Maui vs NYC and Chicago at Christmas

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.

This holiday lights trip pairs two of America's most festive winter cities: three days in New York, then a short flight to Chicago for two more. In Manhattan, stand beneath the Rockefeller Center Christmas tree as skaters circle the rink below, browse the glass kiosks and free-admission ice rink of Bryant Park's Winter Village and walk Fifth Avenue's elaborate department store windows and light shows. Ride the subway to Brooklyn for Dyker Heights, where homeowners cover entire houses in lights, inflatable Santas and animated nutcrackers. In Chicago, sip hot spiced wine from a boot-shaped mug at the German-style Christkindlmarket in Daley Plaza, stroll the Magnificent Mile beneath trees strung with more than a million lights, skate at the McCormick Tribune Ice Rink in Millennium Park and end at Lincoln Park ZooLights, a glowing, family-friendly tradition. The best window is mid-November to early January: markets generally run from mid-November to Christmas Eve, the Rockefeller tree is lit in early December and most displays stay up into the new year. Visit before December 23 to catch everything open. Pack a warm coat, hat and gloves, because Chicago nights often dip into the 20s, and book hotels early.