Since the mid 1990s, San Francisco has been remodeled as an upper middle class Shangri-La for white suburbanites who, in equal parts, hate the uninspiring blandness and FOMO of living outside a major city, and who are also deathly terrified of inner-city crime, poverty, and bad schools. As such, San Francisco has been transformed into the perfect infrastructure of uninterrupted luxury, built on the backbone of a struggling service class (which almost entirely lives in Oakland), tied together by iPhone apps, against a backdrop of unimaginable natural and architectural beauty.
Go Thrifting, Buy a Jacket
You invariably forget to bring a jacket to SF because you had a preconceived notion that California is all sunny all the time. Well, San Francisco is overcast and windy all the time, and you need a jacket all the time, dummy. Lucky enough, that means you have the opportunity to comb through Frisco's 60-plus thrift stores, which are almost entirely supplied and run by the city's artist underclass, who have made a career buying and selling well-tailored, aggressively trendy clothing.
Just like in Los Angeles and New York, the best bang for your buck comes from known resellers like Buffalo Exchange, Crossroads, and Wasteland, where all the hard work of sorting out JINCO jeans from APC is done well in advance. If you want an even cheaper option, traditional thrift stores like Mission Thrift and Goodwill are a dime a dozen, and represent the rapidly dwindling working class population of San Francisco. The epicenter of these two worlds is at Community Thrift, a nonprofit shop on 17th and Valencia in the Mission, where you should find yourself anyway if you're keen on San Francisco's flavor.
Walk Up a Hill and Look Around
Effectively every view in the city offers a long series of Victorian homes breaking into lush, dark treetops cutting through a heavy blanket of fog. From the confusing but palatable mix of Victorian design tacked onto bay windows, to the steel, glass, and cement modern condominiums erupting out of demolished historical landmarks, the flavor of this city taken in all at once is heady and intoxicating. There is literally no shortage of steep hills to climb, and they'll all provide the perfect backdrop to your most viewed Snapchat or Instagram of the day.
The walk to Land's End, a park near Golden Gate bridge, is the most stunning, refreshing, worth-the-hassle hike in the city. To get there, drive to the Coastal Trail entrance. (Or, because parking there is so bad, take the 38/R to its last stop on 48th Street and walk northwest for five minutes and you're there.) On your way down the trail, the trees will filter the light in the most beautiful way, and everything will feel less shitty. Then you'll hit a clearing and look out over a cliff, the Pacific Ocean, and the ruins of Sutro Baths, a saltwater swimming pool complex that burned down in 1967 and almost touches the shore. All in all, it takes about an hour and a half.
Poetry and Stand-Up
San Francisco is a Greek Siren. It promises tolerance, community, creative freedom, chill vibes, and big salaries. But for the thousands of creative writing, art history, and theater majors here, the city is a big fat dead end. Crammed six per apartment, and desperately working to support SF's service industry, leaves many artists here frustrated and unfulfilled. Lucky for you, the best artistic expression comes from desperately trying not to feel like a failure, meaning that community-built live shows are exactly the right place to hear disgruntled talent baring its soul. The city's poetry and comedy scenes are renown for up-and-comers on their way to Los Angeles or New York, and there is never an empty night at impermanent venues in bookstores and video rental shops (there are still at least two in the Mission).
But while venues like Adobe Books (See Music and Nightlife), and Alley Cat are great to find comedy and poetry on the spot, the real heart of SF's spoken word scene (that hasn't fled to Oakland yet) is in dingy crowded apartments found via public but unlisted Facebook event invites. To gain quasi-exclusive access, check out open mics at fan favorite spots like Artists' Television Access, and instead of being a wallflower in a strange city, submerge yourself into the slouching, chain-smoking, zeitgeist crowd to score an invite to something fleeting and real in a packed 700 square foot apartment.
Seeing as San Francisco is (or, as is increasingly the case, was) a self-made, self-identified, self-serving stereotype of the gayest city in the world, it's not actually surprising that the Bay hosts the best LGBT+ parties on the West Coast. Although SF used to be a place where queer folks would run away to, the ultra-high rents have made it prohibitive to see the city as a haven instead of an exclusive club that necessitates a buy-in versus an opt-in. But those that've stuck around still clearly know how to have a gay ol' time.
Hard French, located at popular Mission bar El Rio, is one of the events they go to do that. Hard is more for the alt gaybro, but it plays great oldies, and it is full of friendly cute guys #lookin4love. Quick plug for Oakland's Ships in the Night, a favorite of queer POC bae area girls, whose organizers are particularly aggressive about barring cis white straights from attending, so win/win.
Back in the 7x7, the most San Franciscan thing to do in "San Francisco proper" is to waste time at Dolores Park. Jammed right in between the nicest part of the Mission and the nicest part of the Castro, Dolores is perpetually sunny while the rest of the city shivers under the fog. You can spend hours day drinking on the slopes, watching guys with farmers' tans and beards hooping and juggling amid a sea of couples on blankets, and seeing a roaming edibles dealer who has a five star Yelp page.
StrEat Food Park
Food trucks are an integral part of San Francisco's borrowed authenticity, and you can find them en masse, three times a month as part of SF's many street fairs (Cherry Blossom, Folsom Street Fest, How Weird, Bay to Breakers, Carnaval, Pride, Fillmore Jazz, J-Pop Summit, Jerry Garcia Day, Fleet Week, etc.). But San Franciscans are lazy, and for a midday fix, head to StrEat Food Park, an under-the-freeway collection of rotating food trucks, neighboring a large homeless encampment in the SoMa. The location reeks of desperation, but so does the business model behind throwing a kitchen into a van, and that turned out OK, didn't it?
Golden Gate Park
The park is always worth walking or biking through and encompasses every possible aspect of San Fran culture. You can buy drugs on Hippie Hill, wander through the Japanese Tea Garden, check out the de Young Museum while the MoMa is closed, take your kids to the giant outdoor playground, hike Strawberry Hill island, and if you take the right bike path, you'll wind up at the beach. That said, recommending the biggest park in the city is a bit like trying to convince a Trump supporter he or she is wrong: What's the point?
Baker Nude Beach
This frigid shoreline starts in the shadow of the Golden Gate Bridge, and it was once the epicenter of the—now hilariously commercial—Burning Man festival (it moved after four years to Nevada because you can't legally burn a giant effigy in a region that's prone to annual, billion dollar wildfires). In this creative spirit, Baker is also "technically" a nude beach, although, like all nude beaches, is mostly populated by elderly men who may or may not be aware they're nude. When the weather picks up a little, you'll see more bushy moms and #sorrynotsorry Academy of Art students stripping down, but at a five-to-one ratio of gawking tourists to peens and hoo-has. Nonetheless, nude beaches are far and few between, so get your fill of non-sexual naturism. But bring a jacket, because it is always 55 degrees.
Vintage shop buyers from Tokyo make trips to Painted Bird for the perfect black Bowie tee they can mark up 800 percent back home. That fact is half because the shop's owners don't charge too much, half because they just edit their donations really well and send the other crap down the street to Buffalo Exchange. You'll find anything from well-worn Levis and slinky sweaters to overalls and housecoats from extinct French labels. Everything is arranged by color, and you'll be hard-pressed to spot anything non-monochromatic. The vibe is basically 90s normcore to the extreme.
This Moorish building from the early 1900s was originally built to house the San Francisco National Guard. Then, in 2006, porn site Kink.com paid $14.5 million for the place, so it could film videos of naked humans hogtied by their ankles or cramming things into their bodies. The company hosts tours that walk you through the history of the building and various BDSM sets: dungeons, interrogation rooms, infirmaries, and good-old fashioned boudoirs with slings. It's located in a busy part of the Mission, so have a perfect stranger from an app drive you there, or take the bus.
San Francisco's Japantown is only a few blocks radius and one of three of its kind left in the US. Its most notable fixture is the Japan Center, a gloriously dumpy five-acre mall from the 60s that is full of weird beauty counters, dollar stores, boba tea shops, arcades, book stores, ramen bars, and izakayas. It often hosts various cultural events where Japanese people and white people appropriating Japan culture gather to sumo wrestle or wear traditional geisha clothing for visitors. If you want to make a day of it, go across the street to Kabuki Springs spa, a Japanese bathhouse that locals hit to get butt naked and unwind.