The enemy is hogging the sunset. There it is, six miles to the west, shoving its high-rise, overly familiar towers into the early-evening orange – the Millennium Tower muscling in with its 58 storeys of blue-grey glass; the Transamerica Pyramid like some Seventies idea of a 22nd-century spaceship, waiting for take-off into the glow. Away on the other edge of the water, Oakland sighs and sinks back into the gloaming. It has become used to being overshadowed.

Perhaps the word “enemy” is too strong. But there is a marked rivalry between the twin cities that bestride the opposing flanks of San Francisco Bay – the sort of one-upmanship that, as with all sibling relationships, is defined by a narcissism of small difference.

For there is little between San Francisco and Oakland: in distance – catch a BART (Bay Area Rapid Transit) subway train east on the Richmond-Millbrae line from Embarcadero in the Financial District of San Francisco and the next stop is West Oakland; in history – San Francisco was incorporated as a city in 1850, its neighbour in 1852; in sporting glory – baseball titans the Oakland A’s have nine World Series titles to the San Francisco Giants’ eight, while the San Francisco 49ers have won five Super Bowls to the Oakland Raiders’ three).

And yet, it is San Francisco which shines as the superstar of California’s central coast – while its neighbour suffers from a perception gap.

The view towards San Francisco from Oakland

Perhaps this goes back to the Sixties, when both cities were part of the counterculture movement but were also flipsides of the coin. For while San Francisco had the Summer of Love and the rainbow optimism of Haight-Ashbury, Oakland had something darker. It was one of the epicentres of biker machismo, to the extent that Sonny Barger, leader of the Oakland chapter of the Hells Angels – a charismatic but violent figure – featured heavily in left-field journalist Hunter S. Thompson’s 1966 tome Hell’s Angels: The Strange and Terrible Saga of The Outlaw Motorcycle Gangs.

And where San Francisco had girls with flowers in their hair, Oakland was the gateway to Altamont, the now-defunct speedway track, 45 miles east, where the Rolling Stones held their notorious free concert on December 6 1969, and the hippy dream is said to have died via the fatal stabbing of an 18-year-old fan by (Hells Angels) security.

“Oakland is a magnet for people who want hour-wage jobs and cheap housing, who can’t afford to live in Berkeley, San Francisco or any of the middle-class Bay Area suburbs,” Thompson wrote in his book. “It is a noisy, ugly, mean-spirited place.” Some of this mud stuck in the last half-century but the slur has lost plenty of accuracy in the interim. The “cheap housing” element is fading, erased by new residents from across the Bay seeking more competitive rents and pushing up prices.

And Oakland has shed some of its image as an inward-looking entity, partly because it is now easy for outsiders to reach it. Next week sees the start of a new direct British Airways service (four times a week) from Gatwick. This will complement the five-times-weekly connection from the same airport by the low-cost carrier Norwegian last May.

The advantages of touching down on the east bank of the Bay are a quicker immigration process at a smaller airport and less traffic-choked access to the wine regions of Sonoma and Napa, if your plan is to head north for viticulture. But there are also reasons to linger in a place that, contrary to Thompson’s assassination, shows itself as warm and intriguing.

The advantages of touching down on the east bank of the Bay are a quicker immigration process at a smaller airport and less traffic-choked access to the wine regions Credit: (C) 2014 TOGNONIPhotography.com/Gary C Tognoni

It is a hot Sunday afternoon when I approach Lake Merritt. The sky is flicking through shades of blue above this Y-shaped lagoon and the city is basking in the heat, picnickers on the grass, families and pushchairs inching around the waterside path. There is no sense of Thompson’s “mean-spirited place”, nor of leather and motor oil. Indeed, the only hint of rebellion comes from teenagers using the steps of the adjacent Alameda County Courthouse as a jump-ramp, in wilful defiance of the sign which declares “Skateboarding Prohibited”.

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Further up the lake all is calm in the culinary context of Lake Chalet, which serves a seafood-focused menu from a building overlooking the water. Further on still, the Cathedral of Christ the Light seems to compete with the lagoon for beauty, its walls a curved crescendo of green glass, its modernity the fruit of its recent completion, in 2008.

Here is a reminder that Oakland is susceptible to the destructive forces which often rattle California. It was built as a substitute for the Cathedral of St Francis de Sales, which was so badly hit by the Loma Prieta earthquake of October 1989 that it could not be salvaged. This threat from the wider environment is underscored nearby at the Oakland Museum of California, where Richard Misrach’s photo Oakland Fire #107-91 – a child’s tricycle half-melted amid debris – shows the impact of the East Bay Hills Fire of October 19-20 1991.

Inside the Cathedral of Christ the Light Credit: © Thomas Winz 2012/Thomas Winz

On another wall, Marius Dahlgren’s Alameda County Courthouse East Oakland shows the same institution I saw being misappropriated for teen fun – but in 1882, a horse and cart trundling past. The painting is no more representative of the metropolis of 2017 than Thompson’s bleak summary but some of its softness has been reborn of late.

On the Bay, Jack London Square salutes the author (of The Call of The Wild and White Fang) who grew up in the city in the 1880s, toiling as an oyster fisherman from its docks. He would not recognise it now, even if the bar where he drank, Heinold’s First And Last Chance Saloon, is preserved as a wooden relic. True, there is yet an earthiness to the area, Second Street awash with warehouses, rail tracks set in the tarmac on Embarcadero West and Amtrak trains rolling by.

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But gentrification is fixing the windows and fluffing the cushions: in Bocanova, a Latin American fusion grill serving rock-cod ceviche; in Rosenblum Cellars, one of the 10 independent wine producers which comprise the Oakland Urban Wine Trail.

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The same brushstrokes are being applied to Downtown. When I stroll Telegraph Avenue, I can see the ghosts of a grim mid-20th century being banished. The Fox, a concert venue of kitsch Spanish-Moorish architecture and 1928 origins is alive once more, reopened in 2009 after being shut down in 1965.

The Fox, a concert venue of kitsch Spanish-Moorish architecture Credit: Credit: Phillip Bond / Alamy Stock Photo/Phillip Bond / Alamy Stock Photo

There are cocktails to be sipped at US$9 (£7) a glass at style-bar, Make Westing (the “French Muse” splices vodka, lemon, mint, absinthe and prosecco), and diners galore at Michelin-suggested Duende, across the way on 19th Street.

For all this, it is simple to slip away, uphill to Berkeley – once decried by Thompson as “middle class”.

His opinion holds – but, amid boutiques and eateries, this is no bad thing. And the view west from Tunnel Road is a joy. From this height, both Oakland and San Francisco are visible – this time not as rivals and incompatibles, but as intriguing equals.

Getting there

British Airways (0344 493 0787; ba.com) flies to Oakland from £422 return; Norwegian (0330 828 0854; norwegian.com) from £334 return.

Staying there

The Waterfront Hotel (001 510 836 3800; waterfronthoteloakland.com) has doubles from US$263 (£212), room only. The Claremont Hotel & Spa in Berkeley (001 510 843 3000; fairmont.com/claremont-berkeley) offers doubles from US$276 (£223), room only.

More information

visitoakland.com; visitcalifornia.co.uk