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:
  • Detroit Cops and Mobsters Bus Tour
  • Two James Spirits
  • River Prohibition Cruise
  • Little Italy
  • JP Wisers- Hiram Walker & Sons Distillery
  • Ambassador Duty Free Detroit
  • Murder Mystery Dinner
  • Chicago's Original Gangster Tour
  • Al Capone's Gravesite
  • Old Joliet Prison
  • Nitti's Supper Club
  • Unholy Toledo Tour

Sample Itinerary
  Day 1 - The Detroit Cops and Mobsters Tour, Two James Spirits, & A Prohibition Cruise
  • Arrive in Detroit.
  • Take the Felonies and Misdemeanors: The 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 this tour, escape into the city's criminal underworld as we explore the history of the prohibition. You'll hear the stories of the mob families, explore the illegal liquor war of the 1910's, and traverse the city to learn about the speakeasies and their most memorable raids.
  • Enjoy an included lunch at Tommy's Detroit Bar and Grill then get a tour of the joint. Tommy's Detroit was built in 1840 and has a tunnel entrance that was used to smuggle liquor from the Detroit River during prohibition.
  • Visit Two James Spirits. Two James is located 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 source 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. Bonus, you will get to take home a souvenir glass!
  • Board the Diamond Jack Boat for a Guided Prohibition Cruise. During Prohibition, Detroit took advantage of its location on the international border. With 75% of liquor entering the U.S. through the "Detroit-Windsor Funnel," the Detroit River became the epicenter of the booze smuggling trade. On this cruise, travel from the eastern end of the Detroit River to the Ambassador Bridge. Enjoy dinner, desert, coffee, and soft drinks while your guide regales you with smuggling stories from the era. There will be prizes and every attendee receives a Prohibition themed gift.
  • Check in to your local hotel.
Day 2 - Ontario Canada, Little Italy Tour, & JP Wisers-Hiram Walk & Sons Distillery
  • Enjoy breakfast at your hotel.
  • Depart for Windsor, Ontario, Canada. You will need a valid certified U.S. Passport or Valid unexpired passport or True driver's license to enter Canada as a U.S. citizen.
  • After clearing customs, take a drive through Little Italy. Stop and pick up Benny and Yorkie - 2 gentlemen in dire need of assistance. 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. Then Benny and Yorkie will run off as an officer boards the bus and takes you to Old Sandwich Town and the hidden coves where the bootleggers loaded up their boats and waited for the signal to speed across the river. You'll get a close-up look of the Ambassador bridge which connects Canada to the United States. Next, visit Bedford United Church where "The Fighting Parson," Reverend Leslie Spracklin will tell the story of how he fought the bootleggers and owners of the blind pigs and speakeasies with fits and guns.
  • The tour will conclude with a buffet lunch. 
  • Tour the JP Wisers-Hiram Walker & Sons Distillery. Experience the story of Canadian whisky. You'll learn the history of Canadian whisky and the process of making it, from the grains of harvested by local farmers to you pouring it into a glass to enjoy. The distillery tour concludes with a tasting of 4 award-winning whiskies.
  • Check in to your local hotel.
  • Take advantage of free time to have dinner and explore on your own.
Day 3 - Ambassador Duty-Free Detroit, Chicago, & Murder Mystery
  • Enjoy breakfast at your hotel.
  • Visit Ambassador Duty-Free Detroit which is a full-service Duty-Free Store located at the foot of the Ambassador Bridge in Detroit. 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.
  • Have lunch on your own while shopping at the Ambassador.
  • Depart for Chicago.
  • Check-in to your local hotel.
  • Arrive at Wildfire Restaurant for dinner and a Murder Mystery. This is the perfect opportunity for costume party and contest.
Day 4 - Chicago's Original Gangster Tour, Old Joliet Prison, & Nitti's Supper Club
  • Breakfast at your hotel.
  • Depart with your Untouchables Tour Guide for Chicago's Original Gangster Tour. Enjoy this top-notch educational and historically accurate bus tour. Listen to an accurate account of the crimes and activities that were going on in Chicago during the 1920's and 30's. You will hear about the exploits of Capone, Moran, Dillinger, and the rest of the boys. Sites include, the St. Valentine's Day Massacre, Biograph Theatre, Holy Name Cathedral, & Al Capone's gravesite.
  • Lunch is included at a local restaurant.
  • Visit Old Joliet Prison and take a 90-minute docent-led walking tour. The docents worked at the Prison while it was still in operation until its closing 2002. You will hear about the daily life at the Prison during their time there.
  • After a refreshing stop at your hotel, depart for Nitti's Supper Club for dinner and a show.
Day 5 - Unholy Toledo Tour & Toledo 419 Brew Tour
  • Prior to checking out, enjoy breakfast at your hotel.
  • Depart for Toledo, OH.
  • Lunch at a local restaurant.
  • Take the Unholy Toledo Tour: Gambling & Gangsters in Glass City. In 1931, during the era of G-Men, speakeasies, and Pretty Boy Floyd, a gang of Detroit wiseguys led by Thomas "Yonnie" Licavoli arrived in Toledo an brought with them a wave of violence unseen in Toledo's past: 14 murders in 36 months. Get ready for a trip back in time with this tour. With your guides, you'll explore Toledo from World War I through the Prohibition Era and the end of World War II.
  • Next, take the Toledo Brew Tour. Along the way, you'll sample gin, vodka, rum, and mead!
  • Enjoy dinner at a local restaurant.
  • Check in to your local hotel.
Day 6 - Depart for Home
  • Prior to checking out, enjoy breakfast at your hotel.
  • Depart for home.
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