Arrive at Oakland International Airport, just across the bay from the city, and follow the signs for the SuperShuttle desks, which are located in the baggage claim area; the trip into downtown San Francisco in your own non-stop van will take just under an hour and cost $70. Your destination is The Argonaut, a nautical-themed family-friendly hotel where kids 17 and under stay free with an adult.
For brunch you'll all be happy at the Hollywood Cafe on North Point Street, just four blocks from The Argonaut. Open from 7 a.m. to 1:45 pm daily, they serve a down-to-earth menu of eggs, bacon, french toast, and bagels, including a fun kids menu with chocolate chip pancakes. The prices are low and the portions are large enough to keep everyone fueled for the day of sightseeing ahead.
Next you're off to City Lights Bookstore, birthplace of the Beat Movement and publisher of Allen Ginsberg's Howl and Other Poems, the groundbreaking work that gave voice to a generation of gay men. This sprawling two-floor space is perfect for people-watching and browsing; the kids can check out the art and comic books while you pick up a map of the city.
From here take a quick walk to the corner of Taylor St. and Columbus Ave., where you can catch the Powell-Mason cable car south towards Market Street. This isn't just public transportation, it's the most exciting way to take the kids around town. Make sure everyone is hanging on tight, and be sure to look around as you descend the hill.
Take the cable car back to its starting point at Fisherman's Wharf, the bustling tourist center of the city. Here you'll find any number of kid-friendly attractions, including the Ripley's Believe It or Not Museum, the Ghirardelli Chocolate Marketplace and Factory, and the Wax Museum. If you have the energy, you can walk a bit further east for the Aquarium of the Bay and the ferry to Alcatraz.
Then it's your chance to stroll through the Maritime Park, just across the street from your hotel, which has a small beach, museum and multiple green spaces with benches. Don't miss the array of historic ships from the 1800s permanently docked on one of its two piers; they're a remarkable collection of vessels from schooners to paddlewheel tugs. Wander the gravel paths and enjoy the sunshine, or hunker down with an ice cream cone and a burger to take in the view.
Head back towards The Argonaut to rest up for tomorrow, but if you feel like a nightcap, settle the kids in with a movie and make your way to Winery Collective, a wine tasting room just around the corner from the hotel. A boutique venture that focuses on small-batch, organic bottles, you can try a flight of local wines curated by their expert in-house sommeliers.