Looking for the perfect spot to sip and savour this festive season? From elegant lounges to cosy neighbourhood gems, Boston’s bar scene has something for every mood and occasion. Whether it’s a cocktail, a glass of New England’s finest craft beer, or a glass of wine, we have you covered. Raise a glass and explore the city’s top bars with our curated list of the 5 must-visit spots. Thank us later.
Il Casale
Step into rustic Italian charm at Il Casale, the first bar to grace the town of Belmont. Chef Dante deMagistris brings a blend of family recipes, culinary travels, and Michelin-starred techniques to this intimate restaurant, which also has a sister location in Lexington. Il Casale is a warm and inviting haven where authentic Italian dining meets modern sophistication. Housed in a beautifully restored firehouse, the space exudes cozy elegance with exposed brick walls, rustic wood finishes, and ambient lighting.
The menu celebrates Italian tradition, with cocktails like the Belmont 1959 cocktail, a nod to the town’s founding year, paired perfectly with starters like Polpette, Nonna’s classic meatballs in tomato ragu, and the creamy Burrata, served with prosciutto di Parma, kabocha squash, and grilled bread. For mains, don’t miss the Tagliatelle alla Bolognese, a rich, traditional meat ragu from Emilia Romagna.
During the holidays, Il Casale takes it to the next level with its Feast of the Seven Fishes ($89/person), featuring dishes like Grande Antipasto di Mare (fried calamari, shrimp cocktail, octopus salad) and Spigola (grilled striped bass with walnut stuffing). We cannot recommend it enough.
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Porto Boston
Porto Boston is where coastal elegance meets modern sophistication. Situated in the Back Bay area, this Mediterranean-inspired bar and restaurant exudes a chic, oceanic vibe with contemporary interiors and a light, breezy atmosphere that feels like a luxurious escape. Perfect for intimate gatherings or a refined night out. The drinks menu is a masterpiece, with highlights like the Tears of Chios cocktail—a delicate yet complex mix of Kleos Mastiha Spirit, reposado tequila, spiced pear, and lemon. For those interested in mocktails, Porto also offers a robust selection of zero-proof cocktails, alongside an impressive lineup of wine and beer.
Start with a full dozen oysters, perfectly fresh and briny, with a mix of Cotuit and Norumbega varieties. Continue your journey with roasted mushroom mafalde, featuring tender, house-made pasta in rich garlic butter and Parmigiano Reggiano sauce with a hint of Aleppo pepper for spice. Seafood lovers will swoon over the octopus a la plancha, served with fingerling potatoes, aioli, smoked tomato, and a bright celery relish. Another must-try is the tuna tartare, elevated by a seaweed yogurt base, a touch of sweet pear, spicy ginger, and the crunch of rice crackers. Cap off your meal with their warm chocolate chip cookie, gooey in the center, crispy on the edges—topped with vanilla gelato and a sprinkle of sea salt for the perfect sweet and salty finish.
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The Wellington
Located directly across from Il Casale, The Wellington offers a distinct yet complementary dining experience crafted by the DeMagistris brothers. This modern and sophisticated neighborhood eatery blends everyday American cuisine with eclectic twists and an elevated craft cocktail menu. The interior boasts a stylish mix of yellow, black, brown, and gray tones, topped by high ceilings, exposed beams, and vibrant finishes. The open-concept design allows diners to view the kitchen, adding energy to the space, while the sleek bar area invites guests to linger over expertly crafted drinks.
Start your experience with the Harry’s Bar Fellini, a sparkling blend of prosecco and peach nectar that’s as refreshing as it is elegant. Continue with the Smash Burger, a perfectly cooked flat patty topped with juicy tomatoes, pickles, and a touch of house flair, served with golden, crispy French fries. For dessert, do not forget to try the passion fruit cheesecake, a creamy, tangy finale to your meal that strikes the perfect balance between sweet and tart. The Wellington offers Friday night live band performances, but it also shines during the holiday season, offering memorable dining experiences perfect for celebrating with family and friends. On Christmas Eve, the restaurant will serve its a la carte menu with festive nightly specials, while New Year’s Eve features a luxurious four-course prix fixe dinner ($89 per person) and New Year’s Day brings a lively jazz brunch from 11:30 a.m. to 3:00 p.m., complete with standout dishes and festive drinks.
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Oak Bistro
A cozy gem that opened in 2023, Oak Bistro has quickly become a standout destination for farm-to-table American cuisine and perfectly crafted cocktails. Situated in Cambridge, this charming spot is perfect for those seeking small bites with big flavors in an inviting setting. Oak Bistro’s interior exudes warmth with a vibrant palette of yellow and pink accents, creating a welcoming ambiance that feels both fresh and intimate. During the summer, the experience extends outdoors with comfortable patio seating, perfect for enjoying a cocktail al fresco.
The menu celebrates local sourcing with creative small plates and expertly crafted drinks. Start with the buttermilk fried oysters, featuring a crisp, golden exterior complemented by a tangy lemon aioli, chili oil, and a sprinkle of sea salt. Another must-try is the crispy halloumi fries, a delightful combination of salty, chewy halloumi paired with chili sauce and a touch of honey drizzle. To drink, the Tia Maria cocktail is a revelation—a perfectly balanced blend of Sobieski vodka, St. Germain, Earl Grey tea, allspice honey, coconut whey, and lemon. Refreshing yet complex, this cocktail is as memorable as the dishes.
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XOXO Sushi Bar
XOXO Sushi Bar in Brookline combines modern elegance with a relaxed, unhurried vibe. With dim lighting, an open sushi bar where chefs craft dishes in full view, and a sleek bar area, it’s a great spot for unwinding over sushi and cocktails.
The menu features a variety of hot and cold dishes alongside sushi options like the 7-piece chef’s choice nigiri, showcasing fresh and delicate flavours. For drinks, the Jolly Rancher cocktail, made with Casamigos Reposado (hi there, George Clooney), blackberry, Thai basil, lime, and agave, that blends bold and refreshing flavours, is a must-try. The atmosphere at XOXO is easygoing, making it a great choice for those looking for a stylish yet laid-back evening. Great for catching up with friends or enjoying a casual date night.
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Images: Brands respectively
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