Boston: Mobsters, Mayhem and Murder Walking Tour

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Take a scenic walk through the heart of Boston and learn about some of the city's most famous organized crime figures and dark history on this walking tour.


  • Escape into Boston's secret underworld on a crime and mob tour
  • Get the inside scoop from local guides who know the city inside out
  • Step into the shadows to learn about the history of the Boston mob
  • Listen to stories of notorious mobsters such as James “Whitey” Bulger
  • Enjoy a well-paced and entertaining walking tour with plenty of laughs


Embark on a walking tour around Boston’s center and learn about the city's dark and violent past. See landmarks that are tied to the city’s organized crime history as you listen to stories of notorious gangsters from a local guide. Meet your guide on the waterfront. As you stand across the street from where the 'crime' that helped found this country, and made the harbor a little more caffeinated, turn your gaze to the courthouse. Here, one of America's most notorious mobsters run from the law ended. Next, hear the baffling saga of Whitey Bulger, a criminal who had the FBI as muscle. Walking along the harbor, learn about pirate history before entering Boston's own Little Italy, the North End. Take in the smells and sights as you hear about what was once the largest robbery in American history. Find out about two criminals who struck fear into the hearts of people living in Boston. End with a scammer, and another Revolutionary crime that changed history.


Guide Walking tour

Important Information

  • Tour contains mature language Tour may be cancelled due to weather The total distance is about 3.5 mi/5.5 km. You will get to sit down at each stop to rest

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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