Maui vs Route 66

Maui packs an astonishing range of Hawaii into one island: a 10,023-foot volcano where the sun rises above a sea of clouds, a rainforest coastline threaded by the famous Road to Hana, and golden beaches where green sea turtles graze on the reef a few feet from shore. In five days you can snorkel the clear waters of Molokini Crater, watch dawn break from the summit of Haleakala, wind past waterfalls and black-sand coves on the way to Hana, and end each evening with a sunset over Lanai and Molokai from Kaanapali or Napili Bay. Plan ahead, because Maui now runs on reservations: Haleakala sunrise entry, Waiʻānapanapa State Park and Iao Valley all require advance bookings for visitors. Base yourself in Kihei or Wailea for the south shore and upcountry, then move to Kaanapali or Napili for West Maui. Travel with care and respect for local communities, too. Lahaina is still rebuilding after the August 2023 wildfire, and the burn zone is not a sightseeing stop; the best way to help is to spend with open West Maui businesses, follow posted closures, and keep to the island's slower, aloha-minded pace.

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.