The Ultimate Kentucky Derby Experience
The Kentucky Derby is so much more than a horse race; it is the original springtime sports party of extravagance, tradition, and celebrity! Every year in attendance are some of the biggest names in Hollywood as well as the music and sports world, as everyone who’s anyone descends upon Churchill Downs and the historic Twin Spires for the Run for the Roses. You need not be a horseracing fan to enjoy the most exciting two minutes in sports, and whether you are attending for the races, the star sightings, the fashion or the famous mint juleps, the Derby is unlike any other sporting event in the world!
Below you will find a suggested sample itinerary, please remember that we will completely customize your itinerary based on your tastes, desires and budget.
Day by Day
Day 1 – Wednesday, May 3, 2023
Upon arrival at Louisville Airport, you will be met by your personal chauffeur who will take you to The Brown Hotel, your home for the next four nights. Since being restored to its classic, English Renaissance opulence, The Brown Hotel has been one of Louisville’s most treasured landmark luxury hotels. With its genteel Southern charm and ornate finery, the hotel offers the comforts of home in an environment of sophistication and grace, and a fantastic location for your Kentucky Derby experience.
After you have checked-in and freshened up from your travels, you will be met by your Roadtrips Onsite Host for a welcome drink to review your personalized itinerary and the opportunity to ask your host any questions or make any requests.
This evening you have a reservation for dinner at the English Grill. Conveniently located within your hotel, the English Grill is The Brown’s signature restaurant. Enjoy award-winning contemporary American cuisine crafted by executive chef James Adams. It’s the perfect spot for your first night in Louisville.
Day 2 – Thursday, May 4, 2023
Enjoy breakfast at your leisure in The Brown Hotel’s J. Graham’s Café before meeting your guide for a tour of spectacular Kentucky Horse Country. Kentucky is home to hundreds of working thoroughbred horse farms covering miles of the stunningly beautiful Kentucky countryside. You will have the opportunity to get up close to the amazing horses, speak to the grooms that care for some of the world’s most valuable horses, and get insight into what goes into developing a Triple Crown hopeful.
After you’ve rested up from your Horse Country tour, you’ll be treated to a wonderful Italian dinner at Vincenzo’s. Located just a few blocks from your hotel, Vincenzo’s has been serving up authentic Italian cuisine for over 35 years and boasts a long list of celebrity clients.
Day 3 – Friday, May 5, 2023
After breakfast, your chauffeur will meet you in the hotel lobby and transport you to the historic Churchill Downs for today’s Kentucky Oaks. The Kentucky Oaks features some of the world’s best three-year-old fillies, and has been run since its founding with the Derby by Meriwether Lewis Clark, Jr., the grandson of William Clark of the Lewis and Clark expedition, in 1875. Along with the competition on the track, today, ladies of all ages are invited to enter a competition of another kind, the Kentucky Oaks Fashion Contest. Participants walk the “Pink Carpet”, showcasing their finest attire, but if you’re hoping to snag the win, be sure to wear the Kentucky Oaks official color, pink, in recognition of the Oaks’ official flower, the stargazer lily.
Once you arrive at the track, make your way to Millionaires Row and your premium seating. You will be able to enjoy the day’s races from a luxurious, climate-controlled environment with expansive views of the track so you don’t miss one second of races. Once you are ready to depart Churchill Downs, your chauffeur will be ready and waiting to return you to your hotel to get ready for this evening’s exclusive Barnstable Brown Party.
Louisville’s quintessential Derby Eve party, the Barnstable Brown Party has been held on the eve of the “Run for the Roses” for over two decades. Each year, this black-tie gala is attended by some of the world’s brightest film, television, music, fashion, and sports stars, and you will be there to see it all. Your chauffeur will take you to the Barnstable’s famous mansion for this evening’s party, and once you’ve had your fill of this evening’s festivities, will return you to your hotel.
Day 4 – Saturday, May 6, 2023
Today is the day to don those fabulous hats and seersucker suits in preparation for this year’s Kentucky Derby. The Kentucky Derby pits some of the world’s best thoroughbreds against each other in the race for the first jewel in the Triple Crown series. When you’re ready, your chauffeur will meet you in the lobby of the hotel for transportation to Churchill Downs. Once you arrive at the track, make your way again to your premium seats in Millionaires Row. Enjoy evaluating the field for your favorite to win the Kentucky Derby race and be sure to try a mint julep, the quintessential Derby beverage. Once you are ready to depart Churchill Downs, your chauffeur will be ready and waiting to return you to your hotel.
Day 5 – Sunday, May 7, 2023
Enjoy your breakfast in the beautiful surroundings of The Brown Hotel once more before preparing to return home. When you’re ready, your chauffeur will be ready and waiting to transfer you to the airport and your journey home.
The 4-night Ultimate Kentucky Derby Experience as described above is $21,203 per person (Custom 3-night packages start from $4,355 per person). However, our specialty is custom packages tailored to fit you perfectly. To customize the Kentucky Derby experience of a lifetime, please contact one of our sports travel specialists at 1-800-465-1765 (weekdays between 8:30 a.m. and 5:00 p.m. CST) or submit a custom trip request.
*Rates are per person in USD based on double occupancy. Single occupancy rates are available. Triple and Quad occupancy may be available. A 50% deposit will hold your spot. The balance will not be due until three months prior to departure. Rates include all local and state taxes. Availability and pricing subject to change prior to booking.
Kentucky Derby Disclaimer
Roadtrips is in no way associated with the Kentucky Derby, the Kentucky Oaks, or Churchill Downs. The terms Kentucky Derby and Kentucky Oaks are used only for the purpose of properly describing certain events and without the specific permission of event organizers. Roadtrips’ travel packages and services are not affiliated with the Kentucky Derby, Kentucky Oaks, or Churchill Downs.
“Had some of the best seats in the house.”
Had some of the best seats in the house for the most exciting two minutes in sports!
Overall Rating / 79 Total 1st-Party Reviews
RoadtripsPowered by GatherUp
Sign up to our newsletter