It was only a matter of time before the Woodstock generation found the country’s new live-music capital. In the past three years, the riverside college town has seen its 55-plus population jump a staggering 83 percent. More than 200 jazz, blues, country, and rock venues, endless road cycling in the surrounding Hill Country, 300 annual days of sunshine, and average January temperatures of 60 degrees could explain why.

Relax. This isn’t the Florida your aunt’s bunco group retired to. Pre–Civil War and Victorian homes, art galleries, and Southern manners balance the hardworking fishing heritage of Apalachicola. Instead of playing shuffleboard, spend your days kayaking the Forgotten Coast barrier islands, fishing for redfish and tarpon, or hiking through 571,088-acre Apalachicola National Forest. And in lieu of early bird specials, keep your nights free for sampling the specialty at Boss Oyster and checking out film festivals at the Dixie Theater.