Lucky's Lounge Bar / Live Music Venue / Lounge / Restaurant

Waterfront / Fort Point, Boston –

Tucked into the basement of an unmarked brick building, Lucky's Lounge is a cool little hideaway where the unusual mix of hipsters and business types can get a taste of Rat Pack glam.

Early evenings draw a well-dressed and easygoing crowd of bankers, brokers, and business people, who slide into the red banquettes in the dining area, while artsy types and couples sip martinis at the polished wood bar or cozy up by the faux fireplace in back.

As the night progresses, the place swells with lively music lovers and birthday partiers ready to dance to DJs or live bands performing everything from rock and R&B to soul, while Sinatra Saturdays ensure elbow room is at such a premium that signature drinks like Lucky’s Sidecar and the Pear O’Dice see more of the floor than patrons' taste buds.

Ol’ Blue Eyes keeps them coming back for the Sinatra Brunch on Sundays, when the Ron Poster Duo makes sure all the guys and dolls in attendance enjoy French toast and Bloody Marys with plenty of Guys and Dolls.

Prior to the Duo, the brunch was helmed by Al Vega, a sixty-year veteran of Boston’s music scene who had become a staple at the lounge until passing in December 2011 at the ripe old age of ninety.

Lucky’s Lounge may be hard to find, but the venue’s smooth music and hip speakeasy vibe is definitely worth the effort.