Kentucky Derby
Yellow Clubhouse Box Tickets to the 2025 Kentucky Derby & Kentucky Oaks, VIP Fast Access Pass, In‐Track Concessions, Tickets to Fillies & Lilies, Event Transfers, 3‐Night Stay for 2
Please note that this package has limited inventory and can only be used in fundraising events prior to March 1, 2025.
This Experience Includes:
- 2 Yellow Clubhouse box seat tickets to the Kentucky Derby on Saturday, May 3, 2025, with in-track concessions
- 2 Yellow Clubhouse box seat tickets to Kentucky Oaks on Friday, May 2, 2025, with in-track concessions
- 2 tickets to the exclusive Fillies & Lilies Party, Friday, May 2, 2025
- VIP Fast Access Pass
- 3-night stay at select hotel accommodations in Louisville
- Daily continental breakfast for 2
- Round-trip ground transfers between your hotel and both events
- Winspire booking & concierge service
Kentucky Derby
Enjoy two Yellow Clubhouse box seat tickets to the Kentucky Derby on Saturday, May 3, 2025 in the completely remodeled Churchill Downs! From Section 111 you’ll have a view of the Finish Line, 1st and 2nd turns.
The Kentucky Derby is a Grade I stakes race for 3-year-old thoroughbred horses, held annually in Louisville, Kentucky. The race is known as “The Most Exciting Two Minutes in Sports” for its duration and is also called “The Run for the Roses” for the blanket of roses draped over the winner. It is the first leg of thoroughbred racing’s Triple Crown and draws over 155,000 fans each year. 2025 marks the 151st running of the Kentucky Derby.
Kentucky Oaks
Enjoy two Yellow Clubhouse box seat tickets (reserved seating: box seats of 6, Section 111) to the Kentucky Oaks on Friday, May 2, 2025.
Fillies & Lilies
This exclusive event features gourmet cuisine, premium open bar, live music, bourbon tastings, roaming live performers, and more.
VIP Fast Access Pass
This will allow for faster and more secure access to Churchill Downs’ gates.
Hotel Accommodations
Enjoy a 3-night stay (check-in Thursday, May 1; check out Sunday, May 4, 2025) including daily continental breakfast for 2 at the Courtyard by Marriott, Hilton Garden Inn or comparable hotel, subject to availability.
Ground Transportation
Enjoy round-trip transfers between your hotel and both events.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Starting Gate Courtyard Tickets on Friday and Saturday for the 2026 Kentucky Derby, VIP Fast Access Pass, Premium Concessions, Event Transfers and 3‐Night Stay for 2
Please note that this package has limited inventory and can only be used in fundraising events prior to March 1, 2026.
This Experience for 2 Includes:
- 2 Starting Gate Courtyard tickets, Friday, May 1, 2026
- 2 Starting Gate Courtyard tickets, Saturday, May 2, 2026
- VIP Fast Access Pass
- Premium All-Inclusive concessions with unlimited options, unique small vendors, and premium alcoholic and non-alcoholic beverages.
- 3-night stay at select hotel accommodations in Louisville
- Daily breakfast for 2
- Round-trip ground transfers between your hotel and Churchill Downs
- Winspire booking and concierge service
The Kentucky Derby is one of the most iconic horse racing events in the world. With its rich history, colorful traditions like the mint julep and extravagant hats, the Derby has become a celebration of sportsmanship, style, and southern hospitality. It’s not just a race; it’s a spectacle that captures the heart and spirit of Kentucky.
Kentucky Oaks
Enjoy 2 Starting Gate Courtyard tickets (covered section 8-10) with Premium All-Inclusive concessions, to the Kentucky Oaks on Friday, May 1, 2026. The Kentucky Oaks is a renowned horse race held annually at Churchill Downs in Louisville, Kentucky, the day before the Kentucky Derby. Exclusively for three-year-old fillies, it features the top female thoroughbreds vying for a prestigious title in front of an enthusiastic crowd. The event is a vibrant celebration of excitement, fashion, and camaraderie, honoring the elegance and power of the horses and their jockeys.
Kentucky Derby
Enjoy 2 Starting Gate Courtyard tickets (covered section 8-10) with Premium All-Inclusive concessions, to the Kentucky Derby on Saturday, May 2, 2026. The Kentucky Derby is a Grade I stakes race for thoroughbreds, held annually in Louisville, Kentucky. Known as “The Most Exciting Two Minutes in Sports” due to its thrilling duration, it’s also called “The Run for the Roses” for the blanket of roses draped over the winner. As the first leg of the Triple Crown, it attracts over 155,000 fans each year. In 2026, the Kentucky Derby will celebrate its 152nd running.
VIP Fast Access Pass
This will allow for faster and more secure access to Churchill Downs’ gates.
Hotel Accommodations
Enjoy a 3-night stay (check-in Thursday, April 30; check out Sunday, May 3, 2026) including daily continental breakfast for 2 at the Courtyard by Marriott, Hilton Garden Inn or comparable hotel, subject to availability.
Ground Transportation
Enjoy round-trip transfers between your hotel and both events.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
Starting Gate Courtyard Tickets on Friday and Saturday for the 2026 Kentucky Derby, VIP Fast Access Pass, Premium Concessions, Event Transfers, 3‐Night Stay and Airfare for 2
Please note that this package has limited inventory and can only be used in fundraising events prior to March 1, 2026.
This Experience for 2 Includes:
- 2 Starting Gate Courtyard tickets, Friday, May 1, 2026
- 2 Starting Gate Courtyard tickets (covered section 8-10), Saturday, May 2, 2026
- VIP Fast Access Pass
- Premium All-Inclusive concessions with unlimited options, unique small vendors, and premium alcoholic and non-alcoholic beverages.
- 3-night stay at select hotel accommodations in Louisville
- Daily breakfast for 2
- Round-trip ground transfers between your hotel and Churchill Downs
- Roundtrip economy air for 2
- Winspire booking and concierge service
The Kentucky Derby is one of the most iconic horse racing events in the world. With its rich history, colorful traditions like the mint julep and extravagant hats, the Derby has become a celebration of sportsmanship, style, and southern hospitality. It’s not just a race; it’s a spectacle that captures the heart and spirit of Kentucky.
Kentucky Oaks
Enjoy 2 Starting Gate Courtyard tickets (covered section 8-10) with Premium All-Inclusive concessions, to the Kentucky Oaks on Friday, May 1, 2026. The Kentucky Oaks is a renowned horse race held annually at Churchill Downs in Louisville, Kentucky, the day before the Kentucky Derby. Exclusively for three-year-old fillies, it features the top female thoroughbreds vying for a prestigious title in front of an enthusiastic crowd. The event is a vibrant celebration of excitement, fashion, and camaraderie, honoring the elegance and power of the horses and their jockeys.
Kentucky Derby
Enjoy 2 Starting Gate Courtyard tickets (covered section 8-10) with Premium All-Inclusive concessions, to the Kentucky Derby on Saturday, May 2, 2026. The Kentucky Derby is a Grade I stakes race for thoroughbreds, held annually in Louisville, Kentucky. Known as “The Most Exciting Two Minutes in Sports” due to its thrilling duration, it’s also called “The Run for the Roses” for the blanket of roses draped over the winner. As the first leg of the Triple Crown, it attracts over 155,000 fans each year. In 2026, the Kentucky Derby will celebrate its 152nd running.
VIP Fast Access Pass
This will allow for faster and more secure access to Churchill Downs’ gates.
Hotel Accommodations
Enjoy a 3-night stay (check-in Thursday, April 30; check out Sunday, May 3, 2026) including daily continental breakfast for 2 at the Courtyard by Marriott, Hilton Garden Inn or comparable hotel, subject to availability.
Ground Transportation
Enjoy round-trip transfers between your hotel and both events.
Airfare
This package includes roundtrip economy class service for two from any major metropolitan airport, in the contiguous United States. Subject to availability. Airfare taxes and a $25 per person processing fee are the responsibility of the purchaser.
Business and First-Class upgrades are available at the time of booking for an additional fee. Use of frequent flyer miles for upgrades is dependent on specific ticket restrictions as determined by the airline’s frequent flyer program.
Package Redemption
Winspire Travel packages and experiences must be booked within one year of the purchase date. The actual travel date must occur within two years of the purchase date.
Booking & Concierge Services
Winspire provides a team of seasoned travel professionals to help you redeem your experience. We will book all travel-related details and reservations for every part of your experience. Included within our services, Winspire can assist with extra hotel nights, airfare, and additional guests as a full-service travel agency.
Additional Information
Reservations are subject to availability, blackout dates, and major holidays. Reservations must be booked 60 days in advance of travel. Purchases through charity fundraisers are non-refundable.
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