Santa Maria

Santa Maria

Santa Maria has its own style of barbecue (tri-tip cooked over red oak with pinquito beans and salsa), which is a legitimate regional tradition that locals will fight you about. The surrounding Santa Maria Valley is becoming serious wine country (especially Pinot Noir and Chardonnay). It's quieter and more affordable than its central coast neighbors. The Pacific is right there.

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.