Naples

Naples

Naples brings wealthy retirees to the Gulf coast for genuinely some of the prettiest beaches in Florida, and the sunsets at the pier are a community ritual (everyone gathers, no one talks). The downtown along Fifth Avenue is pastel and breezy. Mercato has the upscale restaurants. The Everglades' western edge starts just south of town. Affluent, sunny, and quieter than the east-coast Florida cities.

Charleston

Charleston is pastel rowhouses, cobblestone streets, the smell of pluff mud at low tide, and shrimp and grits that should be illegal everywhere else. The historic district is a working postcard, the food scene punches way above its size, and the porches are made for sitting. Spoleto Festival every spring brings world-class arts. It's small, dense, and absurdly photogenic.