Contessa Boston

Contessa sits on the rooftop of 3 Newbury St, high above the busy intersection of Boston’s most famous retail corridor. It is a ten-minute walk from the stone facade of Trinity Church and the open lawns of Copley Square. The restaurant holds a Wine Spectator Excellence Award.

The room runs smart, leaning into the formality of classic Italian service rather than the casual bustle common to its street-level neighbors. Choosing Contessa over the surrounding cafes means trading the pedestrian crush for a vantage point over the city skyline. While Newbury Street is defined by its window-shopping pace, this rooftop offers a deliberate contrast, favoring a slower, more structured tempo that feels removed from the sidewalk. It is a calculated alternative for those who prefer their contemporary Italian cooking with a sense of perspective.