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Union Square

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History: A public park as old as the city itself (originally used for sandlot baseball games), Union Square was later named for the pro-Northern rallies that assembled here throughout the Civil War, sparked by the Unitarian minister whose church faced the square. The centerpiece pillar, 79 feet tall and topped with a statue of the goddess of victory (supposedly modeled on local heiress and philanthropist Alma de Bretteville Spreckels) was added in 1903 to commemorate American naval victories in the Spanish-American War. The neighborhood’s central location made it a natural hub of commerce. In 2002, the square was redesigned to be more open, the result of a five-year design competition that attracted entries from around the world.

Don’t Miss: There is no more iconic symbol of San Francisco than the cable car. From the cable car terminus at Market and Powell Streets, the mobile museums clang their way up Powell. Hop off at Geary Street, where to the west you’ll find the rest of San Francisco’s downtown theater district, including the American Conservatory Theater, San Francisco’s largest and most ambitious company and San Francisco Playhouse, specializing in homegrown big-banner productions. On the other side of the square, the narrow semi-hidden stretch of Maiden Lane is a veritable window-shopper’s paradise, internationally modeled after New York’s SoHo by the ambitious jeweler who named it. Here you’ll find the big names: Prada, Hermes, Gump’s, and Marc Jacobs, plus local indies within spitting distance of each other.

Around Union Square, the best eating happens in the same places as the best shopping. The Rotunda at Neiman Marcus offers a stained-glass dome with your afternoon tea, while the flagship Macy’s building serves incredible views and burgers at the sixth floor Burger Bar and amazing pastries on the third floor at Tout Sweet Patisserie. If you’d rather eat on the go, there’s a hot dog stand on every corner- even Union Square doesn’t have to be haute all the time. Finally, don’t forget to take a ride in the historic Westin St. Francis glass elevators for a 32-story gander at the city. And grab a coffee at Emporio Rulli on the way out.