Redwood Room

One of San Francisco’s last Art Deco-era interiors, the Redwood Room in The Clift Hotel near Union Square remains one of the most dramatic and atmospheric bars in town. Opened the day after the repeal of Prohibition in 1933, the bar and lounge—with panelled walls said to be carved from a single redwood tree, chevron sconces, and elaborate chandeliers—drew an immediate crowd. Then, as now, an elegant back-lit bar was the centerpiece, surrounded by original paintings by Austrian Art Nouveau master Gustav Klimt (technically, they are Klimt designs completed by his studio artists in 1929). A refresh five years ago restored some of the elegance the Redwood Room had lost over time, including the addition of an 800-year-old redwood bartop and mid-century-inspired grey seating. The effect is stunningly sophisticated, a space that’s virtually dripping with history. Craft cocktails channel the Redwood Room’s vintage vibe with signature twists on classics like Manhattans, old fashioneds, and mules. Food runs the gamut from artisan cheese and charcuterie to a croissant bread pudding with salted caramel.

// 495 Geary St. (Lower Nob Hill), redwoodroomsf.com

The House of Shields

They call it the place “where time stands still”—this historic bar in SoMa. And indeed, there’s no clock or TV at The House of Shields, nothing to keep patrons from leaving the outside world at the bottom of a whiskey glass. The moody, wood-paneled, high-ceilinged bar has more than a few stories to tell, including bearing witness to the death of President Warren G. Harding in the arms of his mistress in 1923 (though official records claim he passed across the street in the Palace Hotel). Presidential consorts notwithstanding, women weren’t allowed inside this men's-only watering hole until the 1970s—not even when it was an underground speakeasy (supposedly) connected to the Palace via secret passage during Prohibition. Since then, The House of Shields has maintained the bar’s original Victorian charm, with a menu of drinks like the Boothby cocktail (bourbon, vermouth, bitters, prosecco) and the Martinez, that are nods to the early days. Women are welcome now, too, and the view from the intimate mezzanine level is worth as lovely as it ever was.

Pied Piper

Across the street from The House of Shields lives another timeless beauty, the Pied Piper. Named for Maxfield Parrish’s bizarrely whimsical mural of the magnetic children’s musician, the Pied Piper has mosaic tile floors and rich wood-panelled walls that lend it an ornate warmth. In business since 1909 as the house bar for the enchanting Palace Hotel, the space today boasts a modern fireplace, cozy armchairs, and mirror-topped marble coffee tables—plus, a cut-glass ceiling that is a companion piece to the hotel’s crowning Garden Court glory. The Pied Piper doesn’t just do cocktails and late-night bites—the former reminiscent of early SF, the latter sandos and a few other dishes that hit the spot long after dark. It also doubles as a full-service restaurant from 5pm to 10pm, with fare like pan-roasted sea bass and braised beef short ribs.

Hotel Utah

On the southern edge of SF’s downtown core today, the Hotel Utah was a rough-and-tumble saloon on a lonesome stretch of the city’s waterfront when it opened in 1908. Still, the Deininger family spared no expense in the construction of their business, commissioning furniture makers in Belgium to create an extravagant wooden barback. (In those early days, Hotel Utah served Fredericksburg, the beer many considered the best in town, delivered straight from the brewery by horse and carriage in sturdy wooden kegs.) When the Bay Bridge was completed in 1936, the Hotel Utah was perfectly poised to take advantage of the new river of traffic flowing across it. The saloon and the hotel upstairs initially catered largely to longshoremen, merchants, metalsmiths, and furniture makers. By the 1950s and ‘60s, Hotel Utah was slinging cocktails for the likes of Bing Crosby, Joe DiMaggio, Marilyn Monroe, and the poets of the Beat Generation. The saloon remains a site of pre-Prohibition nostalgia, hosting live music and open mic nights nearly every night of the week, as well as four-hour long happy hours daily with $5 well drinks.

// 500 4th St. (SoMa), hotelutah.com

Li Po Lounge

Among the first neighborhoods to develop in SF, it’s no surprise that Chinatown is home to one of downtown’s last prewar bars. Wilbert Wong and Jack Chow, major players in the early 20th century Chinese community, opened Li Po Lounge on Grant Avenue on Chinese New Year’s Eve in 1937—the first bar to open legally there after Prohibition’s end. There’s no debate that what’s left nearly 90 years later is a dive, but traces of an earlier elegance remain: ornate wooden fixtures, battered paper lanterns, painted Chinese motifs on the walls and ceiling. Popular with Pacific-bound GIs in World War II and rumored to have discreetly served as a meeting place for gay patrons, everything in Li Po today—including its wraparound bar and memorable golden Buddha—is original, save for one. It wasn’t until the late 1990s that Li Po’s current owner, Kenneth Lee, invented the bar’s famous “Chinese” mai tai, made with three kinds of rum, pineapple juice, and Chinese wine. The bartenders here still specialize in the dangerously delicious, trademarked recipe—a favorite among locals and tourists.

Old Ship Saloon

The Old Ship Saloon doesn’t look much like it did when it first opened in 1851. Back then, it was literally an old ship—the Arkansas—which ran aground on Alcatraz Island in 1849. After being hauled to the city’s shore, some intrepid Barbary Coast entrepreneur cut a hole in its side, added a gangplank, and began selling liquor in its hull. Over the years, as the city filled in Yerba Buena Cove, the saloon lost both its waterfront view and its ship shape. But while the Old Ship Saloon no longer looks like one of only four Gold Rush-era bars left in SF, it still wears some of its history on its sleeve—or, rather, its walls. Pieces of the original vessel are still there too, seen by archaeologists but left buried beneath the foundation to preserve them. The bar’s sign is said to be a replica of the ship in its more seaworthy days.