San Francisco Walking Tour: 10 Highlights

The beauty of San Francisco is best appreciated from the highest points. The city’s 43 rolling hills offer spectacular scenery. Sandwiched between the Pacific Ocean and San Francisco Bay, the city was built between 1849 and the early 20th century, despite its challenging landscape. Many streets are so vertiginous that the sidewalks are actually pedestrian steps (used by locals instead of StairMaster). The dramatic topography also accounts for some of San Francisco’s most iconic images. Lombard Street owes its famous curves to the road’s steep incline; the red brick hairpin bends make it safer to drive up and down. Ziplines are also designed to tackle the extreme slopes.

This self-guided walking tour traverses San Francisco’s steepest streets in quaint, historic neighborhoods that are full of character. More of an urban walk, the tour is physically demanding, but each step is rewarded with beautiful sights: pastel Victorian houses clinging to vertiginous hillsides; thriving stairway gardens tucked away in side streets; view of the majestic bridges and sailboats gliding across the bay on a sunny day. Enjoy the panoramas as you visit the highlights of San Francisco in about four to five hours.

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1 Chinatown Gates

Chinatown Gates

Start the walk at the Dragon’s Gate , at the intersection of Bush and Grant streets. Visitors can arrive in San Francisco’s Chinatown from any of the adjacent neighborhoods: the Union Square shopping district on Bush Street, the posh residential streets of Nob Hill on Powell Street, Little Italy (North Beach) on Columbus Street, or the bustling financial district of Kearny Street. However, the Dragon Gate marks the official entrance. Built in 1970, the green-tiled pagoda-style gate features two small dragon statues on each side. It has Chinese writing that translates to ‘Everything under heaven is for the good of all people’.

2 Chinatown stores and authentic Chinese cuisine

Chinatown shops and authentic Chinese cuisine
Chinatown shops and authentic Chinese cuisine

As you walk along the tourist souvenir shops on Grant Avenue , contemplate the turbulent history of this compact area, the most populous part of the city. Dating back to the Gold Rush period, this neighborhood is the oldest Chinatown in the United States and the largest Chinese community outside of Asia. During the 1800s, Chinese immigrants faced problems of discrimination and overcrowded housing. In 1882, the United States passed the Chinese Exclusion Act, which restricted immigration from China. This xenophobic law remained in effect until 1942. Even so, the Chinese labor force built much of the city during the 19th century.

Continue on Grant Avenue until Washington Street, turn left and turn right onto the narrow pedestrian street. Ross Alley . The small nondescript building #56 is the Golden Gate Fortune Cookie Factory, where tourists can stop to view fortune cookies and purchase cookies. This small factory has been producing delicious fortune cookies since 1962 and the cookies are still made by hand. Fortune cookies were actually invented in San Francisco and are not from China, although some historians believe the inspiration came from 14th century moon cakes. The round cakes concealed messages from Chinese soldiers used to coordinate a revolt against Mongol invaders. In fact, the history of military messages hidden in baked goods goes back to ancient Greece in the time of Alexander the Great. Today’s fortune cookies contain optimistic Confucius-esque sayings designed to surprise diners after a meal.

From Ross Alley, continue one block west and two blocks north to Stockton Street on Broadway, revealing the sights, sounds, and smells of Chinatown. Between Stockway and Broadway, on Columbus Avenida, are grocery stores and markets frequented by locals, many of whom speak only Chinese. Peek into the shops (photos are prohibited) to see the exotic Asian fruits and vegetables, fresh seafood, as well as live fish, turtles and chickens. An easy way to experience authentic Chinese cuisine is to dine at one of Chinatown’s best restaurants. Just off Stockton Street, Michelin-designated Z&Y Restaurant(655 Jackson Street) has a world-renowned chef and serves excellent Sichuan-style Chinese food. The restaurant’s distinguished guests include the presidents and foreign ministers of the People’s Republic of China and US President Barack Obama.

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3 Jackson Square Historic District

From Stockton Street follow Broadway and walk south to Jackson Street (turn left). Keep walking east on Jackson Street until you reach Montgomery Street to explore the historic Jackson Square area. This district also overlaps with the Barbary Coast Trail that marks Gold-Rush-era sites with bronze sidewalk medallions. Jackson Street has distinguished brick buildings from the 1850s and 1860s that survived the 1906 earthquake. Full of old world charm, Jackson Street is lined with shady trees and quaint cast iron street lamps. Many of the buildings house prestigious art galleries, fine antique shops and interior design boutiques. The area also has several excellent fine dining restaurants.

4 Telegraph Hill

Telegraph Hill
Telegraph Hill

Go uphill on Montgomery Street to Telegraph Hill. At Montgomery and Broadway, turn around and admire the view of the Transamerica Building. The next several blocks have a steep incline with steps along the sidewalk to help pedestrians navigate the uphill climb. At Filbert Street, turn left onto Filbert Steps, a lovely stairway with lush, tranquil gardens on either side and pretty houses nestled against the slope. are built. Climb up the stairs of 80 steps and then take another flight of 30 steps leading to the Coit Tower landing . One of the city’s most iconic landmarks, the tower stands on the former site of the telegraph station for which the district is named. Surrounding Coit Tower is the Pioneer Parkrecreation area, nearly five acres of wooded parkland with sensational vistas of the city and San Francisco Bay. Walk the park’s trails and enjoy the beautiful vistas and listen to the sounds of exotic birds. The legendary flock of parrots, featured in the Wild Parrots of Telegraph Hill movie, make their home on these wooded slopes.

5 View from Coit Tower

View from Coit Tower
View from Coit Tower

Located at the top of Telegraph Hill, Coit Tower is a beacon in the San Francisco skyline. This famous landmark is visible to visitors when taking the ferry from the East Bay or driving across the Bay Bridge and from other points in the city. Built in 1929, the tower was funded by and named after Lillie Hitchcock Coit, a wealthy San Francisco socialite and patron saint of firefighters. Although the tower’s fluted shape is said to resemble that of a firefighter’s hose, the architect Arthur Brown Jr., who designed it, did not intend this effect. The openings at the top that resemble the spout of the mouthpiece are actually windows. Take the elevator to Coit Tower’s Observation Deck(admission fee) to admire sweeping views of the bay and downtown San Francisco. The observation deck offers 360-degree panoramas, and each window’s vantage points offer a different view, such as the Bay Bridge, the Transamerica Building, and the picturesque hills of North Beach.

Before or after visiting the observation deck, take a look at the murals in the base of the tower. The series of Depression era murals were painted in 1934 in a thematic style reminiscent of the work of celebrated artist Diego Rivera. At the time the murals were painted, the content was considered radical as it depicts laborers and farm workers as the central subject.

6 Beatnik Heritage op Columbus Avenue

Beatnik Heritage on Columbus Avenue | Photo Copyright: Lisa Alexander
Beatnik Heritage on Columbus Avenue | Photo Copyright: Lisa Alexander

The block of Columbus Avenue between Pacific Avenue and Broadway was the stamping ground of Beat poets in the 1950s. This area once buzzed with counter-culture energy and attracted the beatnik literati. Jack Kerouac author of On the Road, one of the most celebrated works of the Beat generation, and Allen Ginsberg, who wrote the maverick rant Howl, once read their poetry at City Lights Bookstore . Beat poet Lawrence Ferlinghetti founded (and still owns) this legendary bookshop and still possesses a decidedly bohemian attitude. After visiting City Lights, stroll through adjacent Jack Kerouac Alley, a 60-meter cobbled pedestrian street with vibrant murals and old-fashioned street lamps. Chinatown begins at the Grant Avenue end of the alley, while the Columbus Avenue end is in the heart of North Beach’s historic beatnik district. Befitting the location, the alley has sidewalk medallions with literary quotes from great writers, such as Jack Kerouac, John Steinbeck and Maya Angelou.

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If you want to learn more about Beatnik culture, take a short detour to visit the Beat Museum at 540 Broadway. The museum is dedicated to sharing the idealism of the Beat Generation. Defined by its individualistic spirit, this 1950s artistic movement included a collection of poets, writers, thinkers and artists engaged in creativity, tolerance, courage and compassion. The Beat Museum displays an extensive collection of memorabilia from Beat authors, including letters, photographs, original manuscripts and valuable first editions.

7 North Beach: Little Italy

North Beach: Little Italy | Photo Copyright: Lisa Alexander
North Beach: Little Italy | Photo Copyright: Lisa Alexander

San Francisco’s colorful Little Italy dates back to the late 19th century. Charming residential homes line the steep streets of this historic district, intersected by the more modern and busy thoroughfares of Columbus Avenue and Broadway. A beach to border the neighborhood, but the area was developed with landfills, though the name stuck. North Beach is full of old-school Italian restaurants, with red-checkered tablecloths, serving huge portions of pasta, and atmospheric cafes where patrons go and be seen enjoying authentic Italian espresso. It’s also a great place to shop at boutiques, visit a gelato shop, or sample treats at an Italian bakery. Columbus Avenue has the highest concentration of restaurants and cafes, and is usually very touristy,

Continue this walk on Columbus and Broadway, just north of Jack Kerouac Alley. Stop for a snack, coffee or lunch in one of the bustling cafes. Favorites include Caffe Puccini (411 Columbus Avenue) and Caffe Greco (423 Columbus Avenue) as well as the legendary Caffe Trieste (601 Vallejo Street, one block from Columbus), a popular hangout for locals. After the café break, wander past Columbus (to the north) until you reach Washington Square Park . This pleasant, shady green space is located in the heart of North Beach. It’s a peaceful place that’s great for sunbathing and picnicking or playing volleyball and Frisbee. View of the park is impressiveSaints Peter and Paul Church with its gothic towers serving as a focal point in North Beach. The ornate building of this Roman Catholic church was completed in 1924. In addition to its architectural beauty, the church is the location where Marilyn Monroe and Joe DiMaggio took their wedding photos. Today the church reflects the multicultural character of the neighbourhood; mass is offered in English, Italian and Chinese.

8 Russian Hill Staircases

Ina Coolbrith Park Wendy Harman / photo modified
Ina Coolbrith Park Wendy Harman / photo modified

Go back on Columbus Avenue until Vallejo, turn right and enter Russian Hill. In the 19th century, the graves of Russian soldiers were on the hill that is now Vallejo Street, giving the neighborhood its name. As you climb Vallejo Street , you will come across two sets of stairs that are surrounded by gardens with beautiful views. After crossing Mason Street, the next block of Vallejo surprises visitors with a small but delightful green space – the Ina Coolbrith Park . Stop smelling the roses, then continue another block on Vallejo and turn right onto Jones Street. From the intersection of Jones and Green streets, enjoy the incredible panorama of the bay, including Alcatrazon the front. Turn left onto Green Street and then right onto Hyde Street. Stroll three blocks north on Hyde through an elegant residential area to Lombard Street.

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9 Lombard Street: The Crookedest Road

Lombard Street: The Crookedest Road
Lombard Street: The Crookedest Road

Arrive at one of the most popular tourist attractions in San Francisco, the city’s famous winding road. From the top of this winding road at Hyde and Lombard is a sensational viewpoint looking back towards Coit Tower. The only part of Lombard that appeals to tourists is between Hyde and Jones Streets. Known as the Crookedest Street in the World, this section of Lombard has a steep angle of 27 degrees. The road was paved with switchbacks in the 1920s to make it safer for cars to drive up and down. The street also has pedestrian steps on both sides, ideal for a leisurely ramble with the other groups of tourists you’re likely to see here. On either side of the stone-paved winding curves are beautiful homes in Edwardian, faux Tudor, and contemporary architectural styles. Lush geranium-filled flower beds bloom between the hairpin bends, making the street look like a garden. From Lombard Street, take a cable car on Hyde Street and enjoy a scenic ride to Fisherman’s Wharf.

10 Fisherman’s Wharf

Fisherman's Wharf
Fisherman’s Wharf

A descent or cable car from Hyde at Lombard leads to Fisherman’s Wharf. This nostalgic waterfront neighborhood delights visitors with refreshing sea breezes and beautiful coastal scenery, while tantalizing foodies with fresh sourdough bread, fish & chips, clam chowder, and locally caught crab. In the 1800s, the area was a hub for recently immigrated Italian fishermen. Although Fisherman’s Wharf still has many commercial fisheries, it is now a major tourist destination filled with souvenir shops. So it would be easy to overlook the small picturesque wharf on Jefferson Street between Leavenworth and Jones, which was part of the historic fishing villagewhich predates the Gold Rush of 1949. The small boats docked at the wharf are traditional Italian fishing boats called feluccas. Note that the hulls are painted with the names of Catholic patron saints. Try to imagine the fishermen on these small boats ushering in the misty bay. The fishermen were known for singing Italian opera songs while sailing in the fog. After taking a stroll along the wharf, stop to sample the sourdough bread at Boudin Bakery , grab a bite to eat at a fish shack, or try the fresh cracked crab sold from the curbside on Jefferson Street when it’s in season.

San Francisco Fisherman's Wharf Map
San Francisco Fisherman’s Wharf Map
  • Fisherman’s Wharf
  • Pier 39
  • Ghirardelli-plein
  • The Cannery
  • Fort Mason
  • National Maritime Museum
  • Maritime State Historic Park
  • USS Pampanito
  • Art Institute
  • Telegraph Hill
  • Coit Memorial Tower
  • St Peters and Paul

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