Just west of and high above Chinatown, Nob Hill became accessible with the invention of the cable car in 1873 and it was selected by the Big Four (railway magnates Charles Crocker, Mark Hopkins, Collis P. Huntington and Leland Stanford), and several of the silver barons of the Comstock Lode, as the site of the most expensive homes ever seen in California. The 1906 earthquake and fire finished off the millionaires’ mansions but Nob Hill is still the city’s most prestigious address, with a cathedral, a park, and several very elegant hotels occupying the spots where the great houses once stood.

This route starts from Grace Cathedral at the crest of Nob Hill, tours the adjacent buildings of interest and descends to the cable car barn – a museum devoted to the city’s most romanticized form of transportation. From here, the walk (which may be combined with a cable car ride) leads north into Russian Hill, passing an excellent collection of San Francisco’s varied residential architectural styles, and finishes in Pacific Heights at the very chic shops that fill the quaint Victorian buildings of Union Street.

 Start: Junction of California Street and Jones Street. The building of Grace Cathedral began in 1910 when a corner stone was laid on the former site of the Crocker mansion. The construction, to a design based on Paris’s Notre Dame, was not completed until 1964, however. Though a pleasing neo-Gothic pile, the cathedral has few notable features save for its stained-glass windows depicting Californian history, a pair of gilded bronze doors from a Lorenzo Ghiberti cast, and the 15thC French altarpiece and Flemish reredos found inside the Chapel of Grace (only open for services). A few strides from the cathedral, the small but restful Huntington Park occupies the former plot of the Huntington mansion. Overlooking the park are stylish high-rise apartment blocks, luxury hotels and – directly across Cussman Street – the brownstone mansion built by silver-baron James C. Flood and the sole Nob Hill survivor of the 1906 fire. Since 1911, the Flood Mansion has belonged to the Pacific Union Club, an ultra-exclusive male-only haunt for California’s very seriously rich.

The Pacific Union Club is strictly off limits to non-members, but a couple of the neighbouring hotels can happily be explored. At 950 Mason Street, the Fairmont Hotel (www.fairmont.com/san-francisco) was founded in 1902 by the daughter of another Comstock Lode silver mine beneficiary, James G. “Bonanza Jim” Fair. Walk through the grand lobby and sink into a comfy armchair to admire the ground floor’s wealth of Beaux Arts features, then ride the tower’s glass-sided elevator for dizzying views of the city.

Directly across California Street, the Intercontinental Mark Hopkins Hotel (www.intercontinentalmarkhopkins.com) opened in 1926 on the site of the Hopkins mansion. A noted high-society rendezvous, the hotel has often hosted U.S. presidents and in 1945 staged the meetings that led to the founding of the United Nations. The equally high-class but much less ostentatious Huntington Hotel (www.thescarlethotels.com/huntington-hotel-san-francisco), 1075 California Street, was raised on the site of Leland Stanford’s mansion. With few showy features to encourage sightseers, this hotel finds favour with those who like to enjoy their wealth discreetly.

Descend from the crest of Nob Hill to the Cable Car Museum (www.cablecarmuseum.org) at the corner of Washington and Mason Streets. Nowadays the cable cars are more of a tourist attraction than a viable means of getting around, but from 1873 to 1982 they were an essential part of the San Francisco public transportation system. Exhibits at the barn explain the development and the workings of the system: on the lower level, the cable-winding gear can be seen (and heard) in operation, pulling the 11 miles of steel cable that lie beneath the city’s streets.

 After viewing the barn, conserve your strength by hopping aboard a northbound cable car on the Powell-Hyde Line to climb the steep streets of Russian Hill. Many fine examples of the architectural styles that have shaped San Francisco are scattered throughout this district, and several contrasting buildings are grouped together on the 1000 block of Green Street. The English Tudor look of number 1088, the Beaux Arts villa at number 1055, and the South western pueblo-style house at number 1030, being just three in close proximity. The oddest house on Green Street is the 1859 Feusier Octagon House, number 1067, partly hidden behind a large hedge: its eight sides are believed to bring luck and health to the occupants. Six blocks east at 2645 Gough Street stands another octagonal house, built in 1861 and now owned by the Colonial Dames of America.

Immediately north of Green Street, Union Street is the showpiece thoroughfare of Pacific Heights, lined by the boutiques, clothing stores and restaurants where the predominantly well-heeled and fashion-conscious residents like to buy expensive ornaments for their homes, to dress themselves in European-designer clothes, and be seen dining on pricey French and Italian food. Many of the businesses occupy carefully preserved buildings – decorated by wrought-iron work and imitation gas lamps – which date from the late 1800s, when the area was dairy farmland and nicknamed Cow Hollow. Number 2040 Union Street was the three-story home of one early dairyman, James Cudworth. At number 1980 are the twin houses – identical bungalows joined by a common wall – which Cud-worth built as wedding presents to his two daughters.

Browsing the Union Street speciality shops captures the chic mood of contemporary Russian Hill. Three blocks north, the section of Lombard Street between Hyde and Leavenworth Streets is usually marked by camera-pointing tourists aiming their lenses at what is famously known as the “crookedest street in San Francisco.” The steepness of the gradient made the street impassable for vehicles until a series of gardens were installed in the 1920s, enabling traffic to make the descent in corkscrewing fashion. The intention to raise the value of the street’s properties backfired as publicity spread. The procession of cars weaving downwards, observing the 5 mph speed limit, is seemingly endless. Walk down Lombard Street by its staircase pavement and cross into Chestnut Street for the San Francisco Art Institute, (www.sfai.edu) number 800. The West Coast’s oldest art school, the Institute was founded in 1897 and moved into these vaguely monastical-style buildings in the 1920s. Inside is a tremendous Diego Rivera mural, several galleries with noted temporary exhibitions, and a cafe with splendid views. The tower is said to be haunted by the creative spirits of former students who never realized their full potential.

Civic Centre

The beautiful Beaux Arts buildings of the Civic Centre were raised in the early decades of the 20thC as part of a grand plan to reshape San Francisco in the image of the great cities of Europe. The plan was thwarted by profit-hungry property speculators, however, and only this tight grouping of public buildings gives an indication of what might have been. None is more imposing than the 1915 City Hall, topped by a dome modelled on St. Peter’s in Rome and its entrance dominated by a flowing baroque staircase The Civic Centre is safe to explore on foot, although many of the city’s homeless congregate on its grassy plazas, and just north lies the seedy Tenderloin area.