Selecting a wine at The Earle Restaurant isn't as simple as choosing between a red and a white. A recipient of Wine Spectator's Best of Award of Excellence for 20-plus years, The Earle's wine list heaves under the weight of its more than 1,200 listed bottles and from all those bricks weighing it down. Some of those varietals are even available by the glass at The Earle's wine bar, where the menu of light bites includes handmade pizzas crowned with pesto and shrimp.

In the main dining room, wines likewise complement dinners of award-winning French and Italian cuisine, from linguini tossed with crumbled garlic sausage to sautéed duck breast in apple brandy and cider. Those feasts unfold amid the room's romantic lighting and the historic building's exposed brick walls. Once the home of a jazz club, the Earle now spotlights jazz five nights a week with trios on weekends and solo guitarists or pianists on select weekdays.