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.

Orlando

Orlando is theme parks plus lake-dotted residential neighborhoods, a surprisingly good food scene, and one of the fastest-growing tech hubs in the south. Winter Park is a charming brick-street pocket of art and brunch. The summer afternoon thunderstorms roll in at 3pm like clockwork. There's a swamp boardwalk within 15 minutes of wherever you are.