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.

Boulder

Boulder is the Flatirons rising right behind town, the Pearl Street Mall pedestrian shopping, and a population that runs more, climbs more, and bikes more than basically any other American city. CU keeps it young, the foothills keep it active, and the food scene leans organic-virtuous. The access to the Rockies is unmatched and the sunshine is relentless, and locals invest in the city like it's a lifestyle, not just an address.