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.

Washington

Washington DC is power dressed in seersucker. The monuments glow at night, the Smithsonian museums are all free (yes, all of them), and the cherry blossoms in April make even cynical lobbyists pause for a selfie. It's one of the most international cities in America (embassies from everywhere), with food scenes to match. The vibe shifts every four years and the architecture stays magnificent through all of it.