By Matt Markovich

BARS ARE HISTORY . By the nature of their business, they tend to generate income as steadily as any funeral parlor. (In fact, in Ireland it's not uncommon for the two concerns to share the same building.) With a decent location and relatively reliable managers, a bar can stay in business for generations, and thanks to the powerful thirst of San Francisco's denizens, there are many such old-school joints around town. Some have maintained their youth, while the world-weary nonchalance of others is reflected in the patina of their bar stools. Still others, owing to some particular convergence of events and reputation, have become tourist traps.

It's no surprise that many locals make a habit of avoiding such places. For one thing, those holding down straight jobs often find themselves lacking time to devote to a serious exploration of the city and its drinking establishments. And it's standard operating procedure for locals to avoid all tourist habitats. A dilemma may arise, though, when one considers that the reason tourists congregate in certain areas is that those places have (or have had) serious historical merit.

Of course, tourists often fall prey to outdated guidebook copy. Case in point: Scoma's at Fisherman's Wharf. Unless you have an advanced Naugahyde-and-plaid pants fetish, there's no urgent need to patronize its bar – no matter how hip it once was, as evidenced by wall photos of '70s luminaries like Gavin "Captain Stubing" MacLeod. Still, while many bars have woefully gone south in this manner, others have retained the character that made them a solid draw to begin with. And the fact is, we're missing out by detouring around them. It's high time we reclaimed some of these joints.

A good place to start – if only to see what you're up against – is Union Square, and the best place in Union Square to begin is on Powell Street, under an odd, theme park-style marquee bearing the name Gold Dust Lounge (247 Powell, S.F. 415-397-1695), which seems to draw wide-eyed tourists like a tractor beam. But the kinds of characters the Dust attracts at happy hour are nothing compared to the late-nighters, who tout Herb Caen's lionizing of the bar as a prime nightcap spot. While other places like Lefty O'Doul's around the corner have piano bars that allow patrons to literally sit around the instrument, the Dust offers a Dixieland bar. Belly up to the banjo player, order a Cutty Sark, and you'll be learning German from the crew next to you in no time. Reopened at its current location following prohibition, the bar was once a haunt of Jackie Gleason, was redecorated in the '50s by MGM, and in the early '60s had its ceilings painted for Hitchcock's The Birds.

Naturally, learning your bar lore is thirsty work, but when you get hungry too, hang a left out of the Dust, another left at the corner of Geary, and yet one more left into the door of the aforementioned Lefty O'Doul's (333 Geary, S.F. 415-982-8900) for a walk through San Francisco sports history. Plastered with old-time photos, clippings, and mementos, the eponymous O'Doul's was opened by the San Francisco baseball legend after he retired from the game, so the San Francisco Seals memorabilia on the walls is the real deal. Hearty and affordable hofbräu-style dining is on offer (kraut, turkey sandwiches cut from the bird, etc.), more than a dozen TV screens show all the games, and a solid beer selection whets your pipes for the seemingly obligatory "Piano Man" sing-along.

The next lesson for locals: always remember hotel bars. To many, the words conjure grim scenes in some HoJo's lounge off the Pennsylvania Turnpike. But bars at San Francisco's grand old hotels once benefited from the largesse of Gilded Age moguls like William Ralston, whose Palace Hotel, at Market and New Montgomery Streets, was one of the largest and most opulent of its day. At one time home to lodgers such as Rudyard Kipling and Oscar Wilde, the Palace was also the scene of President Warren G. Harding's untimely demise. Harding's wife forbade an autopsy, and many suspected her of poisoning the president. Speaking of poison (the kind that's legal to serve), it's tough to beat the (now Sheraton) Palace's Pied Piper (2 New Montgomery, S.F. 415-512-1111, www.sfpalace.com), named for the 1909 Maxfield Parrish painting, The Pied Piper of Hamlin, that hangs behind the bar and is valued at $2.5 to $3 million. Opened virtually as the stroke of the gavel fell on prohibition's repeal (you can even check out the actual prohibition inventory sheet in the display case outside), the Piper retains the old-school elegance of classic San Francisco – when it's not packed with techno-conference attendees.

You'll have to look across the street, though, for the Pied Piper's original bar, in a place on New Montgomery that could only truthfully be termed a "saloon": the House of Shields (39 New Montgomery, S.F. 415-495-5436), a richly wood-paneled relic of a bygone era in which tippling was a primary occupation. The bar that dominates the modest space was originally crafted for the Pied Piper; however, the expert carpenter who designed it failed to take into account the dimensions of the Parrish painting it was intended to showcase. Rather than demolish it, the Palace's owner sent the bar to the neighboring establishment. Though the place has passed through several hands, the interior of the House of Shields has remained largely intact, and its most recent owner (an affable member of the drinking classes) has undertaken some respectful restorations – while nixing the animal heads that once adorned the walls – and brought a new generation to this classic watering hole. Gentlemen and/or adventurous ladies will marvel at the truly colossal urinal in the men's room, whose size may or may not be directly proportional to that of the massive cocktails served up here.

Though not properly a hotel bar per se, the mahogany- and green leather-shod confines of the bar at Huntington Hotel's Big Four Restaurant (1075 California, S.F. 415-771-1140, www.huntingtonhotel.com) restaurant offer the ne plus ultra of elegantly understated indulgence. The neighboring Fairmont Hotel and Mark Hopkins InterContinental Hotel are the more standard tourist draws, thanks to their well-trod Tonga Room and Top of the Mark bars, respectively. Luckily, their proximity keeps the riffraff away from the Big Four. Named in honor of the four railroad barons of the 19th century (Huntington, Stanford, Crocker, and Hopkins), the bar now attracts a clientele prone to wearing the lightly rumpled linen ensembles and perpetual sunburn the yachting class adopts when compelled to perambulate on terra firma. A snifter of cognac by the fire is the order of the evening at Big Four, as the dim lighting and soothing accompaniment of the pianist accent the low murmur of your fellow patrons' conversations.

From the peak (in all senses) of California Street, it's all downhill (in all senses) to Red's Place (672 Jackson, S.F. 415-956-4490). It would be a project in itself to determine whether a bar could offer fewer frills, but Red's holds the distinction of being Chinatown's oldest bar (indeed, older than the relatively green Big Four). And those willing to brave the wiry dice players at the entrance are welcomed by the good-natured bartendrix, whose disposition is as sweet as her drinks are strong. Be prepared to drink your Courvoisier from a shot glass.

Rolling out of Red's, continue rolling down the street to the corner of Columbus and Kearny, where the San Francisco Brewing Co. (155 Columbus, S.F. 415-434-3344, www.sfbrewing.com) is home to not one but two of the best happy hours in the city ($1 pints from 4 to 6 p.m. and midnight to 1 a.m.). Established in 1985 when the space was acquired by Telegraph Hill resident and brewer Allan Paul, the S.F. Brewing Company was originally one of only three brew pubs in the United States and the first in San Francisco. But the bar that still does service there dates to 1907, when future World Heavyweight Champion Jack Dempsey was the bouncer and the space was known as the Andromeda Saloon. Gangster Babyface Nelson was captured there, and the place weathered prohibition by serving as a café and oyster bar, with alcohol available for "medicinal purposes only." Eventually the space fell into disrepair, and it wasn't restored until 1977, when two local restaurateurs reopened it as the Albatross Saloon. (And lastly, it has the dubious honor of being the first place I drank a beer in San Francisco.) If you're worried you've drunk so much that your liver is in danger of floating away, have no fear: the day bartender (the indomitable Paddy) is also a local scuba instructor.

By the time you leave the Brewing Company, you'll be in need of some bracing sea air and some serious coffee – of the Irish variety. So muster your courage and head to the Wharf for a dose at the Buena Vista Cafe (2765 Hyde, S.F. 415-474 5044), the first place the famous eye-opener was mixed stateside. The story goes that a seaplane, attempting to leave the Emerald Isle in 1943, was turned back due to inclement weather. To calm the nerves of the rattled passengers, the chef at the Shannon airport whipped up a warm drink of coffee, sugar, cream, and just a touch of Irish whiskey. Some years later, San Francisco Chronicle columnist Stanton Delaplane passed on the recipe to the owner of the Buena Vista – by which time the proper proportions had been sorted out – and the bar has been home to the spiked coffee drink ever since.

Now that you're awake again, you might as well hop on a ferry to Oakland's Jack London Square for the last and oldest bar on the tour, Heinold's First and Last Chance Saloon (48 Webster, Oakl. 510-839 6761). (Not entirely fitting for a journey through San Francisco's taprooms but worth the haul for the history.) Purchased by one Johnny Heinold in 1883 for $100, the Melvillian structure was built from the salvaged timbers of a whaling ship right on the Oakland docks. The bar's name was inspired by the fact that it was (and still is) literally the first place to find a drink upon coming to shore and the last place to get one when shipping out. Memorabilia covers the walls – including a key to aid the curious in deciphering what's what – and it was at these same tables that a young Jack London did his homework, leading Heinold to lend London college tuition for his brief stint at UC Berkeley. Inevitably, the bar made its way into the author's work: Heinold and the bar are mentioned 17 times in London's John Barleycorn – and it's also where he began both The Sea Wolf and The Call of the Wild. Luckily, it only takes two rounds to fulfill the promise of Heinold's name, so get one when you come in and another before you hop back on the ferry to carry you home.