The Liberty Hotel in Boston, Massachusetts

The luxurious Liberty Hotel in Boston is the former Charles Street Jail.

This name of this gorgeous hotel that opened in 2007 at the foot of Boston’s posh Beacon Hill neighborhood, is ironic. You see, the Liberty Hotel is the former Charles Street jail. Among the guests that checked into the jail (against their wills) were some well-known inmates including James Michael Curley, Malcolm X, Sacco and Vanzetti, suffragists imprisoned for protesting when President Woodrow Wilson visited Boston in 1919, and World War II prisoners of war from the German submarines.

If you’re wondering how a former jail could end up a luxury hotel, the answer is: good bones. The jail was designed by prison reformer Rev. Louis Dwight according to a 1790s humanitarian scheme. Granite walls form of a cross with four wings that from a central octagonal rotunda, 90-ft above a spacious atrium. Thirty huge, arched were added to provide natural light and ventilation.

Much of the jail’s beautiful structure was incorporated into the Liberty Hotel. Today, beneath the atrium are five dining and drinking establishments, CLINK, Alibi, Scampo, the Liberty Bar, and Catwalk. Above, cell blocks have been replaced with 300 luxurious guestrooms. A landscaped courtyard is the former exercise yard and what was once the “drunk tank” is now a bar called Alibi. Irony or no?

The Liberty Hotel made Conde Nast’ Traveler’s 2014 Gold List of the World’s Best Hotels.