Contessa Boston: Rooftop Italian Dining with Iconic Views at The Newbury Hotel

Perched atop The Newbury Boston, one of the city's most prestigious addresses, Contessa is more than just a meal with a view, it's a moment. Major Food Group’s debut Boston venture has cemented itself as a top-tier destination for refined Italian dining, attracting both well-heeled locals and globe-trotting gourmands. Known as one of Boston’s most celebrated restaurants, Contessa delivers classic trattoria elegance reimagined through a luxe, whimsical lens.

Arriving at Contessa feels like being transported. With a dedicated entrance and elevator leading guests to the rooftop, the experience starts with anticipation and ends in awe. Designed by celebrated interior maestro Ken Fulk, the dining room glows with natural sunlight pouring in from the glass roof, complemented by retractable panels that open to the breeze when weather allows. It's a secret garden in the sky, with colorful florals, greenery, and a mix of pink, teal, and green chairs that evoke playful grandeur. The panoramic view of the Boston skyline and Public Garden made our lunch feel less like a meal and more like a reverie. Sitting by the window, I felt like I was floating.

Despite the high design, there’s nothing stiff about the setting. Vintage art, fresh florals, and a buzzing energy keep things grounded and warm. Service was exceptional, attentive, friendly, and incredibly well-informed. The staff guided us through the menu like seasoned storytellers, adding a layer of ease to the upscale atmosphere.

We kicked things off with two classics: the Daily Imported Burrata and Meatballs Aldo. The burrata, impossibly creamy, practically begged to be scooped up with crusty bread. The meatballs came smothered in a tangy mustard sauce that added unexpected depth to the comforting favorite.

But the standout starter, both visually and flavor-wise, was the Squash Carpaccio. Known as one of the most Instagrammed dishes in Boston, this colorful plate is a mosaic of shaved squash, arugula, pumpkin seeds, and a delicately sweet agrodolce dressing. It’s light, bright, and texturally dynamic, a modern riff on tradition that lives up to the hype.

It would be remiss to dine at Contessa and not order pasta, and in Boston, that means one thing: lobster. The Spicy Lobster Capellini was everything you want from a signature dish—al dente strands coated in a buttery, chili-kissed sauce that clung to every bite of sweet, tender lobster. It was spicy, silky, and totally addictive.

We also sampled the Grilled Mediterranean Branzino, which arrived perfectly charred and delicate, and the Chicken Francese, another classic made modern with zippy lemon notes and a crispy exterior that gave way to juicy meat inside. Both entrees balanced richness and restraint, a hallmark of Contessa's style.

There’s only one way to finish a meal this good: Crema di Boston. Contessa’s signature dessert pays homage to the city’s iconic Boston cream pie, layering vanilla custard, chocolate ganache, and lady fingers into a reimagined masterpiece. It was rich, creamy, and unapologetically indulgent, a fitting final note to a symphony of flavors.

Inspired by Northern Italy’s grand villas and old-world resorts, Contessa manages to be both timeless and timely. It’s a place where elegance doesn’t come at the expense of joy, where refined Italian cuisine meets laid-back glamour, and where every meal feels like a special occasion, even if it’s just lunch on a Tuesday.