California’s City by the Bay has plenty of rewarding views for willing pedestrians. Its 42 hills and more than 600 stairways add an extra challenge, says Aaron Dence, a personal trainer and walk leader for the nonprofit organization Walk SF, but locals and tourists alike learn to love them for the built-in workouts and breathtaking vistas they provide. “Give yourself more time than you think you need for these walks,” says Dence, “since you’ll want to take your time on your way up.”
Best Walk: Chinatown, North Beach, Telegraph Hill, and Jackson Square
Begin this three-mile walk at San Francisco’s iconic Transamerica Pyramid Center, at the intersection of Merchant and Montgomery streets. Walk south on Montgomery and then right onto Clay Street. At the end of Portsmouth Square Plaza, turn right onto Walter U. Lum Place. Walk to the end of the plaza, then turn left on Washington Street. Make a right onto Ross Alley (grab a sample at the Golden Gate Fortune Cookie Factory!), a right onto Jackson Street, and a left onto Grant Avenue. Turn right on Jack Kerouac Alley to pass the famous beat poet hangout City Lights Booksellers, then turn left on Columbus Avenue. At Broadway Street, make a left and walk about 250 feet, then turn around and look up to catch a glimpse of the “Language of the Birds” sculpture, a collection of books seemingly frozen in thin air. Walk back to Columbus Avenue, making a left. Bear right at Stockton Street and walk along—or stroll through—Washington Square Park. At its northern border, turn right on Filbert Street. Follow Filbert Street as it twists and turns and becomes the Filbert Steps, and wander down the intersecting alleys to see picturesque San Francisco homes and gardens. In Levi’s Plaza, bear left at the circle and head north. Make a right onto Battery Street, then a quick left onto Greenwich Street. Follow the road (and stairs) to Telegraph Hill Boulevard, where you can check out a statue of Christopher Columbus overlooking the city. Turn back and head southeast on Telegraph Hill Boulevard to explore Coit Tower and its surrounding grounds. Return to Greenwich Street and turn left (west) out of the park. Turn left on Grant Avenue, then left on Vallejo Street. After the Vallejo Street stairs, turn right on Montgomery Street. Make a left on Gold Street, a right on Balance Street, a right on Jackson Street, and a left on Hotaling Street. Finally, make a left on Washington Street and a right into Transamerica Redwood Park, where your tour comes to an end. To access the map, click here.
Alternate Walk: Nob Hill and Russian Hill
This walk starts outside of Grace Cathedral, at the corner of Sacramento and Taylor streets. Head east on Sacramento Street and turn left on Mason Street, where you’ll pass the San Francisco Cable Car Museum. Turn left on Vallejo Street and follow it up one set of stairs, through Ina Coolbrith Park, and then up another set. Turn right on Jones Street, right on Green Street, left on Taylor Street, and left on Macondray Lane. Continue zigzagging through Russian Hill, turning right on Leavenworth Street, left on Greenwich Street, right on Larkin Street, left on Chestnut Street, and right on Polk Street. From here, turn right on Francisco Street, which curves north into Russian Hill Park. At the end of the park, turn right on Hyde Street and left back onto Francisco Street. Turn right on Leavenworth Street to head south, then make a right on Lombard Street to travel down the city’s “crookedest street,” consisting of eight hairpin turns and flanked by beautiful homes and gardens. To finish the 3.3-mile tour, turn left on Hyde Street, left on Filbert Street, right on Jones Street, left on Vallejo Street, right on Florence Street, left on Broadway Street, and right on Taylor Street to return to Grace Cathedral.
Embrace San Francisco’s historic hippie subculture with psychedelic and rock favorites.