The Liberty, Beacon Hill
Boston’s Charles Street Jail was remodeled into a luxury hotel that relishes its roots; the cellblock rooms and original catwalks lining the atrium remind you that a prison always has stories to tell. For instance, a captured German U-boat captain killed himself while imprisoned here in 1945, and one can only imagine what was going through Malcolm X’s head during his time inside. When a court ruled that conditions here were so poor that they violated the prisoners’ constitutional rights, it took nearly 20 years to relocate the inmates. For more on the history of the old jail, ask for a tour at the concierge desk. Afterwards, grab a drink at Alibi — probably the only time you’ll ever be able to get a drink in a drunk tank.