56 days in Kentucky Itinerary

Created using Klarna Trips Kentucky trip itinerary planner
Make it your trip
Fly to Cincinnati Northern Kentucky International Airport, Drive to Covington
1
Covington
— 5 nights
Drive
2
Louisville
— 14 nights
Drive
3
Owensboro
— 5 nights
Drive
4
Paducah
— 7 nights
Drive
5
Hopkinsville
— 6 nights
Drive
6
Bowling Green
— 7 nights
Drive
7
Lexington
— 11 nights
Fly

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Covington — 5 nights

Covington is a city in Kenton County, Kentucky, located at the confluence of the Ohio and Licking Rivers. Change things up with these side-trips from Covington: Kentucky Gateway Museum Center (in Maysville), Brianza Gardens and Winery (in Crittenden) and EarthJOY Tree Adventures (in Germantown). There's still lots to do: learn more about the world around you at Creation Museum, sample the fine beverages at Boone County Distilling Co., do a tasting at Wooden Cask Brewery Company, and have some family-friendly fun at Purrfect Day Cafe Covington.

To find more things to do, other places to visit, where to stay, and other tourist information, use the Covington trip itinerary planning site.

Exeter, UK to Covington is an approximately 16.5-hour combination of flight and car. The time zone difference moving from Greenwich Mean Time to Eastern Standard Time is minus 5 hours. In September, daytime highs in Covington are 31°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Louisville.
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Breweries & Distilleries · Parks · Wineries · Museums
Side Trips
Find places to stay Sep 5 — 10:

Louisville — 14 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Change things up with these side-trips from Louisville: Clermont (Bernheim Arboretum & Forest & James B. Beam Distilling Co.), Maker's Mark (in Loretto) and Bardstown (Lux Row Distillers, Willett Distilling Company, &more). Next up on the itinerary: savor the flavors at Food & Drink, see the interesting displays at Muhammad Ali Center, take in the views from The Big Four Bridge, and test your problem-solving skills at popular escape rooms.

For more things to do, where to stay, ratings, and other tourist information, go to the Louisville trip itinerary planner.

Traveling by car from Covington to Louisville takes 2 hours. In September in Louisville, expect temperatures between 32°C during the day and 19°C at night. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to Owensboro.
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Side Trips
Find places to stay Sep 10 — 24:

Owensboro — 5 nights

Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. You'll find plenty of places to visit near Owensboro: Henderson (John James Audubon Museum, Audubon State Park, &more), Bill Monroe's Home Place (in Rosine) and Everly Brothers Monument (in Central City). And it doesn't end there: brush up on your knowledge of spirits at Green River Distilling Co., hunt for treasures at Preservation Station Market And Event Center, admire the masterpieces at Owensboro Museum of Fine Art, and walk around Panther Creek Park.

To find ratings, photos, and tourist information, use the Owensboro trip itinerary planner.

Drive from Louisville to Owensboro in 2 hours. You'll gain 1 hour traveling from Louisville to Owensboro due to the time zone difference. In September, plan for daily highs up to 32°C, and evening lows to 19°C. Wrap up your sightseeing on the 29th (Thu) early enough to drive to Paducah.
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Parks · Shopping · Museums · Historic Sites
Side Trips
Find places to stay Sep 24 — 29:

Paducah — 7 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Explore Paducah's surroundings by going to Mineral Mound Golf Course (in Eddyville), Kuttawa Harbor Marina (in Kuttawa) and Fort Jefferson Memorial Cross (in Wickliffe). There's lots more to do: explore the world behind art at The National Quilt Museum, explore the engaging exhibits at River Discovery Center, see the interesting displays at Paducah Distilled Spirits, and take an in-depth tour of Lloyd Tilghman House and Civil War Museum.

To see where to stay, photos, reviews, and tourist information, read Paducah day trip planner.

Traveling by car from Owensboro to Paducah takes 2.5 hours. In September, daytime highs in Paducah are 34°C, while nighttime lows are 18°C. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Hopkinsville.
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Parks · Museums · Historic Sites · Shopping
Side Trips
Find places to stay Sep 29 — Oct 6:

Hopkinsville — 6 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Change things up with these side-trips from Hopkinsville: Adsmore House & Gardens (in Princeton), Woodlands Nature Station (in Cadiz) and Pennyrile Forest State Resort Park (in Dawson Springs). There's lots more to do: sample the fine beverages at Casey Jones Distillery, sample the tasty concoctions at Hopkinsville Brewing Company, see the interesting displays at Robert Penn Warren Birthplace Museum, and see some colorful creatures with Pennyroyal Scuba Blue Springs Resort.

For traveler tips, where to stay, maps, and other tourist information, refer to the Hopkinsville planning app.

Drive from Paducah to Hopkinsville in 1.5 hours. In October, plan for daily highs up to 26°C, and evening lows to 12°C. Wrap up your sightseeing on the 12th (Wed) early enough to drive to Bowling Green.
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Parks · Wildlife · Breweries & Distilleries · Museums
Side Trips
Find places to stay Oct 6 — 12:

Bowling Green — 7 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Explore Bowling Green's surroundings by going to Diamond Caverns (in Park City), Mammoth Cave National Park (Echo River, Mammoth Cave, &more) and Dog Creek Recreation Area (in Cub Run). There's lots more to do: see the interesting displays at National Corvette Museum, explore the fascinating underground world of Lost River Cave, walk around Basil Griffin Park, and steep yourself in history at Riverview at Hobson Grove.

To find reviews, other places to visit, traveler tips, and tourist information, refer to the Bowling Green online route planner.

Traveling by car from Hopkinsville to Bowling Green takes 1.5 hours. In October, daytime highs in Bowling Green are 26°C, while nighttime lows are 11°C. Wrap up your sightseeing on the 19th (Wed) to allow time to drive to Lexington.
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Parks · Nature · Outdoors · Museums
Side Trips
Find places to stay Oct 12 — 19:

Lexington — 11 nights

Horse Capital of the World

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
Explore Lexington's surroundings by going to Frankfort (Floral Clock, Castle & Key Distillery, &more), Versailles (Sun Valley Farm & Woodford Reserve Distillery) and Ark Encounter (in Williamstown). The adventure continues: stroll through Kentucky Horse Park, experience rural life at Old Friends at Dream Chase Farm, try to win big at Keeneland, and sample the fine beverages at James E. Pepper Distillery.

For ratings, traveler tips, more things to do, and more tourist information, you can read our Lexington driving holiday planner.

Drive from Bowling Green to Lexington in 3 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Bowling Green to Lexington. In October, daytime highs in Lexington are 24°C, while nighttime lows are 11°C. Finish your sightseeing early on the 30th (Sun) so you can fly back home.
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Side Trips
Find places to stay Oct 19 — 30:

Kentucky travel guide

4.6
Caves · Distilleries · Specialty Museums
The Bluegrass State
A diverse region of sprawling farmland and rich cultural heritage, Kentucky is the birthplace of American horse racing and home to the world-famous Kentucky Derby. While the cities of Lexington and Louisville experience the majority of the state's tourism, Kentucky is also a favorite among outdoor enthusiasts with its array of natural attractions, including the Cumberland Gap and the world's longest cave system at Mammoth Cave National Park. Take a tour through original Civil War battlefields to delve into the nation's history, or head to one of the many bourbon distilleries to learn more about Kentucky's most famous export.
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