Contessa Boston
Italian restaurant · Back Bay ·
Italian-inspired rooftop dining with opulent decor and city views
Italian-inspired rooftop dining with opulent decor and city views
"One of Boston’s toughest reservations since opening in 2021, this glitzy Italian rooftop spot from Major Food Group draws celebrity sightings (Emily Blunt, Chris Hemsworth, Robert Downey Jr.) and delivers sparkling city views at night, consistent and friendly service, and a menu tuned for crowd-pleasing. Perched atop the Newbury Hotel at the corner of the Public Garden, the room is a glass box lined with opulent booths and velvet-covered chairs; soft lighting and low chatter create the feeling of a very exclusive party. Start with the butternut squash carpaccio—thin toasted squash layered and topped with arugula, crunchy pumpkin seeds, and a sweet agrodolce, the greens kissed with excellent olive oil and pepper—and the tonnato crudo, where hunks of juicy red raw tuna get a satisfying salty crunch from artichoke hearts and anchovies. Salt-pressed buttery San Daniele prosciutto comes with fresh seasonal fruit (recently thinly sliced pears). The spicy lobster capellini doesn’t run hot, but its rich, creamy sauce with a mild peppery flavor and a decadent amount of lobster meat more than compensates. Insider tip: if there’s a black truffle-topped pasta on special, it’s worth ordering for the tableside truffle shaving—exciting and dramatic, like everything else here." - Tanya Edwards
"Opened in 2022 as a glamorous rooftop destination that quickly became one of Boston’s hardest-to-score reservations and later expanded with a Miami outpost, this restaurant was the subject of an arbitration settlement after 68 current and former employees alleged years-long mishandling of tip money. Workers say the venue ran a tip pool using a points system to allocate tips to front-of-house staff, but allegedly diverted tips to ineligible back-of-house employees for over a year and repeatedly shorted the pool over multiple years — practices that violate Massachusetts rules tying tips to the lower front-of-house minimum wage. The employer paid out employees as part of the settlement while denying any admission of wrongdoing, and former staffers described both frustration at having to fight for owed wages and fond memories of service nights, urging diners to tip more generously in light of what happened behind the scenes." - Erika Adams
"For the views, make sure to grab drinks or dinner around sunset at this rooftop." - Todd Plummer
"While this posh Italian restaurant doesn’t have an actual roof deck, as it’s actually on the roof, you can sink into the plush surroundings while basking in the birds-eye views of Newbury Street. On days when the weather is nice, the team will retract the restaurant’s windows for breezy open-air dining." - Tanya Edwards
"Operated in Boston by Major Food Group as a restaurant in the Newbury Hotel, cited as an example of New York groups bringing Italian concepts to the city." - Erika Adams