5 days in Kentucky Itinerary

5 days in Kentucky Itinerary

Created using Inspirock United States vacation planner

Make it your trip
Drive
1
Middlesboro
— 1 night
Drive
2
Mammoth Cave National Park
— 2 nights
Drive
3
Louisville
— 1 night
Fly

S M T W T F S
23
24
25
26
27
28
29
30
31
1
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5

Middlesboro

— 1 night
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 28th (Fri), explore the striking landscape of Cumberland Gap National Historical Park.

To plan Middlesboro vacation without wasting time, ask Inspirock to design an itinerary.

Chicago to Middlesboro is an approximately 5-hour combination of flight and car. You can also drive. In May, daily temperatures in Middlesboro can reach 76°F, while at night they dip to 53°F. Finish your sightseeing early on the 29th (Sat) to allow enough time to travel to Mammoth Cave National Park.

Things to do in Middlesboro

Nature · Parks

Mammoth Cave National Park

— 2 nights
Mammoth Caves National Park is the longest cave system in the world so far discovered.
Bring the kids along to Mammoth Cave and Cedar Sink Trail. The adventure continues: stroll through Fat Man's Misery, explore the activities along Echo River, explore the fascinating underground world of Diamond Caverns, and learn about wildlife with up-close encounters at Kentucky Down Under Adventure Zoo.

To see ratings, other places to visit, more things to do, and more tourist information, use the Mammoth Cave National Park trip itinerary builder tool.

Traveling by car from Middlesboro to Mammoth Cave National Park takes 3.5 hours. In May, daily temperatures in Mammoth Cave National Park can reach 76°F, while at night they dip to 56°F. Finish up your sightseeing early on the 31st (Mon) so you can go by car to Louisville.

Things to do in Mammoth Cave National Park

Parks · Nature · Outdoors · Trails

Side Trips

Louisville

— 1 night

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
On the 1st (Tue), take in the views from The Big Four Bridge and then explore the fascinating underground world of Louisville Mega Cavern.

For traveler tips, photos, reviews, and tourist information, go to the Louisville visit planner.

Traveling by car from Mammoth Cave National Park to Louisville takes 2 hours. Alternatively, you can 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 May, daytime highs in Louisville are 77°F, while nighttime lows are 58°F. Wrap up your sightseeing on the 1st (Tue) to allow time to travel back home.

Things to do in Louisville

Nature · Parks

Kentucky travel guide

4.5
Caves · Specialty Museums · Distilleries
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.