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

If you’re looking for a tour that combines history, intrigue, and authentic storytelling, the “Crooked” St. Paul Gangsters Private Riding Tour offers a compelling glimpse into the shadowy world of 1930s gangsters, bootleggers, and lawless characters that once roamed the Twin Cities. For just $480 per group (up to two people), you’ll spend about two hours in a private vehicle with a knowledgeable guide, exploring both Saint Paul’s streets and hidden corners that hide stories of daring escapes and notorious figures like John Dillinger.

What makes this experience stand out? First, the personalized nature of the tour means you get a tailored adventure, with your guide adjusting stops based on weather and your interests. Second, the focus on local legends and secret sites offers a level of detail seldom found in generic city tours. It’s perfect for history buffs, crime story enthusiasts, or anyone curious about the colorful, gritty past of Minnesota’s capital.

However, it’s worth noting that this tour is not a sprawling “see everything” sightseeing bus — it’s a focused, intimate exploration that requires a bit of riding in a car. If you’re looking for a quick, no-fuss introduction to Twin Cities’ gangster lore with a maximum of personalized attention, this could be ideal. It’s especially suited for those who enjoy storytelling that feels authentic and immersive, rather than overly polished.

Who Should Consider this Tour?

This tour suits travelers with a keen interest in American crime history, those who appreciate personalized, behind-the-scenes narratives, and anyone eager to see the city through a different lens — one filled with historical scandals and legendary figures. It offers insight into Saint Paul’s neighborhoods, revealing a mix of wealthy enclaves and crime hotspots, and gives a fresh perspective on the city’s past.

Key Points

• Personalized & Private: Focused attention from your guide ensures a tailored experience.
• Rich Local Lore: Learn stories about John Dillinger, speakeasies, and gang hideouts.
• Convenient: Includes hotel pickup and drop-off, making it easy to fit into your schedule.
• Flexible & Engaging: The itinerary adapts to weather and your curiosity.
• Affordable for the Experience: For just $480, you get a deep dive into Twin Cities crime history.
• Expert Guides: Knowledgeable narration elevates the experience beyond just looking at old buildings.

An In-Depth Look at the “Crooked” St. Paul Gangsters Tour

The Essence of the Experience: A Private Ride Through Infamous Past

This tour isn’t about crowds or generic sightseeing buses. Instead, it’s a private, two-hour journey designed for your comfort and curiosity. With your guide, likely Douglas Kline, you’ll enjoy round-trip hotel pickup and drop-off, which saves you the hassle of navigating public transit or parking. The only other participant is your companion, making it a very intimate and flexible experience.

What You’ll See and Learn

The tour begins from your chosen starting point — whether your hotel or another convenient location — and takes you on a drive through Saint Paul, where your guide points out sites linked to notorious criminals and the venues they frequented. Highlights include:

• John Dillinger’s residence: You’ll hear the story of how this infamous bank robber managed to escape a gunfight, adding a sense of adventure to the neighborhood’s quiet streets. Dillinger’s daring exploits are a highlight for those fascinated by early 20th-century crime figures.

• A bloody kidnapping site: This shocking event once riveted the nation, and it’s fascinating to see where it happened, giving you a tangible connection to Minnesota’s criminal past.

• A former speakeasy and casino: Hidden behind innocuous storefronts, these spots were popular with both the underworld and local elites. Your guide will share stories of illicit gambling, secret entrances, and the nightlife of the Prohibition era.

• Gangsters’ homes and hideouts: You’ll see where the most infamous figures lived and planned their crimes, offering a glimpse into their luxurious or gritty lifestyles.

Authentic and Engaging Stories

The reviews praise the knowledgeability of the guides — notably Douglas himself — who can fill in details far beyond what a book could offer. As Lyudmila V. exclaims, “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.” This personalized attention makes the experience stand out, giving you a narrative that’s both educational and entertaining.

Tour Format and Pacing

The itinerary is flexible; your guide can adjust stops based on weather conditions or your interests. This flexibility ensures you get the most out of your limited time. Whether it’s a rainy day or a sun-filled afternoon, the experience remains engaging and well-paced.

Value for Money

Although the price of $480 might seem high at first glance, it’s important to realize what you’re getting: a private, curated tour with a dedicated guide and driver, focused entirely on the crime era and hidden city stories. Compared to larger group tours, this one offers a level of intimacy and customization that can make it well worth the investment for history enthusiasts and curious travelers.

Practical Considerations

Most travelers who enjoy local history, crime stories, or unique city perspectives will find this tour fits their interests well. It’s suitable for anyone most travelers can participate in, including those with service animals. Just keep in mind that weather can influence the experience — though the tour goes rain or shine — so dressing accordingly is advisable.

Who This Tour Is Best For

If you’re fascinated by criminal lore or want to see a different side of Saint Paul, this private tour offers an up-close look at historic crime scenes and colorful legends. It’s perfect for history buffs, storytelling lovers, and those who appreciate private, tailored experiences. The tour’s focus on small groups and personalized narration means you’ll walk away with stories that linger long after the ride.

Travelers who enjoy learning from passionate guides and want to see both known and hidden sites of Minnesota’s gangster past will find this tour particularly rewarding. It’s also a great choice for couples or small groups seeking an interactive, memorable experience that’s both fun and educational.

FAQs

Is hotel pickup included?
Yes, the tour offers round-trip hotel pickup and drop-off, making it convenient to start and end your experience without extra hassle.

How long is the tour?
The experience lasts about two hours, providing plenty of time to see multiple sites and hear detailed stories without feeling rushed.

What is the cost?
It’s priced at $480 per group, which covers up to two people. Given the private nature and personalized attention, this can be quite a good value for a focused, intimate tour.

Can I customize the stops?
The tour is designed to be flexible, and the itinerary can be adjusted to fit weather conditions and your interests — just discuss your preferences with your guide.

What sites are included?
You’ll see John Dillinger’s residence, the site of a notorious kidnapping, an illegal speakeasy and casino, and gangsters’ homes and hideouts — some of the most intriguing parts of Saint Paul’s criminal past.

Is this suitable for all travelers?
Most travelers can participate, and service animals are allowed. The tour is great for those interested in history, crime, and local stories.

What should I wear?
Dress comfortably for driving and potentially walking in outdoor settings. Since the tour proceeds rain or shine, check the weather forecast and dress accordingly.

Can I cancel if my plans change?
Yes, cancellations are free if made at least 24 hours in advance. The experience offers flexibility for travel plans.

Final Thoughts

The “Crooked” St. Paul Gangsters Private Riding Tour is a unique, personalized way to explore a fascinating chapter of Minnesota’s past. It’s less about broad sightseeing and more about deep storytelling and exclusive insights, making it a perfect pick for those who want a private, engaging, and educational experience. Through the stories of infamous gangsters, hidden speakeasies, and daring escapades, you’ll see Saint Paul in a light few travelers normally experience.

This tour offers excellent value for history enthusiasts, crime story aficionados, and curious travelers seeking an intimate look at the city’s notorious past. The knowledgeable guides, flexible itinerary, and private setting combine to create an experience that’s both fun and profoundly informative — well worth considering if you want to add a dash of danger and excitement to your Twin Cities visit.

Whether you’re a history buff or simply a fan of good stories, this tour guarantees a memorable ride through the shadowy corners of Saint Paul’s past, revealing stories that will surprise and entertain long after the wheels have stopped turning.