Route 66 vs Savannah and Charleston

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.

Two of the South's most beautiful old cities sit just two hours apart, making them an easy pairing for a four- or five-day trip. Start in Savannah, Georgia, where 22 leafy squares shaded by Spanish moss-draped oaks break up a historic district made for wandering. Stroll to the white fountain in Forsyth Park, tour a historic house that tells the full story of the enslaved people who lived there, and end the day on cobblestoned River Street watching container ships glide past. Then drive about 110 miles up the coast to Charleston, South Carolina. Walk past the pastel facades of Rainbow Row and the grand homes on the Battery, cool off at the Pineapple Fountain in Waterfront Park, and dig into lowcountry seafood: shrimp and grits, she-crab soup and fresh oysters. Plantation tours such as Magnolia, Boone Hall and McLeod Plantation are part of any visit, and the best of them center the histories of enslaved people and the Gullah Geechee culture they built. With extra days, add Sullivan's Island, the beaches of Tybee Island and Kiawah, and the quiet waterfront town of Beaufort. Spring and fall bring mild weather, blooming azaleas and comfortable walking.