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 on Bridgeway (toward San Francisco), 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 climb the hill to wooded neighborhoods filled with both rustic and opulent homes. As you amble along Bridgeway past shops and galleries, you'll notice the absence of basic services. If you need an aspirin or some groceries (or if you want to see the locals), you'll have to head to Caledonia Street, which runs parallel to Bridgeway, north of the ferry terminus and inland a couple of blocks. The streets closest to the ferry landing flaunt their fair share of shops selling T-shirts and kitschy souvenirs. Venture into some of the side streets or narrow alleyways to catch a bit more of the town's taste for 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.
Sausalito had a raffish reputation before it went upscale. Discovered in 1775 by Spanish explorers and named Sausalito (Little Willow) for the trees growing around its springs, the town served as a port for whaling ships during the 19th century. By the mid-1800s wealthy San Franciscans were making Sausalito their getaway across the bay. They built lavish Victorian summer homes in the hills, many of which still stand. In 1875 the railroad from the north connected with ferryboats to San Francisco, bringing the merchant and working classes with it. This influx of hardworking, fun-loving folk polarized the town into "wharf rats" and "hill snobs," and the waterfront area grew thick with saloons, gambling dens, and bordellos. Bootleggers flourished during Prohibition, and shipyard workers swelled the town's population in the 1940s.
Sausalito developed its bohemian flair in the 1950s and ’60s, when creative types, led by a charismatic Greek portraitist named Varda, established an artists' colony and a houseboat community here (this is Otis Redding’s "Dock of the Bay"). Today more than 450 houseboats are docked in Sausalito, which has since also become a major yachting center. Some of these floating homes are ragged, others deluxe, but all are quirky (one, a miniature replica of a Persian castle, even has an elevator inside). For a close-up view of the community, head north on Bridgeway—Sausalito's main thoroughfare—from downtown, turn right on Gate Six Road, park where it dead-ends at the public shore, and enter through the unlocked gates. Keep a respectful distance; these are homes, after all, and the residents become a bit prickly from too much ogling.