America's Best Summer Getaways 2009

Beach Town: Boca Grande, Florida

Stay: This idyllic enclave on the Gulf of Mexico, 60 miles from Fort Myers, is a genuine glimpse of Old Florida, with whimsically named streets such as Damnificare, a postcard-worthy lighthouse watching over Gasparilla Island State Park, and long, quiet beaches lapped by gentle waves.

Eat: Great Value The Innlet, the 33-room sister property of the old-guard Gasparilla Inn, has a dockside restaurant and a relaxed, let’s-go-fishing vibe. Doubles from $110. A certifiably funky Florida joint, Temptation—think murals of leaping tarpon and a neon martini sign—serves local grouper, pompano, and soft-shell crabs. Dinner for two $100.

—Tom Austin