Florida Keys vs Maui

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.

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.