I’d put Mac’s Club Duce, or the Duce Bar, in Miami Beach, and Husong’s in Ensenada, Baja, Mexico on that list. Both are old-school comfortable places to drink and share conversation.
In the meantime, I’ll add two more of my old-school favorites to the list in honor of Ernest Hemingway: Sloppy Joes in Key West, and the Casino Club in Ketchum, Idaho.