Florida Keys vs Hawaii

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.

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.