Start your tour with a slice of pizza in the North End, Boston’s Little Italy and its oldest neighborhood. Then, head to the historic waterfront neighborhood of Charlestown, home to a wooden-hulled frigate named by George Washington (the USS Constitution) and one of the first major battles of the American Revolution, the Battle of Bunker Hill.
Grab another slice before jumping on the 10-minute ferry to Long Wharf pier. Stop by the Old State House, Boston’s oldest public building, and its oldest church, Old North Church. Check out Fan Pier for another great view of the city and head to the Blackstone Block, Boston’s oldest business district. Snag your last slice in the North End before finishing the tour at the Green Dragon, the basement watering hole whose clientele once included John Hancock and Paul Revere, or Bell in Hand, America’s oldest tavern.