A curlicue of islands south of Miami connected by the Overseas Highway, the Florida Keys are a mix of tropical splendor, swashbuckling romance (the spirit of Hemingway looms large), and Southern-tinged pleasures. Begin in Key Largo and Mrs. Mac’s Kitchen, a brightly painted locals’ hangout with fresh yellowtail snapper sandwiches. Half an hour south, Islamorada is renowned for sport-fishing and daily sunset celebrations—starring just-caught stone crab claws—at the Islamorada Fish Company. The Keys’ prettiest beach is about two-thirds of the way down the chain at Bahia Honda State Park, but the underwater scenery is just as gorgeous: Join a guided snorkel tour of Looe Key National Marine Sanctuary, just offshore. Bahia Honda is also handy to Little Palm Island Resort & Spa, an opulent retreat whose waterfront restaurant, open to nonguests, serves French-meets-Latin dishes such as short ribs with black-bean risotto. The end of the line is Key West, a Victorian confection of a town with a vibrant cultural scene and a healthy dose of funk. You can take in readings at the annual Key West Literary Seminar in January (writers including Annie Dillard and Robert Stone call the island home), art exhibits at the Studios of Key West, and first-rate productions at the Red Barn Theatre. Then get down and dirty with a lobster and fried green tomato BLT at Hogfish Bar & Grill, a let-the-good-times-roll joint right on the docks.
Florida Keys Affordable Tip: Many of Key West’s charming guesthouses, including the 1888 Cypress House (601 Caroline St.; 800/525-2488; doubles from $145), can be booked at reasonable rates through the Key West Innkeepers Association (800/492-1911).
Florida Keys Family Tip: John Pennekamp Coral Reef State Park is North America’s only living barrier reef and its first undersea park, with boat rentals, snorkeling, cabins, and campsites.