27014 Bootleggers & Badmen: The Prohibtion Years

Day 1

Day 1: Wednesday, August 11, 2027
On the Road to Michigan
Your adventure begins as you board the motorcoach and set out for a journey into the shadowy, spirited, and surprisingly glamorous world of Prohibition-era history. Convenient departure points include Fort Madison, West Burlington, Mediapolis, Wapello, Muscatine, and Davenport.
As the group travels east, you can settle in, visit with fellow travelers, and let the anticipation build. This is the beginning of a tour that follows stories of bootleggers, gangsters, distillers, riverfront cities, and infamous crime history across Michigan, Ohio, Illinois, and Indiana.
A rest and refresh stop will be made in Davenport while Quad City passengers are picked up. Later, enjoy a lunch stop on your own in Joliet, Illinois, with options nearby including Culver’s and Chick-fil-A.
As the group continues toward Michigan, clocks move ahead one hour to Eastern Time. A rest stop will be made at the Michigan Welcome Center in New Buffalo before continuing to the Detroit area.


Hilton Garden Inn Plymouth
Arrive at the Hilton Garden Inn Plymouth, your home base for the next two nights. This evening, gather for a group dinner at the hotel’s Garden Grille Restaurant and Lounge.
After a day of travel, it is the perfect chance to relax, enjoy a meal, and get ready for the Detroit experiences ahead. Tomorrow brings city history, Gilded Age elegance, distillery heritage, and a sunset cruise with Motown soul.

Day 2

Day 2: Thursday, August 12, 2027
Detroit History, Gilded Age Dining, Distillery Heritage, and Motown on the River
After breakfast at the hotel, depart for a full day in Detroit — a city with grit, grandeur, reinvention, music, industry, and plenty of stories.
Detroit Historical Museum
Begin at the Detroit Historical Museum, where the city’s past comes alive through interactive exhibits, engaging displays, and experiences that celebrate Detroit’s industries, neighborhoods, culture, and people.
Detroit is a city that helped shape America in powerful ways. Its story includes automotive innovation, music, manufacturing, immigration, architecture, labor, sports, civil rights, and cultural transformation. This museum offers a meaningful introduction to the region, helping travelers understand the city beyond the headlines.
It is the ideal first stop before diving into Detroit’s Prohibition and distillery connections later in the day.




Lunch at The Whitney
Next, enjoy a group lunch at The Whitney, one of Detroit’s most iconic dining destinations.
Housed inside a magnificent 1894 Romanesque Revival mansion, The Whitney was originally built for lumber baron David Whitney Jr. The estate is filled with Gilded Age beauty: ornate woodwork, stained glass windows, grand staircases, restored dining rooms, and elegant architectural details that make the entire experience feel special.
Lunch here is more than a meal. It is a step into old Detroit luxury.
Guests can admire the craftsmanship of the mansion, enjoy the atmosphere of a bygone era, and perhaps hear whispers of the building’s colorful reputation. The third-floor Ghostbar adds an extra bit of intrigue, while the mansion’s gardens and historic rooms make this one of the most memorable dining experiences of the tour.
Travelers should note that The Whitney recommends business or country club casual attire. Dress jeans or slacks with a collared shirt or sweater are encouraged for gentlemen, while ladies typically wear dresses, skirts, slacks, or dress jeans. Athletic wear, shorts, sports jerseys, tank tops, flip-flops, ball caps, sweatpants, and overly casual clothing are not permitted.

Two James Spirits Detroit
After lunch, continue to Two James Spirits Detroit in Corktown, Detroit’s oldest neighborhood.
This guided tour introduces travelers to Detroit’s first licensed distillery since Prohibition. That detail alone makes this stop a perfect fit for the theme of the trip. During the Prohibition years, distilling and drinking did not disappear — they simply went underground. A modern distillery visit gives travelers a chance to connect the past with the present while learning about craft spirits, local entrepreneurship, and Detroit’s renewed energy.
Located in historic Corktown, Two James Spirits brings together history, craftsmanship, and neighborhood character in a fun and flavorful way.

Downtown Detroit Free Time
Later in the afternoon, enjoy free time in Downtown Detroit.
Set along the scenic Detroit River, downtown Detroit offers a vibrant mix of historic architecture, entertainment, shopping, restaurants, riverfront views, and revitalized city energy. This is your time to explore at your own pace. Take a stroll, grab a coffee, browse, enjoy the riverfront, or simply take in the movement of the city.
Detroit is full of contrasts — old and new, industrial and artistic, polished and soulful — and downtown is a great place to feel that mix.
Detroit Princess Sunset Motown Dinner Cruise
This evening, board the Detroit Princess for a Sunset Motown Dinner Cruise.
As the boat glides along the Detroit River, enjoy spectacular views of the greater Detroit and Windsor riverfronts and skylines. There is something magical about seeing a city from the water, especially as evening light begins to soften the skyline.
Dinner is served buffet-style, with selections such as fresh Atlantic salmon, baked chicken, marinated portabella mushrooms, cheese tortellini, chef’s choice potatoes, steamed vegetables, Michigan tossed salad, dessert, coffee, hot tea, and ice water. Other beverages are available for purchase by credit or debit card.
The evening is made even more memorable with live entertainment by the Prolifics Live Motown Revue, celebrating the classic sound that made Detroit famous. Motown music has a way of getting people smiling before they even realize it. Add river views, dinner, and the glow of sunset, and you have one of the signature experiences of the tour.
After the cruise, return to the hotel for the evening.

Day 3

Day 3: Friday, August 13, 2027
Toledo’s Underworld Stories and Onward to Chicago
After breakfast, set luggage out for pick-up and depart Michigan for a day that dives deeper into the Prohibition theme.

Garters, Gambling, Gangsters and Gin Tour – Toledo History Museum
Arrive in Toledo for the Garters, Gambling, Gangsters and Gin Tour, presented by the Toledo History Museum.
For two hours, step into a world of gangsters, women of the night, rum running, and police on the take. This guided tour opens up the seamier side of Toledo’s past, exploring the stories that respectable history books sometimes leave in the margins.
It is a colorful, dramatic, and entertaining look at a city shaped by river traffic, industry, vice, politics, and Prohibition-era opportunity. During the 1920s and 1930s, cities throughout the Midwest became part of a broader network of bootlegging, gambling, corruption, and underground nightlife. Toledo’s stories add another layer to the tour’s exploration of crime, vice, and law enforcement during this complicated era.
This is history with a wink, a raised eyebrow, and maybe a little gin in the back room.

Downtown Toledo – Lunch on Your Own
After the tour, enjoy lunch on your own in Downtown Toledo.
Set along the Maumee River and home to the city’s central business district, Downtown Toledo offers cafes, casual bars, restaurants, shops, and local businesses. It is a nice opportunity to stretch your legs, enjoy a meal, and explore a bit before continuing west.

Travel to Oak Brook
In the afternoon, continue toward the Chicago area. A rest and refresh stop will be made at the Henry Schnicker Travel Plaza in Elkhart, Indiana.
As the group travels west, clocks move back one hour to Central Time.

Marriott Chicago Oak Brook
Arrive at the Marriott Chicago Oak Brook, where luggage handling is available. This evening, enjoy a group dinner at a local restaurant before returning to the hotel.
You are now in the Chicago area — and tomorrow, the tour steps straight into the legends of Al Capone, John Dillinger, gangland rivalries, and Prohibition-era Chicago.

Day 4

Day 4: Saturday, August 14, 2027
Chicago Crime, Deep-Dish Pizza, and The Magnificent Mile
After breakfast at the hotel, depart for a day filled with Chicago’s most infamous stories.



Chicago Crime Tour
Board the motorcoach with a step-on guide for the Chicago Crime Tour, a guided journey into the legendary tales of Chicago’s most notorious criminals, mobsters, and gangsters.
Few cities are as closely linked to Prohibition-era crime as Chicago. During the 1920s, the city became a battleground of bootlegging empires, rival gangs, speakeasies, political corruption, and dramatic violence. Names like Al Capone and John Dillinger still echo through the city’s history.

Tour highlights include:
Biograph Theater, connected to the final steps of John Dillinger.
St. Valentine’s Day Massacre Site, tied to the violent beer wars and Al Capone’s era.
Chicago River, with stories connected to Prohibition architecture and the city’s development.
Holy Name Cathedral, associated with North Side and South Side gangland shootouts.
This tour is fascinating because it blends crime history with real city places. You are not just hearing stories. You are seeing the streets, buildings, and neighborhoods where legends, rivalries, and headlines unfolded.
It is gripping, entertaining, and one of the defining experiences of the trip.





Chicago-Style Deep-Dish Pizza Lunch
No Chicago visit is complete without pizza, and today includes an authentic Chicago-style deep-dish pizza lunch.
Enjoy one of the city’s signature foods, served with pizza, salad, and soft drinks. Deep-dish pizza is hearty, cheesy, saucy, and unapologetically Chicago. It is the kind of meal that fits perfectly after a morning of mob stories and city sightseeing.
The Magnificent Mile
In the afternoon, spend time on The Magnificent Mile, Chicago’s premier commercial district along Michigan Avenue.
This vibrant area is known for upscale shops, fashion outlets, restaurants, hotels, architecture, and city energy. The rest of the afternoon and early evening is yours to enjoy on your own.
Browse the shops, enjoy the atmosphere, admire the architecture, people-watch, or choose a restaurant for dinner. The Magnificent Mile offers something for every traveler, whether you want a lively meal, a sweet treat, a souvenir, or simply a memorable Chicago stroll.
After dinner on your own, return to the hotel for the evening.

Day 5

Day 5: Sunday, August 15, 2027
Old Joliet Prison and the Journey Home
After breakfast, set luggage out for pick-up and depart the Chicago area for the final featured stop of the tour.




Old Joliet Prison – Guided Tour
Arrive at Old Joliet Prison for a 90-minute guided walking tour led by knowledgeable guides from the Joliet Area Historical Museum.
This historic prison opened in 1858 and closed in 2002. Over nearly a century and a half, it became one of Illinois’ most recognizable correctional facilities. Its limestone walls, imposing cell houses, and stark corridors have a powerful presence, making it a memorable final stop on a tour focused on crime, law, punishment, and the stories behind the headlines.
During the tour, you will learn about the prison’s general history and significance while stepping inside key areas of the facility as available, including the West Cell House, North Segregation, Dining Hall, and other buildings.
There is something undeniably gripping about visiting a place like Old Joliet Prison. It is historic, haunting, and deeply atmospheric. You can imagine the sounds of doors closing, footsteps echoing, and lives lived behind stone walls. It is not just a building — it is a place that holds stories.
This final tour brings the theme full circle, connecting the world of gangsters and crime with the institutions built to contain those who crossed the line.
Lunch in Joliet and Return Home
After the prison tour, enjoy lunch in Joliet before beginning the return journey.
As you travel home, you will have plenty to talk about: Detroit’s Gilded Age mansion, the first licensed distillery since Prohibition, Motown on the river, Toledo’s vice history, Chicago’s mob legends, deep-dish pizza, Magnificent Mile lights, and the stone walls of Old Joliet Prison.