Contessa Boston

Contessa sits on the rooftop of 3 Newbury St, perched above the boutiques that line the city's most famous shopping stretch. It holds a Wine Spectator Excellence Award, a recognition that tracks with the gravity of the room’s contemporary and classic Italian menu.

The room runs smart, trading the sidewalk bustle of Newbury Street for a vantage point that feels removed from the density below. While it shares the Italian focus of many spots in this part of Boston, it is the only one that makes the skyline the primary course. You go here for the contrast; the city feels like a diorama from this height, making it a better choice than the basement-level alternatives if you prefer your dinner with a sense of scale. A ten-minute walk from the crowds at Copley Square, it succeeds by being both a landmark and a departure from the street-level activity.