Free-wheeling the Frisco way

Cycling in San Francisco: not the most obvious form of transport. After all, one of the motifs of the city – besides the Golden Gate Bridge, the cable cars, the fog and the hippies – is its hills. The long, and sometimes preposterously steep, hills. But among the cycling fraternity, San Francisco is also famous as a cradle of "fixie" culture: those gearless, fixed-wheel bikes beloved of cycle messengers, who first scaled Frisco's gruelling gradients during a mail-delaying rail strike in 1894.

Today, the colourful professional cycle couriers compete for Tarmac with thousands of thick-thighed amateurs. As a cycle commuter in London, I need no convincing that it's the best way to see any city. And so I found myself, one sunny morning, at Bike and Roll, a cycle-hire firm at the corner of Columbus and Lombard streets in the North Beach district.

Now, I'm not one of those mad weekend cyclists who completes mountain stages of the Tour de France in their spare time, but at home in comparatively contourless London, I ride to work every day (almost) on a swift, single-speed bike that cycling nerds consider adequate, and which non-cyclists seem to find snazzy. The rental bike with which I was presented at Bike and Roll was like an armchair by comparison: an armchair that I planned to ride through the urban equivalent of the Pyrenees. Thankfully, it did have gears.

The morning began with a group bike tour led by one of the firm's friendly guides. We rolled down to Fisherman's Wharf and along the shoreline to Fort Mason, a former military base that now houses a youth hostel. Then we glided to the desirable Marina District, where house prices are high despite their vulnerability to tectonic shifts (the area was flattened in the 1989 earthquake). We were headed, however, for the Golden Gate Bridge. It's a gentle, winding climb up to Route 101 (the freeway that crosses the bay on its way up the Californian coast) and, once on the bridge's pedestrian pathway, a saddle is a better place than a car seat from which to appreciate this engineering achievement, and the views that it affords.

Our destination, on the far side, was the birthplace of mountain biking: Marin County. It was here, during the 1970s, that local cyclists began modifying their rides for freewheeling down the long mountain trails in Mount Tamalpais State Park. We, however, were just freewheeling down the road into Sausalito, a pretty waterfront town that faces back across the bay to San Francisco. It's worth a trip, if only to buy lunch from the plainly named eatery, Hamburgers. The line for food here stretches down the street for two simple reasons: first, the burgers are spectacular (lucky, since they are the only item on the menu); and second, there is no space in the restaurant to eat them. So we took them across the street to eat in the park beside the ferry port.

The ferry across the bay accommodates bicycles and takes passengers within a key's throw of Alcatraz Island on its way back to Fisherman's Wharf. Here, I split from the group to continue my afternoon expedition alone. Heading south along the Embarcadero took me close to the City Lights bookshop, haunt of the Beat poets. But I was aiming for a more modern literary landmark on the other side of the city: 826 Valencia is a writing centre for children aged between eight and 18, run by the author Dave Eggers and his miniature publishing empire, McSweeney's.

Because 826 is a retail location, the powers that be demanded a shop there. Thus, the front of the writing centre is a wonderfully charming "Pirate Supply Store", selling eyepatches, scurvy medication, messages in bottles and other such treasures – along with most of the recent McSweeney's back catalogue.

The area surrounding Valencia Street is known as The Mission, an up-and-coming hipster district filled with super bookstores and bars. The man dressed as a snow leopard who trundled past me on roller skates as I locked up my bike outside 826, with a ghetto blaster playing the Rocky theme tune, may have been on his way to a carnival, but here he wouldn't be too out of place on an average Tuesday.

Valencia Street is also home to Mission Bicycle, a specialist store selling custom-built, fixed-gear bikes, whose advisory board includes the two-wheeled top brass from some of the Bay Area's biggest technology companies: Google, Digg and Vimeo. From the Mission (I discerned using my basic city map) I could cycle up through the Castro district to Haight-Ashbury, once a haven for hippies.

This, however, proved more of a challenge than I expected. Getting to Castro is simple enough. As anyone who saw the Oscar-winning Milk will know, this is the centre of San Francisco's gay community, where the activist Harvey Milk lived prior to his untimely death. What the film didn't demonstrate was that getting from Castro to Haight-Ashbury involves climbing some of the steepest hills in a city full of them. Determined to reach Amoeba Records – the world's largest independent record store – I started out strongly enough. But two-thirds of the way up into the foothills below Haight-Ashbury, the going proved too tough: I got off and pushed. It was worth it, however – both for Amoeba's apparently endless racks of second-hand CDs, and for the apparently endless downhill freewheel towards downtown.

So this, I reassured myself, is what those fixie fanatics are missing: the more that gravity assists, the more frantically their pedals spin. On my way across town to return the mobile armchair to the hire shop, I passed my hotel – the Clift on Geary Street, just around the corner from Union Square. By now my legs were yearning for a sit down in its sumptuous lobby, my sweat glands for a shower in my 15th-floor suite with its great view of the city skyline, and my throat for a drink from the impressive Velvet Room bar (designed, like the rest of the hotel's interiors, by Philippe Starck).

Unfortunately for my legs, my glands and my throat, there was one last near-vertical hill to summit before I reached the bike shop. In fact, I had to cross Filbert Street to get there. At a gradient of 31.5 per cent (for every yard you travel horizontally, you climb a foot vertically), it is one of the steepest navigable streets in the western hemisphere. The ascent involved another walking/pushing combo. Despite this, and glistening with the day's perspiration, I returned my bike to the lady behind the counter at Bike and Roll with a certain degree of triumph, as if I had not merely cycled the city, but conquered it.

"How was it?" she asked. "Great," I replied (and it was). "Although I think I underestimated a couple of those hills!" "Yeah," she replied, not especially impressed, as she wheeled the bike towards its rightful stand, "Well those maps aren't topographical, you know." Oh, I know.

Travel essentials San Francisco

Getting there

* The writer flew with British Airways (0844 493 0758; ba.com/sanfrancisco), which offers three nights' room only at the five-star Clift in San Francisco from £797 per person with return flights from Heathrow; based on two travelling together for October departures.

* San Francisco is served non-stop from Heathrow by BA, United (0845 8444 777; unitedairlines.co.uk) and Virgin Atlantic (0844 874 7747; virgin-atlantic.com).

Getting around

* Bike and Roll doesn't just rent out armchairs; it also has mountain bikes and racers (001 415 229 2000; bikeandroll.com). Rental starts at $8 (£5.30) per hour.

* Ferries between Fisherman's Wharf and Sausalito are operated by the Golden Gate Ferry Service (001 415 455 2000; goldengateferry.org) and the Blue and Gold Fleet (001 415 705 8200; blueandgoldfleet.com).

Staying there

* Clift, 495 Geary Street (001 415 775 4700; clifthotel.com). Room-only doubles from $249 (£166).

Visting there

* Hamburgers Sausalito, 737 Bridgeway Avenue (001 415 332 9471; hamburgersausalito.com).

* City Lights Books, 261 Columbus Avenue at Broadway (001 415 362 8193; citylights.com).

* 826 Valencia, Valencia Street (001 415 642 5905; 826valencia.org).

* Mission Bicycle Company, 766 Valencia Street (001 415 683 6166; missionbicycle.com).

* Amoeba Music, 1855 Haight St (001 415 831 6400; amoeba.com).

Red tape and more information

* US visitors require a $14 (£9.30) ESTA permit ( esta.cbp.dhs.gov).

* San Francisco Tourism: 001 415 391 2000; onlyinsanfrancisco.com