Insider tours 2026 Kentucky Derby Itineraries

Insider Tours offers a 3 and 4 night tour package option. The 3 night package includes (as highlights) a Welcome Party on Thursday Night, Kentucky Oaks on Friday, and Kentucky Derby on Saturday, along with a mimosa bar, bourbon tasting, and a Welcome Basket. The 4-night package means arriving one day early for a fun-filled day of tours on Thursday! Tours include a visit to the Louisville Slugger Museum for a factory tour and Bourbon blending experience, lunch, tour and a whiskey tasting at Jim Beam Distillery, and a bourbon and chocolate tasting at Stitzel Weller Distillery. Both feature a stay in the Bourbon District of Downtown Louisville at the Springhill Suites by Marriott, and both include daily breakfast, private transportation to all events and tours, and Insider Guides present every step of the way, making sure you’re having the absolute time of your life!

3-Night Stay Itinerary:

4-Night Packages with Tours Include 3-Night Package + All Items Below:

  • 1 Additional Night Stay at Springhill Suites by Marriott, includes Breakfast Buffet (arrive 1 day earlier than the 3-Night Package guests).

  • Louisville Slugger Museum and Factory Tour.

  • Louisville Slugger Bourbon Experience – Partake in Louisville's only custom bourbon experience, a 45-minute class that teaches you how to blend your own bourbon recipe. Optionally purchase a bottle of your custom bourbon recipe & have it blended on-site.

  • Jim Beam Distillery Tour & Whiskey Tasting.

  • Lunch is served at Jim Beam Distillery’s Restaurant, the Kitchen Table.

  • Bourbon & Chocolate Tasting Experience at Stitzel-Weller Distillery.

  • Private Transportation & Insider Guides present at all events to lead the way!

Ticket Details, Info on Your Kentucky Derby & Oaks Reserved Seats:

Your Reserved Seating for Oaks and Derby will be located in the Starting Gate Courtyard at Churchill Downs. Seats are uncovered. Seats in the Starting Gate Courtyard provide an exceptional experience focused on the exciting moments at the start of the race, plus the homestretch dash, combined with premium, all-inclusive food, drink & amenities. 

Key Benefits Include:

  • Prime Starting Line Views: Enjoy an unparalleled, “front-row” view of the horses as they are loaded into the gate & break at the start of the race.

  • Trackside Location: This area is located directly next to the dirt & turf racetracks & overlooks the beginning of the homestretch, ensuring a close-up, "courtside” experience.

  • Horses Pass You Twice: Experience both the excitement of the start of the race & the homestretch portion of the race. The horses pass by the Starting Gate Courtyard seats twice for double the excitement & double the fun!

  • Comfortable Seating: Relax in new, comfortable padded fold-down stadium-style seating that provides spectacular views of the racetrack.

  • Elevated Social Atmosphere: The area features an updated and upscale ambiance, designed for socializing & enjoying the day's events in a modern setting with premium finishes.

  • All-Inclusive Food and Beverage: Your ticket includes an all-inclusive menu of food (including a Chef's Table buffet in some adjacent pavilion areas) & a wide selection of alcoholic and non-alcoholic beverages.

  • Facility Access: Ticket holders have access to the first-floor frontside & paddock viewing areas of the facility.

** Please note: Seating is uncovered. To upgrade to a covered seating option, please inquire for pricing.

Derby Fun Facts & Traditions:

  • The Race: The Derby is a Grade I stakes race for top three-year-old Thoroughbreds, run at a distance of 1 and 1/4 miles. The field is limited to 20 horses, which qualify through a points system in a series of preparatory races.

  • "Run for the Roses": The winning horse is draped in a spectacular blanket of over 400 red roses, a tradition that began officially in the 1930’s.

  • Fashion and Atmosphere: The event is a grand cultural and social spectacle known for its unique style. On race day, women typically wear large, ornate hats - every hat is unique and each hat is more grand than the next! Men typically wear colorful suits and bow ties. The atmosphere is electric, a lively mix of high fashion with an abundance of fancy food and drink, exciting race moments, and celebrity sightings!

  • Traditions: In addition to race day fashion, a few other ong-standing traditions include mint juleps and the singing of Stephen Foster's song "My Old Kentucky Home" as the horses parade to the starting gate.

  • Triple Crown: The Kentucky Derby is followed by the Preakness Stakes and then the Belmont Stakes. A horse must win all three races in the same year to achieve the prestigious Triple Crown title.