Lucky's Lounge
About
Lucky's Lounge is an underground bar at 355 Congress Street in Fort Point with, in the bar's own words, no sign out front: you follow the red lights down the stairs. Below street level it plays the speakeasy theme with dim light, vintage booths, cocktail classics and what it calls an homage to Sinatra, down to a Sinatra Brunch on Sundays. The kitchen runs late, until 1:30 a.m. on most nights.
It suits a group that wants food and drinks under one roof, a birthday, or colleagues looking for somewhere after a day at the Boston Convention and Exhibition Center, a crowd the bar courts openly. Getting there is simple: the bar puts South Station on the Red Line at a 10-minute walk, and the Silver Line SL2 stops at World Trade Center a few blocks away.
Drinks
The cocktail list sticks to crowd-pleasers made the Lucky's way: an espresso martini, a Lucky's Mai Tai, the Speakeasy Spritz with Aperol and elderflower, and a Naked & Famous for mezcal drinkers. Beer runs from Lone Pine's Oh-J double IPA and Bent Water from Lynn to Narragansett and Miller High Life, with ciders, seltzers, wine and a short Champagne list.
Food
The menu is comfort food: smash burgers in single, double and triple stacks, pork belly bao, dumplings, nachos, flatbreads, a steak and cheese and fish and chips. Lunch runs on weekdays. Lucky Hour, every day from 4 to 7 p.m., brings $5, $6 and $7 bites, for guests dining in only.
Weekly nights
Monday is free standup comedy, and Tuesday is Triple Trivia, with a gift card for the winners. Both start in the evening after doors open at 4 p.m.; times are in the FAQ.
Groups and private events
The space works for groups of almost any size, from a couch corner for about 20 to a private lounge for up to 140 and a full buyout for 234. Private events are planned and booked through Boston's Best Events.
Sources: Lucky's Lounge, menus, happenings, private events, contact and directions. Checked September 30, 2026.
Contact Information
Boston, 02210
Photo: Rumen Nikolov via Google
Lucky's Lounge
About Lucky's Lounge
Quick answer: Lucky's Lounge is a bar at 355 Congress Street, Boston, MA 02210. Underground bar in Fort Point with a Sinatra theme: cocktail classics, smash burgers until 1:30 a.m., free Monday comedy and Tuesday trivia.
Last updated
Lucky's Lounge is an underground bar at 355 Congress Street in Fort Point with, in the bar's own words, no sign out front: you follow the red lights down the stairs. Below street level it plays the speakeasy theme with dim light, vintage booths, cocktail classics and what it calls an homage to Sinatra, down to a Sinatra Brunch on Sundays. The kitchen runs late, until 1:30 a.m. on most nights.
It suits a group that wants food and drinks under one roof, a birthday, or colleagues looking for somewhere after a day at the Boston Convention and Exhibition Center, a crowd the bar courts openly. Getting there is simple: the bar puts South Station on the Red Line at a 10-minute walk, and the Silver Line SL2 stops at World Trade Center a few blocks away.
Drinks
The cocktail list sticks to crowd-pleasers made the Lucky's way: an espresso martini, a Lucky's Mai Tai, the Speakeasy Spritz with Aperol and elderflower, and a Naked & Famous for mezcal drinkers. Beer runs from Lone Pine's Oh-J double IPA and Bent Water from Lynn to Narragansett and Miller High Life, with ciders, seltzers, wine and a short Champagne list.
Food
The menu is comfort food: smash burgers in single, double and triple stacks, pork belly bao, dumplings, nachos, flatbreads, a steak and cheese and fish and chips. Lunch runs on weekdays. Lucky Hour, every day from 4 to 7 p.m., brings $5, $6 and $7 bites, for guests dining in only.
Weekly nights
Monday is free standup comedy, and Tuesday is Triple Trivia, with a gift card for the winners. Both start in the evening after doors open at 4 p.m.; times are in the FAQ.
Groups and private events
The space works for groups of almost any size, from a couch corner for about 20 to a private lounge for up to 140 and a full buyout for 234. Private events are planned and booked through Boston's Best Events.
Sources: Lucky's Lounge, menus, happenings, private events, contact and directions. Checked September 30, 2026.
Frequently Asked Questions
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Things to do
Book a Boston experience
- Freedom Trail walking tourSmall-group guided walk, about 2.5 hours
- Duck boat tourCity sights by road, then a Charles River cruise
- Whale watching cruiseHalf-day trip from Long Wharf to Stellwagen Bank
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