San Francisco

San Francisco

San Francisco is hills, fog, Mission burritos the size of forearms, and pastel Victorians stacked like dominoes. Karl the Fog has his own Instagram, the cable cars are still mechanically pulled by cables running under the street, and the Pacific shows up at the end of every west-bound avenue. The food is wildly good, the views are theatrical, and yes, you'll get cardio just walking to the corner store.

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.