14 days in Kentucky Itinerary

14 days in Kentucky Itinerary

Created using Inspirock Kentucky tour itinerary builder

Plan created by another user.Make it yours

Route & dates

Start: New York City
Fly:  4 h 30 min
1
Lexington
— 3 nights
Drive:  1 h 30 min
2
Louisville
— 4 nights
Drive:  2 h
3
Bowling Green
— 3 nights
Drive:  1 h 45 min
4
Loretto
— 1 night
Drive:  2 h 30 min
5
Middlesboro
— 2 nights
+2
Drive + Fly + Drive:  6 h
End: New York City

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 Frankfort (Floral Clock, Buffalo Trace Distillery, &more), Ark Encounter (in Williamstown) and Woodford Reserve Distillery (in Versailles). Next up on the itinerary: browse the exhibits of Kentucky Horse Park, indulge your thirst for a good beer at Lexington Brewing & Distilling Co., try your luck at Keeneland, and sample the fine beverages at James E. Pepper Distillery.

To see photos, other places to visit, where to stay, and more tourist information, you can read our Lexington trip itinerary builder.

New York City to Lexington is an approximately 4.5-hour flight. You can also drive; or take a bus. Expect slightly colder evenings in Lexington when traveling from New York City in September, with lows around 59°F. Wrap up your sightseeing on the 7th (Mon) to allow time to drive to Louisville.

Things to do in Lexington

Museums Breweries & Distilleries Parks

Side Trips

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

4
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Change things up with a short trip to Jim Beam American Stillhouse in Clermont (about 32 minutes away). Next up on the itinerary: Head underground at Louisville Mega Cavern, sample the fine beverages at Evan Williams Bourbon Experience, try to win big at Churchill Downs, and examine the collection at Kentucky Derby Museum.

To find other places to visit, more things to do, where to stay, and more tourist information, use the Louisville trip itinerary builder app.

You can drive from Lexington to Louisville in 1.5 hours. Another option is to take a bus. Expect a daytime high around 82°F in September, and nighttime lows around 61°F. Cap off your sightseeing on the 11th (Fri) early enough to go by car to Bowling Green.

Things to do in Louisville

Breweries & Distilleries Museums Tours

Side Trip

Jim Beam American Stillhouse
Highlights from your plan
Louisville Mega Cavern ©
Louisville Mega Cavern
Louisville Slugger Museum & Factory ©
Louisville Slugger Museum & Factory
Churchill Downs ©
Churchill Downs

3
nights
Bowling Green

Bowling Green ©
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Step out of the city life by going to Mammoth Cave and Tall Man's Misery. Get out of town with these interesting Bowling Green side-trips: Mammoth Cave National Park (Cedar Sink Trail, Nature & Wildlife Tours, &more) and The Book Store (in Horse Cave). There's much more to do: examine the collection at National Corvette Museum, explore the activities along Echo River, and Head underground at Lost River Cave.

To see reviews, ratings, photos, and tourist information, refer to the Bowling Green trip tool.

You can drive from Louisville to Bowling Green in 2 hours. Other options are to take a bus; or take a bus. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In September in Bowling Green, expect temperatures between 83°F during the day and 60°F at night. Finish your sightseeing early on the 14th (Mon) to allow enough time to travel to Loretto.

Things to do in Bowling Green

Parks Nature Outdoors

Side Trips

Mammoth Cave National Park, The Book Store
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
Fat Man's Misery ©
Fat Man's Misery
Cedar Sink Trail ©
Cedar Sink Trail

1
night
Loretto

Loretto
Loretto is a home rule-class city in Marion County, Kentucky, United States. On the 15th (Tue), brush up on your knowledge of spirits at Maker's Mark, thenbrush up on your knowledge of spirits at Limestone Branch Distillery, thendo a tasting at Springhill Winery, and finally take in the spiritual surroundings of The Abbey of Gethsemani.

To find more things to do, photos, where to stay, and more tourist information, you can read our Loretto tour itinerary planning app.

Drive from Bowling Green to Loretto in 2 hours. The time zone difference when traveling from Bowling Green to Loretto is 1 hour. Expect little chillier weather when traveling from Bowling Green in September: highs in Loretto hover around 78°F, while lows dip to 56°F. Finish up your sightseeing early on the 15th (Tue) so you can travel to Middlesboro.

Things to do in Loretto

Breweries & Distilleries Wineries Historic Sites

Side Trips

Limestone Branch Distillery, Springhill Winery, The Abbey of Gethsemani
Highlights from your plan
Maker's Mark
Maker's Mark
Limestone Branch Distillery ©
Limestone Branch Distillery
Springhill Winery ©
Springhill Winery

2
nights
Middlesboro

Middlesboro ©
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Start off your visit on the 16th (Wed): explore the striking landscape of Cumberland Gap National Historical Park. Get ready for a full day of sightseeing on the next day: immerse yourself in nature at Cumberland Falls State Resort Park.

To see more things to do, maps, and more tourist information, use the Middlesboro day trip tool.

Drive from Loretto to Middlesboro in 3 hours. Traveling from Loretto to Middlesboro, you'll gain 1 hour due to the time zone difference. In September, daytime highs in Middlesboro are 80°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 17th (Thu) to allow time to travel back home.

Things to do in Middlesboro

Parks Nature

Side Trip

Cumberland Falls State Resort Park
Highlights from your plan
Cumberland Gap National Historical Park ©
Cumberland Gap National Historical Park

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