Tenderloin Bars & Nightlife
Chambers Eat + Drink
Phoenix Hotel, 601 Eddy St., Tenderloin
San Francisco's notoriously gloomy weather means pool parties aren't exactly abundant in the city. But on those rare days that call for a bikini, the poolside patio at Chambers Eat + Drink at the Phoenix is the place to be. The scene can get a little rowdy in the afternoon, so go early (the brunch is good).
Bourbon & Branch
501 Jones St., Tenderloin
While Bourbon & Branch isn't the first bar to play on the speakeasy theme, they expand the motif with a lot of enthusiasm. Located in a bar that was an actual speakeasy from 1921-1933, the space has more than five secret rooms for guests to explore, if they can find them (and remember the password). Plus, a set of "House Rules" prevents anyone from using cell phones or taking photographs, and awesomely cautions: "Don't even think about asking for a Cosmo." Make a reservation in advance, as you'll need to be armed with a password to get in.
495 Geary St., Tenderloin
This historic bar inside the Clift Royal Sonesta Hotel has been open since the '30s, when waiters in white tuxedoes served the drinks (indeed, the Redwood Room's conservative dress code made it an important battleground for clashes between San Francisco's old guard and the long-haired kids of the '60s). The art-deco style space underwent a complete restoration in the early 2000s, bringing the redwood paneling on the walls and the deep bar, which was rumored to have been built from just one redwood tree, back to their former glory. The vibe here can get a little clubby at night, so we like to stop by in the early evening for pre-dinner drinks.
688 Geary St., Tenderloin
For after-dinner drinks, head to Rye where the bartenders will concoct the drink of your choice using the freshest ingredients. It's the kind of mellow place that doesn't use its cool, candle-lit ambiance or stellar reputation as an excuse to hike up drink prices.