15 days in Kentucky Itinerary

15 days in Kentucky Itinerary

Created using Inspirock Kentucky vacation builder

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

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Lexington

— 4 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 Natural Bridge State Resort Park and Kentucky Horse Park. Deepen your sense of the past at sights like Shaker Village of Pleasant Hill and Ashland: The Henry Clay Estate. Change things up with these side-trips from Lexington: Four Roses (in Lawrenceburg), Rock Bridge Trail #207 (in Slade) and Fitchburg Furnace (in Ravenna). And it doesn't end there: explore the different monuments and memorials at Lexington Cemetery, tour the pleasant surroundings at Legacy Trail, get engrossed in the history at Mary Todd Lincoln House, and witness the site of a historic battle at Perryville Battlefield State Historic Site.

For more things to do, traveler tips, maps, and tourist information, use the Lexington trip itinerary planning site.

Newark to Lexington is an approximately 4-hour flight. You can also drive; or do a combination of train and bus. Expect a daytime high around 84°F in June, and nighttime lows around 64°F. Cap off your sightseeing on the 24th (Thu) early enough to travel to Middlesboro.

Things to do in Lexington

Historic Sites · Parks · Museums · Nature

Side Trips

Middlesboro

— 2 nights
Middlesboro is a home rule-class city in Bell County, Kentucky, United States. Kick off your visit on the 25th (Fri): explore the wealth of natural beauty at Cumberland Gap National Historical Park. On the 26th (Sat), you'll have a packed day of sightseeing: stroll through Levi Jackson Wilderness Road Park and then delve into the lush surroundings at Pine Mountain State Resort Park.

For ratings, maps, other places to visit, and tourist information, you can read our Middlesboro online trip itinerary planner.

Traveling by car from Lexington to Middlesboro takes 2.5 hours. Due to the time zone difference, you'll gain 1 hour traveling from Lexington to Middlesboro. Expect a daytime high around 84°F in June, and nighttime lows around 62°F. Wrap up your sightseeing on the 26th (Sat) to allow time to travel to Cave City.

Things to do in Middlesboro

Nature · Parks · Museums

Side Trips

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.
Discover out-of-the-way places like Diamond Caverns and Onyx Cave. Step out of the city life by going to Mammoth Cave and Cedar Sink Trail. You'll find plenty of places to visit near Cave City: Cub Run Cave (in Cub Run) and Abraham Lincoln Birthplace National Historical Park (in Hodgenville). Next up on the itinerary: surround yourself with nature on a nature and wildlife tour, explore the activities along Echo River, examine the collection at Dinosaur World, and explore the fascinating underground world of Hidden River Cave and American Cave Museum.

For traveler tips, reviews, maps, and tourist information, read Cave City trip itinerary builder app.

You can drive from Middlesboro to Cave City in 3.5 hours. In June in Cave City, expect temperatures between 84°F during the day and 64°F at night. Wrap up your sightseeing on the 30th (Wed) to allow time to drive to Louisville.

Things to do in Cave City

Parks · Nature · Outdoors · Trails

Side Trips

Louisville

— 4 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll discover tucked-away gems like Cave Hill Cemetery and Conrad-Caldwell House Museum (Conrad's Castle). Get outdoors at Louisville Mega Cavern and Bernheim Arboretum & Forest. Get out of town with these interesting Louisville side-trips: Bardstown (Barton 1792 Distillery, My Old Kentucky Home, &more) and Four Roses Bourbon - Warehouse and Bottling Facility (in Coxs Creek). There's much more to do: browse the exhibits of Historic Locust Grove, see the interesting displays at Kentucky Derby Museum, look for gifts at A Taste of Kentucky, and brush up on your knowledge of spirits at Kentucky Artisan Distillery.

For ratings, reviews, other places to visit, and more tourist information, you can read our Louisville trip planner.

Traveling by car from Cave City to Louisville takes 1.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of taxi and bus. Due to the time zone difference, you'll lose 1 hour traveling from Cave City to Louisville. In June, daytime highs in Louisville are 86°F, while nighttime lows are 67°F. Finish up your sightseeing early on the 4th (Sun) so you can catch the flight back home.

Things to do in Louisville

Historic Sites · Museums · Parks · Breweries & Distilleries

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.