Contessa

This rooftop oasis perched atop The Newbury Boston is the cherry on top of the city’s most exciting vertical suite of luxurious offerings. From hospitality company Major Food Group, Contessa is a 4,000-square-foot grand trattoria space, luxuriously appointed in Art Deco details that almost—almost—pull you away from the sweeping skyline views. The Italian menu invites you to dine on prosciutto from five different regions, tortellini en brodo, pizzas, and dry-aged bistecca fiorentina. Start with a spritz, move onto a Negroni or martini, and revel in an evening spent with your head literally in the clouds. Just plan ahead, because this is the most coveted reservation in the city; the lunch menu may be your best bet.

A 4,000-square-foot rooftop trattoria space, luxuriously appointed in art deco details that almost pull you away from the sweeping city views (and, oh yeah, your date). The Italian bill invites you and your sweetie to dine on prosciutto from five different regions, tortellini en brodo, pizza, and dry-aged bistecca fiorentina. Start with a spritz, move onto a Negroni or Martini, and revel in a special evening spent literally above it all (just be sure to book way ahead of time).

The best seat in the city on the best day of the year? This is a true gift for everyone lucky enough to attend. On Christmas Day, tuck into a four-course, family-style spread for $195 per person that includes burrata with caviar, spicy lobster rigatoni, grilled Mediterranean branzino, and olive oil ice cream with truffle (gah!).

After a slew of successful ventures in Tel Aviv, Miami, and New York City, the Mario Carbone, Rich Torrisi, and Jeff Zalaznick-fronted Major Food Group has made their first foray into Boston, launching the opulent Contessa atop the Newbury Hotel last year. Flavorful Italian favorites like Veal Milanese and Fusilli Genovese are all up for grabs here, while drink options range from the effervescent Spritz Contessa to the Boulevardier—but it’s the ambiance that really makes Contessa shine. This spot is outfitted with a marble bar, lush plant life, and a retractable glass roof, providing newcomers with a healthy dose of old-school elegance to enjoy as they sip their cocktails.

This rooftop oasis is one of the most coveted dinner tables in town—which is why brunch might be your best chance to get in there. The daytime Italian menu invites you to dine on Florentine Benedict, Panettone French Toast, carbonara scramble, and smoked salmon carpaccio. Start with a spritz, move onto a Negroni if you’re feeling cheeky, and revel in a morning spent with your head literally in the clouds.