Playing Lockdown in the Liberty Hotel in Boston, Massachusetts
It's not for convicts anymore—but step into the Liberty Hotel, and you'll have to walk through a jail cell to get to the bar. What used to be the Charles Street Jail is now a luxury hotel, and a magnificent repurposing of the historic building. Can't afford to get locked down for the night? Just stay for a drink at one of the several bars. Sink deep into an overstuffed armchair in the lobby and gaze up at the 90-foot rotunda ceiling (built in 1851). Slip through iron prison grating on the way to the bathroom and you can get a peek at photos documenting the extensive restoration. Dramatic, uplifting, and otherworldly, this hotel has an odd energy and unique history. Check it out for a night—you may not want to leave—handcuffs are optional.