San Jose

San Jose

San Jose is Silicon Valley's anchor city, much bigger than San Francisco by population, and culturally underrated because everyone drives through it on the way somewhere else. The Vietnamese food scene (especially in Little Saigon) is one of the best in the country. The weather is impossibly mild, the Santa Cruz Mountains rise to the west, and the tech money funds a genuinely excellent restaurant scene.

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.