Route 66 vs San Francisco

Route 66 is the great American road trip: roughly 2,400 miles of the Mother Road from downtown Chicago to the Pacific at Santa Monica, crossing eight states and three time zones. This Chicago to Santa Monica itinerary packs it into 10 days, which is fast. Expect about 200 to 330 miles and five to seven hours behind the wheel most days, mixing interstate stretches with the best surviving original alignments; two to three weeks is ideal if you can spare it. Start with a photo at the Begin sign, then roll past Illinois giants, the bent Chain of Rocks Bridge over the Mississippi and Ozark frozen custard stands. Cross the short Kansas corner and Oklahoma's diners before painting your own stripe at Cadillac Ranch outside Amarillo. In New Mexico, sleep under the glowing neon of the Blue Swallow Motel in Tucumcari, then drive through the badlands of Petrified Forest National Park, the only national park that protects a stretch of Route 66. A day off the road from Williams takes you to the Grand Canyon's South Rim. The finale climbs over the Black Mountains to Oatman, crosses the Mojave and ends with a sunset at the Santa Monica Pier. Book classic motels ahead in spring and fall.

San Francisco packs world-famous sights into a compact, hilly peninsula wrapped in fog and bay views. Ride a clanging cable car up Nob Hill, then drop toward the water for sourdough bread bowls of clam chowder at Fisherman's Wharf. Book Alcatraz well ahead, because the ferry to the former prison island and its gripping audio tour sell out weeks in advance. Walk or bike across the Golden Gate Bridge, coast downhill into Sausalito for seafood by the bay and ride the ferry home past the skyline. Give a full day to wine country, sipping Cabernet in Napa Valley or Pinot Noir in laid-back Sonoma, and save a morning for the towering coast redwoods of Muir Woods, where parking or shuttle reservations are required, or swap in the cliffs and beaches of Half Moon Bay. The city itself rewards slow wandering: dim sum in Chinatown, espresso in North Beach, murals in the Mission and sunset at Ocean Beach. Pack layers whatever the month, since summer fog can drop temperatures into the 50s while the sun shines a few miles inland, and wear comfortable shoes for the steep hills. September and October usually bring the warmest, clearest days of the year.