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.

Riverside

Riverside is where the navel orange got its start in America, with the parent tree from 1873 still alive and producing fruit on a downtown corner. The Mission Inn is a wildly ornate Spanish Revival hotel that hosts the country's biggest holiday lights festival. Riverside's downtown is genuinely walkable, with citrus groves still scattered through the foothills. Summers are dry and bright, with the foothills cooling the evenings.