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The Kentucky Derby 2026

  • Witness the most exciting two minutes in sports with Inspirato during an unforgettable, first-class weekend at the Kentucky Derby
  • Enjoy access to Club SI premium hospitality at Churchill Downs, with views into the Paddock and Paddock runway, along with trackside race viewing
  • Savor gourmet dining, premium bar, and private betting windows at Club SI
  • Stay at Hotel Distil, a chic boutique hotel in downtown Louisville

Itinerary at a Glance

Day 1
Thursday, April 30, 2026 | Arrive in Louisville

• Arrive and check in at Hotel Distil

• Meet and mingle with fellow Inspirato members at our Inspirato Only Welcome Dinner

Meals included: Dinner

Day 2
Friday, May 1, 2026 | Kentucky Oaks Day

• Breakfast at Hotel Distil

• Private transportation to and from Churchill Downs

• Access to Club SI, the premium hospitality venue at Churchill Downs, including views into the Paddock Stalls and Paddock Runway, chef curated food and beverages, along with dedicated betting windows and private restrooms

• Watch the Longines Kentucky Oaks race trackside from the Club SI dedicated viewing area

Meals included: Breakfast and Racetrack Hospitality

Day 3
Saturday, May 2, 2026 | Kentucky Derby Day

• Breakfast at Hotel Distil

• Get Derby-ready with hair, makeup, and barber services (for an additional cost)

• Private transportation to and from Churchill Downs

• Access to Club SI, the premium hospitality venue at Churchill Downs, including views into the Paddock Stalls and Paddock Runway, chef curated food and beverages, along with dedicated betting windows and private restrooms and appearances by Sports Illustrated Celebrity Ambassadors

• Watch the most exciting two minutes in sports with trackside views from the Club SI dedicated viewing area

Meals included: Breakfast and Racetrack Hospitality

Day 4
Sunday, May 3, 2026 | Departure Day

• Breakfast at Hotel Distil

• Checkout and departures

Meals included: Breakfast

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