Party Earth Review 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... ... read full review
355 Congress Street
Boston, MA 02210
Red Line: South Station
M–F 11am–2am, Sa 6pm–2am, Su 10am–2am
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.
Diverse mix of business and finance types, trendy artists, jazz lovers, birthday girls, and young professionals, mid-20s to late 30s.
Live music includes Case of the Mondays featuring acoustic guitar; classic rock covers, jazz, and funk on Thursdays and Fridays; Sinatra Saturdays in the dining room from 7:30pm and Sinatra Brunch Saturdays and Sundays 10am–3pm featuring Sinatra covers. DJ spins a mix of R&B, classic rock, funk, and soul Saturdays in the lounge from 10pm.
Full American menu featuring meatloaf and buttermilk fried chicken. Reservations recommended for brunch.
Brunch $6–$15, appetizers $2.50–$16, soups and salads $4–$15, entrées $15–$28. Beer $5–$9, wine $7–$14, cocktails $9–$11.
Nice casual: t-shirts or dressy tops and jeans for women, and polos, hoodies, button-downs, or t-shirts and jeans for men.
Friday and Saturday nights for the biggest crowds, with a line starting around 9:30pm, or Sundays for the Sinatra Brunch.
Drink (348 Congress Street) is another fun lounge with an excellent menu of specialty cocktails.