5 Best Bars in 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.