In the ornate 1913 basilica, stained-glass windows depict California's 21 missions and the Seven Sorrows of Mary. The basilica's doors are usually only open during services, so you'll need to pass through the original adobe structure and cross a courtyard to enter the basilica's side door. The mission graveyard is the resting place of mission founders Don Luis Antonio Arguello, the first governor of Alta California under Mexican rule, and Don Francisco de Haro, the first mayor of San Francisco.

Hedonism interrupts commutes at this historic transit hub that's become a local sustainable food destination, where crowds happily miss their ferries over Sonoma oysters and bubbly, SF craft beer and Marin-raised beef burgers, locally roasted coffee and just-baked cupcakes. Star chefs are spotted year-round at the Saturday waterfront farmers market, while farm-to-table kiosks line the curb Tuesdays and Thursdays.

Alcatraz: for over 150 years, the name has given the innocent chills and the guilty cold sweats. It’s been a military prison, a forbidding maximum-security penitentiary and disputed territory between Native American activists and the FBI. Today, first-person accounts of daily life in the Alcatraz lockup are included on the award-winning audio tour. But take your headphones off to hear carefree city life across the Bay: this torment made perilous prison escapes into riptides worth the risk.

This triple-decker, brick-walled US military fortress was completed in 1861, with 126 cannons, to protect the bay against a certain invasion during the Civil War…or not, as it turned out. Without a single shot fired, Fort Point was quietly abandoned in 1900. Alfred Hitchcock made it famous in his 1956 film Vertigo – this is where Kim Novak jumped into the bay. Now the fort showcases Civil War displays and knockout panoramic viewing decks of the bridge's underside.

SF's reinforced-concrete Gothic hilltop cathedral took 40 years to complete, with spectacular stained-glass windows celebrating science – look for Albert Einstein amid swirling nuclear particles. Murals commemorate the 1906 earthquake and 1945 UN charter signing, and Grace's Interfaith AIDS Memorial Chapel features a bronze angel altarpiece by artist-activist Keith Haring – his final work before his 1990 death from AIDS.

Market St's traffic-stopping 1937 Mayan deco landmark was built to accommodate 300 wholesale furniture-design showrooms – but, a decade ago, fewer than 30 remained. The city offered tax breaks to Twitter to move here from its South Park headquarters and, after a $1.2-million LEED-certified green makeover including a rooftop farm, Twitter nested here. Only employees can access Twitter's free video arcade and cafeteria, but the ground-floor public space, The Market, offers local gourmet fare.

Rising from the ashes of the 1906 earthquake, this beaux arts landmark echoes with history. Demonstrators protesting red-scare McCarthy hearings on City Hall steps in 1960 were blasted with fire hoses – yet America's first sit-in worked. America's first openly gay official supervisor, Harvey Milk, was assassinated here in 1978, along with Mayor George Moscone – but, in 2004, 4037 same-sex couples were legally wed here.

Heads of state choose the Fairmont for its grand hotel swagger – magnificent marble lobby, opulent mosaic penthouse suite, bacchanalian brunches – plus San Francisco eccentricity, including tiki Tonga Room and deco circus-mural Cirque bar. Guest rooms offer business-class comfort, but comparatively less character and luxury than public spaces. For historic appeal, reserve in the original 1906 building; for jaw-dropping views, go for the tower.

Picture what it was like to be Chinese in America during the gold rush, Beat era, and women's rights movements in this 1932 landmark. Historians unearth fascinating artifacts: 1920s silk qipao dresses, WWII Chinatown nightclub posters, and Frank Wong's Chinatown miniatures. Exhibits share personal insights and historical perspectives on Chinese American historical milestones – including the Civil Rights movement, transcontinental railroad construction, and the 1882 Chinese Exclusion Act.

Free speech and free spirits have rejoiced here since 1957, when City Lights founder and poet Lawrence Ferlinghetti and manager Shigeyoshi Murao won a landmark ruling defending their right to publish Allen Ginsberg's magnificent epic poem Howl. Celebrate your freedom to read freely in the designated Poet’s Chair upstairs overlooking Jack Kerouac Alley, load up on zines on the mezzanine and entertain radical ideas downstairs in the new Pedagogies of Resistance section.