San Francisco is small and steep, and it knows how to make an entrance. It sits on the tip of a peninsula of steep hills, with the Pacific on one side and the bay on the other, and its best-known landmarks are a bridge, a prison island and a cable car system that has outlived every rival. The city grew out of the 1849 Gold Rush, burned after the 1906 earthquake, rebuilt in a hurry, then spent the 1950s to the 1970s reinventing American culture: the Beat poets in North Beach, the hippies in the Haight, the gay rights movement in the Castro. You can still walk through all of it.
Be ready for the other side too. This is one of the most expensive cities in the country, the fog can swallow the Golden Gate Bridge at lunchtime in July, and parts of downtown, mainly the Tenderloin, are hard to look at. It deserves five days because the neighborhoods are so different from each other, and because half of the good stuff, like Muir Woods and Alcatraz, needs booking days or weeks ahead. Five lets you do it without running.
The plan keeps every day in one part of town. Day one is the Presidio and the Golden Gate Bridge, day two Alcatraz, the waterfront, North Beach and Chinatown, day three Golden Gate Park and the Haight, day four the Mission, the Castro and Twin Peaks, and day five a trip north to the redwoods of Muir Woods and the waterfront town of Sausalito. Start on a Monday: Fort Point is open, the de Young is open when you reach it, La Taqueria is open on day four, and the Muir Woods shuttle from Larkspur runs on the Friday that closes the trip. Weekday Alcatraz boats are also easier to book. Driving in? Here's the New York to San Francisco road trip. More on the United States.