I started my journey with a hearty breakfast at an unpretentious-looking restaurant called Sweet Maple in Lower Pacific Heights. The menu cannot claim the same modesty.
The restaurant is known for its "millionaire's bacon," a thick-cut, sweet-and-spicy version of the breakfast staple that costs $4 a slice. Its decadence at least made me feel rich.
Jane coffee shop was packed at midday with shoppers hauling bags and others gazing at smartphones. They nursed cups of Stumptown Coffee and ate house-baked pastries.
The Clay Theater, in business for over a century, is a single-screen movie theater that still hosts regular midnight screenings of "The Room" and "The Rocky Horror Picture Show."
A quick detour off Fillmore Street brought me to Alta Plaza Park, a former rock quarry that now features a large lawn area, two tennis courts, a children's playground, and trails.
In the 1870s, these hills overlooking the San Francisco Bay were filled with laborers enjoying a building boom in what was then the largest city west of St. Louis, Missouri.
After the 1906 earthquake shook San Francisco, fires consumed some 500 city blocks. The wealthy stood around the burned rubble of their homes and wondered where to settle.
The best view in the city was in Pacific Heights, and with that swath of real estate now up for grabs, old-monied families claimed the working-class neighborhood as their own.
Of the 70 billionaires living in the Bay Area, 28 reside in San Francisco, and many call Pacific Heights home. The area's zip code has a median home sales price of $2.09 million.
Jony Ive, Apple's longtime head of design who recently took back the reigns of the company's design team, scooped up this Tudor palace for $17 million in 2012.
Source: San Francisco Chronicle and Redfin
Tech mogul David Sacks, who sold his startup Yammer to Microsoft for $1.2 billion, and wife Jacqueline dropped $20 million on a mansion that towers over Broadway.
Source: Business Insider
Oracle's Larry Ellison, the first tech giant to arrive on Billionaires Row in 1988, lives across the street. He bought a house for $3.9 million but tore it down to build this boxy abode.
Source: Vanity Fair
Ellison has been known to ruffle feathers on the block. He took his neighbors to court because he said their trees obstructed his bay views and hurt his property value.
Source: Vanity Fair
Zynga's Mark Pincus, an early investor in Facebook and Twitter, and his recently separated wife Alison Pincus, founder of One Kings Lane, own a New England-style home nearby.
The couple filed for divorce earlier this year.
While not everyone on Billionaires Row is thrilled to share their slice of San Francisco with the technorati, the newcomers have an ally in socialite and entrepreneur Trevor Traina.
Traina, who has been called "San Francisco's undisputed social king," is a member of one of the city's most established families and founded several startups, including IfOnly and DriverSide.
He is credited with bridging the old-money and new-money families of San Francisco when he tipped off tech moguls to a number of Pacific Heights houses coming on the market in 2012.
