Jacqueline Pirolo knows all about the grind. The Italy-born, Long Island–raised beverage director of Wine Spectator Award of Excellence winner Macchialina in Miami started her career at a grueling, sleep-at-the office film production job in New York City. But when one of her older brothers asked her to help open the Saint Austere restaurant in Brooklyn, she not only found her calling, but connected with her past.

Another brother’s restaurant opening brought her to Miami, where she has since made a name for herself in the growing South Florida wine scene at Macchialina, where the all-Italian wine list showcases many of Italy's indigenous grapes. (Macchialina essentially translates as “little spot.”)