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. 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.
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.