San Francisco's most famous bookstore was the first paperbacks-only bookshop in the USA and has always been at the cutting edge of writing and literature. It was the centre of the Beat scene in the 50s, renowned for it's publishing of Allen Ginsberg's poem 'Howl', and is still owned by its founder, poet Lawrence Ferlinghetti.

Benefit sells glam cosmetics with a retro twist. Started in San Francisco by twin sisters, Benefit offers makeup with a tongue-in-cheek attitude. Say goodbye to your old moisturizer with Dear John facial cream. Get rid of blemishes with Boo Boo Zap. Bum Deal is 'made with pride for your backside.' Being beautiful apparently means being sassy, too.

.Weekends are busy, busy at the Bi-Rite Market which showcases local farmers, vintners, chocolatiers and cheese mongers. Sample the season's best regional organic fruits, then take sandwiches to Dolores Park up the street.

Only locals lunch here, in an industrial shipyard on the eastern waterfront. Sit on the docks at umbrella tables and purge your hangover with Bloodies. The food's OK, mostly sandwiches and salads, but the crowd is a cool cross section, and the not-yet gentrified area shows a side of SF few visitors see. Musicians play weekends and the place become a bar.

Hobnob with the fancy-pants set. Stylish and casual Zuni has remained a standard in the San Francisco culinary parade for decades now. The modern menu changes daily but always features superb oysters (nearly two dozen varieties) and grilled and roasted meats and fish. Zuni's focaccia burger (not available during dinner) is one of the city's best.

One of several good neighbourhood spots along the Hyde St cable-car line, 1550's Euro-Cal cooking uses sustainably grown, local ingredients in its earthy, honest dishes. Locals pack the place every night; make reservations or wait in the tiny wine bar.

Inside the coolly elegant St Regis Hotel, Ame (ah-may) has a spectacular (though pricey) sashimi bar, an impressive selection of sakes and a rich menu of perfectly executed dishes such as sake-marinated black cod with shrimp dumplings, and risotto with eel and foie gras. Service could be better at this price, but the food is incredible.

Long-running Greens raises the standard for vegetarianism, with inventive cooking so good that even hard-core meat eaters leave sated. The former industrial space juts out over the water, with stupendous Golden Gate Bridge views. Or picnic by the bay with salads, sandwiches and fantastic black-bean chili from Greens to Go.

The 'Summer of Love' lives on at the Red Vic. Aside from being a cosy B&B with theme rooms related to harmonious living, the inn has a cafe and gallery with art that promotes peace and a 'change in human consciousness'. Naturally, everything is green and organic, including housekeeping practices.

Every room is different from the next, and each is dedicated to a specific event or theme. The 'Skylight' room - with an actual skylight - is dedicated to the sky and pure air, with soothing deep-purple walls. The 'Summer of Love' room memorialises the 'flower children's vision of peace and love'; it's done up with tie-dye, '60s concert posters and a wild burnt-orange and electric-blue colour scheme. Travelling with kids? Book the 'Playground' room, which pays tribute to America's first children's playground, in Golden Gate Park; the room brims with teddy bears, primary colours and giant crayons. And unlike the hippies, the Red Vic is kept spotlessly clean. Most rooms have private baths, but hallway baths have themes too - don't miss the way-trippy 'Aquarium' bathroom. Morning meditations happen Friday and Saturday mornings and lively conversations occur daily over breakfast.

The pinnacle of luxury, the St Regis honours its neighbour, the Museum of Modern Art, with stunning sculptures and fabulous paintings filling its public areas. Of San Francisco's top-shelf hotels, the St Regis and the Four Seasons run neck and neck for 1st place.

A butler escorts you to your room, where stitched cappuccino-coloured leather walls line the entry foyer. Closets and drawers are recessed behind a wall of white oak, facing a magnificent bed dressed with top-of-the-range Pratesi linens. Bathrooms sport travertine floors and oversized two-person soaking tubs at both ends; separate glass-enclosed showers have ceiling-mounted waterfall showerheads. Expect every conceivable amenity, including ingenious 'guest digital assistants', handheld PDA-like devices next to the bed that do everything from part the drapes and turn on the air-conditioning to tune your 42-inch wall-mounted plasma-screen TV, dock your iPod and check the weather. It's like a Gameboy for grey-at-the-temple CEOs. The only drawbacks are windows that don't open and surround-sound speakers placed behind a closed closet door, effectively muffling the sound.

Live like a local in a fully furnished apartment on a quiet, tree-lined street between the Castro and Mission districts. The historic 1880s Italianate Victorian has been lovingly restored by the architect-owner, and may actually look better than it ever has in its entire 120-year existence. And what a steal!

Every unit is huge - way bigger than a hotel room - and comes with a full kitchen. One of the owners is a stonemason and has outfitted the apartments with details like Brazilian-slate front steps and marble kitchen counters. Wonderful period details like wide-plank wood floors, deep claw-foot bathtubs, turn-of-the-century light fixtures, beadboard wainscoting and plaster ceiling medallions add rich character. Upstairs apartments have peaked ceilings, skylights and rooftop views across the city. The mismatched furniture - from contemporary leather dining chairs to Eastlake Victorian sofas - is typical of San Francisco homes, effectively blending style, comfort and functionality. It may initially seem pricey, but factor in the kitchen and the square-footage, and this is one screamin' deal.

Tosca Cafe did not need a mink coat to become a legend. The old-world bar, the tall espresso machine and the opera on the juke box set a nice stage and the celebrities (local and otherwise) sprinkled in the crowd put on a little show. A great place to sink back in a Naugahyde booth and savour a midweek martini.

This Mission stalwart hosts everything from DJ nights to rock bands to cabaret, but the big draw is Salsa Sundays (from late afternoon in the warmer months), when Latin bands perform outdoors and the whole joint shimmies and shakes. Come early for the free BBQ and dance lessons.

The Saloon is one of San Francisco's oldest bars; it first opened its doors in 1861, and is a rare survivor of the 1906 quake and fire. Today it attracts a mix of dishevelled old-timers, street people and local hipsters. Blues and rock bands perform nightly and on Sunday afternoons.

The place to go when you want to feel like a glamourpuss from a black and white movie, the Drake Hotel's swank top-floor lounge-with-a-view draws an upbeat crowd dressed to the nines. The nightly live music menu typically features a cool jazz starter, a more swinging main course, and something eminently danceable for dessert.

Nights here are full of award-winning, progressive theatre. A little more edgy than its sister at the Geary downtown, they'll do Shakespeare, but they'll also do work by Tony Kushner or Culture Clash. Classic, contemporary and works hot off the page are performed on one of their two stages near the downtown Berkeley BART station.

The most infamous prison in the US sits on an island in the middle of San Francisco Bay. A derelict military institution in the 1920s, it became 'The Rock', a maximum-security prison housing America's most wanted, including Al Capone. It closed for business in 1962, but with so many stories and mysteries, it's a magnet for tourists.

Filling one of the city's grooviest looking buildings, SFMOMA's collection is almost equal to the setting and getting stronger by the acquisition. Twentieth-century art is the clear forte and recent aquisitions include Mark Rothko's No 14, 1960 and Jim Hodges' No Betweens.

The permanent collection includes work by all the great American and European artists but is particularly strong in American abstract expressionism, with major works by Clyfford Still, Jackson Pollock and Philip Guston, and in fauvism, with works such as Henri Matisse's 1905 masterpiece Femme au Chapeau. The permanent collection also contains several works by Mexican painters Diego Rivera and Frida Kahlo and by Bay Area artists Robert Arneson and Richard Diebenkorn. Willem de Kooning, Marcel Duchamp, Rene Magritte, Robert Rauschenberg and Andy Warhol are all represented.

The Golden Gate Bridge is one of the best, and certainly the biggest, art deco constructions anywhere. From its 210m (700ft)-high towers to its 360° views to its 'international orange' colour, selected to blend with the natural environment, it's a spectacular delight - and was designed as much for people as for cars.

The 210ft (60m) high, concrete Coit Tower crowns the top of Telegraph Hill and is a monument to the firefighters of San Francisco. It has views from the Golden Gate to the Bay Bridge, and a sensational view of the slopes of Nob Hill and Russian Hill as they fall into North Beach. The interior is decorated with beautiful 1930s frescoes.

Chinatown is densely packed and colourful. There are some tacky curio shops, but the 30,000 Chinese - most of whom speak Cantonese - live in a tightly knit, distinctly un-Western community. It's a great place for casual wandering through narrow alleys, where on quiet afternoons you can hear the clack of mahjong tiles from behind screen doors.

The most colourful time to visit Chinatown is during the Chinese New Year in late January or early February, with a parade and fireworks and other festivities.

San Francisco's great playground is a cunningly designed rectangle that appears far larger than it is. Woods line the edges, and nature lovers can wander in the fern dell, the arboretum, the Japanese Tea Garden and the tulip gardens. It's hard to believe it's all artificially created on top of sand dunes.

Long taken for granted, the De Young has reasserted itself magnificently with its new building, which opened in 2005. The new twisting tower, standing 144ft (44m) and clad in copper, was controversial in San Francisco, which despite its liberal image can be stodgy when it comes to architecture.

As the city warms to its new landmark, many are beginning to appreciate the new De Young's well lit galleries and pleasant courtyard patios. The museum has a fine collection of pre-20th century American art, and has built a particularly solid collection of African and Pacific Island art. Additionally, selections from SFMOMA's deep photography collection frequently show here.

Cable cars make the everyday getting around the city fun. From the standing room along the sides the world slides by at 9mph as your wooden car climbs up and down the hills above the heart of town. There's fresh air, water views, the sounds of cables and bells, and the smell of burning pine (they use wooden blocks for brakes).