If you truly want to leave your heart in San Francisco, you'll have to take on its storied outlaw past. On the surface, tales of the city shimmer and snap with glossy tech startups, tricked out twitter foodies, and its free wheeling lifestyles. But beneath this awesomeness is a city built along the seamier lines of a former gold mining town. Its frontier mentality, a “Go west and can-do” reinvention swagger, marks the past, as well as informs its present. Come explore these secret byways – revitalized docklands, quirky shops and hidden vistas – that make the city by the bay one of the most magical destination along the great Pacific coastline. 

On the waterfront

Fog. On any given day, billowy puffs truss the city’s fabled bay. But fog also wrote its destiny. Guarding it from the ocean are the Golden Gates, slivers of rocky headlands, constantly shrouded in fog. The native Miwoks, ancient Amerindians who once lived by the coast, knew about this hidden gateway. Not so the clueless land hungry European colonialists. For two hundred years, they sailed pass the foggy entry until an impromptu Spanish land trek uncovered the bay yonder. Oh, snap! From this inglorious founding in 1769, the city trudged on as a minor missionary outpost. That is until a century later when a farmer struck a gold seam in nearby Coloma. Overnight, San Francisco spiked from a sleepy town to a wild west ecstasy of the imagination. And that music hasn’t stopped playing since. 

Start your evening downtown at Comstock Saloon. Back in 1907, it was a ramshackle joint that attracted drunken gold miners and high society gadflies. These days, its mojo are the house made cocktails backed by live Delta blues to attract the hip and restless. Deep in this downtown docklands, Bix broods handsomely with a dark paneled Art Deco bar. Perfect tipples before nipping on prawns ‘a la plancha’ at Bocadillos, an Andalusia meets wine country tapas hideaway.

When the heavy fog rolls in, some streets come eerily alive. Rumour has it a century old dancehall, now an art supply shop on 555 Pacific, channels ghosts of those raucous gold mining days. A secret chamber quivers with cold spells and whispers. Just ask the nonchalant staff who will gladly tell you to turn right by the basement sketchbooks. Be nice and buy something. For more chills and spills, book a Ghost Tour. Or, just quench your fears and stroll over North Beach to the almost centennial Tosca Cafe and its iconic opera jukebox. Saved from the wrecking ball, allegedly by Sean Penn two years ago, local politicos and actors now hobnob in April Bloomfield's mod-Milan supper club vibe. And if you're up for impressing foodie pooh-bahs, grab a rez at Coi. You gotta love the city for having a swanky 2-star Michelin smack amongst the "gentlemen's clubs" and questionable take out joints. 

For the bold, nearby Chinatown beckons with diverse and uninhibited dive bars. Back in the gold mining days, Ross Alley was a hive of opium dens, smuggling tunnels and vice. In the still of the night, the troika of Bow Bow Cocktail Lounge, Buddha Lounge, and Li Po hold ground with non-ironic Mai Tai’s and Normcore local art types. For supper, swing by R&G Lounge for gargantuan live Dungeness crab deep-fried to wholesome tender goodness. When done, kick it up a notch on the other side of Chinatown at Bourbon & Branch, a reservations only speakeasy with a 1920’s Prohibition era flapper feel and cubby booths.

Not all here in North Beach echoes the sound and fury of days past. Contemplative spaces abound, like William Stout Architectural Books on Montgomery Street, a modern paean to all things Design. Nearby, City Lights, the indie bookstore that ignited 1960’s beatnik writings, retains a basement full of radical social literature. On a quiet afternoon, grab a single varietal drip coffee at local roasters Réveillé or Blue Bottle. Take a breather in the Redwood Grove tucked behind the iconic Trans America building. Don’t look up, but think, down. Below, abandoned ships together with gigantic redwood trees were found buried deep in its foundations. For back then, there were few return voyages in the mad dash to the gold mines. These ghost ships became landfill. As the treetops soar with its dramatic architecture, you can literally sense the staccato past of the city under your feet.

Trip the light fantastic

In 1882, a literary ingénue on his first American tour quipped that San Francisco “must be a delightful city that possess all the attractions of the next world.” Today, Oscar Wilde’s bon mot ain’t so absurd. Places and names may have changed, but the city continues to rock a groovy vibe that spins your headspace and dents your wallet.

Take Maiden Lane for example, a throwback to a Parisian left bank shopping street but infused with a distinctly Californian flair. TSE delivers modern cuts drenched in sunlit hues on feather light cashmere. At Oliver Peoples, look for full vintage and collab sunglasses with, of late, hand carved wood frames from musician Ryuichi Sakamoto and Tokyo’s cult following, Maison Kitsuné. Gump’s, that imprimatur for exotic home wares founded in the Gold Rush era for the new rich, displays gawk worthy collections – from Lalique art glass to the fantastical ‘flora danica’ Royal Copenhagen porcelain service – overseen by a two story high Qing dynasty gilded Buddha. Stroll up to a hidden gem on 140 Maiden Lane. Frank Lloyd-Wright designed it as a gallery in 1947. Outside, his famous Prairie School brickwork draws you in. Inside, it’s his only known prototype for the celebrated Guggenheim Museum in New York. For all this, few will remember this serene lane as one of the most notorious brothel strips in the early gold mining days.

 Hayes Valley too transformed from a wildflower creek to a Spanish mission before hitting its hipster fabric stride. Hunt for imaginative techno fabrics at Triple Aught Design, Aether, and Marine Layer, all designed in San Francisco. Nearby,  Azalea and Steven Allen for hyper-curated pieces. There’s also rare FEITAG bags at Public Bike + Gear, the perfect match to the Nordic furnishings at Minimal. For sustenance: brunch outdoors at Monsieur Benjamin, strike a boozy pose at Victoriana gastro pub Two Sisters Bar and Books or, sink into the Boxing Room’s luxe Louisiana food hall brimming with local oysters, jambalaya, and wines from small batch growers.

 The Fillmore came into being after the disastrous 1906 earthquake when fires wiped out eighty percent of downtown. This western addition soon attracted a hotbed of jazz clubs with a rising Jewish enclave. The Elite Café, opened in 1928, retains much of the period vibe, a convivial reminder of the once Harlem of the West. Over the years, the neighborhood sidestepped into a mini Japantown, before reviving as a retail hotspot: from Thom Brown’s postmodern preppy Black Fleece label to outré Victor + Rolf pieces at Curve across the street. For handcrafted scents, Le Labo / Bare Essentials has a west coast outpost here. Down a block is a local food lore outpost, Pizzeria Delfina. Come for the snazzy combos, stay for the brick oven roasted chicken. And for gastro nerds, State Bird Provisions dishes up an award winning small plate carousel for your ever changing moods.

During the Gold Rush, gold barons built massive Nob Hill mansions while workers strove south of the rail slots off the main Market Street. Generations later, the tide has turned. Of the all the city’s spaces, none has seen more dramatic changes than South of Market (SoMa). Today, SoMa is bristling with new money with even newer ideas. Inside this industrial fringe, Bar Agricole is bucking food and space trends. The craft bar menu rakes up the highest tweets, hashtagged with stunning sustainable architecture by way of vast glass tubes, salvaged woods, and urban gardens. And if beauty has a bête noire, welcome to Mr. and Madam S., a cavernous fetish emporium with one of the world’s most advanced gear for those slap and tickle nights that sting the body electric. Between the slipstreams of cutting edge design and game studios are organic cooperatives like Rainbow Grocery, and the nation’s largest grower-led Flower Market. These farm-to-home places complement fervent locales like Radius. Here, chefs take you to elevated taste realms with ingredients strictly sourced within 100 miles. Locavore, much?

Rebels with a cause

San Francisco’s jumpstart as a city of immigrants was fueled by the gold mines’ promised wealth. Broken dreams were daily hard knocks for the new kids on the block. But Ambition was the social leveler and everyone – merchants, workers, hucksters, and dreamers – bought in. From high society rebels like Lillie Coit (of the landmarked tower fame), to the bordello Madam who became Mayor of Sausalito, Sally Stamford. This true grit for constant transformations rolls on to yield wondrous results for you, the intrepid traveler.

 Witness Levi-Strauss, a German immigrant merchant who moved from New York in 1853. He started as a small general supplier to the miners before spotting the need for work clothes that do not fray. Bingo! - A denim retail empire. Get a glimpse of the company’s history in their headquarters in Levi’s Square.  Or, wander the Levi’s main store on Market Street for limited editions from Levi’s Vintage Collection (LVC) and Made & Crafted rarely found outside the U.S.

Few will remember the civic engineer William Hall. But all will enjoy Golden Gate Park. Rent a bike and take in the vast green acres strung with windmills, picnic meadows, museums, and plenty of shy raccoons. Hard to imagine these outer lands were once nothing but sand dunes swirling off the Pacific Ocean. Hall worked hard to fight off the newly minted gold rush millionaires gunning for a mega racetrack for their rich buddies. All bets were off when 60,000 trees were brought in to hold down the sand and greed. From the top floor of the beguiling Herzog de Meuron designed de Young Museum, catch a birds eye view of San Francisco’s magnificent hills rolling into the ocean.

Other secret vistas abound in the city’s hills. Twin Peaks and Buena Vista Park are well trekked, but nearby Corona Heights Park is a hidden gem. Tucked between the hyper gay Castro and hippie dippy patchouli scented Upper Haight, its high point commands a panoramic bay view unlike any other. The park had its darker days as an abandoned quarry owned by the profiteering Gray brothers. One was shot point blank for not paying wages, just another gun slinging showdown in those wild west days. Now, the park’s devoted fans’ quirky full moon peak dancing mitigates that historical trauma. Nearby, kick up your Instagram clout at the Vulcan Steps. Knockout city views and eclectic house styles appear on each twist and turn of the 218 steps that even few locals know about.

And then there are the social dreamers. While the new rich built castles in the hills, Adolph Sutro settled on a home bracing the cold fog along the ocean. As a self-taught immigrant engineer, Sutro made a fortune inventing drainage systems for the gold mines. When he became mayor, in gratitude, he used his skills to drain out an ocean side bath complex in 1896 for the city folk. Sutro Baths near his home was an elaborate system of three football-field sized temperature and salinity controlled pools. This was where the public relaxed before it dramatically burned down in 1966. Hike through the magnificent ruins that are now part of the heritage Land’s End and Sea Cliff walking trails. As you wander deep into the woods, dazzling features of the Golden Gate Bridge start to appear by the ocean’s golden gate. You will not be alone. Go forth, as waves of explorers did, loud and clear in the wind where it all began. Flanked by towering cypress punctuated with welcoming foghorns, the keys to this enchanting city are now yours to explore.