Top Milwaukee Crime Tours

Explore Milwaukee’s criminal underworld on the Mobsters and Mafia Tour, a guided walking experience that uncovers the rise and fall of the Milwaukee Mob and the powerful Balistrieri crime family. Visit historic locations while discovering how organized crime, political influence, and underground enterprises shaped the city throughout the 20th century. Hear captivating stories of power, loyalty, corruption, and betrayal as your guide reveals the real people and events behind one of Milwaukee’s most fascinating chapters. While the tour touches on the city’s Prohibition-era roots, its primary focus is the Milwaukee Mob and the figures who dominated the city’s underworld from the 1960s through the 1980s. Perfect for history enthusiasts, true crime fans, and curious travelers seeking a side of Milwaukee few visitors ever discover.

Step back into Milwaukee’s Prohibition era and uncover a world of speakeasies, madams, gangsters, corruption, and scandal. The Whorin’ 20s Walking Tour explores the city’s notorious vice district during the Roaring Twenties, when bootleggers, brothel owners, politicians, and organized crime figures helped shape Milwaukee’s nightlife and underground economy. Led by expert storytellers, this entertaining and historically grounded walking tour reveals the hidden stories behind the city’s most colorful characters and forgotten locations. Along the way, guests will discover how Prohibition transformed Milwaukee and why the era continues to captivate visitors nearly a century later. Perfect for history enthusiasts, groups, couples, bachelorette parties, and anyone looking for a different side of Milwaukee beyond breweries and ballgames. Bride goes free with qualifying bachelorette party reservations.

One of the most haunted bars in the nation, Shaker’s Cigar Bar—a Milwaukee institution formerly owned by the infamous Al Capone—has a history as wild as its ghostly encounters. On this small-group tour, explore behind the scenes, hearing stories about its Prohibition-era connections, the bar's cemetery and brothel past, and accounts of lingering spirits. Part history tour, part paranormal experience, this tour is not for the faint of heart.

Find out about Milwaukee’s dark history and most haunted places with this ghost-themed tour. Opting for a private tour means you’ll hear your guide clearly and can ask all the questions you want along the way. Find out about the city’s devastating fires in 1892 and the ghosts that are still believed to haunt the city. Learn about apparitions in a pub’s basement and bathroom mirrors, and visit the city’s most haunted location.

Shakers Bar in Milwaukee, formerly owned by the infamous Al Capone, has some gritty stories that have happened behind its walls. Dive deeper into the stories, spirits, and paranormal encounters that have earned this bar a spot among the most haunted bars in the United States. Enjoy this experience with just a small group for company and an included cocktail—an ideal tour for those who want to go beyond the basics.