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.

Bridgeport

Bridgeport is the largest city in Connecticut, sitting on Long Island Sound with a working harbor and a real waterfront. P.T. Barnum lived here and the city's museum still pays tribute to his weird genius. It's a quick train ride to New York, with much cheaper housing and proper New England summers. The food scene punches above its weight, with old-school Portuguese and Brazilian spots packed every weekend.