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.

Ocala

Ocala is the horse capital of the world (it actually has more thoroughbred horses than Lexington, Kentucky), with rolling hills of horse farms unlike anywhere else in Florida. Silver Springs (one of the largest artesian springs in the world) is right next door, with glass-bottom boats and clear blue water. Surprisingly hilly. Slower than the coastal cities, with a quietly strong equestrian economy.