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.

San Antonio

San Antonio wraps the River Walk through downtown like a Venetian canal trail (much shorter, but lined with mariachi and margaritas). The Alamo sits in the middle of it all, the five Spanish missions are a UNESCO World Heritage Site, and the puffy tacos are unlike Tex-Mex anywhere else. Fiesta in April is essentially a 10-day citywide block party. It's bigger and prouder than outsiders expect.