St. Augustine (pop. 12,707) is a rare Florida bird. Not only does this laid-back city offer some of the state's most consistent surfing; you can actually afford to buy a bungalow right on the sand (median price, $225,000). The town pier has a beginner-friendly beach break; you'll find bigger waves at the point break at Matanzas Inlet. Can't work in your pajamas? Jacksonville, 40 miles down the road, is home to several Fortune 500 companies.