1) Horse Farm Tours
I'll admit that I have not taken one of these yet although I had one scheduled last year that was cancelled. You can book these well in advance or when you get to Kentucky and in many cases they'll come and pick you up at your hotel. You can book one here.
This is a must see if you love horses. But be warned you'll need to plan this far in advance to see the big ones - Coolmore, Winstar, Taylor Made and others. For about $20 you can see some of the most expensive horses on the planet. Well worth it!
(Pioneer of the Nile at Winstar)
3) KY Horse Park
The Park is huge and there's much to see here. Museums, the barns, the retired race horses, and of course, there may be an event taking place - a horse show, a three-day event, driving, etc.
This local restaurant chain has something for everyone. I go to Malone's every trip and have never been disappointed. Great food, atmosphere, a real Kentucky landmark.
Don't miss this cute, historic town west of Lexington that's full of antique shops, restaurants, character and charm.
You don't have to like Bourbon to take one of the many tours along Kentucky's Bourbon Trail. Woodford Reserve is divine but make your reservations well in advance. Buffalo Trace in Frankfort is also worth a visit. You can take a week and visit two a day and not see them all.
7) LV Harkness
Also located downtown, if you love horses, china, entertaining and like to shop you'll think you have died and gone to heaven in this place.
Even if they are not racing go by and see this lovely spot. Have breakfast at the track kitchen. And if you are there in April or October go to the races!
9) M's Canvas House
Needlepoint nirvana, located on a side street downtown and full of horse-related needlepoint designs that you won't see anywhere else. Plan to stay a few hours if you stitch.
I hope you are planning your trip!