Florida Keys vs Savannah and Charleston

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.

Two of the South's most beautiful old cities sit just two hours apart, making them an easy pairing for a four- or five-day trip. Start in Savannah, Georgia, where 22 leafy squares shaded by Spanish moss-draped oaks break up a historic district made for wandering. Stroll to the white fountain in Forsyth Park, tour a historic house that tells the full story of the enslaved people who lived there, and end the day on cobblestoned River Street watching container ships glide past. Then drive about 110 miles up the coast to Charleston, South Carolina. Walk past the pastel facades of Rainbow Row and the grand homes on the Battery, cool off at the Pineapple Fountain in Waterfront Park, and dig into lowcountry seafood: shrimp and grits, she-crab soup and fresh oysters. Plantation tours such as Magnolia, Boone Hall and McLeod Plantation are part of any visit, and the best of them center the histories of enslaved people and the Gullah Geechee culture they built. With extra days, add Sullivan's Island, the beaches of Tybee Island and Kiawah, and the quiet waterfront town of Beaufort. Spring and fall bring mild weather, blooming azaleas and comfortable walking.