As Chinatown spills northwards, its borders with the North Beach district become blurred. There’s no diluting of the North Beach’s strong Italian flavour, however: the area having been the base of the city’s Italian community since the 1880s. Our walk reveals the churches, cafes, bakeries and delis that have earned a niche in community folklore. It also explores some of the sites associated with 1950s North Beach when, attracted by cheap rents, cheap wine, and late-night discussions in the cafes, a bunch of disaffected writers and artists colonized the area, soon to be immortalized as the leading lights of the beat generation. The walk leaves the North Beach to climb into Telegraph Hill, a quiet residential area where secluded lanes and stairways hold intriguing buildings, and ends at the major city landmark of Coit Tower.

 Start: Close to Transamerica Pyramid, at the junction of Montgomery and Clay Streets. From the Financial District northwards, Columbus Avenue cuts a diagonal swath through the North Beach, intersecting the otherwise chessboard street pattern and creating sharply angled junctions. There are some triangular-shaped buildings, too, such as the Columbus Tower, a classic flatiron structure dating from 1905 that was bought and restored in the 1970s by film-director Francis Ford Coppola and now a fashionable apartment building. As old as the Columbus Tower and just as well preserved, the saloon bar of the San Francisco Brewing Company, 155 Columbus Avenue, delights discerning beer drinkers with its own brews. Legend has it that boxer Jack Dempsey once worked here, helping drunken brawlers to find the street. Broadway meets Columbus Avenue to form San Francisco’s busiest crossroads.

Just south of Broadway, City Lights, 261 Columbus Avenue, was opened by local poet Lawrence Ferlinghetti in 1953, with the intention of using the profits to finance a small literary magazine. The first all-paperback bookshop in the U.S., City Lights achieved greater fame by publishing Allen Ginsberg’s narrative poem, Howl, in 1956. The controversy which ensued brought worldwide attention to the underground cultural scene flourishing in the North Beach – what became known as the beats (derisively dubbed “beatniks” by a San Francisco newspaper columnist). The shop continues to carry the definitive stock of writings by and about the beats, plus a wide range of political and general titles on its tightly packed shelves. Facing City Lights, Vesuvio Cafe was, and still is, the definitive beat hang out, complete with satirical art and bizarre ornaments. The alley between the bookshop and the cafe has been re-named Jack Kerouac Street to mark one of the beat generation’s leading figures.

Continuing north along Columbus Avenue, the corner with Vallejo Street finds Molinari’s Deli, purveyors of fine cheeses, meats (the salami in particular has many admirers) and pastas – any or all of which will be placed in a sandwich on request. Across the street, St. Francis of Assisi Church was founded in 1849, becoming the first Catholic church established in California since the Spanish missions. Caffè Trieste, 601 Vallejo Street, is another local landmark for its espresso coffee and live opera on Saturday afternoons.

Turn on to Filbert St (number 700), the Victoria Pastry Company has been turning out wondrous Italian cakes and French pastries since 1914. Just north at 678 Green Street, the terracotta-decorated Fugazi Hall was financed by John Fugazi, founder of the Transamerica Corporation, and donated in 1912 to the North Beach’s Italian community. A pocket-sized but much loved patch of greenery, Washington Square has a statue of Benjamin Franklin at its centre and the twin-spired Church of St. Peter and St. Paul on its northern side. The 1924 church reflects the ethnic balance of the community by saying Mass in Cantonese, Italian and English. The park is in constant use by practitioners of tai chi and each weekend sees dozens of artists displaying their wares.

Grant Avenue north of Broadway is lined by numerous one-of-a-kind shops capturing the eclectic spirit of the North Beach. None is better for a lengthy rummage than The Schlock Shop, number 420, which lives up to its name with an enormous stock of second-hand clothes, ornaments, bric-a-brac – and much more that defies description.

Soma

In Soma (South of Market Street), the splendid buildings of Yerba Beuna Gardens area have helped invigorate a former industrial area that used to be littered with disused warehouses. Numerous arts and cultural institutions located here include the excellent San Francisco Museum of Modern Art (www.sfmoma.org), 151 Third Street. Housed in a spectacular building with a black and white truncated cylinder rising from its roof, SFMOMA’s horde of European paintings includes Cubist eye-catchers such as Pablo Picasso’s Head in Three-quarter View. Also prominently featured are architecture, design and photography.

Telegraph Hill

Further north along Grant Street, the noise and commotion that characterizes the North Beach gives way to the sedate Telegraph Hill district, a well-to-do residential area of old and new houses set across a steep hillside. Rising steeply from Montgomery Street the Filbert Steps pass the well-tended gardens of equally well-tended 19thC cottages on a stiff climb to Telegraph Hill’s major landmark, Coit Tower.

When Lillie Hitchcock Coit died in 1929, she left $100,000 for a memorial to the city’s volunteer firemen. The result – uncharitably said to be a fire hose nozzle – was Coit Tower, completed in 1934. The views from the 210-foot-high observation level are spectacular but equally interesting are the 16 murals decorating the tower’s ground floor, a Depression-era Public Works Project.

Alcatraz Island

From the top of Coit Tower, the island of Alcatraz and the buildings of its infamous prison which incarcerated America’s Most Dangerous between 1933 and 1963 are (fog permitting) clearly visible in the bay. Tours reveal the cells, canteen, exercise yard and much more of the former prison using a taped audio commentary recorded by former guards and inmates, who served an average of ten years and rarely received a visitor. The museum describes the island’s earlier history as a fort and military prison and a brief period of Native American occupation before public tours began in 1972. This trip is rightly very popular and early booking is advised at any time; in summer it’s essential, they’ll set you back about $30 per person (www.alcatrazcruises.com).