Florida Keys vs New Orleans

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.

New Orleans moves to its own rhythm, and three days is enough to feel it. Start in the French Quarter, where wrought-iron balconies hang over Royal Street, street musicians play outside St. Louis Cathedral on Jackson Square, and a plate of powdered-sugar beignets at Café Du Monde is a rite of passage. By night, skip the Bourbon Street crowds and head to Frenchmen Street in the Marigny, where small clubs host brass bands, trad jazz and funk for little or no cover. Ride the green St. Charles streetcar under live oaks to the Garden District, a neighborhood of antebellum mansions and shady sidewalks, then browse Magazine Street. Save an evening for a long Creole or Cajun dinner of gumbo, shrimp and grits, crawfish etouffee or redfish, and a morning for the French Market. With more time, spend a full day at the National WWII Museum, glide through cypress swamps on a boat tour, visit Whitney Plantation for an honest look at the lives of enslaved people, and explore the murals of the Bywater and the oaks of City Park. Come in spring or fall for the best weather, and pace yourself: in this city, lingering over lunch is the plan.