San Francisco

San Francisco

San Francisco is hills, fog, Mission burritos the size of forearms, and pastel Victorians stacked like dominoes. Karl the Fog has his own Instagram, the cable cars are still mechanically pulled by cables running under the street, and the Pacific shows up at the end of every west-bound avenue. The food is wildly good, the views are theatrical, and yes, you'll get cardio just walking to the corner store.

Worcester

Worcester (pronounced 'WOO-stuh', please) is triple-deckers, classic American diners (the city helped invent the diner), and a college-heavy student population (Clark, Holy Cross, WPI, and a dozen more). The smiley face was invented here in 1963. It's central Massachusetts' working-class anchor and quietly gaining a real food scene. Cheaper than Boston, an hour away when you need it.