8 days in Kentucky Itinerary

8 days in Kentucky Itinerary

Created using Inspirock Kentucky travel planner

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Route & dates

8 days in Kentucky Itinerary

Start: Chicago
Fly + Drive:  5​h
1
Bowling Green
— 1 night
Drive:  2​h
2
Louisville
— 3 nights
Drive:  1​h 30​min
3
Lexington
— 3 nights
Fly:  3​h 15​min
End: Chicago

1
night
Bowling Green

Bowling Green ©
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Kick off your visit on the 26th (Thu): test your team's savvy at popular escape rooms. Keep things going the next day: see the interesting displays at National Corvette Museum, Head underground at Mammoth Cave, and then explore the fascinating underground world of Lost River Cave.

To see photos, maps, more things to do, and other tourist information, read Bowling Green trip itinerary planner.

Chicago to Bowling Green is an approximately 5-hour combination of flight and car. You can also drive; or do a combination of train and bus. Plan for somewhat warmer temperatures traveling from Chicago in December, with highs in Bowling Green at 51°F and lows at 33°F. Wrap up your sightseeing on the 27th (Fri) early enough to drive to Louisville.

Things to do in Bowling Green

Nature Parks Museums

Side Trip

Mammoth Cave
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
National Corvette Museum ©
National Corvette Museum
Lost River Cave ©
Lost River Cave

3
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Take a break from Louisville with a short trip to Maker's Mark in Loretto, about 1h 10 min away. There's much more to do: explore the fascinating underground world of Louisville Mega Cavern, sample the fine beverages at Copper & Kings American Brandy Distillery, take in the views from The Big Four Bridge, and test your problem-solving skills at popular escape rooms.

For maps, ratings, where to stay, and tourist information, use the Louisville day trip site .

Drive from Bowling Green to Louisville in 2 hours. Alternatively, you can take a bus; or take a bus. You'll lose 1 hour traveling from Bowling Green to Louisville due to the time zone difference. In December, daily temperatures in Louisville can reach 48°F, while at night they dip to 33°F. Finish your sightseeing early on the 30th (Mon) so you can drive to Lexington.

Things to do in Louisville

Historic Sites Museums Tours

Side Trip

Maker's Mark
Highlights from your plan
Louisville Slugger Museum & Factory ©
Distillery Tours
Kentucky Derby Museum ©
Kentucky Derby Museum

3
nights
Lexington

Lexington
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Venture out of the city with trips to Buffalo Trace Distillery (in Frankfort), Ark Encounter (in Williamstown) and Woodford Reserve Distillery (in Versailles). The adventure continues: try your luck at Keeneland, indulge your thirst for a good beer at Lexington Brewing & Distilling Co., sample the fine beverages at James E. Pepper Distillery, and test your problem-solving skills at popular escape rooms.

To find photos, ratings, where to stay, and tourist information, you can read our Lexington trip itinerary builder tool .

You can drive from Louisville to Lexington in 1.5 hours. Alternatively, you can take a bus. In December, daily temperatures in Lexington can reach 48°F, while at night they dip to 32°F. Finish up your sightseeing early on the 2nd (Thu) so you can travel back home.

Things to do in Lexington

Museums Breweries & Distilleries Fun & Games

Side Trips

Woodford Reserve Distillery, Buffalo Trace Distillery, Ark Encounter
Highlights from your plan
Ark Encounter
Ark Encounter
Keeneland ©
Keeneland
Kentucky Horse Park ©
Kentucky Horse Park

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