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.

Orlando

Orlando is theme parks plus lake-dotted residential neighborhoods, a surprisingly good food scene, and one of the fastest-growing tech hubs in the south. Winter Park is a charming brick-street pocket of art and brunch. The summer afternoon thunderstorms roll in at 3pm like clockwork. There's a swamp boardwalk within 15 minutes of wherever you are.