Bougainvillea-covered hillsides and an expansive yacht harbor give Sausalito the feel of an Adriatic resort. The town sits on the northwestern edge of San Francisco Bay, where it's sheltered from the ocean by the Marin Headlands; the mostly mild weather here is perfect for strolling and outdoor dining. Nevertheless, morning fog and afternoon winds can roll over the hills without warning, funneling through the central part of Sausalito once known as Hurricane Gulch.
South of Bridgeway, which snakes between the bay and the hills, a waterside esplanade is lined with restaurants on piers that lure diners with good seafood and even better views. Stairs along the west side of Bridgeway and throughout town climb into wooded hillside neighborhoods filled with both rustic and opulent homes, while back on the northern portion of the shoreline, harbors shelter a community of more than 400 houseboats. As you amble along Bridgeway past shops and galleries, you'll notice the absence of basic services. Find them and more on Caledonia Street, which runs parallel to Bridgeway and inland a couple of blocks. While ferry-side shops flaunt kitschy souvenirs, smaller side streets and narrow alleyways offer eccentric jewelry and handmade crafts.
The ferry is the best way to get to Sausalito from San Francisco; you get more romance (and less traffic) and disembark in the heart of downtown.
First occupied by the Coast Miwok tribe and later discovered by Spanish explorers who called the area Saucito (Little Willow) for the trees growing around its streams, Sausalito was developed as a ranch in 1838 under the ownership of English mariner William Richardson. It served as a port for whaling ships during the 19th century and became a major terminus for transport by rail, ferry, and, eventually, car. By the mid-1800s wealthy San Franciscans had made Sausalito their getaway across the bay and built lavish Victorian summer homes in the hills. Meanwhile, an influx of hardworking, fun-loving merchants and working-class folk populated the waterfront area, which grew thick with saloons, gambling dens, and bordellos. Bootleggers flourished during Prohibition, and shipyard workers swelled the town's population in the 1940s, at the height of World War II.
Sausalito developed its bohemian flair in the 1950s and ’60s, when creative types, including artist Jean Varda, poet Shel Silverstein, and madam Sally Stanford, established an artists' colony and a houseboat community here (this is Otis Redding’s "Dock of the Bay"). Both the spirit of the artists and the neighborhood of floating homes persist. For a close-up view of the quirky community, head north on Bridgeway, turn right on Gate Six Road, park where it dead-ends, and enter through the unlocked gates.