Old Route 66 had its western terminus at the edge of the Pacific Ocean in Santa Monica, on a palm-lined bluff a few blocks north of the city’s landmark pier. The pier holds a small amusement park and a lovely old Looff carousel (as seen in the movie The Sting). A beachfront walkway heads south of the pier to Venice Beach, heart of bohemian LA Near where Santa Monica Boulevard dead-ends at Ocean Avenue, a brass plaque marks the official end of Route 66, the “Main Street of America,” also remembered as the Will Rogers Highway, one of many names the old road earned in its half century of existence. The plaque remembers Rogers as a “Humorist, World Traveler, Good Neighbor”—not bad for an Okie from the middle of nowhere.

Two blocks east of the ocean, stretch your legs at Santa Monica Place and the adjacent Third Street Promenade, an indoor-outdoor shopping area and icon of contemporary Southern California (sub)urban culture. The surrounding streets are among the liveliest in Southern California; people actually walk, enjoying street performers, trendy cafés, bookshops, and movie theaters.

Enjoyable in its own right, Santa Monica also makes a good base for seeing the rest of the LA area. For the full retro-luxury experience, check in to the art deco Georgian Hotel (1415 Ocean Ave., 800/538-8147, $300 and up). Or you can save your money for food and fun by staying at the popular HI-Santa Monica Hostel (1436 2nd St., 310/393-9913, around $45).