3. Alibi at The Liberty Hotel
Though it's carved out of the old Charles Street Prison building, we wouldn't exactly call a visit to Alibi "doing hard time," unless you consider lounging on leather couches, taking in a breeze on the outdoor patio, or sipping on a dirty martini with blue cheese-stuffed olives "punishment." This may be the one time you want to get thrown in the drunk tank.
215 Charles St., Beacon Hill (857-241-1144).