Miami to Key West: about 160 miles
Why go: After leaving Miami, Route 1 heads over a chain of islands linked by 42 bridges surrounded by stunning water views. In Key Largo, John Pennekamp Coral Reef State Park runs glass-bottomed boat rides with views of the reefs, home to 260 species of tropical fish species. Ernest Hemingway fans can tour his former Key West property, now home to more than 40 six-toed cats (descendants of the writer's favored pets).
Where to stay: The Artist House is a restored Victorian mansion in Key West's Old Town (doubles from $115).
What to eat along the way: Keys Fisheries in Marathon supplies stone-crab claws to the famous Joe's Stone Crab in Miami; Eaton St. Seafood Market in Key West makes great crab cakes.