriental fishermen might think.

At the time when Havana was in its prime as the front door to the New World, Las Palmas, Gran Canaria was the back door of Europe. After all, it was from here that Columbus made that historic 1492 crossing to discover the Americas - and founded Havana.

Today Las Palmas is the largest city in the east Atlantic, while Havana is the biggest in the West Indies. The two have striking physical similarities: the huge harbour, the long sweeping waterfront of fortresses, rusty wrecks and tramp steamers lying offshore awaiting orders; the sometimes crumbling Spanish colonial architecture, the areas of seediness, and the tendency to stay wide awake deep into the night.

Unlike Havana, however, Las Palmas is completely ignored by the colour supplements. It is largely ignored, too, by the armies of tourists who invade Gran Canaria every year. Those who do venture into the city look overweight and insecure as they browse the bazaar.

Las Palmas deserves their respect, but it doesn't fit well into brochures keen to promote sun and sand. Islands have a tendency to accumulate the flotsam of humanity, especially those with huge ports, and this one is no exception. "Don't go near La Isleta" said everyone, "you'll get mugged". So I did.

Just as you can't have light without dark, so a city cannot have charisma without seediness - look at Paris, for God's sake. La Isleta is the working class area that fringes the port, known for drugs, prostitution and as the birthplace of many a Canarian politician. In the first hours of daylight the red light street was quiet but for the sound of razors and caged birds, although the occasional door stood ajar to reveal a hairdresser's chair, offering the choice of sex or a blow dry.

From Isleta I commandeered a taxi to show me the port, and Damian - yes, Damian, he said - took me out along the 4km-long outer wall past row upon row of massive, rusty Russian fishing ships. The Chinese were there too, and the Japanese, the Moroccans, and even a fleet from Belize, all milling about. It was like a film-set from a Bond or a Mad Max. Had they just been blown in off the Atlantic? "Eggshactly" said Damian, which is what he always said when he didn't understand my question.

A big port and associated seediness do not together a tourist attraction make, but only a few streets away - on the other side of a narrow neck of land - lies Playa de las Canteras. What other metropolis can claim such a broad sweep of clean sand at its heart, protected by a convenient reef of lava? The paseo is busy in the early morning with elderly swimmers, at lunchtime with office workers and late at night with African women sitting in circles like daubs of luminous paint. "Don't take picture" Damian had warned. "Their men don't like".

I stumbled across the Amigo Camilo at the intersection of La Isleta and Las Canteras, perched above a rocky inlet. A man was pushing a wheelbarrow full of whitebait into the kitchen as I arrived. The Camilo had no menu, just that day's catch; I ordered a mountain of deep-fried squid with boiled potatoes and imagined that this was exactly the sort of earthy seafront bar that Ernest Hemingway would have enjoyed - if he hadn't found his niche in Havana.

Las Palmas has had its would-be Hemingways too. Years ago I came here to visit a chain-smoking British journalist living in a bedsit with a parrot, working on her great novel, and found her speaking French with a very hairy Italian photographer of great talent and supremely bad temper. Sadly, she had since died, so instead I tried out my "Havana of Europe" theory with another former contact, a Scottish lass who'd married locally. "Oh yes", said Meg, "didn't you know that the old man in the Old Man and the Sea was a Canary islander?"

Originally, she explained, the Canarios had helped populate Cuba. Latterly they'd been going there for cheap sex, but now the Cubans were reversing the trend, settling in communities in the north of Gran Canaria.

On Meg's suggestion I went to check out the Pequena Habana - little Havana - a bar on Calle Guanarteme. It turned out to be a dark and steamy salsa club, too loud to earmark anyone for a quiet conversation. I came to the conclusion, sipping a beer conspicuously alone at the bar, that this was the closest I would get to Havana without crossing the Atlantic.

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