13 days in Kentucky & Southeast Missouri Itinerary

13 days in Kentucky & Southeast Missouri Itinerary

Created using Inspirock United States tour itinerary planner

Make it your trip
Drive
1
Louisville
— 3 nights
Drive
2
Lexington
— 5 nights
Drive
3
Middlesboro
— 1 day
Drive
4
Cave City
— 2 nights
Drive
5
Eminence
— 2 nights
Drive

S M T W T F S
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Louisville

— 3 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Eschew the tourist crowds and head to Conrad-Caldwell House Museum (Conrad's Castle) and Bernheim Arboretum & Forest. Visiting Spring Mill State Park and Muscatatuck National Wildlife Refuge will get you outdoors. Next up on the itinerary: walk around Cherokee Park, admire the masterpieces at 21c Museum Hotel, and brush up on your knowledge of spirits at Kentucky Peerless Distilling Co.

For reviews, photos, traveler tips, and tourist information, you can read our Louisville trip itinerary app.

Saint Louis to Louisville is an approximately 4.5-hour car ride. You can also fly; or take a bus. The time zone difference when traveling from Saint Louis to Louisville is 1 hour. In November in Louisville, expect temperatures between 57°F during the day and 37°F at night. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Lexington.

Things to do in Louisville

Parks · Wildlife · Historic Sites · Museums

Side Trips

Lexington

— 5 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.
Get in touch with nature at Unique Horse Farm Tours and Nada Tunnel. Eschew the tourist crowds and head to Raven Run Nature Sanctuary and Lexington Cemetery. Step out of Lexington with an excursion to Red River Gorge Geological Area in Winchester--about 1h 10 min away. Next up on the itinerary: get to know the fascinating history of Waveland State Historic Site, stroll around Jacobson Park, see the interesting displays at Aviation Museum of Kentucky, and brush up on your knowledge of spirits at Barrel House Distillery.

To see where to stay, maps, more things to do, and other tourist information, refer to the Lexington day trip website.

Getting from Louisville to Lexington by car takes about 1.5 hours. Other options: drive; or take a bus. In November, daytime highs in Lexington are 56°F, while nighttime lows are 36°F. Cap off your sightseeing on the 24th (Tue) early enough to travel to Middlesboro.

Things to do in Lexington

Parks · Breweries & Distilleries · Wildlife · Historic Sites

Side Trips

Middlesboro

— 1 day
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. On the 24th (Tue), see the interesting displays at Little Congress Bicycle Museum and then tour the pleasant surroundings at Tri State Peak Trail.

To find maps, ratings, other places to visit, and other tourist information, refer to the Middlesboro travel route planner.

Getting from Lexington to Middlesboro by car takes about 2.5 hours. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In November, plan for daily highs up to 58°F, and evening lows to 34°F. Cap off your sightseeing on the 24th (Tue) early enough to travel to Cave City.

Things to do in Middlesboro

Outdoors · Trails · Parks · Museums

Side Trip

Cave City

— 2 nights
Originally intended as a resort city to serve the Mammoth Cave attraction, Cave City has taken on a life of its own.
Kick off your visit on the 25th (Wed): get a dose of the wild on a nature and wildlife tour, then hike along Cedar Sink Trail, and then stroll through Tall Man's Misery. Keep things going the next day: explore the fascinating underground world of Sand Cave and then admire the majestic nature at Nolin Lake State Park.

Before you visit Cave City, use our trip planner to discover what you can do and see there.

Traveling by car from Middlesboro to Cave City takes 3.5 hours. In November, daytime highs in Cave City are 57°F, while nighttime lows are 36°F. Finish up your sightseeing early on the 26th (Thu) so you can travel to Eminence.

Things to do in Cave City

Parks · Outdoors · Nature · Trails

Side Trips

Eminence

— 2 nights
Eminence is a city in Shannon County, Missouri, United States. Kick off your visit on the 27th (Fri): explore the activities along Blue Spring and then admire the majestic nature at Echo Bluff State Park. On your second day here, don't miss a visit to Ozark Heritage Welcome Center and then tour the pleasant surroundings at Greer Spring.

For maps, photos, traveler tips, and more tourist information, read Eminence road trip planning app.

Traveling by car from Cave City to Eminence takes 6 hours. In November in Eminence, expect temperatures between 58°F during the day and 36°F at night. Finish up your sightseeing early on the 28th (Sat) so you can travel back home.

Things to do in Eminence

Nature · Parks · Outdoors · Trails

Side Trips

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.