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.

Sarasota

Sarasota is the home of the Ringling Brothers Circus (the museum is wild, and yes, there's a vintage clown college history), and Siesta Key's beach is regularly named the best in America for its pure quartz sand. The cultural scene is heavy for a Florida city of its size (theater, opera, art museum). Gulf sunsets here are the brochure shot. The food scene has caught up to the city's wealth and the retirees' time.