16 Best Sights in Union Square, Civic Center, and the Tenderloin, San Francisco

You don't have to be a connoisseur of Asian art to appreciate this newly expanded museum, whose monumental exterior conceals a light, open, and welcoming space. The fraction of the museum's collection on display (about 2,500 pieces out of 18,000-plus total) is laid out thematically and by region, making it easy to follow historical developments.

Begin on the third floor, where highlights of Buddhist art in Southeast Asia and early China include a large, jewel-encrusted, exquisitely painted 19th-century Burmese Buddha and clothed rod puppets from Java. On the second floor you can find later Chinese works, as well as exquisite pieces from Korea and Japan. The ground floor is devoted to temporary exhibits and the museum's wonderful gift shop. During spring and summer, visit on Thursday evenings for extended programs and sip drinks while a DJ spins tunes.

This imposing 1915 structure with its massive gold-leaf dome—higher than the U.S. Capitol's—is as close to a palace as you'll find in San Francisco: the classic granite-and-marble behemoth was modeled after St. Peter's Basilica in Rome. Architect Arthur Brown Jr., who was also behind Coit Tower and the War Memorial Opera House, designed an interior with grand columns and a sweeping central staircase. The 1899 structure it replaced had taken 27 years to erect, but it collapsed in about 27 seconds during the 1906 earthquake.

City Hall was seismically retrofitted in the late 1990s, but the sense of history remains palpable, and you can learn about it on a free tour. Some noteworthy events that have taken place here include the hosing of civil-rights and freedom-of-speech protesters (1960); the assassinations of Mayor George Moscone and Harvey Milk (1978); the torching of the lobby by angry members of the gay community in response to the light sentence given to their killer (1979); and the first domestic partnership registrations of gay couples (1991). In 2004, Mayor Gavin Newsom took a stand against then-current state and federal law by issuing marriage licenses to same-sex partners.

Across Polk Street from City Hall is Civic Center Plaza, with an outdoor café, flower beds, and a playground. This sprawling space is generally clean but somewhat grim, as many homeless people hang out here.

Fascinating and futuristic, this 2,739-seat hall is the home of the San Francisco Symphony. The glass wraparound lobby and pop-out balcony are visible from outside, as is the Henry Moore bronze sculpture on the sidewalk. The hall's 59 adjustable Plexiglas acoustical disks cascade from the ceiling like hanging windshields. Concerts range from typical symphonic fare to more unusual performances, such as singer Al Green and film screenings with a live orchestra performing the score.

Celebrated local architects Bliss and Faville, also responsible for the nearby St. Francis Hotel, designed the neoclassical home of San Francisco's premier repertory theater company. The 1910 structure, which replaced one destroyed in the 1906 earthquake, sustained heavy damage in the 1989 quake but was beautifully restored. A.C.T. is renowned for productions by playwrights such as Tony Kushner (Angels in America) and company favorite Tom Stoppard (The Invention of Love and Indian Ink premiered here), and cutting-edge works such as The Black Rider by Tom Waits, William S. Burroughs, and Robert Wilson.

For a rockin' gospel concert and an inclusive, feel-good vibe, head to Glide, where Reverend Emeritus Cecil Williams, a bear of a man and a local celeb do-gooder, and other engaging pastors lead a hand-clapping, shout-it-out, get-on-your-feet Sunday "celebration." The diverse crowd—gay and straight, all colors of the rainbow, religious and not—is large and enthusiastic. You might recognize the church from the Will Smith filmThe Pursuit of Happyness.

Named for cable-car inventor Andrew S. Hallidie, this 1918 structure is best viewed from across the street. Willis Polk's revolutionary glass-curtain wall—believed to be the world's first such facade—hangs a foot beyond the reinforced concrete of the frame. The reflecting glass, decorative exterior fire escapes that appear to be metal balconies, and Venetian Gothic cornice are notably lovely.

Saucy gold rush–era actress, singer, and dancer Lotta Crabtree so excited the city's miners that they were known to shower her with gold nuggets and silver dollars after her performances. This peculiar, rather clunky gold-colored fountain adorned with regal lions was her way of saying thanks to her fans. Given to the city in 1875, the fountain became a meeting place for survivors after the 1906 earthquake; each April 18, the anniversary of the quake, San Franciscans gather here. An image of redheaded Lotta herself, in a very pink, rather risqué dress, appears in one of the Anton Refregier murals in Rincon Center.

Known as Morton Street in the raffish Barbary Coast era, this former red-light district reported at least one murder a week during the late 19th century, though things cooled down after the 1906 fire. These days Maiden Lane is a chic, designer-boutique-lined pedestrian mall. Wrought-iron gates close the street to traffic most days between 11 and 5, when the lane becomes an alfresco hot spot dotted with umbrella-shaded tables. It's also popular with photographers and Instagrammers for its quaint-chic aesthetic. At 140 Maiden Lane is the only Frank Lloyd Wright building in San Francisco, fronted by a large brick archway. The curving ramp and skylights of the interior, which houses exclusive Italian menswear boutique Isaia, are said to have been his model for the Guggenheim Museum in New York.

Topped with a swirl like an art-deco nautilus, the library's seven-level glass atrium fills the building with light. Local researchers take advantage of centers dedicated to gay and lesbian, African American, Chinese, and Filipino history. The sixth-floor San Francisco History Center has fun exhibits of city ephemera, including a treat for fans of noir fiction: novelist Dashiell Hammett's typewriter.

Head downstairs from the cable-car terminus to the visitor center, where multilingual staffers answer questions and provide maps and pamphlets. Muni Passports are sold here, and you can pick up discount coupons—the savings can be significant, especially for families. If you're planning to hit the big-ticket stops like the California Academy of Sciences and the Exploratorium and ride the cable cars, consider purchasing a CityPass (www.citypass.com/san-francisco) here. The CityPass ($94, $69 ages 5–11), good for nine days, including seven days of transit, will save you 50%. The pass is also available at the attractions it covers, though if you choose the pass that includes Alcatraz—an excellent deal—you'll have to buy it directly from Alcatraz Cruises.

Built in 1904 and barely established as the most sumptuous hotel in town before it was ravaged by fire following the 1906 earthquake, this grande-dame hotel designed by Walter Danforth Bliss and William Baker Faville reopened in 1907 with the addition of a luxurious Italian Renaissance–style residence designed to attract loyal clients from among the world's rich and powerful. The hotel's checkered past includes the ill-fated 1921 bash in the suite of the silent-film superstar Fatty Arbuckle, at which a woman became ill, leading to her death. Arbuckle endured three sensational trials for rape and murder before being acquitted, by which time his career was kaput. In 1975, Sara Jane Moore, standing among a crowd outside the hotel, attempted to shoot then-President Gerald Ford. Of course, the grand lobby contains no plaques commemorating these events. Some visitors make the St. Francis a stop whenever they're in town, soaking up the lobby ambience or enjoying a cocktail at the Clock Bar or holiday tea at the Oak Room Restaurant.

The marquee destination for big-name shopping in the city and within walking distance of many hotels, Union Square is home base for many visitors. Four globular contemporary lamp sculptures by the artist R. M. Fischer preside over the landscaped, 2½-acre park anchored by the monument to Admiral George Dewey. The area also has a café with outdoor seating, an open-air stage, and the city's favorite holiday season ice-skating rink. The square hosts a kaleidoscope of characters: office workers sunning and brown-bagging, street musicians, shoppers taking a rest, kids chasing pigeons, and a fair number of homeless people. The constant clang of cable cars traveling up and down Powell Street helps maintain a festive mood.

Locals know this plaza for two things: the farmers' market held on Wednesday and Sunday—cheap and earthy to the Ferry Building's pricey and beautiful—and the many homeless people, a consistent presence despite numerous efforts by the city to shunt them aside. Brick pillars listing various nations and the dates of their admittance into the United Nations line the plaza, and its floor is inscribed with the goals and philosophy of the United Nations Charter, which was signed at the War Memorial Opera House in 1945. The food-truck gathering Off the Grid (offthegridsf.com) livens up lunchtime on Tuesday and Thursday.

After San Francisco's original opera houses were destroyed in the 1906 quake, architect Arthur Brown Jr. was commissioned to design this stunning Renaissance-style building. Named in tribute to the city's soldiers lost in World War I, it was inaugurated in 1932 with a performance of Tosca. It has since played host to two major historic events: the drafting of the United Nations charter in 1945 and the ceremony six years later in which the United States restored sovereignty to Japan. Modeled after its European counterparts, the building has a vaulted and coffered ceiling, marble foyer, two balconies, and a huge silver art-deco chandelier that resembles a sunburst. The San Francisco Opera performs here from September into December and in summer; the opera house hosts the San Francisco Ballet from December through May.

Performing- and visual-arts organizations occupy much of this 1930s structure. Herbst Theatre (415/392–4400) hosts classical ensembles and dance performances. The street-level San Francisco Arts Commission Gallery (closed Sunday and Monday) displays the works of Bay Area artists; admission is free.