New Orleans vs Route 66

New Orleans moves to its own rhythm, and three days is enough to feel it. Start in the French Quarter, where wrought-iron balconies hang over Royal Street, street musicians play outside St. Louis Cathedral on Jackson Square, and a plate of powdered-sugar beignets at Café Du Monde is a rite of passage. By night, skip the Bourbon Street crowds and head to Frenchmen Street in the Marigny, where small clubs host brass bands, trad jazz and funk for little or no cover. Ride the green St. Charles streetcar under live oaks to the Garden District, a neighborhood of antebellum mansions and shady sidewalks, then browse Magazine Street. Save an evening for a long Creole or Cajun dinner of gumbo, shrimp and grits, crawfish etouffee or redfish, and a morning for the French Market. With more time, spend a full day at the National WWII Museum, glide through cypress swamps on a boat tour, visit Whitney Plantation for an honest look at the lives of enslaved people, and explore the murals of the Bywater and the oaks of City Park. Come in spring or fall for the best weather, and pace yourself: in this city, lingering over lunch is the plan.

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.