Planning a trip to the City by the Bay? Read on to learn about the city-defining districts and ‘hoods that you can’t miss.
Haight-Ashbury
What was once the birthplace of American counter-culture (i.e. incense-burning, acid-dropping, tie-dye-wearing, peace-and-love loving, flower power-era hippies) has declared the affluent yuppie the new Deadhead. At some point after 1967’s Summer of Love, the Haight’s colorful Victorian homes were bought up, and its most prominent shops were turned into upscale vintage boutiques, chic hangouts, and hip restaurants. This isn’t to say that you can’t still find old hippie relics and a mellow fellow smoking a doobie—you just may have to cross the street into Golden Gate Park and wander up famous Hippie Hill before one invites you into his drum circle. Don’t leave without perusing one of the biggest collections of CDs in the world at Amoeba, a former bowling alley-turned-record store whose used selection is so vast that you may never have to buy a new CD again. And it gets better. Give employees a list of your current favorites and they’ll direct you to artists, new and old, who are so well-suited to your tastes that it will blow your mind. They know their stuff. For a more diverse neighborhood with a grittier feel, leave Upper Haight’s commercial shopping zone behind for Lower Haight—an alternate nightlife hub whose mushrooming dance-music scene has made it a hot spot for DJs and ravers.
Tenderloin
You’ve all heard the rumors, and on the surface they appear to be true: streets lined with tattered and homeless bodies, arms shamelessly tied and prepped for injection, clouds of second-hand (crack) smoke, smears of human feces on the sidewalks, and transgendered prostitutes scantily clad in fish nets and six-inch heels are just a few of the uncomfortable everyday sights that contribute to this hood’s rap as the “sketchiest neighborhood in SF.” Don’t let this scare you. Beneath the grime and soul-deadening misfortune of its city dwellers is an intriguing and sordid history that has given rise to the last frontier of San Francisco’s character-defining grit. It deserves your attention. You haven’t truly seen San Francisco until you’ve experienced the indomitable hardship at the foot of its increasingly-gentrified beauty. Visit a former recording studio of the Grateful Dead and Creedence Clearwater Revival at what is now Hyde Street Studios, enjoy spectacular live music amidst marble columns, ornate balconies and a sprawling oak dance floor at the Great American Music Hall, and if you’re really feeling ballsy, dress down for a striptease show at the ever-thriving Mitchell Bros. O’Farrell Theater. Opened by adult film pioneers Artie and Jim Mitchell in the late ’60s, this joint was frequented by lascivious journalists and rock stars before a paranoid and drugged-out Jim shot Artie dead in 1991. To absolve your sins before heading home, stop by Glide Memorial Church for the most romping Sunday celebrations in the city—people congregate from all over the world to hear Glide Ensemble’s gospel and rock songs and soak in the wise words of SF’s most revered minister.
Castro
There’s nothing like dildo displays, penile-shaped baked goods, and neon signs screaming “Lube 4 Less” to set even the most bashful freak flags proudly waving. Nowhere else in the world will you find a community so celebratory of its sexuality and of its sexual liberty now unfettered by the law, and it took a lot of harrowing history to get here. Perhaps most famous was the notorious 1978 assassination of openly gay San Francisco Supervisor Harvey Milk, which along with the impact of AIDS united the Castro community and made activists out of just about everyone. Today, the Castro remains a world-recognized symbol of queer identity with a bustling bar scene that is guaranteed to entertain no matter what your sexual preference or identity may be. While evenings (and the wee hours of the morning) are the best time to see the Castro Theatre’s electric marquee light up the drag, daylight hours are an equally impressive time to experience the Castro’s unbridled energy. Visit on the last Sunday in June to take part in the neighborhood’s annual Pride celebration and witness the epic transformation of Market Street into a rainbow sea of queer power. If you have the time, drop by on the last Saturday in June as well. The equally colorful SF Dyke March, a parade of lesbians from all walks of life accompanied by their children, family members, pets, and the SF Women’s Motorcycle contingent, takes place amidst pre-parade parties galore.
The Mission
Vibrant, eclectic, and burrito-licious are just a few adjectives that can be used to describe one of San Francisco’s most historic and culturally rich ‘hoods. While streets lined with taquerias, produce markets, auto repair shops, and panaderias evidence the heavy Latin influence of Central American and Mexican families that have been settling in the area since the 1950s, many have slowly been displaced by highly paid dot.com professionals (ahem, “hipsters”) and the trendy cafes and thrift shops that they’ve ushered in with them. Today, however, there remains an interesting mix of places that have survived and new places struggling to make a name for themselves. Spanning 24th Street, Valencia, Dolores, 16th Street, and Bryant, each two-block area of the Mission can seem like a distinctly different neighborhood in itself, and each area is teeming with things to see and do. Explore at your own leisure, but make sure to stop for an afternoon nap at Dolores Park—a luscious, quiet, and hilly oasis shaded by palm trees and lined by lovingly restored Victorians—before following the line of trees to a street known as “El Corazon della Misione.” This historic heart of the Mission runs along 24th Street from Mission to Portrero and proudly displays the greatest concentration of murals in the city.
Chinatown
If you’re looking to be delighted, charmed, mesmerized, and gorged in savory Szechuan heaven, then Chinatown is the place for you. Be stunned by Chinatown’s elaborate and iconic entry gate, gawk at antique 1920s streetlights sculpted to look like golden dragons, meander through pocket-sized side streets without an itinerary, shamelessly buy more cheap and kitschy Buddhas than your suitcase will physically allow, and try to conceal your shock and horror upon seeing live animals at the, ahem, “pet” market. An insider’s tip: there are two Chinatowns, and they are not created equal. One is there to enchant the tourists, who outnumber visitors to the Golden Gate Bridge, and the other belongs to locals. Immerse yourself in both for the full Chinatown experience; to avoid one would be a disservice to your perception of the other. Along with Chinatown’s explosively entertaining Chinese New Year festivities, beautifully ornate temples and churches, Chinese calligraphy and brush painting classes, and the (unsurprisingly) best Chinese food in the city, its must-see attraction is the Golden Gate Fortune Cookie Factory. Witness the creation of the only fortune cookies still made by hand as two women, each manning a conveyor belt of what look like mini pancake makers, churn out 20,000 fortune cookies per day. Nom on a bag of 40 for $3 and feel free to watch, but pay to capture: a sign on the door asks for 50 cents per photograph.
Golden Gate Park
As Central Park’s relaxed cross-coast sister, Golden Gate Park is the ultimate safe haven from urban chaos. It’s the perfect place to plop down with a picnic basket and enjoy the side of the city where the grass is always greener. You know who else enjoys grass that’s greener? The bison. Small herds of them have made their stolid presence known since 1982, when the park was a free-range zoo filled with elk, bears, and goats, to name a few. Golden Gate is now covered with more than 75,000 trees and houses state-of-the-art museums like the California Academy of Sciences and the de Young fine Arts Museum, both of which were designed with sustainability in mind by some of the most highly-respected architects in the world. While the de Young is clad in copper plates that will eventually oxidize to take on a greenish hue that mimics the nearby eucalyptus trees, the Academy of Sciences includes a stunning 2 ½-acre living roof on which 1.7 million native plants grow. Don’t miss it. Other notable sights and attractions include a rose garden, the Japanese Tea Garden (free admission before 10 a.m.), paddle and rowboat rental at Stow Lake, disc golf courses, two massive and historic windmills at the east end of the park, and Kezar Stadium—a 10,000-seat outdoor stadium and former home to the San Francisco 49ers and Oakland Raiders, which includes an all-weather track for public use.
Fisherman’s Wharf
Let me tell you something about San Franciscans: they love to complain about Fisherman’s Wharf. “The shops are tacky, the museums are trashy, the tourists are too many, the souvenirs are cheap,” they say. But hidden beneath their outward distaste is deep-seated love for an area that is equally loved by tourists. Ranked as San Francisco’s number-one tourist destination (edging out the Golden Gate Bridge and Chinatown), Fisherman’s Wharf will keep you entertained for hours with stupid “I’m with stupid” mementos, cavorting sea lions, decadent Ghirardelli sundaes, video arcades, street performances and an aquarium with a walk-through shark tunnel at the family-oriented Pier 39. Sure, the Wharf is cheap and kitschy, but cheap and kitschy can be fun—and if you ditch the wax museums whose main attractions look more like examples of botched plastic surgery than notable celebrities, you’re left with fresh Dungeness crab, piping hot clam chowder, and some of the most beautiful views of the city. Which brings me to the greatest attraction of all: Alcatraz. Widely known as a high-security penitentiary that housed infamous criminals like Al Capone, George “Machine Gun” Kelly, and Alvin “Creepy” Karpis, none of the 36 prisoners who attempted to escape were said to be successful. It is interesting to note, however, that the FBI’s investigation of the most elaborate escape plan in Alcatraz history—which involved dummy heads fabricated from a mixture of soap, toilet paper and human hair—was unable to determine whether the three inmates involved escaped or died in the attempt. Call ahead to reserve a tour—they book up quickly.
North Beach
Buon appetito! If you’re looking for some fine Italian wine to complement the city’s most heavenly bruschetta, gnocchi, and spaghetti alla puttanesca, then North Beach is the place for you. Known as San Francisco’s “Little Italy,” North Beach’s densely packed cafes, red-checkered delicatessens, and quaint ristorantes have made it a timeless favorite of both locals and tourists alike. Don’t, however, make the mistake of pigeonholing this San Francisco classic as a one-dimensional festa della italiana; North Beach is also home to some of the liveliest bars and clubs in town, spectacular views, and landmarks steeped in the past. Fans of the Beat movement will be delighted to stroll past the old stomping grounds of Jack Kerouac and Allen Ginsberg before they read the day away at City Lights, the original publisher of Ginsberg’s “Howl” and one of the best bookstores in SF. Stay long enough and you may get a glimpse of City Lights’ 94 year-old founder, Lawrence Ferlinghetti. Also don’t forget to visit San Francisco’s famed Coit Tower, a curious structure donated by an even more curious volunteer firefighter by the name of Lillie Hitchcock Coit. (Coit was often seen disguised as a man in order to gamble at North Beach’s males-only establishments.) A mural created as part of Roosevelt’s Federal Art Project depicts the effects of the Depression on the Bay Area and wraps around the ground floor’s inner circular walls.
Union Square
As one of the world’s premier retail districts with one of the largest collections of department stores, tourist shops, boutiques, and art galleries in the Western United States, how to spend a day in Union Square is a no-brainer: shop your socks off. And then buy some more. But beware, as a commercial mega-mecca with flagship stores for powerhouses like Levi’s, Nike and Apple, there’s seldom (if ever) a time when the streets of Geary and Powell aren’t teeming with tourists and save-savvy shopaholics. Throw in a venerable cable car turnaround where drivers get out and rotate a nearly 8-ton, 18-foot-long piece of San Francisco history, and the masses multiply in ways that you didn’t think were humanly possible. Suit up in a camisole (girls) to avoid insane fitting room lines, nab to-die-for deals at stores like H&M and Forever 21 (you too, guys), and, come Christmastime, don’t miss the view and delectable chocolate tuxedo cream cheesecake at The Cheesecake Factory on Macy’s eighth floor—there’s nothing like a collapsible outdoor ice skating rink and an 80-ft-tall, brilliantly lit, and fully-ornamented Christmas tree to get you in the holiday spirit.
Nob Hill
Named after disparaging British slang for “newly rich,” and oft derisively referred to as “Snob Hill,” San Francisco’s swanky epicenter of wealth and affluence offers far more than its name suggests. Despite being nearly destroyed by the 1906 San Francisco earthquake and ensuing fires, Nob Hill has remained a neighborhood renowned for its beautiful architecture and the famous city landmarks that border its lush and shady Huntington Park—a prominent and peaceful plaza that is situated smack in the middle of some of the most opulent turn-of-the-20th-century buildings that the city has to offer. Feast your eyes on the immaculate Gothic splendor of Grace Cathedral Episcopal Church, the West Coast’s largest Episcopal cathedral, and marvel at the intricate mastery of its bronze doors, which are casts of those sculpted by Lorenzo Ghiberti for the Baptistery in Florence. Don’t stop there. Further your Italian fix by wandering over to the Fountain of Tortoises, a replica of one in Rome that features a pasticcio of rollicking turtles and nymphs. During the holidays, its eight underwater halogen lamps change from clear to red, amber and green.
PHOTO CREDS: Haight: Michael Mullady, Wall Street Journal; Tenderloin: Michael Macor, SF Gate; Castro: Huffington Post; Mission: Peter DaSilva, New York Times; Chinatown: StaySF.com; Golden Gate Park: keepontravellin.com; Fisherman’s Wharf: stock photo; North Beach: Scott Haefner; Union Square: sfgba.com; Nob Hill: stock photo.
