Bridgeport

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.

Washington

Washington DC is power dressed in seersucker. The monuments glow at night, the Smithsonian museums are all free (yes, all of them), and the cherry blossoms in April make even cynical lobbyists pause for a selfie. It's one of the most international cities in America (embassies from everywhere), with food scenes to match. The vibe shifts every four years and the architecture stays magnificent through all of it.