DAY 1: HEART OF HORSE COUNTRY
11:00 AM
Here in the Horse Capital of the World, thoroughbreds are ubiquitous throughout the city. Lexington is surrounded by about 450 horse farms, a number of them -- such as Coolmore's Ashford Stud and Darley at Jonabell -- open for group visits.
1:00 PM
Stop by the Kentucky Horse Park, home to two equestrian museums: the Smithonian International Museum of the Horse and the American Saddlebred Museum (focused on America's only native horse breed).
8:00 PM
End the evening with a genteel Southern meal at Merrick Inn, formerly Merrick Place, where Kentucky Derby winner Exterminator was trained. Now the site specializes in memorable meals, such as the filet mignon and angus ribeye.
DAY 2: HISTORY
11:00 AM
Take a trip through the city's past with a visit to Ashland, the Henry Clay Estate. The 18-room Italianate mansion was built in 1806, and Clay met there with figures such as William Henry Harrison, the Marquis de Lafayette, and Daniel Webster. While touring historic homes, your group may also want to make time for a stop at the Mary Todd Lincoln House, built the same year as Clay's and the first house museum in the country that honors a First Lady.
3:00 PM
After visiting historic interiors, venture into the outdoors at McConnell Springs, "the birthplace of Lexington" and a 26-acre nature preserve that showcases native flora along trails leading to the Blue Hole and The Boils -- Kentucky's natural springs.
DAY 3: BOURBON & BLUEGRASS
1:00 PM
A visit to this region would not be complete without a stroll along the Kentucky Bourbon Trail. Lexington's stop on the trail is Alltech Town Branch Distillery, where tours are available to see how bourbon and rye are made.
4:00 PM
Lexington is also home to a number of wineries. Chardonnay and cabernet grapes have grown hardily in the soil of former tobacco fields. Groups can tour any of a number of the local wineries, such as Equus Run Vineyards, Talon Winery and Vineyards, or Chrisman Mill Winery.
6:00 PM
Take in an evening of grassroots music at the Woodsongs Old-Time Radio Hour, broadcast nationally from the city's historic Lyric Theater every Monday night on NPR and PBS. On Wednesdays, groups can check out Red Barn Radio, broadcast from ArtsPlace in downtown Lexington.