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.

Des Moines

Des Moines is the Iowa State Fair every August (think butter cows, deep-fried everything, and the political circus of every presidential cycle), insurance industry stability, and a downtown that's grown into a genuinely good food and brewery scene. The East Village neighborhood is the cool kid pocket. The whole city is bikeable. Friendly, affordable, and chronically underestimated.