Walking San Francisco

Neiman Marcus’s stained glass rotunda is all that remains of the old City of Paris store.

PARKING: Off-street parking at the Fifth and Mission St. Garage, 1 block south of the start of this tour

PUBLIC TRANSIT: Powell St. BART station; underground Muni light rail, streetcars, and 5, 6, 9, 21, 31, and 71 Muni buses all stop at the starting point for this tour, as do Powell St. cable cars.

With its historical buildings, showpiece retail stores, fine restaurants, theaters, hotels, billboards clamoring for rooftop exposure, and converging public transit lines, Union Square has all the hallmarks of a commercial and cultural hub. It’s a central crossroads that has a way of drawing people and traffic through it. Day and night, the area buzzes with cars and buses starting and stopping at traffic lights, the groaning of cable car brakes, the repertoire of street corner singers, the purposeful clicking of high heel shoes, and the shrill whistles blown by hotel doormen hailing cabs.

This tour will range a bit freely, proceeding from Market Street through the Theater District to Union Square itself in the least direct route possible without leaving the neighborhood. While the neighborhood takes its name from the rallies supporting the Union Army during the Civil War, this onetime sand dune is now a pulsing hive of shoppers, theatergoers, and those who cater to their whims and desires.

Walk Description

Start at the

Powell Street Cable Car Turnaround, on the corner of Market and Powell. If it’s the summer tourist season, a hundred or more people will be lined up here for a ride on the historic cable cars, and a multitude of street performers will be vying for their attention and spare change. Don’t get in line, but wait for a car to come along, and watch how it’s rolled onto the circular platform, then rotated 180 degrees, all by hand, as has been done for more than 130 years.

Overlooking the cable car turnaround is the staunch and impressive

Flood Building, where the huge Gap flagship store occupies the ground floor. Designed by Albert Pissis and built in 1904, the building survived the 1906 earthquake. Dashiell Hammett worked upstairs for the Pinkerton Agency during the early 1920s, a few years before he published the novels that would make him a famous crime-fiction writer. Walk along Powell Street, below the block-long Flood Building, and hook right on Ellis Street. Half a block up you’ll spot

John’s Grill, which has been operating since 1908, when it was the first restaurant to open following the ’06 quake. Hammett reputedly dined at John’s frequently and even mentioned the place in his best novel, The Maltese Falcon. Not one to rest on its laurels, John’s has both changed with the times and stayed true to its roots. The waiters no longer wear tuxes, but the wood paneling remains, and the reviews (and frequent celebrity diners) attest to the high standards in the kitchen.

Return to Powell and turn right. The street is a hodgepodge of shops and hotels geared to tourists and passers-through. In the mix are some age-old establishments that seem to hang on despite the changing vibe of the neighborhood. These blocks of Powell Street not so long ago had some of the Tenderloin’s flophouse atmosphere.

Tad’s Steaks, with its gaudy sign looking like a holdover from the vaudeville era, still purveys shoe-leather cuts, charbroiled and served over the counter. Turn left on Geary; at the corner of Geary and Mason stands the

Pinecrest Diner, a 24-hour eatery that’s been slinging the neighborhood’s hash since 1969 but looks like it’s been here longer than that. It’s the no-nonsense, Edward Hopper–esque atmosphere—not the food—that draws people. The place is genuinely hard-boiled, and a little tragic: in 1997, a grill cook shot and killed a waitress here in a dispute about poached eggs.

The Pinecrest inadvertently ushers us into the Theater District, where swank hotels, art galleries, bars, and performance spaces rub elbows. Two landmark stages stand side by side on this block. The

Geary Theater opened in 1909 and is now home of the highly respected American Conservatory Theater. The building is a beauty clad in terra-cotta tiles, many of them shaped like fruit. To the right of the front entrance a traditional shoeshine stand operates during the business week. The Geary is best admired from across the street, where you can see the entire building. Next door, the

Curran Theater was built in 1922, and it and the Geary make a very compatible pair. Theaters small and large are scattered all throughout the neighborhood.

At the end of the block stands

The Clift Royal Sonesta Hotel, which was recently remodeled under the direction of Philippe Starck and has successfully reentered the ranks of the city’s most sophisticated hostelries. The Clift always had the Redwood Room, a gorgeous, clubby old watering hole, and those in the know long appreciated their martinis here. A velvet rope and a bouncer now maintain order on Friday and Saturday nights. On quieter weeknights, it’s possible to enjoy a relaxed drink here amid early-20th-century splendor. And during the day, it’s fun to pop your head in to admire the arty lobby with its oversize chairs.

Across from the Clift,

The Marker San Francisco is a hip boutique hotel housed in a Beaux Arts building from the steamship era. You need only step into the airy

Tratto, a modern Italian trattoria boasting communal tables and homemade limoncello, to know that this isn’t your grandmother’s hotel. Turn right at Taylor. Halfway up the block look for tiny Isadora Duncan Lane, a dead-end alley that rarely benefits from direct sunlight. A monkey could swing from the fire escapes on one side to the fire escapes on the other side. Named for the legendary dancer who was born within a block of here, it is a model for how all dead-end alleys ought to look.

The stately, ivy-covered redbrick fortress on the corner of Taylor and Post is home of the exclusive

Bohemian Club. The name was once somewhat appropriate, for when it was founded, in 1872, the club’s members were writers, poets, newspaper reporters, and artists. By 1900, however, the club was dominated by businessmen and social elites—all men, of course, and all white. The club hasn’t changed much (it’s now about 2% nonwhite), and US presidents have attended its annual summer fetes, which are held 2 hours north of the city at a club-owned campground called the Bohemian Grove. (In 2000 George W. Bush and Dick Cheney held a powwow at the Grove that supposedly resulted in Cheney joining the Republican presidential ticket.) A plaque on the side of the club has a bas-relief owl on a branch, along with the club’s motto, taken from Shakespeare’s A Midsummer Night’s Dream: “Weaving spiders come not here,” meaning that business deals and other outside concerns are not to be discussed within the sanctuary. Kitty-corner, the

Owl Tree Bar serves up stiff drinks and unpretentious warmth for bohemians of a different generation and pocketbook size.

Turn right on Post and cross Mason. On the north side of the street is

Farallon, one of the city’s best seafood restaurants. Step inside for a look at the outlandish underwater decor—a Jules Verne fantasy with illuminated jellyfish hanging from the ceiling.

At Powell turn left. Two local landmarks face off on this block. On the west side is humble

Sears Fine Food, known the world over for its silver dollar–sized Swedish pancakes. It was opened in 1938 by Ben Sears, a retired circus clown. Opposite is the

Sir Francis Drake Hotel. Cross at Sutter, backtrack to the hotel’s front entrance, and be sure to smile at the Beefeater doorman on your way in. Inside, examine the magnificent staircase with its intricate cast-iron rail, and gape at the molded plaster ceiling above. Then duck downstairs if it’s late afternoon, where an elevator can take you to the Starlight Room, a swanky top-floor nightclub surrounded by plate-glass windows. Back at the bottom floor, exit the Drake through the side exit onto Sutter Street, cross at the light, and turn right.

The office tower at

450 Sutter is populated mostly by doctors and dentists, but the building is a pure flight of fancy. It was designed by Timothy Pflueger, who also designed the magnificent Castro Theatre and the Paramount Theatre in Oakland. The lobby at 450 Sutter looks like a set for a never-made Cecil B. DeMille epic about the Mayan empire. It’s well worth going in for a look-see. From the sidewalk the tower’s jagged columns of bay windows are fine to look at too.

At Stockton turn left and you’re soon facing the southern end of the Stockton Tunnel. The entry looks inviting, despite the sign that says QUIET IN TUNNEL, but it’s just your usual tunnel, dank and dimly lit. Immediately within, a foul-smelling flight of steps leads up to Bush Street, which is where we’re headed.

The

Tunnel Top bar, a refurbished dive that’s kind of hip now, welcomes you to Bush Street. If you’re in a drinking mood, and it’s after 4 p.m., have one of the bar’s signature mojitos. Just past the Tunnel Top, on a wall flanking narrow Burritt Alley, a plaque notes that Sam Spade’s partner, Miles Archer, was done in on this spot by Brigid O’Shaughnessy. (It’s always cool to see completely fictional events get historical markers.) On the other side of the street, another alley is named for Hammett.

Now turn around and walk down Bush. Elegant

Notre Dame des Victoires, a Catholic church, stands at No. 566. It was originally built in 1855, then rebuilt after the ’06 quake. Inside the church, the grand pipe organ is worthy of landmark status, having been built in 1915 by the Johnston Organ and Piano Manufacturing Company. It is renowned for its beautiful tone, which you may hear if you attend a Saturday Vigil, with an organist accompanying a cantor, at 5:15 p.m.

At Grant turn right, stopping for a quick look at

Café de la Presse, a European enclave with brasserie-style cuisine and newsstand titles available in a variety of international languages. The southeast corner of Grant and Sutter is dominated by the building that once housed the White House department store and is now occupied by Banana Republic. It was designed, with Federalist overtones, by Albert Pissis and built in 1908.

Turn right onto slender Maiden Lane, a street that had its name changed in order to obscure a shameful past. Before the ’06 quake, the street, then called Morton Street, was a central thoroughfare for Barbary Coast ruffians and was known for its vicious pimps, weekly murders, and seamy bordellos lining both sides of the street. It’s much calmer and more respectable now. Its main architectural distinction lies within the curved brick archway of the

Frank Lloyd Wright building at 140 Maiden Ln. It was constructed in 1949, and its spiral ramp is often cited as a warm-up for Wright’s more accomplished Guggenheim Museum in New York.

Maiden Lane ends at Union Square. Turn left, walk to the corner of Geary, and enter

Neiman Marcus. Immediately within, stare up at the great rotunda, with its stained glass mosaic of a ship. It’s all that remains of the old City of Paris department store, which formerly stood on this corner. The rest of the building was demolished and replaced by the current modern structure in the early 1980s. Jockey your way past the perfume sprayers to take an elevator to the top floor for a closer look at the glass. If you’re feeling fancy, you can join the ladies-who-lunch crowd and snag a table. Models sporting couture and jewelry for sale often strut through the dining room while you nibble popovers and sip Champagne.

Cross to the square, which was part of the original city plans of 1850 and became a more prominent address as San Francisco expanded south from Portsmouth Square; it gained its name during the Civil War. The Dewey Monument, which rises from the square’s center, commemorates a major victory in the Spanish-American War. The model who posed for the sculpture, Alma de Bretteville Spreckels (see Backstory, opposite), was a work of art in herself. A parking structure—meant to double as a bomb shelter—was dug beneath the square during World War II. The square acquired its current Italian piazza styling in a dotcom-era overhaul, and it’s a good spot to stop for an outdoor coffee or to see occasional midday music performances. During holidays, it’s taken over by a giant tree and skating rink. The surrounding cityscape of department stores, billboards, and the awesome

Westin St. Francis Hotel makes this a pleasant urban space. You’re seeing the St. Francis from its most flattering vantage point.

The St. Francis was built in 1904, gutted by the fire of ’06, and rebuilt a year later. It’s the grand dame of Union Square, but it hasn’t escaped controversy over the years. In 1921 comic actor Roscoe “Fatty” Arbuckle rented a suite of rooms and threw a party that ended with the gruesome death of a young actress, Virginia Rappe. Arbuckle was tried for rape and murder, but he wasn’t convicted.; the scandal nevertheless diminished his comic appeal and put an end to his career. President Gerald Ford was shot at by Sarah Jane Moore in front of the hotel in 1975. She missed, went to jail, escaped, was recaptured, and was paroled in 2007, almost exactly a year after Ford had died of natural causes. Strolling the downstairs hallways, you can delight in pictures of all manner of celebrity guests, including Shirley Temple, Douglas MacArthur, and Dwight Eisenhower. As a testament to the hotel’s old-world class, they retain a coin washer—a literal money launderer, as it were—to ensure that no guest’s pristine paws are sullied by grimy change.

Enter the St. Francis’s main lobby, and look for the elevators. The hotel’s modern high-rise annex was built in the early 1970s, with high-speed glass elevators shooting skyward along the east side of the building. For kicks, end this tour with a ride up to the top. Not all of the hotel’s elevators are glass; head to the rear of the hotel past the reception desk and turn right to find the bank of glass elevators. Send yourself to floor 30 for the jaw-dropping view.