The iconic Market St. runs the length of downtown San Francisco. Beginning at the Ferry Building and turning into Portola Blvd. around Twin Peaks, Market St. catches all of the bustling action of San Francisco. The street runs through the tourist traps of the Ferry Building and Union Square to the New York-paced Financial District, and onward to the impoverished regions of The Tenderloin and South of Market (SoMa). Popular attractions along this stretch include the Westfield Mall and the Trolley Rides in Union Square, San Francisco City Hall in the Civic Center, and the Castro Theater further down in the Castro.
Winding, hilly hairpins make for an exciting car ride, and on a sunny SF day, the reflective windshields of colorful vehicles exploring Lombard make for a peaceful view from the bottom. This road crosses through several historical, high-end neighborhoods, including Russian Hill and the Marina.
Haight St. is another San Francisco icon. It stretches from Market St. to Stanyan St. in Golden Gate Park but it’s most popular intersection is at Haight St. and Ashbury St. Only a few blocks from the infamous Golden Gate Park Panhandle, Haight-Ashbury has been home to generations of San Francisco hippies.
Castro St. is the busiest street of The Castro, San Francisco’s LGBT-loving neighborhood and one of the first openly gay neighborhoods in the United States. This street booms during the vibrant SF Pride Parade every summer, but even when the crowds aren’t around, rainbow flags and paintings decorate the entire district. Look out for Hot Cookie, one of SF’s favorite bakeries known for selling phallic macaroon cookies.
Divisadero is one of the hippest streets in the City. Extending from the Marina District all the way to Lower Haight, this road crosses through some of San Francisco’s trendiest sites. Divisadero is the perfect street to eyeball the quintessential SF hipster: bearded, flannel-clad men, and semi-gothic, business-casual women. If you’re traveling Divisadero, be sure to check out breakfast/coffee hotspot The Mill or soul-food favorite Brenda’s Meat and Three.
The Mission District has recently fallen to what some call a ‘hipsterfication,’ and Valencia Street was hit the hardest. This street houses plenty of bizarre, niche, restaurants, bars, and vintage stores. Hipster restaurants include Tacolicious and Crafstman and Wolves; look further down the road for various secondhand boutiques. Also on Valencia and 15th is Four Barrel Coffee, one of San Francisco’s fastest-growing coffee roasters. This street dead-ends at Market, which will then take you back downtown.