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Cool Gray City

Starts at:

Montgomery & Washington, Financial District


2 hours

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Join best-selling author Gary Kamiya on a rollicking (and stunning) walk through 25,000 years of San Francisco history. As you follow Gary’s path forward in time, you’ll hide from mammoths and walk in the soft footsteps of the area’s first humans. You’ll watch Chinese immigrants play cards in an historic square, then go back in time to meet the ‘Father of San Francisco,’ the first guy to build a house there.

You'll wander through the flea-bitten, forgotten outpost that, when the Gold Rush hit, became the crazy, instant city of San Francisco. You’ll feel your feet sinking into the muddy streets and hear the soundscape of the time. Prostitutes will beckon to you from shadowy corners, gunshots will make you jump. You’ll learn the Turkey Trot.

And then, you’ll emerge into the sunlight of Telegraph Hill (and the 20th century). A tasty Italian sandwich in North Beach; Coit Tower framed by a narrow alley and then a visit to the WPA-era paintings inside. And all along the way, you’ll meet the waves of newcomers who’ve made and remade this city, decade after decade, and gain a deeper understanding of how this fabled city became what it is.

Tips & Hours

  • This Detour is best between 9am - 4pm, but is also beautiful at night and can be taken in the evening if stopping at Molinari's Deli isn't a priority. If you want to see the gamblers of Portsmouth Square in action, best to take this walk in the afternoon.

  • Bring some cash or a credit card for a quintessential Italian deli.