Fascinating hike along San Fran’s improbable slopes

I went for a guided walk in San Francisco. Which, in a city so improbably sloped, really means a hike, and my guide was Alex Kenin, founder of Urban Hiker SF tour company. She used to work for Google, or the "Big G" as she calls it, but hated the commute to Silicon Valley so quit to do something she actually cared about. Alex cares about San Francisco and the novels of Armistead Maupin, so I opted for her Tales of the City walk.

We met on Levi's Plaza in North Beach, named after the jeans manufacturer and site of its global headquarters. Levi Strauss founded his dry goods store here in 1853, selling clothing, bedding and combs. In 1872, local tailor Jacob Davis asked him for help in getting a patent for his denim riveted work pants, and a year later Levi Strauss & Co began selling jeans.

San Francisco’s solution to its ridiculous gradients is to carve steps into its steepest inclines and force residents to learn how to park at 30-degree angles. We climbed a steeple’s worth of steps to reach Coit Tower on Telegraph Hill, past millionaire residences behind thickets of trees, hidden houses tilted so precariously that only the most adventurous could consider them home.

Standing by the art deco Coit Tower, with stunning views of both the Bay and Golden Gate bridges below, Alex told me about the ultimate outlier, Lillie Hitchcock Coit, a 19th-century non-conformist who wore men’s clothing, gambled and smoked cigars. After witnessing a devastating fire on Telegraph Hill when she was 15, she devoted herself to the local fire station, Knickerbocker Engine No 5, going so far as having the number 5 stitched into her underwear. She left a third of her fortune to the city, who thanked her by erecting what looks like a giant fire hose nozzle made out of unpainted, reinforced concrete. Alex told me the resemblance was coincidental.

Down more hills and up more steps, stopping in a handful of “secret” gardens, some no bigger than a viewing platform, but each with beautiful, revealing views of the city and the bay.

We walked the length of Macondray Lane, a wooded enclave in Russian Hill recast as Barbary Lane by Maupin in Tales of the City: it looks more like a country path than a city street, albeit lined with high-priced homes.

Property prices are a San Francisco obsession, and with a basic one-bed kicking off at a cool million, it’s easy to see why. For many San Franciscans, the blame lies with the tech companies and their over-inflated salaries, which has led to angry standoffs: buses transporting workers to Silicon Valley are regularly picketed and a week before, a woman was attacked in a bar for wearing a Google Glass.

Alex and I said goodbye in front of the Church of SS Peter and Paul on Filbert St, where Marilyn Monroe and Joe DiMaggio posed for photos after their wedding in 1954. Where to now? I pulled out my phone and found my way on Googlemaps.
Tales of the City walk is 4.5 miles/2.5 hours; $45; see urbanhikersf.com