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.

Jacksonville

Jacksonville is the largest city in the continental U.S. by land area, which means everything is 20 minutes from everything else and most of those 20 minutes involve a bridge. The St. Johns River cuts the city in half, the beaches are a quick drive east, and the food scene leans seafood and surprisingly excellent BBQ. It's a Florida city without the theme-park vibe.