Prohibition and All That Jazz 2026

Pick Up Locations

7:00 AM - State College
7:30 AM - Philipsburg
8:00 AM - Clearfield
8:30 AM - Dubois
8:00 AM - Lamar

Please arrive at your pickup location 15 minutes prior to scheduled departure.

Day 1

Rest/Brunch Stop Enroute
2:30pm Pick up your Gangster GUIDE at Angelo's Northwood Villa. Enter a world of gangsters, women of the night, rum running and police on the take as the Toledo History Museum opens up the seamier side of Toledo's past on the Glass City Garters, Gambling, Gangsters and Gin Tour.
5:30pm Return to Angelo's Northwood Villa for an included dinner
7:30pm Check in to Courtyard Toledo Maumee/Arrowhead
PLEASE NOTE: Baggage handling is NOT available at this location.

Day 2

7:00am Enjoy breakfast included at the hotel prior to checking out
8:00am Depart
12:00pm CT Enjoy lunch included at Lou Malnati's
1:45pm Arrive at Old Joliet Prison for a self-guided tour. True to its historic and notorious legacy, the Old Joliet Prison now takes it rightful place as an authentic, unique asset which is inextricably linked to the history of Joliet, the state of Illinois, and people impacted by crime and punishment.
3:00pm Depart
4:30pm Check in to SpringHill Suites Chicago O'Hare
5:30pm Depart
6:00pm Arrive at Vito's Vault (5901 W Lawrence Avenue, Chicago, IL 60630). Take a journey back to 1929 and step into a world of secret delights. Give the password at the door to join Vito and the gang for an evening filled with fantastic food and fun. Enjoy a scrumptious three-course meal, savor some of Vito's homemade Hooch, and then be treated to a lively 90-minute stage show featuring glorious tunes from the twenties and hilarious comedy sketches. Our talented mugs and flappers, handpicked by Vito, showcase some of the finest entertainment in the city of Chicago. Get ready for an unforgettable night of speakeasy glamour and good times!
9:15pm Return to the hotel.

Day 3

7:00am Enjoy breakfast included at the hotel prior to checking out.
8:00am Depart
9:00am Pick your GUIDE and continue on the Untouchable's Tour - Chicago's Original Gangster Tour. Your guide will present an accurate account of the crimes and activities that were going on in Chicago during the 1920's and '30's (Prohibition). You will hear the exploits of Capone, Moran, Dillinger, and the rest of the boys on this unforgettable Chicago crime tour! Guests remain on the bus for the duration of the tour. Some sites included are the St. Valentine's Day Massacre, the Biograph Theatre, and the Holy Name Cathedral. The Gangster Guides are professional actors who take on the personas of gangsters and mobsters and bring the world of 1920s Prohibition to life.
11:15am Arrive at Lunch-more surprise fun details to be announced!
2:15pm Depart
Stop for dinner on own at group leader's discretion.
8:45pm ET Check in to Courtyard Detroit Dearborn

Day 4

7:00am Enjoy breakfast included at the hotel.
8:45am Depart
9:30am Arrive at Detroit History Tours. Pick up your GUIDE and begin 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.
12:15pm Drop off Guide
12:30pm Enjoy lunch included at The Whitney The Whitney mansion is world famous for upscale dining in Detroit. Completed in 1894, the Motor City landmark retains the exquisite charm of Detroit's early upper echelon as a venue for all to enjoy. Lunch included at The Whitney
2:00pm Enjoy a champagne tour of the Whitney Mansion!
3:15pm Depart
3:30pm Arrive at Two James Spirits for a guided tour. Located in Corktown, Detroit's oldest neighborhood, Two James Spirit 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.
5:30pm Depart
6:00pm Arrive for boarding at Detroit Princess Sunset Cruise
7:00pm Cruise departs!. Enjoy dinner included and live entertainment on this delightful sunset cruise.
9:00pm Dock and disembark. Depart
9:30pm Return to hotel for the evening

Day 5

7:00am Enjoy breakfast included at the hotel.
9:00am Depart
9:30am Arrive at Ambassador Duty Free Detroit. Become your own "rum runners" before going through customs and entering Canada. 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!
" Enjoy lunch on your own while visiting.
11:30am Meet and go through customs. You will need a valid US Passport to enter Canada
12:30pm Depart
1:15pm 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.
2:30pm Depart
3:00pm Stop at Caesar's Windsor and pick up Benny and Yorkie- 2 gentlemen in dire need of assistance. They board the bus, 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
7:00pm Depart Be prepared to pass through customs again.
8:15pm Return to the hotel.

Day 6

7:00am Enjoy breakfast included at the hotel prior to checking out. (DI)
8:00am Depart for home

Return Times

TBD

FB=Full Breakfast, L=Lunch, D=Dinner