Florida Keys vs Route 66

The Florida Keys are America's most famous road trip island chain, a necklace of coral islands linked by the Overseas Highway as it hops 113 miles from Key Largo to Key West over 42 bridges and turquoise water. Starting from Miami, you can be snorkeling North America's only living coral barrier reef at John Pennekamp Coral Reef State Park within a couple of hours. Farther south, Islamorada is the sportfishing capital with tarpon feeding at the docks, Marathon has a sea turtle hospital and the soaring Seven Mile Bridge, and Bahia Honda State Park offers some of the best natural beaches in the Keys. The road ends in Key West, a colorful, easygoing town of conch houses, Hemingway's cats, and the nightly sunset celebration at Mallory Square. This plan covers the full Key Largo to Key West run in four days, then adds a day trip by ferry or seaplane to remote Dry Tortugas National Park and its giant brick fort. Navigate by the green mile markers, slow down in Key deer zones, eat plenty of fresh fish and key lime pie, and book Key West hotels early in winter.

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.