When Boston’s infamous Charles Street Jail was built in 1851, it served as an international model of prison architecture. Today, the former correctional facility is home to the cheekily-named Liberty Hotel, which opened in 2007. The hotel’s Alibi Bar & Lounge is located in the jail’s former “drunk tank” and has become a popular late-night spot for Bostonians to mingle and sip custom cocktails with prison-inspired names, like “Doin’ Thyme” and “Jail Bait.”

Originally designed by Boston architect Gridley J.F. Bryant, who consulted with prison reform advocate Rev. Louis Dwight, the innovative cross-shaped Charles Street Jail was constructed largely with granite, with massive arched windows supplying abundant natural light and ventilation. A 90-foot high octagonal rotunda in the center of the jail connected the four wings, which contained a total of 220 cells meant for one inmate each.

Over the years, famous occupants of the jail included Boston Mayor James Michael Curley, Frank Abagnale, Jr., Sacco and Vanzetti, and Malcolm X.

However, after being in continuous operation for more than 120 years, the jail’s deterioration became apparent; it was covered in pigeon droppings, prone to overcrowding, and plagued by frequent riots. A federal judge ordered the facility closed in 1973 after inmates sued over the squalid conditions. It ultimately shuttered in 1990 and was bought by the adjacent Massachusetts General Hospital, which sought proposals to preserve the building’s historic character due to its listing on the National Register of Historic Places.

Ultimately, prominent Boston developer Richard Friedman and his firm undertook the project, envisioning the jail as the city’s newest luxury hotel. He enlisted the help of Cambridge Seven Associates to give the derelict jail a $150 million facelift, complete with 300 rooms.

The team worked with the Massachusetts Historical Commission, the Boston Landmarks Commission, the National Park Service, and the Boston Redevelopment Authority to ensure the historical character would not be lost in the conversion.

Of course, every hotel needs a bar. The developers saw a way to playfully integrate the hotel’s theme into the ground-floor watering hole by setting it in the former “drunk tank” of the jail. The Alibi Bar & Lounge retains the jail’s original bluestone floors and brick cell walls, with decorative prison bars barricading the windows and doors.

Wall art pays homage to the bar’s name with celebrity mug shots -- from Frank Sinatra to Hugh Grant to Jane Fonda -- with cheeky alibis underneath.

“We tried to use a sense of humor,” said Friedman. Adding to the theme is a prominently featured work of art combining images of handcuffs, fingerprints, and barbed wire.

Developers were also sure to include luxury details like plush couches, state-of-the-art lighting, and a custom-made bar. Patrons sip on a wide variety of signature cocktails, wines, and liquor drinks, and order “bites” from the Italian-inspired menu. Popular items include thin-crust pizzas like the artichoke and prosciutto or white clam and bacon, as well as the tandori fired scallops.

An expansive, 100-seat outdoor patio was also added, and has proved enormously popular when the weather is nice. And even when it’s not, the bar inside fills up quickly so it’s best to get there early if you want to snag a seat. Here’s what you need to know:

Location: 215 Charles Street, Boston, Massachusetts 02114

Phone: (857) 241-1144

Hours: 5:00pm – 2:00am every night

What to drink: Try the signature cocktails like Single White Female (peach vodka, white grape, peychaud bitters, prosecco) and the Gordon Gekko (rye blood orange liqueur + orange bitters)

What to eat: Thin-crust pizza (lobster; artichoke and prosciutto; white clam and bacon); spaghetti with cracklings and hot pepper; green beans tempura.

Best Yelp review: "The ambiance is kept true to its former self: brick walls, jaill cells are still intact and famous B&W photos of criminals line the walls. The lighting is kept dim for couples on date nights but there's also a large seating area for small group get togethers. The back patio is where its at in the summer time, be sure to check it out."