The Sultry Boston Speakeasy That Feels Straight Out Of A Frank Sinatra Song

There are so many fun nods to the swinging sixties in Boston. From colorful vintage stores and record shops to glamorous hotels and storied bars, you can step back in time in so many different ways across the city. But there's one modern speakeasy you need to visit if you really feel like channeling a Frank Sinatra song: The Red Fox.

Located in the historic North End neighborhood, Boston's answer to Little Italy, The Red Fox is an Italian-American restaurant and lounge oozing with old-school charm. The eatery was opened by the All Day Hospitality Group in 2024, but you'd never guess that from its retro-inspired interior. The dimly-lit space is filled with remnants from a much more luxurious past, like fringed lampshades, crimson leather booths, and wood-paneled walls.

There's even a botanical-print carpet, and a cocktail menu filled with classics like gin martinis, negronis, and rum punch. As for the food? That evokes nostalgia too, because what screams Rat Pack-era more than crispy chicken parmesan, spaghetti and meatballs, and classic shrimp cocktail?

The Red Fox isn't trying to do anything fancy. Yes, the space feels like a speakeasy, and it certainly charges Boston prices, but the team has chosen not to mess with the classics. The menu has an entire section dedicated to red sauce and there aren't any complicated descriptions or accompaniments. This is where you go at night to enjoy prosciutto, rigatoni, and pasta al limone after a long day at work downtown.

The cocktail menu is where things get a little more interesting. There's a pine-infused spritz with vanilla and clove, a sour apple martini with Granny Smith cordial, and a rotating clarified milk punch. Online reviewers say that the drinks and ambiance is where The Red Fox really shines, but people do love the food, too. One Yelp reviewer says, "It feels like eating in your Italian grandma's basement (in the best way)". Another writes, that it "feels like descending into a different era. This is not just a bar; it's a masterpiece of atmosphere and design."

Customers have shared similar experiences on Google, saying, "Approaching the unassuming door to what appeared to be an office of some sort ... we descended the staircase and entered into an entirely different world [...] While the Arancini was probably the best I've ever tasted, the strangolapreti is probably one of the best foods I have ever tasted. Anywhere. Ever." You might just need to put your favorite Sinatra song on and find the place for yourself.