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North Beach: Beats, Broads & Little Italy

Start: Intersection of Montgomery Street, Columbus Avenue, and Washington Street.

Public Transportation: Bus no. 10, 12, 13, 30, or 41.

Finish: Washington Square.

Time: 3 hours, including a stop for lunch.

Best Times: Monday through Saturday between 11am and 4pm.

Worst Times: Sunday, when some shops are closed.

Hills That Could Kill: The Montgomery Street hill from Broadway to Vallejo streets; otherwise, this is an easy walk.

You won’t see any beaches here today, but North Beach got its name because before the addition of landfill, the area was actually a large beach marking the northeast side of San Francisco. Its shoreline extended to what are now Taylor and Francisco streets. (As a result, there are many ships buried under parts of downtown San Francisco—visit the Maritime National Historical Park, to learn all about them and see a map of where they’re buried.) 

To get an idea of what the area looked like during the Gold Rush, before much of the shoreline was filled in the late 1800s, picture a wooden shantytown leading down to a bustling, curved wharf. Over time, the settlement grew and in the 1860s became known as the Barbary Coast, after the pirate-prowling North African coast of the same name.

North Beach (especially Pacific Avenue) was a den of sin, pleasure, and crime. Routinely, after a night of carousing at the saloons and opium dens, young men would pass out and wake up the next day on a ship already well out to sea, where they’d be forced to join the crew for months on end until they could raise enough money to buy passage home. This impression-by-kidnapping method was called being “shanghaied,” and it often involved drugs slipped surreptitiously into beer. It was so common in those days that the police barely kept track of the incidents. The brilliant underworld journalist Herbert Asbury, famous today for his book Gangs of New York, wrote in his book Barbary Coast that the period was “the nearest approach to criminal anarchy that an American city has yet experienced.”

North Beach became the city’s Italian district when Italian immigrants moved “uphill” in the early 1870s, crossing Broadway from the Jackson Square area and settling in. Once the 1906 earthquake demolished the Barbary Coast’s flimsy buildings and infrastructure, new buildings began to spring up, and more Italian immigrants moved in, quickly establishing restaurants, cafes, and bakeries. 

The Beat Generation also helped put North Beach on the map, with the likes of Jack Kerouac and Allen Ginsberg holding court in the area’s cafes during the 1950s. Although most of the original Beat poets are gone, their spirit lives on in North Beach, which is still a haven for bohemian artists and writers. The neighborhood, thankfully, retains its Italian village feel; it’s a place where residents from all walks of life enjoy taking time for conversation over pastries and frothy cappuccinos.

If there’s one landmark you can’t miss, it’s the familiar building on the corner of Montgomery Street and Columbus Avenue (take bus 30 or 41 to get there):

1. Transamerica Pyramid

Technically in the Financial District, but just a few blocks south of North Beach, the Transamerica Pyramid is nearly as iconic as the Golden Gate Bridge. Petitions and protests greeted the plan to build this unusual skyscraper, but once it was completed it immediately became a beloved fixture of the skyline. Noted for its spire (which rises 212 feet above the top floor) and its “wings” (which begin at the 29th floor and stop at the spire), this pyramid was San Francisco’s tallest building until July 2017, with the opening of South of Market’s Salesforce Tower (at an impressive 1,070 feet, it’s now the 11th-highest building in the U.S.). The beloved pyramid, now dwarfed, instantly turned into a quaint reminder of San Francisco’s more small-town, charming past. 

Still, it’s a wonder. There’s a small, bland visitor’s center in the lobby that offers a bit of the history of the building, but the real draw is the exterior and the sweet little park around to the right. A bit more history: the 600 block of Montgomery Street, occupied by the Transamerica Pyramid today, once held the Montgomery Block, the tallest building in the West (when it was built in 1853). San Franciscans called it “Halleck’s Folly” because it was built on a raft of redwood logs that had been bolted together and floated at the edge of the ocean (which was right at Montgomery St. at that time). The building was demolished in 1959 but is remembered as the power center of old San Francisco.

From the southeast corner of Montgomery and Washington streets, look across Washington to the corner of Columbus Avenue. At 4 Columbus Ave. you’ll see the: 

2. Original Transamerica Building

A Beaux Arts flatiron-shaped building covered in terra cotta, this old-fashioned beauty was built in 1909 as a bank. Today, the building houses an outpost of the well-funded Church of Scientology, which may explain why it’s so well maintained. Directly across Columbus, you’ll see an odd, yet tragically hip row of storefronts, including the quirky Space Between Gallery; Iron and Resin, a men’s clothing store geared toward the weekend warrior set; and Blades Co., an upscale yet old-school barbershop.

Cross Washington Street and continue north on Montgomery Street to no. 730:

3. Golden Era Building

Erected around 1852, this San Francisco historic landmark building is named after the literary magazine The Golden Era, which was published here. Some of the young writers who worked on the magazine were known as “the Bohemians” and included Mark Twain and Bret Harte (who began as a typesetter here but later became famous for his stories about the Gold Rush). Backtrack a few dozen feet and stop for a minute to admire the exterior of the annex at no. 722, a historic landmark which after years of neglect and lawsuits has been restored to its former glory. Fittingly, Filson, an outdoorsy men’s clothing store that got its start outfitting miners during the Gold Rush, has taken over the space.

Continue north on Washington Street and take the first right onto Jackson Street, where you’ll find the:

4. 400 Block of Jackson Street

Here you’ll find some of the only commercial buildings to survive the 1906 earthquake and fire. Stop in to peruse some of the very high-end shops that now line this block of Jackson Street, or simply admire the architecture. The Hotaling Building (no. 451), built in 1866, features pediments of cast iron applied over the brick walls. At no. 441 is another building that survived the disaster of 1906; constructed between 1850 and 1852, with ship masts for interior supporting columns, it served as the French Consulate from 1865 to 1876. The building at 415 Jackson St., which dates back to 1853, served as headquarters for the Ghirardelli Chocolate Company from 1855 to 1894.

Cross the street and backtrack on Jackson Street. Continue toward the intersection of Columbus Avenue and Jackson Street. Turn right on Columbus, walk halfway up the block, and look across the street for the small triangular building at the junction of Kearny Street and Columbus Avenue.

5. Columbus Tower

Also known as the Sentinel Building, this structure survived the earthquake by virtue of being under construction at the time (it was completed in 1907). In the late 1940s it was the original site of the legendary nightclub hungry i. The building went to seed in the 1960s, although the basement contained a recording studio where the Grateful Dead recorded its second album. Director Francis Ford Coppola owns the building now, and most of it houses the offices of his film production company American Zoetrope (now co-owned by his son Roman and his daughter Sofia). Downstairs, he sells his Napa and Sonoma county wines, and there’s also a slightly overpriced but good European-style bistro, Café Zoetrope.

Continue north on Columbus Avenue, turn right on Pacific Avenue, then left on Montgomery Street, crossing Broadway, to:

6. 1010 Montgomery Street

This is where Allen Ginsberg lived when he wrote his legendary poem, “Howl.” First performed on October 7, 1955, during the Six Gallery reading—when poets, including Ginsberg, presented their poems in front of a rapt but rowdy crowd in a converted auto-repair shop at 3119 Fillmore St.—“Howl” became the manifesto of the Beat Generation. By the time Ginsberg finished reading, he was crying and the audience was going wild. Jack Kerouac, who refused to read his own work but was drunkenly cheering his friends on, proclaimed, “Ginsberg, this poem will make you famous in San Francisco.” It did, of course, make him famous, and its graphic language resulted in poet and publisher Lawrence Ferlinghetti’s arrest, leading to a landmark trial (Ferlinghetti won) that saw many literary giants coming forward to defend Ginsberg’s work. 

Now head back to:

7. Broadway

As you walk along this part of Broadway between Montgomery and Columbus, you’ll see that the Barbary Coast’s risqué business hasn’t completely died out. It’s usually fairly quiet during the day because the barkers and dancers aren’t standing outside in the sunlight trying to lure men (and couples) inside, but the X-rated stores and “gentlemen’s clubs” (aka seedy strip clubs) continue to attract men at all hours. Strange to think of a porn-shop block as having historical significance, but this one really does.

Keep walking west on Broadway and a little farther up you’ll find the current location of:

8. The Beat Museum

While it is located amid porn shops and strip clubs, this bookstore and museum is a diamond in the rough and a must for Beat fans. You can purchase “Howl” and other Beat works, as well as memorabilia as priceless as a first edition of Kerouac’s On the Road. The museum even has a replica of Kerouac’s 1949 Hudson, featured in Walter Salles’s 2012 film version of On the Road (the car is on permanent loan from Salles). The store is open every day from 10am to 7pm; you can wander around the store for free but tickets to the museum are $8 ($5 students and seniors). The museum screens a series of Beat-centric documentaries, most running 90 minutes or so. 

Continue along Broadway to:

9. hungry i

Now a strip club (at 546 Broadway), the hungry i has switched locations and identities at least four times. Originally located in the basement of Columbus Tower, it was owned and operated by Eric “Big Daddy” Nord, a man whose personality was even bigger than his 6-foot 7-inch stature. He sold the club to impresario/producer Enrico Banducci in 1951, who moved it to a cavernous room at 599 Jackson St. three years later. A who’s who of nightclub entertainers performed at the hungry i, including Lenny Bruce, Billie Holiday (who sang “Strange Fruit” there), Richard Pryor, and Woody Allen. Incidentally, my mom, local jazz singer Faith Winthrop, was the house singer there in its ‘50s heyday, as evidenced in the historically accurate major motion picture Big Eyes (2014), which features the club and her name on its marquee. In 1963, the as-yet-unknown Barbra Streisand convinced Banducci to let her perform, and the series of concerts she gave there helped launch her career. My mom was there for that, too. 

At the corner of Broadway and Columbus Avenue, you will see:

10. The Condor Club

Whether or not you approve (I’m on the fence, myself), the Condor Club deserves recognition as part of San Francisco’s history. The city’s topless scene got its start right here in 1964. The owner, looking for something to liven up his club, asked the chief of police if his waitresses could loosen their bikini tops. They did, and toplessness wasn’t far behind. The mayor at the time tolerated it by saying “fun is part of our city’s heritage.” Within days, every club in the vicinity had also gone topless.

But the person who gets the most credit, to this day, is the voluptuous Carol Doda, who danced a dozen shows nightly at the Condor and was profiled in Tom Wolfe’s The Pump House Gang. Doda remained a fixture on the San Francisco scene for many years, as a chanteuse and the owner of a store in the Marina district that sold—you guessed it—bras. She passed away in 2015.

Note the bronze plaque claiming the Condor Club as birthplace of the world’s first topless & bottomless entertainment.

Cross to the south side of Broadway. You’ll see a mural of jazz musicians painted on the entire side of the building directly across Columbus Avenue. Diagonally across the intersection is:

11. City Lights Booksellers & Publishers

Founded in 1953, initially as the nation’s first all-paperback bookstore, this is one of the best and most historic bookstores in the country: a triangular building stuffed with volumes, including many hard-to-find books by fledgling presses. Back in the 1950s, its owner, poet Lawrence Ferlinghetti, decided that good books didn’t have to be expensive, and he set about publishing new and unknown writers whose voices he felt needed to be heard. As mentioned earlier, one of his choices was Howl and Other Poems by Allen Ginsberg. The book’s homoerotic overtones scandalized some, and the resulting obscenity trial made Ferlinghetti’s bookstore internationally famous. What stands out to this day, however, is the fact that this small publisher continues to produce at least a dozen new titles every year (open daily, 10am–midnight). 

Upon exiting City Lights bookstore, turn right, cross aptly named Jack Kerouac Street, and stop at 255 Columbus Ave., where you’ll find:

12. Vesuvio

Ah, Vesuvio! There’s still nothing quite like this dark little bar, opened in 1948, which somehow manages to feel simultaneously historic and timeless. Because of its proximity to City Lights bookstore, this bar became a favorite hangout of the Beats. Dylan Thomas used to drink here, as did Jack Kerouac, Lawrence Ferlinghetti, and Allen Ginsberg. The building dates from 1913, but maintains the same quirky decor it had during the Beat era. Grab a drink and make your way to a tiny upstairs table for the best view of the bar and the streets.

Facing Vesuvio across Columbus Avenue is another favorite spot of the Beat Generation:

13. Spec’s Twelve Adler Museum Cafe

Located at 12 Saroyan Place, this is one of the city’s funkiest bars, a small, dimly lit watering hole with ceiling-hung maritime flags and exposed brick walls crammed with memorabilia. One of the first nine businesses in San Francisco to be officially designated as a “legacy business,” the bar is also a mini-museum—there are a few glass cases filled with mementos brought by seamen who frequented the pub from the [']40s on—but the real legacy is the ambience. 

From here, walk back up Columbus Avenue across Broadway to Grant Avenue. Turn right on Grant and continue until you come to Vallejo Street. At 601 Vallejo St. (at Grant Ave.) is:

14. Caffe Trieste

Opened in 1956 by Giovanni Giota, Caffe Trieste makes a mean espresso—in fact, it claims to be the first espresso purveyor on the West Coast. Many locals linger for hours inside or at one of the sidewalk tables, sipping and chatting. Francis Ford Coppola is said to have written most of the screenplay for The Godfather here. Stop by for a coffee or just a peek; if you’re not ready to take a break, there are more cafe options farther along your route. 

Look across Columbus, where you’ll see the famed:

15. Molinari Delicatessen

This deli, located at 373 Columbus Ave., has been selling its pungent, air-dried salamis since 1896. Ravioli and tortellini are made in the back of the shop, but it’s the sandwiches and the mouthwatering selection of cold salads, cheeses, and marinades up front that captures the attention of most folks. One Italian sub is big enough for two hearty appetites, and their mouth-watering pecorino cheese studded with pistachios will keep if you want to grab a wedge and save it for later. 

Continue in the same direction on Columbus until you reach 412, home of:

16. Biordi Art Imports

This store has carried imported hand-painted majolica pottery from the hill towns of central Italy for more than 50 years, and it welcomes browsers just as eagerly as serious shoppers. With such a wide selection of brightly painted ceramics at nearly every price point, you may quickly find yourself with the perfect gift for someone back home—and the staff is happy to ship it for you. Biordi handpicks its artisans, and the extensive catalog includes biographies of current artists. 

Walk north to the lively intersection of Columbus and Green Street and go left to no. 678, the home of:

17. Club Fugazi

For more than 40 years, Fugazi Hall has been staging the zany and whimsical musical revue Beach Blanket Babylon. The show evolved from Steve Silver’s Rent-a-Freak service, which consisted of a group of partygoers who would attend parties dressed as any number of characters in outrageous costumes. The fun caught on and soon became Beach Blanket Babylon, now the longest-running musical revue in the nation. 

The show changes regularly, and is often based on current events—think political and pop culture spoofs combined with fantastical costumes. If you get tickets and they’re in an open seating section, you should arrive fairly early because you’ll be seated around small cocktail tables on a first-come, first-served basis. (Two sections have reserved seating, four don’t, and all of them frequently sell out weeks in advance; however, sometimes it is possible to get tickets at the last minute on weekdays.) You’ll want to be as close to the stage as possible. And yes, this supercharged show is definitely worth seeing.

Head back along Green Street and cross Columbus Avenue, turning left on Columbus, proceeding 1 block northwest to 566 Columbus Ave.:

18. Mario’s Bohemian Cigar Store Cafe

Don’t let the name put you off; they haven’t sold cigars in over 20 years. This tiny cafe is the perfect stop for breakfast, lunch, or a little evening nosh. Open daily from 10am to 11pm, Mario’s offers an unusual Italian specialty: Cappuccino con Vov, which puts today’s hazelnut lattes to shame. A traditional zabaglione liqueur, Vov adds a sweet kick reminiscent of eggnog. It’s the perfect treat to follow one of their famous sandwiches, made with fresh focaccia from right across the park at Liguria Bakery (1700 Stockton St.).

Once you’re ready to move on, cross the street to: 

19. Washington Square

Established in 1847, Washington Square is one of the city’s first parks and has been the heart of North Beach since the 1860s. Today you’ll find it at the center of the annual North Beach Festival (held in June) and host to community events throughout the year. The statue of Benjamin Franklin was donated in 1879 by temperance crusader Henry Cogswell. An avid teetotaler, he built similar statues (although usually of himself, not Franklin), fitted with fountains, across the country in an effort to get people to drink water instead of alcohol.

The Roman Catholic Church on the square’s northern side on Filbert Street, Saints Peter and Paul Church (1924), is most often cited as the background of some shots of Marilyn Monroe and Joe DiMaggio after their wedding at City Hall in 1954. DiMaggio married his first wife at this church, but could not marry Marilyn there because he never annulled his first marriage. In true literary North Beach style, the Italian motto on the facade quotes not the Bible but Dante’s “Paradise,” from The Divine Comedy.

Your walking tour is over, but there are still dozens of shops, bakeries, and restaurants to explore. Divertiti!

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.