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

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

When thinking about exploring Minneapolis-Saint Paul, most travelers focus on its vibrant arts scene, beautiful lakes, and historic architecture. But for those with a curiosity about the city’s secret past, especially its notorious gangsters, this private 2-hour tour offers a fascinating glimpse into the criminal underworld that once thrived here.

It’s particularly well-suited for history buffs, fans of true crime stories, and anyone who appreciates a personalized, flexible experience.

Two things stand out about this tour: First, the deep knowledge of the guides — they don’t just show you sights; they tell stories that bring the city’s gangster history vividly to life. Second, the private setting means you can customize your experience and go at your own pace.

One consideration is the price — at $480 for up to two people, it’s a bit of an investment, but the private, tailored approach offers value for those interested in a dedicated, in-depth look at the city’s criminal lore. This tour will appeal most to travelers who love stories of the underworld, historic architecture, and unique local history that most guidebooks don’t cover.

Key Points

• Exclusive Private Tour: Only your group, with tailored commentary from knowledgeable guides.
• Focus on Gangster History: Learn about figures like John Dillinger and notable crimes from the Prohibition era.
• Flexible Itinerary: Stops include both famous and lesser-known sites where gangsters once hung out or lived.
• Included Transport & Water: Private transportation with bottled water keeps you comfortable and refreshed.
• Great for Enthusiasts: Ideal for those interested in crime history, architecture, and local lore.
• Rain or Shine: The tour runs regardless of weather, with adjustments as needed.

An In-Depth Look at the Tour Experience

Starting Point and Overall Atmosphere

The tour kicks off from your preferred pickup point in Saint Paul or Minneapolis, and from there, you’re whisked through the city in private transportation. The benefit of this setup is the personalized attention—your guide can tailor the stops and stories to your interests, making this experience feel like a private history lesson rather than a generic tour.

The tour is designed to last approximately two hours, which might seem brief but is packed with sights and stories. As one reviewer put it, “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,” highlighting how efficiently the tour covers a lot of ground.

What You See and Learn

Your guide will point out exterior views of key locations in Saint Paul linked to the city’s gangster past. Among these are spots where famous criminals like John Dillinger lived and escaped gunfights — stories that will likely fascinate anyone interested in the thrill of early 20th-century crime. You’ll also see the site of a notorious kidnapping that captured national attention, giving you a sense of the city’s darker history.

The tour includes a visit to an illegal speakeasy and casino, once popular among both the underworld and the well-to-do, illustrating how gambling and bootlegging flourished here during Prohibition. Seeing where these clandestine activities took place, even just from the outside, helps paint a vivid picture of what life was like for gangsters and their associates.

Neighborhoods and Homes

Beyond the crime stories, the tour also explores neighborhoods where wealthy residents coexisted with the city’s more notorious figures. This brings an interesting contrast — the same streets that housed bootleggers and gangsters also hosted the city’s elite. One reviewer appreciated this balance, noting the guide’s expertise in both history and architecture, which enriches the experience.

What’s Unique About This Tour?

Unlike some group excursions, this private tour allows you to set your pace and focus on what interests you most. Whether you want to linger longer at certain sites or just listen and absorb the stories, the flexibility adds tremendous value.

Guides and Personal Touch

Our sources highlight Douglas Kline’s knowledgeable and engaging approach. Reviewers consistently praised his ability to weave stories with facts, making the history feel alive. One person said, “Doug and his driver Ron were very knowledgeable in the history, architecture of Saint Paul,” which is a testament to the quality of the guiding.

Comfort and Convenience

The inclusion of hotel pickup and drop-off means you don’t have to worry about navigating public transportation or finding the starting point. Bottled water is provided, adding a small but appreciated touch of comfort.

Valuing the Price

At $480 for a private two-hour experience, the tour positions itself as a premium option. However, considering the personalized attention, exclusive access, and the depth of stories told, many travelers will find it to be good value—especially if they’re interested in the criminal history of the Twin Cities or want a unique, tailored sightseeing experience.

This isn’t a quick overview but a carefully curated journey into a lesser-known side of Minneapolis-Saint Paul. The private nature means you won’t be part of a large bus group, and the flexibility allows for a more engaging and memorable experience.

Who Will Love This Tour?

This experience is perfect for history enthusiasts, true crime fans, and architecture buffs. It’s also ideal if you’re looking for a private, customizable tour that offers insights you won’t find in standard guidebooks. Given the engaging guides and the focus on storytelling, it’s particularly suited for those who enjoy learning through conversation rather than just sightseeing.

Travelers who appreciate a bit of historical drama, or who want to see the city through a different lens, will enjoy discovering the underbelly of Saint Paul’s past.

The Sum Up

For those interested in Minneapolis-Saint Paul’s gangster era, this private tour provides a focused, entertaining look into the city’s criminal history. Thanks to knowledgeable guides and personalized service, you’ll see the sites that shaped the underworld and hear stories that bring them vividly to life.

While it’s a bit on the pricier side, the exclusive, flexible nature and quality storytelling make it a worthwhile investment for crime history fans or anyone seeking a unique, off-the-beaten-path experience. The tour’s focus on authentic sites and stories makes it a compelling choice for those wanting more than just standard sightseeing.

Overall, if you’re after a personalized, story-rich exploration of Minneapolis-Saint Paul’s more colorful history, this tour delivers an engaging snapshot that’s both fun and educational.

FAQ

What is included in the tour?
The tour includes a private guided driving experience, private transportation, and bottled water. No admission fees are necessary as the stops are exterior views only.

How long is the tour?
It lasts about 2 hours, offering a compact but rundown of the city’s gangster history.

Can I customize the stops?
Yes, since it’s a private tour, the itinerary can be adjusted to match your interests and schedule.

Is transportation provided?
Yes, private transportation is included, making the experience convenient and comfortable.

What kind of locations will we see?
You’ll see sites like where John Dillinger lived, locations of famous crimes, former speakeasies and casinos, and neighborhoods where gangsters and the wealthy coexisted.

Are the guides knowledgeable?
Absolutely. Reviewers consistently praise Douglas Kline’s expertise and engaging storytelling.

What if it rains?
The tour runs rain or shine, with adjustments made to ensure your experience remains enjoyable.

Who is this tour best suited for?
It’s ideal for history buffs, crime story enthusiasts, architecture lovers, and travelers wanting a private, customizable experience.

This gangster-themed tour offers a rare peek into the shadowy corners of Minneapolis-Saint Paul’s past — perfect for those who like their history with a bit of intrigue and personality.