8 days in Kentucky Itinerary

8 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

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Route & dates

8 days in Kentucky Itinerary

Start: Chicago
Fly:  3​h 45​min
1
Louisville
— 2 nights
Drive:  1​h 15​min
2
Georgetown
— 1 night
Drive:  2​h 30​min
3
Park City
— 3 nights
Drive:  3​h
4
Paducah
— 1 night
Fly:  3​h 30​min
End: Chicago

2
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll find plenty of places to visit near Louisville: The Great American Dollhouse Museum (in Danville) and Swope's Cars of Yesteryear Museum (in Elizabethtown). The adventure continues: explore the fascinating underground world of Louisville Mega Cavern, indulge your taste buds at Food & Drink, get your game on at Bluegrass Karting & Events, and brush up on your knowledge of spirits at Kentucky Peerless Distilling Co.

Find out how to plan Louisville trip without stress by asking Inspirock to help create an itinerary.

Chicago to Louisville is an approximately 4-hour flight. You can also drive; or do a combination of flight and bus. Traveling from Chicago to Louisville, you'll lose 1 hour due to the time zone difference. September in Louisville sees daily highs of 82°F and lows of 61°F at night. Cap off your sightseeing on the 1st (Tue) early enough to go by car to Georgetown.

Things to do in Louisville

Tours Museums Parks

Side Trips

The Great American Dollhouse Museum, Swope's Cars of Yesteryear Museum
Highlights from your plan
Louisville Mega Cavern ©
Louisville Mega Cavern
Distillery Tours
Swope's Cars of Yesteryear Museum ©
Swope's Cars of Yesteryear Museum

1
night
Georgetown

Georgetown ©
Georgetown is a home rule-class city in Scott County, Kentucky, in the United States. On the 2nd (Wed), relax in the rural setting at Claiborne Farm, experience rural life at Old Friends at Dream Chase Farm, then experience rural life at Pin Oak Stud, and finally relax in the rural setting at Sun Valley Farm.

Start your trip to Georgetown by creating a personalized itinerary on Inspirock.

You can drive from Louisville to Georgetown in 1.5 hours. In October, daytime highs in Georgetown are 70°F, while nighttime lows are 49°F. Finish your sightseeing early on the 2nd (Wed) so you can travel to Park City.
Highlights from your plan
Old Friends at Dream Chase Farm ©
Old Friends at Dream Chase Farm
Claiborne Farm ©
Claiborne Farm
Sun Valley Farm ©
Sun Valley Farm

3
nights
Park City

Park City ©
Park City is a home rule-class city in Barren County, Kentucky, United States. Park City is known for nature and historic sites. Your plan includes some of its best attractions: Head underground at Mammoth Cave National Park, stroll through Cedar Sink Trail, steep yourself in history at Bell's Tavern, and explore the activities along Echo River.

For ratings, maps, more things to do, and more tourist information, refer to the Park City journey planner.

Drive from Georgetown to Park City in 2.5 hours. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In October, daily temperatures in Park City can reach 71°F, while at night they dip to 48°F. Wrap up your sightseeing on the 5th (Sat) to allow time to travel to Paducah.

Things to do in Park City

Parks Outdoors Trails

Side Trips

Mammoth Cave National Park, Detweiler's Country Store, 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
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Kick off your visit on the 6th (Sun): walk around Mike Miller County Park, then do a tasting at Purple Toad Winery, then admire the masterpieces at The National Quilt Museum, and finally pause for some serene contemplation at St. Francis de Sales Catholic Church.

To see ratings, traveler tips, and tourist information, refer to the Paducah trip itinerary planner .

Traveling by car from Park City to Paducah takes 3 hours. In October, daytime highs in Paducah are 73°F, while nighttime lows are 50°F. Cap off your sightseeing on the 6th (Sun) early enough to travel back home.

Things to do in Paducah

Parks Museums Wineries

Side Trip

Mike Miller County Park
Highlights from your plan
The National Quilt Museum ©
The National Quilt Museum
Purple Toad Winery ©
Purple Toad Winery
St. Francis de Sales Catholic Church ©

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