Churchill Downs, Louisville, KY : April 30 - May 3, 2020
experience the kentucky derby in style with our customized derby ticket & hotel packages

experience the kentucky derby in style with our customized derby ticket & hotel packages

Day by Day

Your Ultimate Premium Kentucky Derby Experience

The Kentucky Derby is the original springtime sports party of tradition, grandeur, beauty and excitement! It is honestly so much more than just a horse race. People attend for the fashion, the mint juleps, the horses, the movie stars, the sports stars, the wagering and ... well just the fantastic-ness of it all. Derby weekend is really one of the most exciting parties of the year. 

And of course each year, the venerable Churchill Downs draws in an impressive crowd including the biggest names in the sports world, music, Hollywood and politics. You can be part of that crowd in Louisville for the Run for the Roses. 

Let's get you started with some suggestions based on the ultimate itinerary that we would recommend. These are merely our suggestions, and please remember that we will completely customize your itinerary based on your tastes, desires and budget.

Day 1 – Wednesday

the lobby of the historic brown hotel in downtown louisville

the lobby of the historic brown hotel in downtown louisville

Upon your arrival at the Louisville Airport, you will be met by your own personal driver who will take you to your home for the next four nights. Depending upon your reservation, you will stay at either of two beautiful and grand hotels, the 21C Museum Hotel or the Brown Hotel. Known for their significant contribution to downtown Louisville, these magnificent hotels top Condè Nast Traveler lists of excellence and truly make for a perfect Kentucky Derby racing weekend experience. With genteel Southern charm or cutting edge artistic beauty, these hotels offer more than the comforts of home and serve up Derby tradition with sophistication and grace.

After your driver delivers you to your home for the weekend and freshened up from your travels, you will be met by your local Sports Tickets & Travel Host for a complimentary welcome drink in the hotel bar to review your personalized itinerary with time for you to ask your host any questions or make any special requests.

This evening you have a reservation for dinner at Proof On Main. Conveniently located in the heart of downtown and in the 21C Museum Hotel, Proof On Main features a culinary team that sources the finest local ingredients and serves rich and sustainable cuisine alongside a menu of more than 50 Kentucky bourbons. Relax and take in the electric atmosphere at the hottest spot in town!

Day 2 – Thursday

horse farm tours and bourbon trail tours are available to our guests

horse farm tours and bourbon trail tours are available to our guests

Enjoy breakfast at your leisure in your hotel's Café prior to greeting your guide and driver for your private tour of Kentucky Horse Country or the Bourbon Trail - it is your option to choose which you prefer. Kentucky is home to hundreds of working thoroughbred horse farms and world famous bourbon distilleries covering miles of the stunningly beautiful Kentucky countryside. You will have the day to get up close to the horses, speak to the grooms that care for the world’s most valuable animals or speak personally with the master distillers and learn their secrets at legendary bourbon properties such as Heaven Hill, Four Roses and Makers Mark.

Upon return to Louisville in the early evening, you will have your choice to either attend the Kentucky Derby’s famous Pegasus Parade on the streets of downtown Louisville or to relax at your hotel and reflect upon the day's events in the beautiful Kentucky countryside.

Day 3 – Friday - Kentucky Oaks Day!

After breakfast, your driver will again meet you at your hotel to drive you to Churchill Downs for the historic Kentucky Oaks. The Kentucky Oaks features some of the world’s best three-year-old fillies, which are the female horses. The Oaks has been run since 1875, so you know there is no lack of tradition in what is considered a very special day by those local to Louisville. It has become a tradition for both men and women to dress in their finest fashion with a focus on the color pink in an homage to the fillies. So be sure to wear the Kentucky Oaks official color, pink, in recognition of the Oaks’ official flower, the stargazer lily.

the paddock area at churchill downs is alive with pink on kentucky oaks day

the paddock area at churchill downs is alive with pink on kentucky oaks day

Once you arrive at the Downs, make your way to the top floors of the Clubhouse and Millionaires Row for your premium seats. You will enjoy the Oaks races from the luxurious top of the track with expansive views of the backside and the main stretch so you don’t miss one second of races. There are thirteen races run on Oaks Day beginning at 10:30am, with the final race posting at 7:23pm. Once you are ready to depart for the afternoon, your friendly driver will be ready and waiting to return you to your hotel to get ready for this evening’s exclusive Barnstable Brown Party.

Louisville’s most famous and well-known Derby Eve party, the Barnstable Brown Party has been held on the Friday of Derby Weekend 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 driver will take you to the Barnstable’s famous mansion for this evening’s event, and once you’ve had your fill of festivities, will return you to your hotel.Your driver will take you to the Barnstable’s famous mansion in The Highlands for this evening’s party, and once you’ve decided it's time to rest, you will be returned to your hotel for the night by your dedicated driver.

Day 4 – Saturday - Kentucky Derby Day!

the kentucky derby on saturday is the most famous horse race in the world

the kentucky derby on saturday is the most famous horse race in the world

The Big Day! Today is the day to wear your fabulous hats, dresses and and crisp seersucker suits for this year’s Kentucky Derby. Often called the “most exciting two minutes in sports” for its approximate length, this beloved horse race dates back to May 17, 1875. The Kentucky Derby is packed with the world’s best thoroughbreds bumping and competing against each other in the first jewel in the Triple Crown series. When you’re ready, your private driver will meet you in the lobby of the hotel for the drive to Churchill Downs. Once you arrive at the track, make your way again to your premium seats in Millionaires Row. Enjoy your racing form, private betting window and selecting your favorite horse to win the Kentucky Derby race. Definitely be sure to enjoy a mint julep, the famous Derby drink of choice. As with the previous days’ Oaks, the Kentucky Derby is an all-day affair. Races begin at 10:30am again and the final race is the 14th which posts at 8:10pm. The world-famous Kentucky Derby race is actually the 12th race and this posts at 6:46pm. Of course you may depart or stay as long as you prefer, and your dedicated driver will be waiting to bring you back to your hotel after an exciting day watching perhaps the next Triple Crown winner sweep the field.

Day 5 – Sunday

Enjoy breakfast in the beautiful surroundings of your hotel once more before preparing to return home. When you’re ready, your driver will be waiting to transport you to the airport and toward your memory-filled journey home.

Interested in our Special Kentucky Derby Hospitality options?


Rates are per person based upon Double occupancy. Single occupancy is available. Triple and Quad occupancy may be available. Custom 3-night packages available from $2,195 per person. The 4-night Ultimate Kentucky Derby Experience as described above is $19,876 per person. However, we specialize in custom packages built to fit you perfectly. To customize your Bucket List Kentucky Derby experience, please contact one of our sports travel concierge team members at 1-317-759-3002 (weekdays from 9:00 a.m. to 5:00 p.m. EST) or simply submit the custom package request form on this page. We can tweak the Day-by-Day package described above to include what you like and change what you don't!

*Rates are per person in $USD. Just a 50% deposit will lock in your rate and hold your place for our Ultimate Experience Packages. The balance will be due three months prior to departure. While we can't prevent the 16.07% room occupancy tax that Louisville requires every hotel to charge its guests, we do include that in our customized package pricing so that you don't have to worry about it! Availability and pricing are subject to change at any time, so please consider reserving early.

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“The Kentucky Derby is such a spectacular event! Really it's a 'can't miss' for us. Every year we have used you for our 3rd Floor Clubhouse tickets and hotel and we have been beyond pleased. You guys are great! Thank you for making our experience spectacular!”

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