Best of Boston

One hundred seventeen pages long, with upwards of 32,800 bottles, the Federalist’s wine list is a tome to be reckoned with—if not downright feared. But as inaccessible as the list may seem, sommelier James Flynn navigates it with cool confidence and a breadth of knowledge underscored by a sincere affection for wine and food. He can select a single perfect wine for a table filled with even the most difficult of entrée combinations—say, aged beef sirloin cooked rare, roasted scallops, and poussin—and serve the resulting (and invariably delicious) bottle promptly and at the ideal temperature with barely a bat of his eye.