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

Exploring Minneapolis-Saint Paul’s “Crooked” Gangster History: A Detailed Look at the Private 2-Hour Tour

If you’re interested in a different angle of Minneapolis-Saint Paul’s history, this “Crooked” St. Paul Gangsters Private Riding Tour offers a fascinating glimpse into the city’s criminal past. For two hours, you’ll sit behind the wheel—alongside a knowledgeable guide—and cruise through neighborhoods that once buzzed with illegal speakeasies, daring bank robberies, and notorious gangsters like John Dillinger.

What we really appreciate about this experience is its personalized approach—it’s just you, your companion, and an expert storyteller. This makes the tour both intimate and flexible, letting you soak in the stories at your own pace.

The only thing to keep in mind is that this is a driving tour, so if you’re hoping for a walking or more immersive experience, you might find it somewhat limited. That said, if you’re curious about the shadowy underworld of the Twin Cities and prefer a private, curated adventure, this tour hits the mark.

This experience is best suited for history buffs, crime history enthusiasts, or travelers eager to discover the city’s hidden stories in a relaxed, personalized setting.

Key Points

• Private tour offers personalized attention and flexibility.
• Learn fascinating stories about gangsters and historic criminal hideouts.
• Includes round-trip hotel pickup and bottled water for convenience.
• Ideal for small groups—up to two people for a more intimate experience.
• A two-hour drive that packs in a lot of history, making it great for short sightseeing windows.
• Suitable for all weather conditions, as the tour is mostly exterior and can be adjusted accordingly.

An In-Depth Look at the Tour Experience

What is the Crooked St. Paul Gangsters Private Riding Tour?

This tour is a two-hour private drive through the streets of Saint Paul, Minnesota, focusing on the city’s notorious gangster past. Led by Douglas Kline, a guide praised for his extensive knowledge and engaging storytelling, you’ll visit key locations linked to well-known criminals like John Dillinger, as well as sites where illegal activities once thrived. The tour is designed for up to two guests, making it ideal for couples or close friends who want a personalized, intimate experience.

How does the tour work?

Your journey begins with hotel pickup, ensuring a smooth start and eliminating the hassle of navigating unfamiliar streets. The guide then takes you through both Saint Paul’s historic neighborhoods and some more mundane areas that hide stories of bootlegging, bank robberies, and gangland escapades. The entire experience is around two hours, with flexibility to adapt to weather or personal preferences.

What makes this tour stand out?

It’s the expert storytelling and attention to detail. Reviewers mention how Douglas and his driver Ron are “very knowledgeable” about local history and architecture, which makes the stories come alive. For instance, you’ll see the former home of John Dillinger and learn about his daring escape from a gunfight. The tour also covers infamous events like a bloody kidnapping that captivated the nation, adding depth to what might otherwise be just another sightseeing drive.

What is included?

• Guided tour with a local expert
• Private transportation—your own vehicle for the duration
• Bottled water to keep you refreshed during the drive

It’s a straightforward package that emphasizes comfort, learning, and personalization.

The Itinerary in Detail: What You’ll See and Hear

First Stop: Saint Paul

The tour kicks off with exterior views of various Saint Paul locations—some famous, some more everyday—that are tied to the city’s gangster lore. Expect to see:

• The residence of John Dillinger, one of America’s most infamous bank robbers, and hear how he managed a daring escape during a shootout.
• The site of a brutal kidnapping that made headlines across the country, giving you a sense of the violent undercurrents of the era.
• A former speakeasy and casino, once a hotspot for both underworld figures and city elites, illustrating how crime and high society often intertwined.
• Neighborhoods that historically welcomed both wealthy residents and gangsters alike, showing the city’s complex social fabric during the Prohibition era.

What you’ll learn

Your guide, Douglas, doesn’t just point out buildings but tells stories—about daring escapes, dangerous turf wars, and the social scene of the time. According to reviews, Douglas’s “knowledge of the history and architecture” makes the stories vivid and engaging, making it feel like you’re stepping back in time.

Authentic Insights from Reviewers

Lyudmila, who traveled with her husband, mentioned that the two hours flew by because Douglas and Ron packed their itinerary with so much information. She appreciated how they managed to show her things she would “never be able to see in two days staying in Saint Paul,” highlighting the value of a curated, expert-led experience.

Another reviewer, Paula, described the tour as “the best she’s ever had,” emphasizing how Douglas’s warmth and the customized nature of the experience made it special. She particularly appreciated the blend of gangster lore and Prince attractions, showing how the tour can be tailored for diverse interests.

Why Choose This Tour?

This tour is particularly good for history enthusiasts who enjoy detailed storytelling, as well as those who prefer a comfortable, private experience over large group excursions. Its focus on local stories and architecturally significant sites makes it more than just a crime tour; it’s a cultural window into the city’s past.

The cost of $480 for up to two people might seem steep at first glance, but when you consider the personalized attention, expert guidance, and private transportation, it offers excellent value for those interested in a unique, tailored experience. The inclusion of hotel pickup and bottled water adds to the convenience.

Practical Tips for Your Booking

• Confirm your preferred pickup point; the tour is flexible on location within Saint Paul.
• Keep in mind that the tour runs rain or shine and can be adjusted based on weather conditions.
• The experience is best suited for those who appreciate storytelling and history, not necessarily for those seeking an energetic walking tour.
• Since the tour is private, it’s ideal for couples or small groups looking for an exclusive experience.
• Cancelations are free if you do so more than 24 hours in advance, giving you peace of mind if your plans change.

The Sum Up

The “Crooked” St. Paul Gangsters Private Riding Tour offers a well-balanced mix of history, storytelling, and personalized service. With a knowledgeable guide like Douglas, you’ll gain insight into the city’s criminal past that you simply can’t find in guidebooks. It’s perfect for curious travelers eager to uncover lesser-known stories and enjoy a private, tailored experience.

While not a full-day adventure, the two-hour format makes it a convenient and engaging option for those with limited time but a big appetite for local lore. It’s especially suited for couples or small groups who want a more intimate connection to Saint Paul’s shadowy past.

If you love history, storytelling, and a touch of the legendary, this tour will leave you with plenty of stories to tell—along with a fresh perspective on Minnesota’s twin cities.

Frequently Asked Questions

Is this tour suitable for all weather conditions?
Yes, the tour is designed to go rain or shine. It’s mostly exterior viewing and stories, so adjustments can be made if the weather turns bad.

How many people can participate?
It’s a private experience for up to two guests, making it ideal for couples or close friends who want a more personalized touch.

What is included in the price?
The fee covers the guided tour, private transportation, and bottled water. There are no hidden extras.

Can I customize the tour?
While the standard tour focuses on gangsters and historical sites, reviews suggest that Douglas can tailor the experience, blending in interests like Prince or other local highlights.

How long is the tour?
Approximately two hours, which is enough to see several key sites and hear engaging stories without feeling rushed.

How do I book or cancel?
You can book through the provided platform, and cancellations are free if made at least 24 hours in advance.

In summary, if you’re looking for a personal, story-rich journey into Minneapolis-Saint Paul’s gangster history, this private tour delivers. With a knowledgeable guide, flexible itinerary, and intimate setting, it offers a memorable way to see the city’s darker, more intriguing side. Perfect for history buffs, curious travelers, or anyone wanting a private perspective on Saint Paul’s hidden past.