California | Neighborhood Guides | Road Trip Eats & Restaurants

Eating and Drinking Like the Beats in San Francisco

“What a city of whites and blues!—What air!—Great churchbells bonging, the hint of tinkling flutes from Chinatown markets, the incredible Old Italy scene on Broadway […] “—Jack Kerouac, Desolation Angels

On both ends of the American Beat trail—New York and San Francisco—history has been having a hard time of it. So many vestiges of the era have been remodeled into purgatory, pummeled flat, or scraped away that it’s come to the point where any remaining spots become notable for their very existence.

Luckily, in San Francisco’s North Beach neighborhood, there’s still something to see. Among the crenellated architecture and narrow sidewalks, there’s a lingering, palpable sense of what brought Kerouac, Allen Ginsberg, and Gregory Corso out west to combust spectacularly with the likes of Lawrence Ferlinghetti, Gary Snyder, Philip Whalen, and a host of other writers, artists, and jazz musicians. Climbing through the hilly streets, crisscrossing between bustling Chinatown and Little Italy, you’ll find a few historic spots holding onto the spirit immortalized by Kerouac: “It’s the beat generation, it’s béat, it’s the beat to keep, it’s the beat of the heart, it’s being beat and down in the world […] ”

If you, like me, want to raise a glass to Jack and company when you’re in the city by the bay, here’s a brief list of what’s left and worthwhile in North Beach. Remember, for all his heavy boozing, Kerouac always had a taste for a good meal.

Vesuvio Cafe in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

Vesuvio

In 2007, the alley that cuts between the venerable City Lights bookstore and the equally longstanding Vesuvio Cafe was officially reopened as Jack Kerouac Alley, literally cementing the North Beach block as San Francisco’s still-beating Beat heart. The prow of land draws visitors—really, let’s call them/us pilgrims—from roads near and far, welcoming them with a good stiff drink. As co-owner Janet Clyde remarked on FoundSF, “Vesuvio is everyone’s first bar in San Francisco.”

Vesuvio Cafe in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

Technically, its full name is Vesuvio Cafe, but you won’t find food beyond a bag of chips behind the bar. Comfortably cluttered and collaged with decades of art and ephemera, it doesn’t stand on airs—still opening at 6:00 am to accommodate anyone who might want to while away the day sipping and chatting… or just drinking.

Tosca

Even when a deserving spot is saved from the wrecking ball, new owners can easily doom decades of historic ambience—Minetta Tavern, I’m looking at you. But sometimes angel investors do sweep in and pull off a winning renovation. When April Bloomfield and Ken Friedman (of Spotted Pig fame) took over Tosca Cafe, they managed to maintain a bit of rough charm even while introducing offal to the menu and replacing the usual Ghirardelli chocolate in the house “cappuccino” with Dandelion’s small-batch ganache.

Tosca Cafe in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

Skip the tasty but pedestrian pastas unless you truly need to carbo-load and spend your dough on cocktails and snacks. A few whiskey smashes and a few dishes of pork meatballs, crispy fried potatoes, or chicken heart spiedini can make a whole meal, and the cocktails are worth the price of admission to sit among the restored murals and watch the jacketed bartenders. If you want to go big, the oversized portions of the entrees being whisked out of the open pass looked worthy of another visit. The next time I return, I’m thinking the best bang for my buck is that marsala-roasted chicken for two.

chicken spiedini at Tosca in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

Caffe Trieste

As the first espresso-slinging outpost on the West Coast, Caffe Trieste has parlayed its well-honed coffee chops into a mini-chain with four Bay Area locations, but the original North Beach cafe remains a neighborhood standard—virtually unchanged since 1956. Sunny weekday mornings give regulars the run of the place for spending unhurried minutes or hours reading papers, snacking on pastries, and writing novels or screenplays. If you’re around on a Saturday afternoon, you can catch a little accordion jam with your espresso, as the long-running Caffe Trieste Band does it thing.

cappuccino at Caffe Trieste in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber
Caffe Trieste in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

Li Po

Have you had enough to drink yet? You might need a shot or two before heading over to Li Po. Most of the Beat-frequented greasy spoons of Chinatown are long gone—Sam Wo, Sun Heung Heng, Nam Yuen (though its sign remains in homage above what’s now a housewares shop). The Li Po Cocktail Lounge, however, stubbornly retains its kitschy dive bar status, with its battered but still shining red neon lantern hanging outside and dingy turquoise-walled interior.

Li Po Cocktail Lounge in San Francisco, via www.www.goodfoodstories.com
Photo: Casey Barber

I can’t imagine Kerouac drinking the famous Chinese Mai Tai, but the man did love his sweet port and sweet red wine, so the idea might not be as far-fetched as it sounds. If the spiffied-up bar of Tosca is too much for you, this scruffy spot might be the right way to close out the night.

Looking for a place to crash?

The Hotel SW, formerly the Sam Wong, and known to the Beat crew as the Colombo, is a completely renovated, clean update of the historic beat-down hotel. It’s directly in the thick of things—including the Beat Museum a few blocks away—and if you’re cool with Holiday Inn Express-level lodgings, give it a go. If you’re like us, you’re not spending too much time in the hotel room anyway.

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