Prohibition & All That Jazz

Journey back in time to the days of speakeasies and jazz clubs, when mobsters ruled the streets and the world's most infamous policemen tried to stop them. During this tour, you'll learn all about the Prohibition era - its smuggling operations, gangsters, and justice-men. Visit famous locations in Chicago, Detroit, Toledo, and Windsor, Canada. Taste your share of award winning liquors at historic distilleries, and allow your costumed guides to regale you with stories of the past.

Duration
6 Days /5 Nights

Group size
Customizable

Customization
Available!
Estimated Tour Pricing Inclusions: Roundtrip transportation, 5 nights’ accommodation, baggage handling, 5 breakfasts, 4 lunches, 4 dinners, admissions, entrance, and guide fees as stated in the itinerary, including taxes, and gratuity (excluding gratuity for guides and driver, unless requested).
  Highlights:
  • Glass City Garters, Gambling, Gangsters and Gin Tour
  • Old Joliet Prison
  • Vito’s Vault
  • Chicago's Gangsters Tour
  • Wildfire Luncheon
  • Murder Mystery
  • Felonies and Misdemeanors, Detroit Cops, & Mobsters Tour
  • David Whitney House & Champagne Tour
  • Two James Spirits
  • Detroit Princess Sunset Cruise
  • Duty Free Shopping Store
  • Windsor, Canada
  • Wolfhead Distillery
  • Benny & Yorkie Tour
  • The Rockstar Music Hall

SAMPLE ITINERARY:

This itinerary is based on an actual, executed tour custom created from a specific location.  Your group's itinerary can be customized and tailored to fit your group's originating location or arrival into the area.  It's easy! We can help you!
 

Day 1
  • Arrive in Erie, Michigan and meet your Gangster Guide.
  • Embark the Glass City Garters, Gambling, Gangsters, and Gin Tour. This 3-hour tour includes a stop at the Toledo Police Museum. There will be tastings of Gin and Rum along the way.
  • Depart for Toledo, OH.
  • Upon arrival, enjoy a delicious Welcome Dinner included at a local favorite restaurant, before checking-in to your local area hotel.
Day 2
  • Enjoy breakfast at your hotel prior to checking out.
  • Depart for Illinois, with a stop along the way for a delightful lunch included.
  • Explore the Old Joliet Prison and embark on a 90-minute Docent-led Walking Tour. Hear about the daily life at the Prison – a more personal take on the site’s history. This tour takes you into the East and West Cell Houses, North Segregation, Cafeteria, Chapel, and Honor Dorm.  They will gear this towards Prohibition - Baby Face Nelson was there. Public Enemies movie filmed there.
  • Continue your adventure to Chicago where you'll enjoy an experiential dinner before checking-in to your local hotel for the night.
Day 3
  • Enjoy breakfast at your hotel this morning prior to checking out.
  • Meet your Gangster Guide and embark on a Chicago Gangster Tour.  Your guide will present an accurate account of the crimes and activities going on in Chicago during the 1920’s and ’30’s (Prohibition era). You will hear the exploits of Capone, Moran, Dillinger, and the rest of the boys on this unforgettable Chicago crime tour! Some sites included are the St. Valentine’s Day Massacre, the Biograph Theatre, and the Holy Name Cathedral.
  • Delight with a special luncheon today.  You'll dine on delicious food while you and your traveling partners try to solve a Murder Mystery Performance. In this “married to the mob” event, you’ll never know who to trust. With the two families merging, someone is bound to lose power, which means someone else will lose their life! solve this case with your fellow detectives.
  • Depart for Detroit, Michigan, with a stop for dinner on your own en route.
  • Upon arrival, check-in to your local hotel.
Day 4
  • Enjoy breakfast included at your hotel this morning.
  • Meet your Step-on Detroit History Tour Guide and embark on the Felonies and Misdemeanors, Detroit Cops and Mobsters Bus Tour.  Some of the world’s most notorious criminals, mobsters, and gangsters bamboozled their way through Detroit. Meanwhile some of history’s most infamous, brilliant, or honorable policemen tried to stop them. On your Tour, escape into the city’s criminal underworld as you investigate stories about Jimmy Hoffa, Prohibition, The Purple Gang, “Joe the Hood”, The Gotham Hotel, and the Detroit Mob families. You’ll hear the story of "La Mano Nera" or black hand extortionists, in Detroit at the turn of the century. You’ll explore the illegal liquor war of the 1910’s. You’ll visit an iconic bar where you learn about the police chief who resigned from his appointment as a judge to bring “civility back to the police”. You will traverse the city and learn the history of mobster owned speakeasies and some of their most memorable raids. From riots to rolling men into the river, from African American gambling rackets to Italian mobsters fixing professional football games, from hookers, madams, and street corner pimps, to cops, mounted police, and mayors of all types - welcome to the criminal side.
  • Arrive for an included lunch at the David Whitney House. The Whitney, Detroit's grandest restaurant, is topped by the 3rd-floor Ghostbar and surrounded by the pristine Oasis in the City Gardens.
    • Delight with a Champagne Tour of the Whitney Mansion.
  • Visit Two James Spirits in Corktown, Detroit’s oldest neighborhood, and is the first licensed distillery in Detroit since Prohibition. Two James is committed to producing only the highest quality environmentally conscious handmade spirits utilizing locally sourced agricultural products with the aim of revitalizing the community and reinforcing the craft product movement. You will learn all about the distilling process, and even get to try a few samples! Take home a souvenir glass.
  • This evening, relax in luxury and style as you board the Detroit Princess for a Sunset Dinner Cruise complete with live entertainment, a delicious meal, and beautiful views from the water.
  • Return to your hotel for the evening.
Day 5
  • Prior to checking out, enjoy breakfast at your hotel.
  • Arrive at Duty Free Shopping and become your own “rum runners” before going through customs and entering Canada.  A full-service Duty-Free Store located at the foot of the Ambassador Bridge in Detroit, Michigan.  The Ambassador Bridge serves as North America’s #1 Border Crossing. As a Duty-Free Store, items are sold for export and are exempt from certain taxes and duties that would typically be applied to the merchandise sold at a regular domestic retail store. Taxes such as state sales tax and import tariffs are not applied at the point of sale when an item is sold for export.  When a traveler leaves the country, they have the opportunity to shop at a duty free store where they can take advantage of these savings and save money on hundreds of items!
  • After going through Customs at the border, depart for Windsor.
  • Arrive at Wolfhead Distillery. Learn about the distilling process of Whisky, Vodka, & Gin. Check out their maturation room & visit the bottling line. Tours include a tasting of four of their best-selling products.
  • Check-in to your local hotel to rest and refresh to prepare for the evening.
  • Late afternoon, meet Benny & Yorkie, two gentlemen in dire need of assistance.  Being the kind group that you are, you allow them to board your bus.  They climb aboard and your Rum Runners Journey begins! You will travel along the riverfront making several stops as Benny and Yorkie begin to tell the secrets of the bootleggers and the ingenious methods, they used to smuggle liquor across the river in the dark of night and over the windswept ice in the dead of winter. They’ll tell of the bootleggers’ hideouts and divulge the location of the Speakeasies and Blind Pigs where the Purple Gang and Al Capone made their deals.
    • Your tour will end with an included buffet dinner at The Rockstar Music Hall.
  • Return to your hotel for the evening.
Day 6
  • Prior to checking out, enjoy breakfast at your hotel.
  • You're departing for home today, but you'll make a stop en route at the Jackson Square Food Court Ontario with free time to explore and enjoy lunch on own white visiting.
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