Formerly the Charles Street Jail, book some days and nights at the Starwood Luxury Collection Hotel. Built in 1851, the former imposing prison is now a first-class hotel and a national historic landmark. Instead of guys in striped uniforms, those confined inside these days are welcomed guests in regal surroundings, accommodations and dining.

The nearly 300 rooms and suites display the city skyline and Charles River through vintage wrought-iron window bars. Exteriors, interiors and raised catwalks where guards once strolled still entice guests to wander and sight-see the former stone buttresses. thelibertyhotel.com