Tentative dates: April 29 - May 2, 2027

Join Holly Johnson and James Boling as we lead another group to the Kentucky Derby in 2027. We are excited to watch you experience the Fastest Two-Minutes in Sports in this time-honored tradition of the Derby. Our tour will lead us to Louisville on Thursday, where we will have a guided tour of the famous Louisville Slugger Museum before dining with our group.

On Friday, we will tour enjoy a guided tour of Keeneland with a knowledgeable guide that will answer all your questions and then some! After learning the history of Keeneland, we will head to the Old Friends Farm to visit some of the most famous and award-winning thoroughbreds, like 1997 Kentucky Derby and Preakness winner Silver Charm! Get up close to the horses (with some carrots) and enjoy them living their best lives!

Of course, a trip to Kentucky wouldn’t be complete with a bourbon tasting and tour! We’ll have a guided distillery tour and tasting before heading to the Derby on Saturday. If the Kentucky Derby isn’t on your Bucket List, it should be! Join this tour as we help to preserve the history and legacy of the Kentucky Derby, the longest continuously running sporting event in the country dating back to the first Derby in 1875. 

This tour will include coach transportation, hotel accommodations, most meals, Kentucky Oaks and Derby tickets (First Turn Club), Keeneland tour, Old Friends Farm tour, Louisville Slugger Museum tour, Bourbon tour & tasting, and expert guides. Approximate tour price: $3500/person based on double occupancy.

Pre-registrations are accepted by emailing holly@hollitudeholidaytravel.com or by completing the inquiry form below.