“Crooked” St. Paul Gangsters Private Riding Tour (2 hrs)

Discover the Dark Side of Minneapolis-Saint Paul with the “Crooked” Gangsters Private Riding Tour

If you’re looking to add a little intrigue to your visit to Minneapolis-Saint Paul, this private 2-hour gangster tour offers a fascinating look into the city’s criminal past. While it’s not a typical sightseeing experience, it’s perfect for history buffs or anyone curious about the shadowy side of the Twin Cities.

What we really appreciate about this tour is how personalized it is—only your group, customized to your pace. Plus, the stories you hear are far richer than what you’d find in any guidebook, thanks to the knowledgeable guide, Douglas. On the flip side, the tour’s focus on gangsters and crime lore means it’s probably not ideal if you’re traveling with kids or looking for a family-friendly outing.

This experience is well-suited for curious adults who enjoy history, true crime, or local culture, and who want a behind-the-scenes look at a different facet of Minneapolis-Saint Paul.

Key Points

• Private and personalized for your small group, ensuring a flexible and intimate experience
• Rich storytelling from a knowledgeable guide that goes beyond typical historical facts
• Focus on gangster lore, including homes, hideouts, speakeasies, and notable crime events
• Convenient pickup and drop-off at your hotel, making logistics smooth
• Weather-friendly with the itinerary able to adjust to rain or shine
• Cost is $480 for up to 2 people, which offers a private, tailored experience

What is the “Crooked” Gangsters Private Riding Tour?

This tour offers a two-hour journey through the streets of Saint Paul and Minneapolis, focusing on the infamous figures and criminal activities that once shaped the city’s underworld. It’s a private experience, so it’s just for you and your companion—perfect if you’re into niche history or want a more exclusive look at the city’s past.

The tour is designed to go at your own pace and includes others’ reviews praising the depth of knowledge shared and the engaging storytelling. It’s a chance to see the city from a different perspective—one that reveals its underbelly of gangsters, bootleggers, and exotics like speakeasies.

What Makes This Tour Stand Out?

Compared to typical city tours that focus on landmarks, this one zeroes in on Minneapolis-Saint Paul’s gangster past. Learning about famous criminals like John Dillinger, their escapes, and notorious crimes brings a gritty, human element to the city’s history.

We love that the tour covers both the criminal side and the social context—from gangster hideouts to neighborhoods that blended wealth and crime. One reviewer mentioned the guide’s ability to show so much in just two hours, making it a compact but surprisingly comprehensive look into the city’s darker history.

The Itinerary in Detail

Starting Point: Saint Paul

The tour begins with a pickup from your hotel or preferred location. From there, your guide takes you on exterior views of key sites. Expect to see:

• John Dillinger’s former residence and hear how he famously escaped a gunfight. This part really captures the daring and audacity of 1930s gangsters.
• The site of a notorious kidnapping that stunned the nation, giving you a sense of the violent crime stories that played out in the city.
• An illegal speakeasy and casino—a glimpse into the illegal nightlife that thrived during Prohibition, popular with both the underworld and high society.
• Neighborhoods that hosted both the wealthy and the criminal, illustrating the stark contrasts within Saint Paul’s urban fabric.

The guide is quite flexible—if bad weather hits, the stops can be adapted so you get the best experience possible.

What’s Included and How It Feels

Your private tour includes a guided experience in a comfortable vehicle, with the option of hotel pickup and bottled water, making it all quite convenient and low-stress. It’s a chance to learn stories that go beyond the surface, with your guide providing context and details that you might not find elsewhere.

Why Travelers Love It

Reviewers consistently praise the knowledgeable guide, Douglas, and his driver, Ron, for making the experience memorable. One reviewer said, “Doug was able to show us so much in these 2 hours, that we would never be able to see it all in 2 days staying in Saint Paul.” This highlights how much history and local color can be packed into just a couple of hours.

Another expressed that it was “the best tour I’ve ever had,” emphasizing not just the content but the personalized attention and storytelling.

Is It Worth the Price?

At $480 for up to two people, this tour isn’t cheap, but considering it’s a private experience with a tailored itinerary, it offers good value for those interested in niche history. For the price, you get a customized, intimate look at the city’s gangster past—a perspective you won’t get on a typical city tour.

Who Should Consider This Tour?

• History buffs looking for a unique angle on Minneapolis-Saint Paul
• Crime and gangster enthusiasts eager for stories of infamous criminals and their exploits
• Travelers who like private, flexible tours and personalized attention
• Those interested in local culture and architecture, as the guide also shares insights into the neighborhoods and history of Saint Paul
• Probably not suitable for kids or families seeking a light or traditional sightseeing tour, given the crime-focused content

Final Thoughts

This private gangster tour offers a rare glimpse into a grittier side of Minneapolis-Saint Paul’s history, driven by a knowledgeable guide who shares stories with enthusiasm and insight. It’s a good pick if you want a personalized experience that combines history, intrigue, and a sense of adventure.

The fact that it’s private means you can focus on the aspects you find most interesting, and the flexible itinerary makes it suitable for weather concerns or specific interests. Just keep in mind the price point, which is on the higher side, but for many, the exclusivity and depth of storytelling make it worthwhile.

If you’re a fan of true crime, historical stories, or just enjoy discovering hidden stories in a city, this tour is likely to be a memorable highlight of your trip.

FAQ

Is this tour suitable for families with children?
Since the focus is on gangster stories and crime, it might be more suitable for older teens or adults interested in historical crime stories. It’s not specifically tailored for young children.

Can I cancel the tour if my plans change?
Yes, cancellation is free if done at least 24 hours in advance. You’ll receive a full refund if you cancel within that window.

What’s included in the price?
The tour includes a private guide, transportation, and bottled water. It’s a private experience, so only your group will participate.

How long is the tour?
It lasts approximately 2 hours, making it a quick but packed experience.

Is hotel pickup available?
Yes, pickup and drop-off at your hotel are included, which makes logistics easier.

What if it rains?
The itinerary can be adjusted for weather, so rain or shine, you should get a meaningful experience.

Who is the guide?
The guide is Douglas Kline, known for his knowledge and engaging storytelling.

All in all, if you’re after a unique, tailored look at Minneapolis-Saint Paul’s gangster past, this private tour could be just what you’re looking for. It’s a niche experience that packs a punch—perfect for those who crave more than just surface-level sightseeing.