1. Tour the city by cable car
A few dollars in San Fran can buy you a roller coaster ride of the city. San Francisco's cable cars are a cute relic of a time before buses and cars – and they give a great retro-style tour of the city's hills, and neighbourhoods: Union Square, Chinatown, Fisherman's Wharf and the other districts.
Catch one going up the precipitous Nob Hill, and for extra thrills, hang off the running boards, Doris Day-style.
2. Escape to Alcatraz
Pay your respects to one of the world's most infamous prisons. The ominous buildings are no longer in use (its last inmate left in 1963), but thanks to Hollywood films, such as 'Birdman from Alcatraz' in 1962, and 'Escape from Alcatraz' in 1979, Alcatraz remains a popular attraction, luring over a million visitors a year. The audio tour, which features interviews with former inmates and guards, is powerful, chilling and evocative.
3. Take in an incredible view
If there’s one classic San Francisco view – in a city with a multitude – it is the vista across the Bay from Pacific Heights and the northern waterfront. What sets this view apart from all the others is the presence of the iconic Golden Gate Bridge.
4. Soak in art for cheap
San Francisco's Museum of Modern Art is second only to New York's in size and the collection includes works by artists as varied as René Magritte, Jeff Koons, Piet Mondrian (characteristically geometric) and Marcel Duchamp (a urinal). However, the special exhibits are the real draw.
Get it all for less on a Thursday night when museums go easy on the pocket. Admission to San Francisco MOMA is half price between 6-8.45pm, and the Asian Art Museum – a soaring beaux-art building that houses 17,000 Asian art treasures – offers reduced admission after 5pm (February and September only).
5. Line up for studs and trannies
San Francisco is the beating gay heart of America and its hedonistic gender-benders throw good parties. Try omnisexual techno rave Endup or drag venues such as Asia SF, a restaurant and lounge where sexy 'gender illusionists' run the bar. Stud club prides itself on being open to partygoers of all stripes and hosts the best drag in town at the hair raising Trannyshack. For a taste of old-school drag catch glittery weekend performances by the grandé dames of Hot Boxxx at Aunt Charlie's Lounge. June's month-long Gay Pride, the largest gay carnival in the world, is the highlight of the year.
6. Hit a nostalgic note
Some accuse San Franciscans of being mired in musical nostalgia – fixated on 1950s Beat bohemia or stuck in a Summer of Love flashback. Perhaps they have a point, but in a city with a musical history this extraordinary, it would be harsh to criticise a music-lover for wanting to explore the iconic, still-raging hotspots where it all happened.
The town’s grandest beauty is the Great American Music Hall. Constructed in 1907, this erstwhile bordello has maintained its baroque, gilded beauty well. Further east on Geary is the Fillmore, once a jazz-era big-band venue that went by the moniker the Majestic Ballroom, it saw memorable shows by the likes of the Who, Eric Clapton and Santana. Opposite, The Boom Boom Room was named by John Lee Hooker who held court here until his death in 2001. Further south in Downtown stands the ex-movie palace the Warfield, where Louis Armstrong once shared the bill with the talkies. And finally, towards Fisherman’s Wharf, Bimbo’s 365 Club sets the scene for early ’50s supper-club glamour with a parquet dancefloor, leather booths and kitsch-cool girl-in-a-fishbowl theme.
7. Dig into organic cuisine
Demand for seasonal food and sustainable agriculture kicked off back in the 1970s and it has fuelled an array of Organic treasure-troves. Traci Des Jardins of Jardinière oversees the menu at Acme Chop House, and her commitment to sustainability and organically raised meat sets it apart from most steakhouses. In the drinks department, the chic and intimate Fish & Farm has an all-organic cocktail list, while Millennium has one of the best all-organic wine lists in the US and puts out an admirable vegetarian and vegan menu too.
8. Feel the 'Beat'
To get up to speed on the Beats and their legacy, check out the Beat Museum (540 Broadway, at Columbus Avenue, 399 9626, www.thebeatmuseum.org) before heading over to what was both the head and the heart of the Beat movement, City Lights bookshop. The legacy of Beat anti-authoritarianism lives on in this publishing company and bookshop, co-founded by poet Lawrence Ferlinghetti in 1953. Be sure to head upstairs to the Poetry Annex, where books by the Beats sit beside contemporary small-press works and the photocopied ravings of ’shroom-addled hippies, raging punks and DIY indie voices. Readings here are real events. Step across Jack Kerouac Alley just next door to Vesuvio, which welcomes mad poets and tourists in equal measure, much as it did when Kerouac and crew drank here in the 1950s. Tosca was another favourite watering hole of the Beats, and today attracts actors and filmmakers.
9. Toast with designer tipples
Mushroom Martini anyone? Chefs at top SF restaurants have been making a name for themselves by drawing on top-shelf spirits and seasonal produce to create some mixologie masterpieces. Expect harrissa, lemongrass, infused sugars and chrysanthemum blossoms in your cocktails. Try absinthe and all manner of exotic tipples at Absinthe; Vietnamese-fusion cocktails at Slanted Door; a simply head-spinning array of boutique beers and single malts in Alembic; or all-organic cocktails at Fish & Farm.
10. Enjoy a world record musical
Be teased, amused and shocked by Beach Blanket Babylon, the longest running musical revue in theatrical history. It sells its formulaic blend of songs, puns and outrageous headgear with such irresistible conviction that it has become an institution. Poking fun at current political figures and celebrities, it's an irreverent queer take on the straight world that still plays to full a house most nights.
11. Have a 'Bullitt' moment
No film buff will be able to resist driving down the street on which Steve McQueen has a high-speed car chase in the 1968 film 'Bullit'. Dubbed the world's most crooked street, Lombard Street snakes steeply down from Hyde Street to Leavenworth passing Victorian mansions and landscaped blocks along the way.
12. Slip on some vintage threads
Old is the new new in San Fran, a city with a vibrant vintage clothing scene. Get bargain basement prices at thrift stores or step into one of the amazing vintage boutiques. Painted Bird is an extremely well priced, brilliantly edited vintage outpost selling granny sundresses, glam disco bags, flash but cute jewellery and styling shoes and boots from the 1980s, ’70s and earlier eras. Climbing up the price ladder Ver Unica sells unique retro finds.
13. Popcorn up for alfresco cinema
San Francisco truly loves its cinema and hosts a dozen or so film festivals every year, which screen film fodder including animation, Jewish films, lesbian and gay films and silent films. But best of all are those that bring the viewer out of the theatre and into the fresh air. Grab a picnic basket, a blanket and a bottle of wine and you're set for a romantic or family-friendly experience like no other.
The largest of the outdoor festivals is Film Night in the Park (www.filmnight.org) featuring classics like Casablanca. For more subversive fare take your picnic to the Overcooked Cinema Film Festival (www.overcookedcinema.com), which shows shorts and videos every second Monday in June, July and August.
Every night is alfresco night at Foreign Cinema. This restaurant is dominated by a film screen on one side of the outdoor courtyard dining room, on which classic foreign films are projected.
14. Skate through Golden Gate park
Roughly three miles in length and half a mile wide, Golden Gate Park is one of the largest man-made parks in the world and a testament to human dominion over nature. Join the locals by skating, jogging, walking or biking around it and you'll see a multitude of fantastic sights: paddocks, bridges, the white-domed Conservatory of Flowers, the Japanese Tea Garden, where fortune cookies were supposedly invented, and Hippie Hill – the sun-kissed epicentre of '67's Summer of Love. Skates and bikes can be hired at Golden Gate Park Skate & Bike.
15. Drink hard, speak easy
One of the institutions that resulted from the Prohibition Era (1920-1933) has recently been revived: the speakeasy.
The venerable Café du Nord started life as a speakeasy in 1907, and its basement bar and music venue retain their classic Victorian interiors. The House of Shields started by one Eddie Shields in 1908, is still said to house a subterranean network of tunnels once frequented by surreptitious tipplers. Bourbon & Branch has somehow managed to rekindle the spirit of the speakeasy. Reservations are required (that's also when you'll learn the password to gain entry) and the only indication that there is anything housed in the dark, corner building is the 'Anti-Saloon League' sign (a nod to an actual organisation) that hangs outside.
At one of the most notorious speakeasies in San Francisco, Coffee Dan's, patrons would access the basement bar by riding down a 15-foot slide. Featured in the 1927 Al Jolson movie, The Jazz Singer. Coffee Dan's is now home to the aptly named Slide, as it is still accessed in the same bizarre manner.
16. Root for the San Francisco Giants
Even if you know nothing about home runs and fly balls, being part of a baseball audience is still a quintessentially San Fran experience. The two Bay Area teams are the Giants, whose roster is stacked with veterans, and have a middle-class following and a lovely Downtown stadium (San Francisco Giants). Oakland Athletics, on the other hand, have a younger team and a more working-class fan base. You can often bag cheap tickets at the game on game days, or catch a few innings for free via the viewing window behind right field.
17. 'Pop your collar' with a hyphy
There may be a passing linguistic resemblance, but the blinged-out party animals of the Bay Area hyphy mvement counldn't be more differnet from the hippies who danced on these same streets almost half a century ago.
Okay, so there are similarities – the rabid anti-authoritarianism and semi-theatrical dress code, but they are unlike hippies in every other way. Advocates of hyphy (pronounced 'high-fee') take pride in 'going dumb' or 'getting stupid' and have patented countless acts of pointless flamboyance, like getting out of cars and running beside them as they roll driverless down the street. Look out for 'stunna' shades and mega-long sports jerseys.
The best way to check out the Bay Area's stars is to keep tabs on their myspace pages, although their records to get aired at local hip-hop nights in clubs like Milk, Duplex and Transfer.
18. Walk the streets with a salmon
In an effort to raise spirits during the arduous and lengthy rebuilding process that followed the 1906 earthquake and fire, Randolph Hearst's San Francisco Examiner started the Bay to Breakers Foot Race in 1912. At the height of its popularity, the race attracted more than 110,000 participants. These days, weekend warriors dressed as salmon, jog-walkers pushing kegs of beer in shopping carts, and footloose nude zanies run, walk or stumble from the foot of Howard Street (bay), a distance of about 7.5 miles to Ocean Beach (breakers). The race takes place from Howard & Spear Streets, SoMa, to Ocean Beach, Golden Gate Park on the third Sunday in May (359 2800/www.baytobreakers.com).
19. Notch your culture up a pointe
Home to America's longest running professional ballet company, the San Francisco Ballet, founded in 1933, has a lot to offer the dance enthusiast both classical and contemporary.
The San Francisco Ballet mixes traditional works and new choreography. The Smuin Ballet (www.smuinballet.org) specialises in contemporary dance and is known for its innovative repertory and The Alonzo King's Lines (www.linesballet.org) is famous for the vulnerability and tenderness of its pieces.
20. Try out old school Americana
The ice cream sodas are frothy, the mac and cheese is magnificent and the table tops are Formica; go to St Francis Fountain diner for a retro eating experience. On York Street in the colourful Mission & Castro district, it links the past of the area with the trendy present, after new owners gave the ancient soda fountain a 21st century revamp.
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