Cedar Key, Florida
Funky, old Florida endures in this ramshackle hamlet set three miles into the Gulf of Mexico, about 50 miles southwest of Gainesville. No cookie-cutter condos or mega-developments here — just stretches of white-sand beaches and unspoiled marsh and mangrove bayous that are perfect for paddling. Be sure to row a half mile to the abandoned Atsena Otie Key, where you can explore the ruins of the Faber pencil factory circa 1868 — when Cedar Key was a logging capital and the second-largest city in Florida. Stay at the Low-Key Hideaway, a quirky but clean motel where you won't see kids (they're not allowed), but you will see epic sunsets from the tiki bar on the back porch. When you're done exploring the estuaries, clam beds, and shell mounds, have a drink in town at the delightfully shabby Island Hotel, built in 1859, where an unknown singer-songwriter named Jimmy Buffett used to play impromptu sets back in the early 1980s.
Getting there: From Gainesville, drive about an hour southwest.