Your expert Derby guides, Holly Johnson & James Boling
If you are interested in this Bucket List Tour, you won’t want to miss this FUN Information Session! Make sure to register for this session and confirm your booking at checkout! There is no fee, but registration is recommended!! Easy Registration Here.
Tentative Trip dates: April 29 - May 2, 2027
Click here to save your spot now for the Free Information Session that will be held on Sunday, May 17th at 1pm at Didi’s – located inside the Ingleside Hotel, Pewaukee.
Back by popular demand, Holly and James invite you back to Kentucky for an unforgettable blend of excitement, education, and Southern charm—centered around the most thrilling two minutes in sports. From our premium seats, you’ll enjoy splendid views of the horses as they parade between the barns and paddock before and after each race—including the winner’s celebrated victory walk.
Beyond race day, we’ll dive into Kentucky’s rich traditions with a guided bourbon distillery tour and tasting, offering insight into the craftsmanship behind this iconic spirit. We’ll also visit the Louisville Slugger Museum & Factory, where you’ll see how the famous bats are made—and even take home a special souvenir.
Our journey offers an in-depth look at Kentucky and the industries that have shaped this Bluegrass State. An expert guide will lead us through the historic Keeneland Racecourse, followed by a heartwarming stop at Old Friends Farm, where you’ll meet some of racing’s most beloved retired champions. Don’t forget—a carrot or two is always appreciated by our “old friends”!
This thoughtfully curated getaway includes comfortable coach transportation with drinks, snacks, and onboard entertainment, accommodation at the Hilton Lexington, most meals, and tickets to both the Kentucky Oaks and the Kentucky Derby. Your Derby seating is in a covered area with unlimited food and beverages for a truly elevated experience.
What started as a bucket-list trip has quickly become a guest favorite—one you may find yourself returning to year after year. Care to place your bet?
This tour includes:
3 nights hotel accomodation
Roundtrip coach transportation from Goerke’s Corners Park n Ride
Most meals! Daily breakfast, group dinner on first night, lunch/dinner at Derby
Guided tours of Louisville Slugger, a bourbon distillery/tasting, Keeneland, Old Friends Farm
Kentucky Oaks and Kentucky Derby tickets – seating in First Turn
Your expert guides – Holly & James – can help you place bets too!
This tour is anticipated to be approximately $3700-$3900, depending on transportation expense.
Highlights
- Keeneland Race Track Tour
- Old Friends Farm Tour
- Kentucky Oaks and Derby Tickets
- Bourbon tour and tasting
