7 Best Sights in Union Square, San Francisco

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.

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.

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.