Day 1 – Bootleg Beginnings:

From Templeton Rye to Galena’s Historic Charm Begin your adventure with convenient departures from Fremont, Lincoln, and Omaha. Kick things off at the Templeton Rye Distillery, where the spirit of Prohibition lives on. After a stop in Dubuque—including a glimpse of Al Capone’s old stomping grounds at the Julien Hotel—you’ll arrive in charming Galena. Check into the historic DeSoto House Hotel and enjoy an included dinner with your fellow travelers. (L, D) 

Day 2 – Mob Bosses & Hidden Rooms:

Chicago Arrival and Nitti’s Speakeasy Start with a trolley tour through Galena’s storybook streets before continuing on to Chicago. Upon arrival, check into the elegant Knickerbocker Hotel, a 1920's era hotel often frequented by famous mobsters. Tonight, savor dinner at Harry Caray’s Steakhouse, once owned by Capone’s enforcer Frank Nitti. Step through a hidden bookcase into Nitti’s Speakeasy, a reconstructed 1920s hideout that immerses you in vintage mob history. End the night with an illuminating Mob Tour of Chicago. (B, L, D)

Day 3 – Skylines, Stories & Speakeasies:

Exploring Chicago’s Underworld After breakfast, glide along the river on a world-renowned Architectural Cruise, taking in Chicago’s stunning skyline. Then, taste your way through history on a Gangster Food Tour, sampling dishes while learning about the city’s underworld past. Go behind the scenes at Wrigley Field, then stroll Michigan Avenue’s Magnificent Mile, filled with shops, architecture, and energy. Dinner awaits at Volare, a classic Italian restaurant, before a nightcap at the storied Green Door Tavern, one of the city’s oldest speakeasies. (B, L, D) 

Day 4 - The Getaway:

Saying Farewell to the Windy City Enjoy a final breakfast together before departing Chicago. On the way home, relax with friends and share your favorite memories from this one-of-a-kind adventure. Return to Omaha by evening, bringing back stories and experiences you’ll never forget. (B, L)