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.

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.