Boston has always been a city of firsts: America’s first public school (Boston Latin School), subway system (the “T”), public park (Boston Common), American University (Harvard), and even the first gay marriage license issued in America (in 2004). The petite colony, founded by English Puritans in the 1630, has evolved as an iconoclastic freedom-fighting juggernaut from the infamous events of the American Revolution to the controversial victory in Goodridge v. Department of Public Health, which legalized gay marriage in Massachusetts.

The revolutionary spirit and legacy live on through the city’s 250,000 students, a $4.8 billion dollar ephemeral force spread over 50 plus campuses on both sides of the Charles River. Year after year, this academic arena lures fresh, virginal sycophants to enter a world of scholarship and sagacity, well endowed with countless opportunities for rebellion against Puritan ways. With such blossoming creativity and burgeoning intellect in the air, it’s no surprise that Boston has pioneered yet another first in the United States – the conversion of a decrepit prison into a luxury hotel. Drop the bar of soap jokes aside, this is one Boston prison you may never want to leave! The gay man prison fantasy takes on a new meaning at The Liberty Hotel.

The former Charles Street Jail cum 5 star architecture and design masterpiece is quintessentially Boston – historic, eclectic, fashionable, and meticulous. The entrance captivates patrons with contemporary mosaics rising in tandem with dueling escalators to the jail’s open center – now the hotel’s bustling lobby. Tiers of wrought iron and original weathered brick envelop the lobby’s full 360 degrees, cast over 5 levels and 90 feet, illuminated by chain-linked chandeliers and natural light peering through elaborate ocular windows and tri-story glass panes. The mahogany panels strategically blend into the subtle burgundy/black/white contrasts over a series of plentiful couches and fabulous chairs, ideal for absorbing the hotel’s warmth and splendor. Curious guests repeat visits to the lobby long after the complimentary champagne experience upon check in. The awe-inspiring reinvention and re-interpretation of one of Boston’s most notorious prisons reveals a functioning oversized work of art – easily venerated for hours.

The prison motif tapers off upon entering the joining hotel tower, shifting attention to the immaculate views over the Charles River from all 298 rooms. Floor to ceiling windows peer over the verdant crossroads of Boston and Cambridge, painting postcard perfect scenes of stacked sailboats fading into the horizon. The rooms themselves are simple yet elegant, technologically profound, and scrumptiously comfortable.

Adjacent to the jail cell entrance, the award-winning restaurant, Scampo, has foodies and gourmets trekking over from neighboring states to sample chef Lydia Shire’s gastronomic magnum opus. Lydia’s renowned lobster dishes - lobster pizza, sea salted butter poached lobster with red swiss chard gnocchi, and lobster latte – are just a microcosm of her creative culinary ingenuity and prowess. The menu offers vast vegetarian, meat, seafood, and carb comma options, with descriptions and unlikely combinations seductive enough to warrant several courses (e.g. warm burrata with beet crudo & crushed marcona almond; fresh corn agnolotti del plien with whipped parmesan butter and sherried chanterelles; grilled Vermont quail over roasted peach risotto and pistachio pesto). The gleefully frenetic pace of the open kitchen, the talk of bedazzled patrons, and the undeniable upbeat vibe lend to an unforgettable dining experience.

Just upstairs, the hotel’s second restaurant, CLINK., takes no prisoners!  The vestiges of original cells set the backdrop for modern American cuisine, heavily focused on local and sustainable products. The half dozen artisan cheeses are pure dairy utopia, merging the savory fruits of New England’s finest utters with sweet home-made preserves. The raw bar presents top regional catch on the half shell, including Thatch Island Oysters from Barnstable, MA and Littleneck Clams from Cape Cod. The hearty mains satisfy carnivorous cravings with such dishes as the Natural Venison Loin (with sweetbreads, pistachio puree, braised endives and raisin jus) and the Red Wine Braised Shortribs (with potato puree, maitake mushrooms and horseradish gremolata).

In three short years The Liberty Hotel, its restaurants and its trendy bar, Alibi, have risen from the ashes of a defunct jailhouse junkyard, preserving and re-defining a major historical link to Boston’s dark side. Indeed, The Liberty Hotel is a rare one-of-a-kind in the hotel industry. It’s not part of any chain or any cookie-cutter blueprint. It’s a true original, a flawless modern reincarnation of a notorious historic site, a compulsory experience on any visit to the irresistible city of Boston.