Lucky's Lounge

Bar / Live Music Venue / Lounge / Restaurant
Lucky's Lounge Sinatra lives on at Lucky's Lounge on Boston's Waterfront, with great live music, brunch, and themed cocktails. Check out this great Boston bar at Party Earth. Boston United States 42.350314 -71.04853
4.27 6
Lucky's Lounge - Bar | Live Music Venue | Lounge | Restaurant in Boston.
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Adriana
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Emma

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

  • Hours:

    M–F 11am–2am, Sa 6pm–2am, Su 10am–2am

  • Recommended as:

    • Day Spot
    • Night Spot

Party Earth Lucky's Lounge Review

The Scene

Sinatra lives on at Lucky's Lounge on Boston's Waterfront, with great live music, brunch, and themed cocktails. Check out this great Boston bar at Party Earth.

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.

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Tip from Emma:

If you’re with a group of friends, you’ll definitely want to share an order of the Kobe sliders. And don’t forget to wash them down with a Lady Luck cocktail – you know Sinatra would approve!

  • Crowd

    Diverse mix of business and finance types, trendy artists, jazz lovers, birthday girls, and young professionals, mid-20s to late 30s.

  • Entertainment / Music

    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.

  • Food / Miscellaneous

    Full American menu featuring meatloaf and buttermilk fried chicken. Reservations recommended for brunch.

  • Prices

    Brunch $6–$15, appetizers $2.50–$16, soups and salads $4–$15, entrées $15–$28. Beer $5–$9, wine $7–$14, cocktails $9–$11.

  • What to Wear / Dress Code

    Nice casual: t-shirts or dressy tops and jeans for women, and polos, hoodies, button-downs, or t-shirts and jeans for men.

  • Hot Nights / When to Go

    Friday and Saturday nights for the biggest crowds, with a line starting around 9:30pm, or Sundays for the Sinatra Brunch.

  • Close By

    Drink (348 Congress Street) is another fun lounge with an excellent menu of specialty cocktails.

Lucky's Lounge User Reviews

Average rating:
Lucky's is a great place to go at any point during the week, for any reason, great for large groups and private parties.
Corry H. Apr 13, 2013
Purposefully unmarked, Lucky's Lounge draws a certain type of crowd and vibe. Completely different from day to night, coming here at different times and hours during the week, you are going to get a completely different atmosphere. Lunch will be quick and satisfying, mostly business men and women popping in during their lunch breaks. The after work crowd is fun, light hearted and always sure to be cackling up a storm. Friday and Saturday nights are sure to be wild, never a cover charge which is a huge bonus, with young professionals letting off steam from a long work week. Live music will fill the restaurant until 11 when a DJ will take over and keep the night going strong. Sunday brunches have a fresh and lively atmosphere, the cocktails flow just as much as they do on Saturday night and the live Sinatra band will be sure to keep you in the mood for a Sunday fun-day.
A not-so-hidden gem
Alicia F. Nov 21, 2012
I LOVE Lucky's Lounge. Great music. Fun atmosphere. Terrific dirty martinis. For a bar with a speakeasy vibe, Lucky's Lounge is fairly busy during all hours of operations. Locals and out of towners alike come for everything: the atmosphere, delicious comfort foods (Kobe sliders!), and live jazz. The live jazz includes my personal favorite, the Sinatra Brunch. The weekly tribute to ol' Mickey Blues is the perfect way to kick off a Saturday or Sunday morning, and the tater tots that comes with my breakfast are just the icing on the cake. Brunch aside - a night a Lucky's Lounge can be either low-key or pretty rowdy, depending on the night you want to have. For a more chill time, try to grab a table in the dining area. Bands typically set up on the other side of the space where a boisterous crowd forms as the night progresses.
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