North Beach is San Francisco's Italian quarter and its literary one, stacked on the same few blocks, and the walk through it is short, steep at the end, and full of espresso. Start at the corner that matters: City Lights, where Lawrence Ferlinghetti published Howl in 1956 and won the obscenity trial that followed. The shop is still independent, the poetry room still up the stairs.
Next door across Jack Kerouac Alley is Vesuvio, the Beats' bar, the alley underfoot set with their lines. From here walk the diagonal of Columbus Avenue, stopping at Caffe Trieste for the cappuccino — the first espresso bar on the West Coast, and still the right one. Push on to Liguria Bakery on the corner of Washington Square for focaccia, sold by the bag until it's gone, then eat it on a bench in the square under the spires of Saints Peter and Paul.
Then the climb. Filbert Street goes up hard toward Telegraph Hill, and Coit Tower stands at the top of it. Walk it slow or take the 39 Coit bus; the bay widens behind you the whole way.