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Created in the 1920's as a way to deal with the extreme forty-degree slope of Russian Hill, the block of Lombard Street from Hyde to Leavenworth has long been known as "the crookedest street in the world." Much of the pleasure of Lombard Street is due to the beautiful flowers and shrubs that border the eight switchbacks and the smashing views of the city and the Bay available from any point along the block. There are stairs (without curves) on either side of the street for pedestrian access.
Less well known than Lombard Street but at least as challenging is Vermont Street off 20th Street, in the Potrero Hill section of the city. There are just six curves on this 14.3 percent grade, but they're very sharp. There's also a backdoor view of the city skyline and of Twin Peaks and Mt. Davidson from the small park at the top of the hill.
Twin Peaks offers another opportunity for winding roadways and spectacular vistas. Follow Twin Peaks Boulevard from the intersection with Clarendon Avenue up to the top of the hill, then down to Portola Drive. Be sure to stop at the top for a 360 degree panorama of the entire bay area. The view is especially beautiful at night, when the city is a sea of twinkling lights, or at sunrise, when you can watch the city slowly emerge from sleepy darkness into the light of day.
Just in case you're wondering: the steepest street in the city (no curves) is Filbert Street between Hyde and Leavenworth. Its 31.5 percent grade makes even native San Franciscans gasp.