"Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) in Minneapolis-Saint Paul
Minneapolis-Saint Paul, United States

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

Outty Ranking 50 5.0 · 2 traveler reviews2 hoursFrom $480

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September 2026

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Adults

Age 13 and over

2

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Age 12 and under

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From, per person$480
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Outty Ranking

50/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 2 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) worth booking?

"Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) is a 2-hour experience in Minneapolis-Saint Paul, United States, from $480 per person. It scores 50 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 5/5 rating across 2 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
50 / 100
Rating
5/5 (2)
Duration
2 hours
From
$480 per person

We'll connect at a location and hour convenient for you and step back in time during this private, 2-hour riding tour. You'll hear how St. Paul, Minnesota became a haven for the nation's most notorious gangsters, includi

What you get

    About this experience

    We'll connect at a location and hour convenient for you and step back in time during this private, 2-hour riding tour. You'll hear how St. Paul, Minnesota became a haven for the nation's most notorious gangsters, including John Dillinger, during the first decades of the 20th Century, and the impact of that legacy on life today in the "Saintly City. " How could bank robbers and bootleggers run their crimes while "hiding in plain sight"? This private riding tour will show the homes, nightclubs, hangouts - and even the courthouse - where these professional thugs lived, planned, played and were prosecuted. We'll also see other St. Paul highlights, including Summit Ave, cathedral and Capitol. Private transportation is a professionally chauffeured "town car" sedan or Cadillac Escalade SUV. Want to entertain locals or out-of-towners? Old enough to remember those lurid headlines or young enough to be amazed? Ready for a new twist on a town you thought you knew? This tour is for you.

    What's included

    Included

    • Private transportation
    • Bottled water
    • Guided tour

    Not included

    • Gratuities

    What you'll see and do

    1. Saint Paul

      Starting from your desired pickup point, the private riding tour will include exterior views of many St. Paul locations - some famous and some blandly "everyday" - where yesterday's gangsters lived their lives while planning and committing horrendous crimes. You'll see: - Where the wanted criminal John Dillinger lived and learn how he escaped a gun shootout - The site of a bloody kidnapping that riveted the nation - A former illegal speakeasy and casino popular with both the underworld and elite - Neighborhoods that welcomed the city's wealthiest citizens alongside the nations' hoodlums This tour is engaging and informative rain or shine. The itinerary can be adjusted to accommodate changing weather and your personal schedule.

      120 minutes here

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers.

    Options you can book

    • Two-hour tour; 3 or 4 people

      Group size - 3 or 4 people: Transportation is a private, executive-class Cadillac Escalade SUV with a professional, licensed & uniformed driver Pickup included

    • Two-hour tour; 1 or 2 people

      Group size - 1 or 2 people: Transportation is a private, chauffeured "town car" luxury sedan with a professional, licensed & uniformed driver Pickup included

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Douglas Kline

    Know before you go

    • Infants are required to sit on an adult’s lap
    • Service animals allowed
    • Public transportation options are available nearby
    • Infants and small children can ride in a pram or stroller
    • Suitable for all physical fitness levels

    Photos

    "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) in Minneapolis-Saint Paul, photo 2Lurid headlines in 1934 helped expose St. Paul's gangster haven to the world. During this tour, learn why gangsters flocked to St. Paul and hear tales of their exploits.This 1905 police revolver was used by St. Paul police to injure John Dillinger in a shootout at his home in 1934. You won't see this gun during the tour, but you'll see where the shootout happened.Bootlegging, bank robberies and kidnapping were part of an open secret that thrived in St. Paul for 35 years. The heavy toll of that legacy will be explained during this tour.For 1 or 2 people, provided transportation is a chauffeured "town car" Lincoln Continental sedan with a professional, licensed and uniformed driver.For 1 or 2 people, provided transportation is a chauffeured "town car" Lincoln Continental sedan with a professional, licensed and uniformed driver.

    Traveler reviews

    2 verified traveler reviews for "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs). Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    2
    4 star
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    3 star
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    Lyudmila_V · September 2023

    Lovely Saint Paul.

    I and my husband were very happy with our tour. 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. Doug and his driver Ron were very knowledgeable in the history, architecture of the Saint Paul. Saint Paul is very lovely city. The car was very comfortable. After the tour we went to Capitol and Cathedral as was suggested by Doug. And what a wonderful experience it was. I definitely recommend this tour with Doug.

    Response from the operator: I appreciate your comments. I made sure that our short time together was packed, productive and fun. Thank you.

    via Viator

    Paula_R · June 2022

    Best Tour I’ve ever had!

    Our Tour guide Douglas Kline and his driver we’re absolutely fantastic! We we’re picked up right from our hotel and given a 3 hour custom tour. It truly exceeded our expectations as we learned so much about Minnesota and it’s colorful background. Douglas is a very warm & delightful person and his knowledge was outstanding. Our experience was worth every penny because the memories we walked away with is priceless.

    Response from the operator: Thank you! I had hoped that you would like the customized tour created for you – with the special gangster lore and the added Prince attractions blended-in to our itinerary. The specialized combination seemed to work well for both you and your brother. We had a fun time!

    via Viator

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Price range
    $480 to $550
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    1
    Verdict
    Worth a Look

    Why this scores 50

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)78
    Review evidence (18% weight)19
    Booking momentum (14% weight)15
    Value for money (12% weight)0
    Listing quality (10% weight)85
    Local standing (8% weight)54
    Booking flexibility (8% weight)100

    "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs): questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Minneapolis-Saint Paul.

    How much does "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) cost?

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    Prices start at $480 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Minneapolis-Saint Paul usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) take?

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    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Minneapolis-Saint Paul is not rushed.

    Is "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) worth it?

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    It holds an Outty Ranking of 50 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 2 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Minneapolis-Saint Paul, and how flexible the cancellation terms are.

    Can I cancel or reschedule "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs)?

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    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs)?

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    Around 1 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Minneapolis-Saint Paul can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

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    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Minneapolis-Saint Paul and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does "Crooked" St. Paul Gangsters Private Riding Tour (2 hrs) start and how do I get there?

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    The exact meeting point and directions are on your voucher once you book, and they sit in central Minneapolis-Saint Paul within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Minneapolis-Saint Paul?

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    The Twin Cities cover Mississippi mill district history, chain of lakes bike and paddle tours, Mall of America trips, brewery crawls in Northeast and winter ice experiences. Seasonal swing is extreme, so honest weather guidance matters. On Outty we rank every Minneapolis-Saint Paul experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Escape Game: Epic 60-Minute Adventures at the Mall of America, Narrated Scenic Tour on the Minneapolis Trolley, St. Paul Historic Cave Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Minneapolis-Saint Paul?

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    June to September, with winter activities from December to February. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Minneapolis-Saint Paul?

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    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

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    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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