22 days in Kentucky Itinerary

Created using Inspirock Kentucky trip itinerary maker
Make it your trip
Fly
1
Lexington
— 7 nights
Drive
2
Middlesboro
— 1 night
Drive
3
Cave City
— 4 nights
Drive
4
Louisville
— 6 nights
Drive
5
Paducah
— 3 nights
Fly

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1

Lexington — 7 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.
Step off the beaten path and head to Distillery Tours and Mary Todd Lincoln House. Explore the numerous day-trip ideas around Lexington: Slade (Natural Bridge State Resort Park & Kentucky Reptile Zoo), Red River Gorge Geological Area (in Winchester) and Shaker Village of Pleasant Hill (in Harrodsburg). And it doesn't end there: explore the galleries of Ashland: The Henry Clay Estate, stroll the grounds of Lexington Cemetery, brush up on your knowledge of spirits at James E. Pepper Distillery, and take a peaceful walk through Berea Pinnacles.

To see other places to visit, where to stay, more things to do, and other tourist information, use the Lexington trip maker website.

Portland to Lexington is an approximately 8-hour flight. You can also drive; or do a combination of train and bus. You'll lose 3 hours traveling from Portland to Lexington due to the time zone difference. In September in Lexington, expect temperatures between 81°F during the day and 59°F at night. Finish your sightseeing early on the 15th (Thu) so you can drive to Middlesboro.
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Breweries & Distilleries · Parks · Historic Sites · Tours
Side Trips

Middlesboro — 1 night

Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 16th (Fri): explore the wealth of natural beauty at Cumberland Gap National Historical Park.

For photos, more things to do, maps, and other tourist information, use the Middlesboro route planner.

Drive from Lexington to Middlesboro in 2.5 hours. The time zone difference when traveling from Lexington to Middlesboro is minus 1 hour. In September in Middlesboro, expect temperatures between 80°F during the day and 58°F at night. Finish your sightseeing early on the 16th (Fri) to allow enough time to drive to Cave City.
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Nature · Parks

Cave City — 4 nights

Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
You'll explore the less-touristy side of things at Fat Man's Misery and Limestone Branch Distillery. Explore Cave City's surroundings by going to Swope's Cars of Yesteryear Museum (in Elizabethtown) and Abraham Lincoln Birthplace National Historical Park (in Hodgenville). The adventure continues: meet the residents at Kentucky Down Under Adventure Zoo, examine the collection at Dinosaur World, and explore the fascinating underground world of Onyx Cave.

To find other places to visit, where to stay, traveler tips, and tourist information, read Cave City sightseeing planner.

You can drive from Middlesboro to Cave City in 3.5 hours. In September in Cave City, expect temperatures between 81°F during the day and 59°F at night. Finish up your sightseeing early on the 20th (Tue) so you can go by car to Louisville.
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Parks · Nature · Zoos & Aquariums · Museums
Side Trips

Louisville — 6 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll explore the less-touristy side of things at Cave Hill Cemetery and Conrad-Caldwell House Museum (Conrad's Castle). You'll find plenty of places to visit near Louisville: Bardstown (My Old Kentucky Home & Distillery Tours) and Owensboro (Green River Distilling Co. & Smothers Park). The adventure continues: glide peacefully along the water with some of the best stand-up paddleboarding in the area, make a trip to Zachary Taylor National Cemetery, stroll around Cherokee Park, and sample the fine beverages at Copper & Kings American Brandy Distillery.

To find traveler tips, other places to visit, photos, and tourist information, read our Louisville online road trip planner.

You can drive from Cave City to Louisville in 1.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of taxi and bus. The time zone changes from Central Standard Time (CST) to Eastern Standard Time (EST), which is usually a 1 hour difference. In September, daily temperatures in Louisville can reach 82°F, while at night they dip to 61°F. Finish your sightseeing early on the 26th (Mon) to allow enough time to drive to Paducah.
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Breweries & Distilleries · Parks · Tours · Historic Sites
Side Trips

Paducah — 3 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Step off the beaten path and head to Paducah Riverwalk and Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium. Explore the numerous day-trip ideas around Paducah: Casey Jones Distillery (in Hopkinsville) and Kentucky Lake (in Gilbertsville). The adventure continues: have fun and explore at River Discovery Center, look for gifts at Hancock's of Paducah, and do a tasting at Purple Toad Winery.

To see traveler tips and tourist information, you can read our Paducah driving holiday planning website.

You can drive from Louisville to Paducah in 3.5 hours. Other options are to take a bus; or fly. You'll gain 1 hour traveling from Louisville to Paducah due to the time zone difference. September in Paducah sees daily highs of 84°F and lows of 60°F at night. Finish your sightseeing early on the 29th (Thu) to allow enough time to fly back home.
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Parks · Breweries & Distilleries · Nature · Wildlife
Side Trips

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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