Best of the New

Celebrating a wedding in the former Charles Street Jail gives new meaning to the phrase "the old ball and chain." When the prison building was converted into a hotel in 2007, the architect added a new tower of luxe guest rooms but, fortunately, omitted the cell doors. The hotel has a cleverly named lounge, Alibi, and two restaurants-celebrity chef Lydia Shire's Scampo, and Clink, run by executive chef Joseph Margate, who also offers a catering menu. The lobby bar, an extension of Clink, provides plenty of seating for elegant lounging and surreptitious star-gazing.

Standout Features: Undoubtedly, its award-winning architecture and two world-class restaurants make the Liberty a choice wedding destination. The original brick walls and enormous period chandeliers decorate the hotel's five-story octagonal atrium, and most guest rooms offer rare Charles River views. Cocktails are typically served on the fifth-floor catwalk overlooking the atrium, where wedding guests can savor sushi and tapas. A dinner in the Liberty Ballroom, whose three-tiered chandeliers mimic the larger lobby fixtures, can include entrées like short ribs and veal osso bucco, and desserts such as truffled rice pudding and panna cotta. From the ballroom floor, you can gaze through enormous windows that afford views of Beacon Hill. Outside, the hotel's courtyard functions as another swank ceremony location.

Capacity: 180 seated; 300 for cocktails

Catering: Must be provided by the hotel, except for wedding cakes from outside bakers

Food and Beverage Fee: Starts at $20,000

Find it: 215 Charles St., Boston, 617-224-4000, libertyhotel.com