The Kentucky Bourbon Trail

Join us as we visit 5 distilleries both on and off the famous Kentucky Bourbon Trail and learn about the craft that started in the 1700’s with the first settlers of Kentucky! Visit the Kentucky Derby Museum, and see the backside of Churchill Downs Racetrack with a behind-the-scenes view of thoroughbred racing including breakfast in the Horsemen’s Track Kitchen. Along the way we’ll have a chance to explore enjoy the thriving downtown Louisville plus stop at some historic eateries for lunch.

Included on the tour is:

Day 1 (Friday, October 5, 2018)
• In route to Louisville, we will stop for lunch at the Gray Brothers Cafeteria which has been serving Indiana some of the best home cooked meals and desserts since 1944.
• We will start our weekend with a tour of Copper & Kings American Brandy where they sonically age their spirits. Our tour includes three tastings and a souvenir tasting glass. After all, as they say at Copper & Kings, “happy brandy makes happy drinkers!”
• After we get checked into the Hilton Garden Inn Louisville Downtown we will be hosted for a rooftop welcome at 8UP Elevated Restaurant & Bar which includes appetizers and an open bar.
• After the reception, you’ll have the rest of the evening to explore the many establishments in the vibrant surrounding neighborhood.

Day 2 (Saturday, October 6, 2018)
• We will start the day by welcoming our very own guide from Kentucky Bourbon Boys. They pride themselves on loving good times, good bourbon and our guide will tell us more about Kentucky and the history for bourbon.
• We join the Kentucky Bourbon Trail at Barton 1792 Distillery named in honor of the year Kentucky joined the United States.
• Next, we’ll head to Heaven Hills Distillery and the Bourbon Heritage Center where we will learn about the aging process of Bourbon and the magic that takes place inside the barrel. In addition to our educational tasting we will discover why Heaven Hill Distillery is the only producer of all five styles of American Whiskey.
• For lunch, we will eat like a local at Mike Linning’s famous seafood restaurant. Open since 1925, Mike Linning’s dishes up tasty fried fish and seafood nestled in a shady grove along the Ohio River. If you don’t like seafood, don’t worry, we will have other options on our menu.
• Bulleit Frontier Whiskey is our next stop. Inspired by his great-grandfather, Augustus Bulleit, who made a high-rye whiskey between 1830-1860, Tom Bulleit, Jr. left a successful law practice and risked everything to experience life on the frontier. Rye has always been their cornerstone.
• We will head back in time to meet Kentucky’s first licensed distiller at the Evan Williams Bourbon Experience. On our tour and tasting we will see Whiskey Row along Main Street from the 1890’s through the present. You’ll learn how Heaven Hill’s modern Bernheim Distillery operates and discover how it is different from distilling in Evan William’s era. Then, you will see a combination of the two—a state-of-the-art, modern, operating distillery utilizing the same type of pot stills as the early bourbon-making days.
• For dinner, you will have time to explore the neighborhood surrounding Evan Williams on your own. Located just a mile from our hotel there is no shortage of delicious places to try!

Day 3 (Sunday, October 7, 2018)
• To wrap up our visit, we will get the once-in-a-lifetime chance to spend a morning on the backside at Churchill Downs Racetrack where we will get a behind-the-scenes view of thoroughbred racing at the “World’s Most Legendary Racetrack.” Unopen to the public, we will enjoy breakfast in the Horsemen’s Track Kitchen and will get an up close and personal view of the horses, jockeys, trainers, and other connections who live the sport of horseracing! During our visit we will also have a historic walking tour and time to explore the Kentucky Derby Museum.
• We’ll depart for home and along the way, stop for a late lunch at Hollyhock Hill for an Indiana fried chicken dinner served family-style before our 6:30 pm Milwaukee arrival / 7:30 pm Sheboygan arrival back home.

This trip includes Discovery Coach transportation to/from Louisville, KY, and all items as noted in the itinerary found on the reverse. You will also receive an exclusive shopping tote from Milwaukee Food & City Tours for all of your Kentucky treasures.

Download PDF Registration Form register online HERE


  • WHEN: Friday October 5 - Sunday October 7, 2018

  • DURATION: 5 AM departures from Sheboygan; 6 AM departures from Milwaukee on Friday, October 5th. Returning on Sunday, October 7th by 7 PM to Sheboygan drop off locations.

  • PRICE: $600 Double / $750 Single

  • LOCATION: Motorcoach picks up at Sheboygan Park & Ride (5 AM), Brown Deer Park & Ride (5:45 AM), Amtrak Station in Downtown Milwaukee (6 AM), College Avenue SW Park & Ride (6:10 AM), Chicago (7:30 AM). You will be asked to select your pick up location during the ticket purchase process.

  • ACCESSIBILITY: This is a bus tour.

    • We are able to accommodate for food allergies. Please call 414-255-0534 ext 3 with your specific requests.