13 Best Nightlife in Union Square, Civic Center, and the Tenderloin, San Francisco

Although this spot reeks of Prohibition-era speakeasy cool, it's not exclusive (though it's highly recommended to book a reservation). The place has sex appeal, with tin ceilings, bordello-red silk wallpaper, intimate booths, and low lighting; loud conversations and cell phones are not allowed. The menu of spirit-forward cocktails and quality bourbon and whiskey is substantial. A speakeasy within the speakeasy called Wilson & Wilson is more exclusive but just as funky.

Euro-chic yet comfortable, this rooftop lounge serves up jaw-dropping skyline views along with sophisticated small bites and expert cocktails—it's not hard to reach the $65 per person minimum spend. The indoor space is cozy and intimate, and the outdoor tables with personal fire pits are popular, so reservations are a good idea.

In the rough-and-tumble Tenderloin, around the corner from the Polk Street bars, transgenders and their admirers come here for the racy entertainment. Naughty Schoolgirls night (Wednesday) is a major fave. This multilevel space has separate areas for stage performances, dancing, and quiet chats. It's not a drag bar, as there is no sense of irony or camp about the place; the girls here are charming, and the fun is in the titillation.

Work off your fish-and-chips and Scottish brew with a turn at the dartboard or pool table at this decades-old divey pub. It's popular with locals and Brits, who congregate at the long bar or in the scattered seating areas, downing single-malt Scotch or pints of Fuller's. The pub holds weekly trivia nights and occasional Scottish cultural events (January's Robert Burns celebration is a favorite). Be aware that the surrounding neighborhood is gritty.

You'll find top-drawer entertainment at this eclectic venue. Acts range from the best in blues, folk, and jazz to up-and-coming alternative artists. The colorful marble-pillared club, built in 1907 as a bordello, accommodates dancing at some shows. Pub grub is available most nights.

Tucked away on lovely Maiden Lane, this warm and welcoming two-level space offers respite from the bustle of Union Square. Talented bartenders make good use of fresh fruit in reasonably priced seasonal cocktails, while muted jazz, dim lighting, and oil paintings in gilded frames create an intimate vibe. Upstairs tables overlooking the lane are particularly cozy.

Down an easy-to-miss alley off Taylor Street is what appears to be a two-story plantation house in the center of the city. Without being kitschy, the top-floor bar successfully evokes French-colonial Vietnam, thanks to creaky wooden floors, wicker Victorian sofas, and a patio with potted palms. It's open Friday and Saturday only, when live music accompanies tasty French-Vietnamese food and tropical cocktails.

PCH for short, this neighborhood hangout with a convivial aura and industrial-chic decor hits all the right notes. Plus the well-chosen and unique ingredients mean there’s a little something for everyone, and the glassware is as dazzling as the elixirs inside. The must-try cocktail is the Oh Snap!, a concoction of gin, sugar snap peas, citrus, and absinthe.

Retro tiki kitsch meets tropical sophistication at award-winning PCH, a lively favorite for evening cocktails. As the name suggests, Asia Pacific flavors—shiso, ume, li hing mui, pandan—abound on the booklike cocktail menu, and the talented bartenders make reliable recommendations. Fun theme nights and whimsical mugs are common.

Opened in 1933, this lounge at the Clift Hotel is a San Francisco icon. The art-deco bar itself and the wood-paneled room are constructed from a single old redwood tree, giving a distinct only-in-California sense of place. Cocktails are a mix of high-quality classics and slightly creative newcomers.

If you weren't of legal drinking age during the '80s, now's your chance to experience the era's ambience. The Romper Room, bubbling over with neon pink and leopard print, is a funky little bar and quasi-dance club located in the city's somewhat cookie-cutter and label-driven Union Square district. The cocktail menu is small and simple, but they guarantee you won't have to wait longer than 90 seconds to get one.

During Prohibition, one of the city's more notorious speakeasies was accessible only via a secret-wall passage and a 15-foot slide that whisked patrons into the basement "restaurant" known as Coffee Dan's (it wasn't really a restaurant). That space has been reclaimed, restored, and aptly renamed Slide. A swanky, modern version of its former self, the place still has a slide, though stairs are also available. On the weekends, DJs spin a mix of hip-hop, downtempo, and Rat Pack–era hits from a 1920s baby grand piano that has been converted to a DJ booth. Like similar-themed bars within the city, the facility is completely unmarked.

A former movie palace is now one of the city's largest rock venues, with folding chairs or standing space (depending on the event) downstairs and theater seating upstairs. The historic venue has booked everyone from Prince and the Grateful Dead to the Killers.