16 days in Kentucky Itinerary

16 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

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Route & dates

16 days in Kentucky Itinerary

Start: Chicago
Fly:  3​h 45​min
1
Newport
— 1 night
bus:  1​h 30​min
2
Lexington
— 4 nights
Drive:  1​h 30​min
3
Louisville
— 5 nights
Drive:  2​h
4
Bowling Green
— 3 nights
Drive:  2​h 30​min
5
Paducah
— 2 nights
Fly:  3​h 30​min
End: Chicago

1
night
Newport

Newport ©
Newport is a home rule-class city at the confluence of the Ohio and Licking rivers in Campbell County, Kentucky, in the United States. On the 27th (Sat), try your luck at JACK Cincinnati Casino and then meet the residents at Newport Aquarium. Here are some ideas for day two: identify plant and animal life at Spring Grove Cemetery & Arboretum, browse the eclectic array of goods at Jungle Jim's International Market, and then identify plant and animal life at Cincinnati Nature Center.

To see more things to do and tourist information, read Newport road trip planning website .

Chicago to Newport is an approximately 4-hour flight. You can also drive; or do a combination of flight, taxi, and bus. You'll lose 1 hour traveling from Chicago to Newport due to the time zone difference. July in Newport sees daily highs of 84°F and lows of 64°F at night. Finish up your sightseeing early on the 28th (Sun) so you can catcht the bus to Lexington.

Things to do in Newport

Parks Wildlife Fun & Games

Side Trips

Cincinnati, Jungle Jim's International Market, Cincinnati Nature Center
Highlights from your plan
Jungle Jim's International Market ©
Jungle Jim's International Market
JACK Cincinnati Casino ©
JACK Cincinnati Casino
Cincinnati Nature Center ©
Cincinnati Nature Center

4
nights
Lexington

Lexington ©
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Step out of the city life by going to Kentucky Horse Park and Salato Wildlife Education Center. Give yourself a bit of retail therapy at Kentucky Artisan Center at Berea and Damselfly Gallery. Change things up with these side-trips from Lexington: Shaker Village of Pleasant Hill (in Harrodsburg), Buffalo Trace Distillery (in Frankfort) and Four Roses Bourbon - Warehouse and Bottling Facility (in Coxs Creek). There's much more to do: try your luck at Keeneland, brush up on your knowledge of spirits at Bluegrass Distillers, look for all kinds of wild species at Raven Run Nature Sanctuary, and sample the tasty concoctions at Woodford Reserve Distillery.

For reviews, ratings, other places to visit, and more tourist information, read Lexington trip planner .

You can take a bus from Newport to Lexington in 1.5 hours. Alternatively, you can drive. In July, daily temperatures in Lexington can reach 85°F, while at night they dip to 67°F. Finish your sightseeing early on the 1st (Thu) to allow enough time to drive to Louisville.

Things to do in Lexington

Parks Museums Breweries & Distilleries

Side Trips

Berea, Frankfort, Midway, Woodford Reserve Distillery, Shaker Village of Pleasant Hill
Highlights from your plan
Keeneland ©
Keeneland
Buffalo Trace Distillery ©
Buffalo Trace Distillery
Woodford Reserve Distillery ©
Woodford Reserve Distillery

5
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Step out of the city life by going to Louisville Mega Cavern and Muscatatuck National Wildlife Refuge. Change things up with these side-trips from Louisville: Maker's Mark (in Loretto), Jim Beam American Stillhouse (in Clermont) and The Glendale Antique Mall (in Glendale). And it doesn't end there: try your luck at Churchill Downs, look for all kinds of wild species at Starve Hollow State Recreation Area, sample the fine beverages at Copper & Kings American Brandy Distillery, and see the interesting displays at Louisville Slugger Museum & Factory.

To find reviews, photos, where to stay, and other tourist information, use the Louisville online holiday planner .

Getting from Lexington to Louisville by car takes about 1.5 hours. Other options: take a bus. August in Louisville sees daily highs of 86°F and lows of 68°F at night. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Bowling Green.

Things to do in Louisville

Parks Wildlife Theme Parks

Side Trips

Muscatatuck National Wildlife Refuge, Jim Beam American Stillhouse, Starve Hollow State Recreation Area, The Glendale Antique Mall, River Run Family Waterpark
Highlights from your plan
Churchill Downs ©
Churchill Downs
Maker's Mark ©
Maker's Mark
Jim Beam American Stillhouse ©
Jim Beam American Stillhouse

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. Take a break from the city and head to Mammoth Cave National Park and Lost River Cave. You'll find plenty of places to visit near Bowling Green: Fat Man's Misery (in Mammoth Cave National Park) and Cave City (Onyx Cave & Kentucky Action Park). There's still lots to do: examine the collection at National Corvette Museum, cool off at Beech Bend Park & Splash Lagoon, and explore and take pictures at NCM Motorsports Park.

To see ratings, traveler tips, reviews, and other tourist information, read our Bowling Green trip itinerary maker app .

Traveling by car from Louisville to Bowling Green takes 2 hours. Alternatively, you can take a bus; or take a bus. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. In August in Bowling Green, expect temperatures between 87°F during the day and 67°F at night. Wrap up your sightseeing on the 9th (Fri) to allow time to drive to Paducah.

Things to do in Bowling Green

Parks Theme Parks Nature

Side Trips

Cave City, Mammoth Cave National Park
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
Fat Man's Misery ©
Fat Man's Misery
Lost River Cave ©
Lost River Cave

2
nights
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 10th (Sat): explore the world behind art at The National Quilt Museum, then make a trip to Floodwall Murals, then take an in-depth tour of Lloyd Tilghman House and Civil War Museum, and finally do a tasting at Purple Toad Winery. On the 11th (Sun), you'll have a packed day of sightseeing: take a leisurely stroll along Paducah Riverwalk, see the interesting displays at Paducah Distilled Spirits, then look for gifts at Newsom's Old Mill Store, and finally stroll around Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium.

For traveler tips, other places to visit, photos, and other tourist information, read Paducah trip maker app .

Traveling by car from Bowling Green to Paducah takes 2.5 hours. Alternatively, you can take a bus. August in Paducah sees daily highs of 87°F and lows of 67°F at night. Wrap up your sightseeing on the 11th (Sun) to allow time to travel back home.

Things to do in Paducah

Museums Parks Wildlife

Side Trips

Newsom's Old Mill Store, Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium
Highlights from your plan
The National Quilt Museum ©
The National Quilt Museum
Purple Toad Winery ©
Purple Toad Winery

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