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Sightseeing sans Fisherman’s Wharf, Telegraph Hill or Alcatraz

The first time I visited San Francisco’s famed Castro neighbourhood, I half-expected to run into Harvey Milk at a bacchanalian club night brewing with radical politics and unexpected pleasures.

But it was the mid-1990s, and what I found were bric-a-brac shops offering more rainbow candles that I could fit in my suitcase. San Francisco’s red-hot gay utopia had much earlier congealed into a pleasant bourgeois enclave. Despite the city’s beauty, I felt like I had shown up on the sidewalk long after the parade had passed.

Since then, the Disneyfication of San Francisco has grown even more intense. Downtown is occupied primarily by tourists, the very rich and the very poor. But whatever money has done to the city’s social fabric, it surprisingly hasn’t torn its urban fabric. Rather than raze neighbourhoods for glass condo towers, filthy rich San Francisco has polished up what it has—quirky low-rise houses and apartments that sit right on the sidewalk, historic trams, lush parks, quaint neighbourhoods with offbeat shopping—to a mesmerizing sheen.

On a visit this spring, I just couldn’t bring myself to spend time in oversold tourist haunts like Fisherman’s Wharf, Telegraph Hill or Alcatraz. Castro was under construction, getting new sidewalks, trees and fancy benches, expected to be in working order by this fall. So I went looking for some sort of alternative San Francisco, hidden in the cracks of the obvious. I can’t say I went off the beaten path—San Francisco has so much beaten path to get off of. But I learned 11 things about the city that I couldn’t have learned from mainstream depictions of the city by the bay.

1. Health mania
For almost an hour, I eavesdropped on the four attractive women in their mid-20s who occupied the table next to me at an Indian restaurant in the Castro. They do not talk about their careers, politics, boyfriends, girlfriends, TV or pop music. They don’t gossip or tell jokes. Instead, they talk about their health concerns with excruciatingly dispassionate detail. And it wasn’t like they had gonorrhea or were sharing fad diets. It was all cancer all the time. “So you’re saying it might be pre-cancer?” one asked. “No, but it could be pre-pre-cancer,” said another. Is pre-pre-cancer actually a thing or just “life?”

2. Constant testing
In fact, Californians talk about their health all the time. In gay bars, men talk about disclosing their HIV status much like gay men used to tell coming out stories. And it seems that all gay San Franciscans know exactly what their status is. With places like Out of the Closet (outofthecloset.org/), an AIDS charity thrift store, offering free testing, few sexually-active guys seem to go more than two weeks without it. And the city’s emphasis on “test and treat” seems to be working. The number of new HIV diagnoses in San Francisco declined between 2007 and 2011, levelling off in 2012.

3. Groceries galore
In Canada, we see Whole Foods as a fancy splurge. Pricewise, Whole Foods is San Francisco’s bargain basement grocery store. But the novelty and quality of what’s available is worth it. California does food like no other place on Earth. What’s fresh is super fresh and what’s processed is… stuff you’ve never encountered before. Many big grocery stores are devoid of Nestlé, Unilever and Procter and Gamble products. Locally produced fizzy water brand Hint is sometimes easier to find than Coke. Here’s a real hint: Eat as many avocadoes as you can when in California; you’ll find none better.

4. Distinctive districts
Although downtown shopping is Main Street anywhere (oh, what a surprise, Banana Republic!), neighbourhoods work hard to keep themselves indie. Camp franchise Hamburger Mary’s, for example, is currently trying to prove it’s not a generic chain outlet in order to open a Castro location.

5. Windswept beaches
To be honest, the local beaches aren’t so great. They’re big and sandy, sure. But the weather on the city’s Pacific side is much foggier and colder than in the rest of the Bay area. The beaches are about bracing, meditative walks—not tanning.

6. Old media
Considering that Silicon Valley is doing its best to put booksellers, DVD and music stores out of business with digital media devices, San Francisco, perversely, has an enviable selection of independent old-media retailers. Amoeba Music (amoeba.com) has massive locations in Berkeley and The Haight selling new and used CDs and vinyl. In the Richmond neighbourhood, jam-packed Green Apple Books (greenapplebooks.com) might be the most fun bookstore I’ve ever set foot in. Though Castro’s A Different Light is no more, Books Inc. (booksinc.net/sfcastro) and Aardvark Books offer, respectively, new and used LGBT literary treats, including more Armistead Maupin than you ever imagined.

7. Tall Tales
Speaking of Armistead Maupin, a visit to Macondray Lane, upon which Tales of the City’s Barbary Lane is based, is required for any book-loving queer visitor, if only for the cardio (Anna Madrigal couldn’t have staggered home in heels). Walk past some rather unromantic garage doors to find a hidden footpath where you might imagine Michael Tolliver successfully persuading Mary Ann Singleton to smoke a joint….

8. Historic spirits
… And then Michael Tolliver wandering over to cruise nearby Polk Street. A hub of gay life in the 1970s, when Maupin’s series began, Polk is now home only to three gay bars. Two of them, Cinch Saloon and Gangway, are the oldest in the city and probably the two least glossy establishments you’ll find in present day San Fran. Across the bay, Oakland’s White Horse Inn (whitehorsebar.com), an ideal spot for a mid-afternoon bourbon break, bills itself as the nation’s oldest gay bar, having opened its doors in 1942.

9. Happy hours
In a city where an okay one-bedroom in a so-so ’hood can set you back more than $3,000 a month, San Francisco’s happy hours provide brain-addling value—and perhaps a welcome reprite from sharing a basement apartment with four other people. Regularly running from 4pm to 9pm most days of the week, the happy-hour culture fills Castro dance floors as early as 8pm on a Friday night; your one-night stand could be over by midnight.

10. Beer busts
As if the happy hours weren’t enough, Castro Saturdays and Sundays are dominated less by brunch than by fundraising beer busts, with all-you-can-drink beer for about $10. I swung by a softball team beer bust and before I knew it, a drag queen was measuring my arm span for some sort of raffle. In such a boozy town, no wonder San Franciscans are so obsessed with their health (see item #1).

11. Eccentric curation
With the San Francisco Museum of Modern Art (sfmoma.org) closed for renovations till 2016, art lovers must find another way to spend an afternoon with objects of beauty. I tried the de Young museum (deyoung.famsf.org), passing by the tai chi-ers and salsa dancers of Golden Gate Park to enter into a prison-like building filled with one of the most eclectic collections I’ve ever stumbled across. Paintings of American war history and arts and crafts furniture share space with sculpture and “exotic” artifacts from Papua New Guinea, eastern Sudan and other parts of Africa, as well as textiles from Central Asia and glass fantasias by Dale Chihuly. This is what art curation must look like after a beer bust too many.


Castro bars sort clients strictly by age and sexual predilection. While Lookout (lookoutsf.com) is mid-20s to early 30s, anyone under 45 is going to look like chicken at The 440 (the440.com). Badlands (sfbadlands.com), with its early ‘90s resort-town vibe, is the closest thing to come-one-come-all.

A short tram ride from downtown, Sunset District’s 9th Avenue, between Lincoln and Judah, has a wide array of good restaurants and coffee shops. In a city full of burrito joints, Nopalito (nopalitosf.com) offers a sophisticated and organic twist on Mexican classics. And the focaccia at the worker-owned Ariz Mendi Bakery (arizmendibakery.com) may change your life.

Why throw yourself off the Golden Gate Bridge (which, incidentally, is to get a suicide barrier) when you can pedal across it in a bikes-only lane? Once on the other side, it’s a short cycle to Sausalito, a charming waterfront suburb where it’s impossible to find parking on a sunny day.

Little has changed since the 1960s in The Haight, where tie-dye is still work casual. Drop by hipster/hippy hangout Hobson’s Choice (hobsonschoice.com) for a daytime bowl of punch, a tradition that allegedly goes back to Victorian times. Three fruity flavours to choose from.