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.

After a slew of successful ventures in Tel Aviv, Miami, and New York City, Major Food Group from Mario Carbone, Rich Torrisi, and Jeff Zalaznick, made their first foray into Boston in 2021, launching the opulent Contessa atop the Newbury Hotel. 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 Raspberry Cobbler—but it’s the ambiance that really makes this spot shine. Outfitted with a marble bar, lush greenery, and a retractable glass roof, expect a healthy dose of old-school elegance while sipping on cocktails.

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!).