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.

Portland

Portland Maine is lobster rolls, lighthouses (Portland Head Light is the brochure), a working waterfront where fishing boats still come in, and a food scene that has the same per-capita acclaim as the much bigger Portland Oregon. The Old Port's brick streets, breweries, and harbor views are walkable in an afternoon. Casco Bay's islands are a ferry ride away. Tiny, dense, and seriously delicious.