5 Best Sights in San Francisco, California

The block-long "Crookedest Street in the World" makes eight switchbacks down the east face of Russian Hill between Hyde and Leavenworth Streets. Join the line of cars waiting to drive down the steep hill, or avoid the whole mess and walk down the steps on either side of Lombard. You take in super views of North Beach and Coit Tower either way—though if you're the one behind the wheel, you'd better keep your eye on the road lest you become yet another of the many folks who ram the garden barriers. Can't stand the traffic? Thrill seekers of a different stripe may want to head two blocks south of Lombard to Filbert Street. At a gradient of 31.5%, the hair-raising descent between Hyde and Leavenworth Streets is one of the city's steepest. Go slowly!

San Francisco has no shortage of impressive, grand homes, but Macondray Lane is the quintessential hidden garden. Enter under a lovely wooden trellis and proceed down a quiet, cobbled pedestrian lane lined with Edwardian cottages and flowering plants and trees. A flight of steep wooden stairs at the end of the lane leads to Taylor Street—on the way down you can't miss the bay views. If you've read any of Armistead Maupin's Tales of the City books, you may find the lane vaguely familiar; it's the thinly disguised setting for parts of the series.

Originally called Calle de la Fundación, Grant Avenue is the oldest street in the city, but it's got plenty of young blood. Dusty bars such as The Saloon mix with independent boutiques, odd curio shops, and curated gourmet shops. While the street runs from Union Square through Chinatown, North Beach, and beyond, the fun stuff in this neighborhood is jammed into the four blocks from Columbus Avenue north to Filbert Street.

On October 6, 1967, hippies took over the intersection of Haight and Ashbury Streets to proclaim the "Death of Hip." If they thought hip was dead then, they'd find absolute confirmation of it today—the only tie-dye in sight on the famed corner is a Ben & Jerry's storefront.

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.