Beneath its skyscrapers and tidy rows of brightly painted Victorians, San Francisco still is a pioneer town at heart. Although far smaller than New York or Los Angeles, it has exerted an outsize influence as the home of social revolutions felt around the nation.
In the bustling downtown, where most hotels and convention facilities are located, San Francisco's iconoclasm isn't apparent. But a foray outside the commercial center leads you to legendary neighborhoods such as North Beach, Haight-Ashbury, and the Castro, where the beat, counterculture, and gay and lesbian movements flowered. History is being made today in a loft district south of Market Street known as Multimedia Gulch, home of Internet media startups.
Begin your walking tour of San Francisco's cultural icons with North Beach, the lively cafe district near the bay that gave rise in the 1950s to the Beats. Best enjoyed at night, when the streets fill with revelers, the area is a 15-minute walk from Union Square north on Grant Avenue through Chinatown. Don't miss City Lights Bookstore (261 Columbus Ave.), the intellectual centEr of the literary set that included Allen Ginsberg, Jack Kerouac, and Lawrence Ferlinghetti. The Beats also hung out next door at Vesuvio's bar (255 Columbus St.), or at Enrico's (504 Broadway), a crowded sidewalk cafe. For more North Beach flavor, stop for a cappuccino at Caffe Treiste (601 VallejO St.), where the jukebox plays opera, and then swing up Grant Avenue to Washington Square Park.
Fast forward 10 years to the counterculture era in the Haight. Reached by the N-Judah trolley line, the Haight is now best enjoyed by day for its funky boutiques. (At night, it's unsavory.) While few of the landmarks of the 1967 Summer of Love remain, you can find the old pads of The Grateful Dead at 710 Ashbury St. and Jefferson Airplane across the Panhandle park at 2400 Fulton St. Spend the night amid '60s artifacts at the Red Victorian Bed, Breakfast & Art at 1665 Haight St. (415 864-1978).
By the early '70s, the gay rights movement was growing just over the hill from the Haight in a formerly Irish district now known as the Castro. To get there from downtown, hop on the F-Market trolley. At the corner of Market and Castro is the Twin Peaks Tavern, the first local gay bar with windows that didn't hide its patrons. In the next block, at 575 Castro, is the former site of Harvey Milk's camera shop, now a skin care boutique. Milk, California's first openly gay elected official, ran his campaigns from the store before being assassinated in 1978.
TECH TALK. Finish your tour of revolutionary spots with a step into the future. South Park, created in 1856, is now the center of a district housing more than 400 digital media companies. Fifteen minutes south of downtown, the park is tucked between 2nd and 3rd Streets south of Bryant Street. It's best seen at midday, when hordes of programmers talk tech while sipping their lattes from Caffe Centro (102 South Park) or munching bean burritos from Pepito's Parrilla (24 South Park).
More formal eateries include South Park Cafe (108 South Park, 415 495-7275), Ristorante Ecco (101 South Park, 415 495-3291), and Infusion (555 2nd St., 415 543-2282), which features vodkas infused with exotic flavors. Nearby is the new Museum of Modern Art and the Yerba Buena Center for the Arts. Waiting for a message from the office? Stop in at the Club-i Internet cafe (850 Folsom St.) and check your E-mail on one of its 32 workstations. You might even be inspired to draw up plans for the city's next revolution. Just pick a neighborhood suitable for walking.