Afoot & Afloat in San Francisco: Great Walking Tours and SF Bay Boating Venues

Ask a native European traveler about their favorite U.S. city, and you’ll often hear the answer, "San Francisco...and the Bay." The answer is even more likely to be the City by the Bay for U.S. residents. San Francisco’s unbeatable allure grabs you with each new view -- the bay’s constant parade of watercraft, the Golden Gate Bridge peeking through a fog bank, or the city’s steep hills wrapped with Victorian homes. Then there’s the City’s friendly and varied cafes, restaurants, galleries, museums, and clubs. What more could a traveler want?

It’s a special combination of land and water that gives San Francisco it’s uniqueness, so there is no better way to enjoy it than both "afoot and afloat." As previous long-time residents who often return to our favorite city, we always find something new and exciting here. Come share some cherished San Francisco walking and boating discoveries. Mix some of these ideas into your own itinerary grab bag for your next stay in the world’s most beautiful city.

Pacific Heights to Union Street: Victorians, Views, & Shops. (Map preview). This walk starts in lower Pacific Heights at the corner of Sutter and Octavia. The striking facade of the Queen Anne Hotel welcomes you inside for a glimpse of its lobby/salon with period antiques and furnishings recapturing San Francisco’s golden turn-of-the-century. Walk up four short, steep blocks on Octavia to tiny Lafayette Park. Along the way you’ll see some interesting churches and Victorians. The park was the center of early San Francisco’s first suburb in 1855. Climb up the path to the treed summit and peer down across two miles of city streets to the glistening bay.

From the park head west along Clay Street, strolling five blocks to Alta Plaza. Then climb the stairs at the corner of Clay and Pierce Street into the Plaza. All around you are multi-colored Victorians. You’re at the center of Pacific Heights.

It’s all down hill from here as you descend Steiner Street, going five short, steep blocks, then, turning right onto Union Street. Now you’re in the center of the relatively flat Cow Hollow district. This region was once the home of truck gardens and dairy farms. Take your time exploring and browsing both sides of energetic Union Street, along the five blocks between Steiner and Octavia. You'll be enticed to stop and enjoy breakfast or lunch at one of the many cafes. Linger in the boutiques and galleries which tickle your fancy. A recommended dining spot is Prego’s, 2000 Union Street, with a great Northern Italian and pizza menu.

Fisherman’s Wharf to Aquatic Park. (Map preview). Start at Pier 39, the long wharf of shops and restaurants extending into the bay. Browse the pier, and then wind west along the Embarcadero to Fisherman’s Wharf. Here you’ll find fresh-seafood street vendors and famous multi-generation restaurants such as Alioto’s and Sabella’s. As you walk along the wharf bordering Jefferson Street, take in the sights and sounds of the boats that pull in daily catches of San Francisco’s world-famous Dungeness crab.

Two blocks farther west you’ll come to the Cannery, now remodeled into a tiered network of bricked shops and plazas. You’ll likely catch a good musical group here in the main plaza of open air cafes. Leaving the Cannery on Beach Street, you’ll cross cable car tracks and come upon the Buena Vista cafe, birthplace of Irish Coffee. The long bar and scattered tables are always busy. If you can find a free spot, enjoy a lunch break of corned beef with a glass of Irish stout. Just a block farther west, you’ll come upon Ghirardelli Square, a converted chocolate factory that now houses a great array of shops and restaurants. Here again you’ll hear some good musicians, playing tunes with the inspiration of bay views.

If you have the energy, two great options still await. You can walk out along the curved Aquatic Park pier for vistas of the bay and city. Or you you can retrace your steps to the Cannery and rent a bicycle for a flat pedal west past the pier and along the Marina to wave-pounded Fort Point, situated at the foot of the Golden Gate. This is one of the most enjoyable city bicycle rides you can experience. En route you’ll pass Crissy Field’s wind-surfing beach and catch views of white-cap-leaping sailboarders.

Cable Car Excursions — Union Square, Nob Hill, Chinatown, Russian Hill, North Beach. (Map preview). You can take advantage of the City’s cable cars to connect you with a variety of districts. Start by exploring San Francisco’s most exclusive shopping district around Union Square, on Post Street and Maiden Lane. Pick up the cable car on Powell Street from Union Square up to Nob Hill, home to mansions of early California barons and four exclusive hotels. Exit at California Street and walk two blocks west to appreciate Grace Cathedral’s neo-Gothic architecture. The east front doors are cast from Ghiberti’s doors in Florence, Italy. Take the California Street cable car downhill five blocks to Grant Street. Browse your way through Chinatown for six blocks along Grant. Then veer left on Columbus Street into the North Beach district. An interesting stop is the City Lights Bookstore at 261 Columbus, a haven for poets and authors during the 60’s beatnik era. When you reach Green Street, walk east for a good variety of original Italian restaurants such as New Pisa and Green Valley. Walk back to Columbus and continue on past lovely, neighborhood Washington Park back to Mason Street to pick up the cable car back downtown. You’ve just experienced some exciting slices of San Francisco.

Don’t miss the opportunity to view San Francisco and its bay from the deck of a boat. The Red and White Fleet’s one-hour bay cruise leaves from Pier 43-1/2. The Blue and Gold Fleet’s variety of ferries leaves for Alcatraz, Sausalito, Tiburon, Vallejo, or Oakland from Pier 39 and Pier 41. But if you are a sailor, there is no better way to appreciate the Bay then via a sailboat. South Beach Harbor at Pier 40, a mile south of the Ferry Building, has mooring for sailboats coming into San Francisco. The firm, Spinnaker Sailing of South Beach Harbor, also provides sailing lessons and rents 22 to 43-foot bareboat charter sailboats. (Pier map preview).

My father and I enjoyed some windy August days on the Bay last year on his 34-foot sloop. The west winds from the Golden Gate were ripping at 25 knots through "The Slot" between Alcatraz and Angel Island. We at first underestimated the Slot's wind strength, sailing with just a little too much mainsail. We experienced a rollicking, white-water ride, with the deck rail dipping from wave to wave. Although we loved the action, we decided to reef the mainsail just a little lower before crossing the exciting Slot in the opposite direction.

Throughout our sails we enjoyed the sunny Bay and views of the City's skyline, the Gate, and the Bay Bridge. It’s hard to find better sailing than what the Bay serves up. South Beach Harbor provided clean, safe mooring, with a good selection of restaurants within a short walk along the Embarcadero. We also had enjoyable sailing to harbors in the San Francisco Bay towns of Oakland, San Rafael, and Vallejo.

Afoot and afloat, San Francisco is one of the world’s most beautiful and exciting cities. On each visit you’ll make new discoveries of neighborhoods, restaurants, entertainment, or of neighboring waters and towns. The hills and waters of San Francisco await your exploration!