5 days in Kentucky Itinerary

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.

On the 16th (Thu), explore the fascinating underground world of Louisville Mega Cavern. Keep things going the next day: examine the collection at Louisville Slugger Museum & Factory, sample the fine beverages at Jim Beam American Stillhouse, and then sample the fine beverages at Maker's Mark.

For reviews, traveler tips, photos, and tourist information, read our Louisville planner.

New York City to Louisville is an approximately 5.5-hour flight. You can also drive; or take a bus. While traveling from New York City, expect a bit warmer days and about the same nights in Louisville, ranging from highs of 77°F to lows of 58°F. Finish up your sightseeing early on the 18th (Sat) so you can go by car to Lexington.

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.

Start off your visit on the 19th (Sun): take in the exciting artwork at Kentucky Artisan Center at Berea, brush up on your knowledge of spirits at Woodford Reserve Distillery, then brush up on your knowledge of spirits at Buffalo Trace Distillery, and finally take in the exciting artwork at Damselfly Gallery. Here are some ideas for day two: contemplate the long history of Mary Todd Lincoln House, then sample the fine beverages at Barrel House Distillery, then bet on a winner at Keeneland, and finally sample the tasty concoctions at Lexington Brewing & Distilling Co..

For maps, other places to visit, more things to do, and more tourist information, read Lexington road trip planning tool.

Getting from Louisville to Lexington by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 76°F in May, and nighttime lows around 55°F. Finish up your sightseeing early on the 20th (Mon) so you can travel back home.