Derby weekend with the extra day. Oaks day on Friday, the Derby itself on Saturday, and time either side for bourbon country and the horse farms.
The Kentucky Derby is two minutes long. The weekend around it is four days, and if you are going all that way, the extra day is the one worth having.
Arriving Wednesday means you are settled before the city fills up. It gives you Thursday and Friday for the things people always mean to do and then run out of time for. Bourbon country. The horse farms with the white fences. Churchill Downs itself when it is quiet enough to actually look at.
Friday is Oaks day, which locals will tell you is the better day of the two. Smaller crowds, the same track, and the lilies instead of the roses.
Then Saturday, and everything that comes with it. The hats, the juleps, My Old Kentucky Home, and two minutes that empty the lungs of a hundred and fifty thousand people.
If you would rather come for the Derby alone, the shorter package starts Thursday. Both are on the calendar.
The day the locals prefer. Same track, smaller crowd, and the lilies instead of the roses.
Churchill Downs, the twin spires, the hats, and the most exciting two minutes in sports.
Distillery tours and tastings through the rolling country outside Louisville.
White fences, bluegrass, and thoroughbreds. Some of the prettiest farmland in America.
Make your way to the Marriott Griffin Gate Golf Resort and Spa, a four-star property in the heart of Lexington and your home for the next four nights. It sits in Kentucky's Bluegrass country, about seventy-five minutes from Churchill Downs. There is a championship golf course, a full-service spa, indoor and outdoor pools, pickleball courts, and walking trails, which makes it a genuinely restful base between the busy days. This evening, a Kentucky-inspired welcome reception with local flavors and a chance to meet everyone.
After breakfast, into the heart of Kentucky's horse racing industry. First to Keeneland Race Course, founded in 1936 and one of the most respected tracks in the country, for the history and the morning workouts, where you watch future champions being put through their paces. Then out through the Bluegrass countryside to one of Kentucky's premier stud farms to meet the people who run it and get close to some celebrated stallions. Lunch on your own, then a second stud farm and more on breeding, training, and why this region is called the Horse Capital of the World. The evening is yours at the resort.
To Louisville for the first of two days at Churchill Downs, and dress to impress, because Oaks Day is one of the most fashionable days of the racing year. On the way we stop at the Woodford Reserve Distillery for a guided tour and tasting. Then Churchill Downs, where your premium hospitality package includes all-inclusive food and beverages through the day. A full program of racing builds to the Kentucky Oaks, the Lilies for the Fillies. Back to Lexington in the evening.
The moment you have been waiting for. We transfer to Churchill Downs early so you have time to take in the atmosphere, the traditions, and the pageantry before the racing starts. Premium hospitality again, all-inclusive through the day, and then the most famous two minutes in sport.
A final breakfast at the resort, then check out and home, with a Derby weekend behind you that had rather more in it than just the Derby.
The extra day at the front. You arrive Wednesday instead of Thursday, which gives you Oaks day on Friday plus more time for bourbon country and the farms before the weekend takes over.
Same Derby, same city. The Derby Package runs Thursday to Sunday. This one adds Wednesday night and Oaks day. Call me and I will talk you through which suits you.
Soon. This departure is still being finalized. Send me a note or call me at 931-801-9900 and you will hear the moment pricing and the full itinerary are set.
Not a thing. Asking for information is just asking. No deposit, no obligation, and it helps me size the trip.
No, but sharing brings the cost down. I am glad to match you with a roommate from the group.
I recommend it on every trip, and I recommend buying it at deposit rather than waiting. The pre-existing condition waiver window closes early, and once it does I cannot reopen it.
Pricing per person, land only. Airfare to Kentucky is not included.
$1,000 non-refundable deposit per person
Booking is handled securely through our Trips Unlimited reservation system. Prefer to talk it through first? Call me.
Button not opening your email? Write to frances@tripsunlimited.com or call 931-801-9900.
Travel insurance recommended at the time of deposit.
The complete day-by-day for The Ultimate Derby Package, with what is included and what to expect. Print it, save it, or pass it to someone who should come along.
Browse our full lineup of trips, day adventures, and members-only gatherings.
See All Trips →