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.

Orlando

Orlando is theme parks plus lake-dotted residential neighborhoods, a surprisingly good food scene, and one of the fastest-growing tech hubs in the south. Winter Park is a charming brick-street pocket of art and brunch. The summer afternoon thunderstorms roll in at 3pm like clockwork. There's a swamp boardwalk within 15 minutes of wherever you are.