Best Lounge in Boston


Lucky’s Lounge

South Boston

A lounge used to be a place where you could mingle with strangers and tie one on at any time of day. Now it’s usually just home to overdressed scenesters…Read More

2008 Best Lounge

The Enormous Room


The bouncer’s low-key; the door, unmarked. In fact, nearly everything about Central Square’s paradoxically named Enormous Room—including the plush furnishings and easy-on-the-ears music (old-school funk, Euro electro)—is deeply chill: The...Read More

2007 Best Lounge

Middlesex Lounge


The vibe, the feel—that’s what you’re looking for when you’re with friends and dressed for a Night Out. It’s also what the Middlesex does best. The intimate space is minimalist...Read More

2006 Best Lounge

Foundation Lounge


We’ve never understood the phrase “so hip it hurts.” A bikini wax—now that hurts. But a night spent amid lacquered wood and PYTs, drinking mango martinis while dipping into small...Read More

2005 Best Lounge

Middlesex Lounge


Rolling furniture, textured wood-grain walls, Kobe burgers: Few spots in bookish Cambridge offer West Coast atmosphere like the Middlesex. What burst onto the scene with a flurry of red-roped parties...Read More

2004 Best Lounge

Lucky’s Lounge

South Boston

Lucky’s easy-to-miss subterranean location in the Fort Point area and its lack of signage do little to thin the crowds that pack the retro hangout, looking to swill cocktails and...Read More

2003 Best Lounge



If Bogart and Bacall could hop off the screen of the Brattle Theatre, they’d make a beeline for this sexy Harvard Square gin joint around the corner. There in the...Read More

2002 Best Lounge

The Enormous Room


After centuries of sit-up-straight rigidity, it is now possible for Bostonians to lie back, sip on high-octane martinis, nibble on North African goodies, and maybe steal a kiss or two....Read More

2000 Best Lounge

The Milky Way

Jamaica Plain

The Milky Way looks the picture of a suburban basement lounge—if only a basement could be this cool. Tucked beneath Bella Luna restaurant in J.P.’s Hyde Square, the space is...Read More

1999 Best Lounge

B-Side Lounge


Take one part funky restaurant and one part festive bar scene. Sprinkle it with urban hipsters, geeky academics, and East Cambridge natives. Shake gently to the beat of Sinatra or...Read More

1998 Best Lounge

Wonder Bar


Who needs comfort food when you have comfort drink? Lurking beneath the floorboards of the stiff-backed, black-attired glam scene at the Wonder Bar is a comfortable lounge downstairs. It has...Read More

1997 Best Lounge

Frank’s Steakhouse


Sadly, the rediscovery of the cocktail culture has perverted the once noble activity of drinking, reducing it to a runway show for an unfortunate breed of baseball cap-sporting frat rats,...Read More

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