WHY HERE: Other cocktail spots in the city might have a retro vibe, but Vito’s is as real as they come. “Behaving badly since 1953” is the slogan, and the padded red banquets and sultry bar encourage a bit of wickedness. Naturally, you can get a Martini or Manhattan, but consider also well-crafted modern creations, like the Bitter Tears (pisco, rum, barolo chinato, Campari and chocolate bitters). Excellent pasta and pizza dishes round out your evening.
WHY NOW: This is where Sinatra and his buddies might have celebrated the night away (in the private Cougar Room) if he was gigging in Seattle. Catch contemporary and classic live jazz, blues and soul to complete the mood.