Named for a semaphore telegraph that once stood on its summit, Telegraph Hill has been the home of poor immigrants, inspired artists, and wealthy investors. Its stairways traverse some of the city's most charming terrain, but if you'd prefer to skip the climb up the 284-foot hill, you can take a bus or taxi directly to Coit Tower and start the tour from there. Nearby, North Beach still pulses with its Italian-immigrant heritage and Beat movement history.
Take the F-line historic streetcar to the Embarcadero and Greenwich Street stop. Head west into (1) Levi Plaza, where this tour begins. The brick building complex bordering this quiet city refuge houses the headquarters for jeans-maker Levi Strauss & Co., which got its start in San Francisco in 1853 when Strauss sold canvas overalls to gold miners.
Walk west (crossing Battery and Sansome streets) to continue the tour along Filbert, a street so steep it turns into a stairway. Make your way up the Filbert Street steps to reach (2) Napier Lane, a wooden plank sidewalk lined with private dwellings that date from the 1870s and 1880s. Keep climbing those stairs, listening for the caw of Telegraph Hill's famous flock of wild parrots as you pass Victorian-era cottages and private gardens tumbling with blossoms.
At Montgomery Street, go right to reach (3) Julius' Castle, a 1922 restaurant known for its spectacular views. Look for the brick stairway adjacent to the restaurant and ascend the Greenwich Steps to (4) Coit Memorial Tower. Dedicated in 1933, the 210-foot tower honors Lillie Hitchcock Coit, an eccentric San Francisco philanthropist. Inside you'll see a series of colorful murals painted in 1934 by local artists under the Public Works Art Project.
After you take in the panoramic view from the top of Coit Tower, follow the sidewalk down Telegraph Hill Boulevard to the first intersection, Kearny Street. Walk three blocks and turn right onto Vallejo. Walk another block to reach Grant Avenue. On the left, local writers and artists frequent (5) Caffe Trieste (www.caffetrieste.com), a Beat poet hangout in the 1950s and the first espresso coffee house on the West Coast. On the right sits (6) St. Francis of Assisi Church (www.shrinesf.org). Built in 1860, this Norman Gothic beauty bears the name of the city's patron saint. Across Columbus Avenue, (7) Molinari Delicatessen has sold Italian essentials like mozzarella, straw-bottled Chianti, cannoli shells, and salami since 1896.
Next, walk down the east side of Columbus and turn left on Grant Avenue to find (8) the Saloon, San Francisco's oldest continuously operating tavern (since 1861). Walk back to Columbus Avenue and turn left to reach (9) City Lights Bookstore (http://citylights.com). Co-founded in 1953 by poet Lawrence Ferlinghetti, the store soon became a favorite meeting place of Beat poets, including Allen Ginsburg and Jack Kerouac. Today, its narrow entryway opens to a warren of books with large collections of poetry, world literature, and political nonfiction.
Just across Jack Kerouac Alley, (10) Vesuvio (www.vesuvio.com), which opened in 1949, served those same Beat poets in the 1950s. You may wish to step into this bohemian bar for a well-earned end-of-the-tour drink.
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