Fox's Sherron Inn
Centered around a beautiful oil painting of a jet taking off, this is a classic Miami cocktail lounge with aviation-themed décor and an aren't-the-fifties-great ambience. It's the kind of sympathetic joint where everyone—from construction workers and businessmen to University of Miami students—knows your name, but stays out of your business. Order a whiskey sour from the friendly (but not too friendly) staff, settle back on your stool at the bar, and get the night started.
Tip: Avoid weekends, when too many students frequent the place and upset the balance of the clientele.