Make the most of Boston's nightlife!

Photo By Harshad Jadhav


By Harshad Jadhav

December 15, 2021

Library Lounge Paintings at Yvonne's | Photo by Harshad Jadhav

Apart from its food, culture, and history, Boston has a lot to offer.

Modern-day Bostonians like to drink, and what better place to try some new cocktails than the speakeasy bars in the city. There are plenty of reasons to try these bars — retro-style setting, good cocktails, the budget that fits everyone's pockets, their hidden nature, and word-of-mouth publicity. Whether you want to dine in and have an Espresso Martini at the end, or you want to have a couple of beers, these camouflaged bars offer them.

There are a handful of bars that paint the essence of prohibition-era speakeasies in the city. Sometimes these can be at locations where you might not expect them.

Some are well-known and sometimes raise doubts about being speakeasy, but one thing they share amongst themselves is, they all have the retro-themed ambiance.

People awaiting the opening of Krazy Kat Klub | By National Photo Company Collection - Library of CongressCatalog: url:, Public Domain,

What is a speakeasy bar?

A speakeasy is an illicit liquor shop or a drinking bar, or nowadays, a retro-style bar that replicates aspects of historical speakeasies.

In the image on the left, several patrons and a flapper await the opening of the Krazy Kat Klub, a speakeasy, in 1921.

"When I found out about this [speakeasies], ... interest in seeing many more [grew] because it [is] sort of a part of history in which people of all moralities gathered secretly in these places to feel free. That's what usually happens when a goverment puts in a law which is not agreed by most people," said Joseph, 24, who was enjoying his IPA with hot chicken wings.

Why is it called speakeasy?

In the 1880s, Kate Hester, a saloon owner, ran an illegal bar, like many others, in McKeesport, Pennsylvania, due to a hike in-state fees for saloon licenses from $50 to $500. She had a custom of raising her finger deprecatingly and saying, "shh... speak easy boys, speak easy," to quiet her rowdy customers speaking loudly. Soon the expression became common in the city and spread to Pittsburgh, Pennsylvania.

Many years later, during the prohibition era (1920-1933, longer in some states), where the manufacture, transportation, and sale of alcohol were illegal, speakeasy became a general term to describe a place to get illicit drinks.

The speakeasy-style trend began in 2000 with the opening of the bar Milk & Honey.

Some of the prohibition-era speakeasies today

New York's 21 Club.

By David Shankbone - English Wikipedia, CC BY 2.5,

Inside the Mystery Room of the Arizona Biltmore Hotel.

By Marine 69-71 - Own work, CC BY-SA 4.0,


The Gallery, hidden from Yvonne's exuberant main floor, is concealed behind a secret bookshelf at the back of the Library Lounge.

Rose Thorn Cocktail at Yvonne's | Photo by Harshad Jadhav

Labeled as pricy, they provide some good cocktails like Rose Thorn to favorites like Espresso Martini, which is worth the taste as it adds up to the shimmering ambiance. Book your tables online ahead of time to avoid waiting at the bar.

Located at 2 Winter Place, Boston, Yvonne's was inaugurated in 2015. Build on the landmark restaurant Locke-Ober, Yvonne's offers aesthetics that will make you fall in love with them.

Must-try cocktails: Espresso Martini and Rose Thorn

Don't miss: The bar at the Gallery (through the secret pathway behind the bookshelf).

Location: 2 Winter Place, Boston

Budget: $$$$

Lucky's Lounge

Being almost hidden in Fort Point, Lucky's Lounge is a classic retro-style bar known for its well-made cocktails and food. It is so discreet that you won't notice any attractive boards except for a small one, saying "Lucky's," which will lead you to a stairway to enter the bar.

"I think the drinks are good. I like the live singer and the decorations, very holiday-themed, very fun! I will try other speakeasies in the city, [and] I look forward to them," said Jackie, 24, who was sipping her Rye and Ginger cocktail drink.

Only sign to the entrance to Lucky's | Photo by Harshad Jadhav

Don't get confused with Lucky's Lounge and Lucky's Strike Fenway. Though not necessary, booking is recommended during weekends.

Lucky's, a Sinatra-esque lounge, with no-signage, and word-of-mouth publicity, this pocket-friendly bar will give you a traditional bar experience. From a wide menu, you could try Fire Cracker, made with lime, habañero simple syrup, and cranberry along with the strong flavor of grapefruit vodka. If not in the mood for cocktails, you can explore a wide variety of beers.

Must-try cocktails: Fire Cracker and Rye and Ginger

Don't miss: There are two bars, so don't forget to check out the other one too.

Location: 355 Congress St., Boston

Budget: $$$$

Modern Pastry - Underground

There's a bar underneath the Modern Pastry?

With astonishment on their face, this is usually what people say after they hear about the Underground bar at Modern Pastry. It's not their fault, no one could guess that there's a bar beneath a pastry shop! Look for the sign saying "Underground," when you get inside which is to the right-most side of the shop. That will take you to an underground stairway to a bar. A tiny place to grab sliders, wings, and beers.

Make sure to check out the timing of the bar if you're planning to visit it. It is closed on Mondays and Tuesdays and closes early on Sundays.

Must-try cocktails: Martinis (Espresso or Bread Banana)

Don't miss: Cannoli from the pastry shop

Location: 257 Hanover St., Boston

Budget: $$$$


Yvonne's Main floor decorations for Christmas

Yvonne's Main floor decorations for Christmas | Photo by Harshad Jadhav

Main floor bar at Yvonne's | Photo by Harshad Jadhav

Rose Thorn cocktail at Yvonne's | Photo by Harshad Jadhav

Boston Nightlife | Photo by Harshad Jadhav

Bar at Lucky's Lounge | Photo by Harshad Jadhav

Espresso Martini at Yvonne's | Photo by Harshad Jadhav

Bar at Lucky's Lounge | Photo By Harshad Jadhav

Lucky's Lounge Entrance | Photo by Harshad Jadhav

Lucky's Lounge speakeasy setting | Photo by Harshad Jadhav

Outside Modern Pastry | Photo by Harshad Jadhav