City Guide for a Flâneur: San Francisco

Walking Map guide to the city

It’s an east coast meets west coast, European city on the Pacific with an eternal springtime, it’s a port town with a rich, yet comparatively recent history. Each neighborhood carries with it a distinctive architecture and atmosphere. Foreign languages hum on the sidewalks, in cafés and in restaurants.

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Despite its delightful weather and inviting architecture, San Francisco is as international and sophisticated as it is wrought with a very palpable problem of homelessness en masse and drug addiction in the streets. Young and old, shoed and barefoot, you will see—see people who do not appear to be aware that they are among your world, conversing with the invisible, sleeping in parks or on the sidewalks. It’s a very sad and real part of the SF populous.

September and October are the summer months in San Francisco. Still, it’s an pleasant mid-70’s during the day and an agreeable low-60s in the night. The sun shines brightly every day. It’s blue skies as far as the eye can see from the center of the city and then “Karl the Fog” lurks over the surrounding hills off the ocean and encircles  the bay with the evening sunset. The second week of October also marks Fleet Week in San Francisco which means fighter jets zoom up, down and in figure eights around the city breaking sound barriers and stopping locals and tourists alike in their tracks with their echoes, booms and aerial dances.

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For all you flâneurs out there, who like me, love to experience a day in the life of a city, and to stroll the most swell streets and boutiques — here is your guide on which neighborhoods to check out and which streets to saunter.


There is no shortage of great coffee shops with large indoor and patio workspaces, beers on tap and bar food like you haven’t tasted before in San Francisco’s most hipster hood. Walk Valencia Street, Folsom Street, and 18th Street. Read more about what to do in the mission here. Plan your day’s stroll over coffee and breakfast in the delightful Stable Café‘s outdoor patio and succulent garden.

The Mission District on Roadtrippers


Walk up Fillmore Street and peep the storefronts of all your favorite global brands like Sandro, Rag & Bone, and Steven Alan. There are several restaurants and cafés on the sloping block—check out Palmer’s for a bite and cocktail. Continue north on Fillmore into Pacific Heights and walk passed the stately homes on Vallejo which peer from high on the hill at the San Francisco Bay.

Lower Pacific Heights on Roadtrippers


The Hayes Valley is a charming stretch of unique boutiques and quaint cafés with a northern European feel. The area also boasts its own biergarten and an art piece on which you can freely sign your name in Patricia Green Park.

Hayes Valley on Roadtrippers

Head up the hill on Hayes Street to Steiner Street and snap a pic of the Painted Ladies.

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They’re not actually ladies but rather, these homes which look like dollhouses.


The Haight-Ashbury district, named for its intersection of Haight and Ashbury Streets gained fame as the birthplace of the summer of love. The hippie movement grew out of this community and influenced the nation. Check out this recollection piece in Rolling Stone.

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Haight-Ashbury on Roadtrippers

You can follow Haight Street all the way into Golden Gate Park.


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In the late 1800s, millionaire Adolph Sutro built the Sutro Baths at the edge of Point Lobos and the Pacific Ocean in the area of Land’s End. Intended to be recreational and educational, Sutro had built these huge bathhouses for San Franciscans but was never able to get them to make the trek in enough numbers to keep the facilities sustained. He was desperate to build attendance and in the extravagance, even built an ice skating rink in the facilities. Ultimately the buildings were left unsustained and empty and what was left of them burned to the ground in the 1960s. Since 1973 it’s been a national recreational area and the Sutro Bath ruins seem to draw more tourists than they ever did as baths.  Walk on trails by the baths or along the whole of the designated Land’s End area. Ominous Karl the Fog and rough Pacific waves make for a dramatic setting and for a break, stop at the Cliff House for a libation and oysters. To learn more about the Sutro Baths, check out this awesome 99% Invisible podcast episode.

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Photo credit: National Parks Service

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This is one of the more posh neighborhoods of San Francisco. Stroll Union Street for eateries, wine bars, shops and Soul Cycle. Head to famed Lombard Street for a stroll or a drive down the most “crooked” street in America. Built among the steepest of the steep hills, the curves act like traverses as you might ski down a black diamond making your way to a more comfortable blue. Ease your legs after the steep hills with a night of jazz at the Big 4, named for four men from the Central Pacific who rose to the top and were the most talked about gents in the town.

Russian / Nob Hill on Roadtrippers


This is the financial district of San Francisco.  The Ferry Building is a sort of larger version of Chelsea Market with more natural light. It’s built on the waterfront with its own bike path akin to the West Side highway’s with a view onto the San Francisco Bay Bridge and the hills of Oakland. My lunch date in the area was Google (yum!). Head northwest toward Nob Hill and get lost in the City Lights Bookstore and eat in nearby Chinatown or Little Italy.

Embarcadero on Roadtrippers

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The area of the Castro is most well known for its gay community—as a home to activism for equality and civil rights. Notably, Castro Street was home to the offices of Harvey Milk—and also the location of his assassination. The area continues to be adorned with rainbow crosswalks and pride flags in every window. A local launder is called “Sit & Spin.” While here, check out Café du Nord’s downstairs for live jazz and a delicious old fashioned.

The Castro on Roadtrippers

If you enjoy this guide to San Francisco, you can take it with you. Using the GPSmyCity app guides can be downloaded to your phone for offline use.

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By the way, if you do download it, I’d love to hear from you. Did you enjoy using GPSmyCity? I want to make sure scouts and findings on Maidstone Buttermilk are as helpful to you as possible.