San Luis Obispo

San Luis Obispo

San Luis Obispo (SLO to locals) sits halfway between LA and San Francisco on the central coast, with Cal Poly students, gorgeous wine country (Edna Valley and Paso Robles nearby), and a Thursday night farmers market that takes over downtown. It's been called the happiest city in America (multiple studies, Oprah included), and the vibe really does back that up. Bubblegum Alley is exactly what it sounds like. Mellow and beautiful.

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.