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.

Sarasota

Sarasota is the home of the Ringling Brothers Circus (the museum is wild, and yes, there's a vintage clown college history), and Siesta Key's beach is regularly named the best in America for its pure quartz sand. The cultural scene is heavy for a Florida city of its size (theater, opera, art museum). Gulf sunsets here are the brochure shot. The food scene has caught up to the city's wealth and the retirees' time.