Hawaii vs Route 66

Hawaii is the ultimate winter escape for Americans: no passport, no currency exchange and 80°F (27°C) days while the mainland shivers. Choosing an island is the first decision. Oahu is the energetic hub, with Waikiki's beach scene, the moving USS Arizona Memorial at Pearl Harbor, the Diamond Head crater hike and the North Shore, where winter swells send 30-foot waves rolling into Waimea Bay and the Banzai Pipeline. The Big Island is raw and vast, with active volcanoes at Hawaii Volcanoes National Park, night snorkeling with giant manta rays off Kona and stargazing near the summit of Mauna Kea. Maui, with the Road to Hana and Haleakala sunrise, is the romantic middle ground and deserves its own trip. This 7-day plan pairs 3 nights on Oahu with 4 nights on the Big Island, linked by a short inter-island flight of about 45 minutes. Book the key reservations early: Pearl Harbor's USS Arizona Memorial program, Diamond Head entry for non-residents, and a manta ray tour. Pack a light jacket for volcano evenings, mineral reef-safe sunscreen for the reefs, and plenty of patience for traffic in Honolulu.

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.