It may be hard to believe an old slammer for drunks could attract Boston's crème de la crème, but Alibi, located on the first floor of the recently converted Liberty Hotel, does exactly that.

Once filled with public drunks as the Charles Street Jail, Alibi now caters to the city’s upper crust, from politicians like John Kerry to Hollywood actors taking a break from set.

Attractive young professionals fill the space after work, eager to relax with friends at the candlelit tables or lounge on the russet couches. Details like the bluestone floors, bare brick walls, and barred windows recall the venue’s darker past, topped off by an original cell door that leads to the dimly-lit bar.

Alibi's theme creates a nostalgic atmosphere spiced with temptation and seduction, perfect for the well-dressed doctors and lawyers who show up to mingle with groups of flirtatious women or cozy up on cushy sofas late into the night.

An outdoor patio keeps guests cool in the summer as they share animated conversation over powerful cocktails such as the Walk of Shame and Jailbait,…

Tucked away in a residential area, Trina’s Starlite Lounge is a laid-back spot with a touch of punkish zing.

The ultra-chill hipsters and art students filing past the basic black-and-brick exterior will find a lively front room, where helpful bartenders behind the stainless steel bar mix up innovative cocktails with names like Blow My Skull Off and Death in the Afternoon.

A smaller anteroom sporting retro artwork and collages of old catalogs provides space for a diverse group of tattooed young professionals, local residents, and grad students to chow down on corn dogs and fried chicken.

Once the weekend rolls around, the Parlor Room opens up to savvy partiers looking to bask in the dark lounge vibe created by the curving marble bar and tattoo art on the walls.

Featuring comfort food and cheap suds without losing its sense of style, Trina’s Starlite Lounge is a cool destination for hip city dwellers who like their dives with a touch of class.

Named for the neighborhood joint frequented by the characters in the TV show Three's Company, the Regal Beagle gives Brookline residents an equally homey bar to call their own.

Nestled among the many shops and restaurants in Coolidge Corner, this mellow single-room bistro provides a comfy and dependable place for area professionals and Boston University grad students to grab brunch, lunch, or after-work drinks, or for couples to huddle around intimate tables aglow with reflected light from the mirrors.

A long burgundy leather banquette offers space for chatty groups of hipsters to sprawl out, while young professionals and artsy types tend to congregate in the back lounge where they can relax on high leather benches and sip creative cocktails like The Sassy Coworker and The Ladies’ Man, chosen from the blackboard on the wall.

A six-mile stretch of trails offering spectacular views along the Charles River, the Boston Esplanade is a year-round destination for Bostonians of all stripes.

Early morning sees suited bicycle commuters and joggers passing each other on the picturesque riverbank, while later in the day, fit young professionals take to the tennis courts, playing fields, and waterways for activities as diverse as rugby and windsurfing.

Although bustling with activity in all seasons, the park is really at its best in the summer, when warm nights draw everyone from couples in the mood for a romantic stroll to movie buffs settling in for an outdoor film screening.

Patrons looking to do time in a relaxed lounge and restaurant can head to Clink, a unique venue in the lobby of the Liberty Hotel that once housed the Charles Street Jail.

Situated under a series of spotlighted guard catwalks, the intimate space features exposed brick, arched windows, and large iron chandeliers that create a surprisingly sultry atmosphere.

Consisting of two rooms divided by a brick wall and several barred windows and cell doors, the restaurant attracts a sophisticated but laid-back clientele of designers, finance types, and young professionals who gather in the jail-cell alcoves to chat over dinner and drinks, while those interested in culinary matters can watch the chefs at work in the open kitchen in the larger room.

Lunch time finds the place filled with hotel guests and staff from the neighboring hospital, while evenings see an influx of after-work media professionals and off-duty doctors looking to unwind over a cocktail or two.

Later on, a more glamorous clientele shows up to chill out on the cushy wingbacks and sofas, dance to live jazz, or watch a…