57 days in Kentucky Itinerary

57 days in Kentucky Itinerary

Created using Inspirock Kentucky sightseeing planner

Make it your trip
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1
Lexington
— 9 nights
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2
Pikeville
— 5 nights
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3
Loretto
— 1 night
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4
Paducah
— 8 nights
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5
Hopkinsville
— 7 nights
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Bowling Green
— 7 nights
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Louisville
— 12 nights
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Covington
— 7 nights
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Lexington

— 9 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 out of town with these interesting Lexington side-trips: Frankfort (Castle & Key Distillery, Salato Wildlife Education Center, &more), Claiborne Farm (in Paris) and Versailles (Woodford Reserve Distillery & Sun Valley Farm). There's still lots to do: indulge your thirst for a good beer at West Sixth Brewing, see the interesting displays at The Great American Dollhouse Museum, take a memorable drive along Old Frankfort Pike, and experience rural life at Old Friends at Dream Chase Farm.

To find photos, reviews, ratings, and more tourist information, you can read our Lexington sightseeing planning site.

Cincinnati to Lexington is an approximately 1.5-hour car ride. You can also take a bus. In December, daytime highs in Lexington are 48°F, while nighttime lows are 32°F. Wrap up your sightseeing on the 8th (Wed) early enough to travel to Pikeville.

Things to do in Lexington

Breweries & Distilleries · Parks · Museums · Nature

Side Trips

Pikeville

— 5 nights
Pikeville is a city in and the county seat of Pike County, Kentucky, United States. Explore the numerous day-trip ideas around Pikeville: Samuel May House (in Prestonsburg), Cumberland Gap National Historical Park (in Middlesboro) and Walking Bridge (in River). The adventure continues: indulge your thirst for a good beer at Dueling Barrels Brewery & Distillery, get outside with Visit Harlan County, get engrossed in the history at Khribet el-Maqatir & a Journey through Biblical History, and gain insight at Hindman Settlement School.

To see photos, more things to do, and more tourist information, read our Pikeville road trip planning app.

Traveling by car from Lexington to Pikeville takes 3 hours. Traveling from Lexington in January, you can expect nighttime temperatures to be a bit warmer in Pikeville, with lows of 31°F. Wrap up your sightseeing on the 13th (Mon) early enough to travel to Loretto.

Things to do in Pikeville

Nature · Parks · Outdoors · Historic Sites

Side Trips

Loretto

— 1 night
Loretto is a home rule-class city in Marion County, Kentucky, United States. On the 14th (Tue), sample the fine beverages at Maker's Mark, then contemplate in the serene atmosphere at The Abbey of Gethsemani, and then do a tasting at Springhill Winery.

To see maps, ratings, where to stay, and other tourist information, go to the Loretto trip planner.

Getting from Pikeville to Loretto by car takes about 4 hours. Traveling from Pikeville in January, you can expect nighttime temperatures to be slightly colder in Loretto, with lows of 23°F. Wrap up your sightseeing on the 14th (Tue) early enough to travel to Paducah.

Things to do in Loretto

Breweries & Distilleries · Wineries · Historic Sites

Side Trips

Paducah

— 8 nights
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Venture out of the city with trips to Kentucky Lake (in Gilbertsville), Kuttawa Harbor Marina (in Kuttawa) and Ben E. Clement Mineral Museum (in Marion). There's lots more to do: do a tasting at Purple Toad Winery, walk around Mike Miller County Park, take in the architecture and atmosphere at St. Francis de Sales Catholic Church, and look for all kinds of wild species at The Arboretum at Murray State.

Discover how to plan a Paducah trip in just a few steps with Inspirock's itinerary builder.

You can drive from Loretto to Paducah in 3.5 hours. The time zone changes from Eastern Standard Time (EST) to Central Standard Time (CST), which is usually a -1 hour difference. In January, daily temperatures in Paducah can reach 44°F, while at night they dip to 25°F. Finish your sightseeing early on the 22nd (Wed) to allow enough time to drive to Hopkinsville.

Things to do in Paducah

Parks · Museums · Historic Sites · Nature

Side Trips

Hopkinsville

— 7 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Get out of town with these interesting Hopkinsville side-trips: Henderson (Farmer and Frenchman Winery, Ruby Moon Vineyard & Winery, &more), Golden Pond (The Elk and Bison Prairie & Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium) and Robert Penn Warren Birthplace Museum (in Guthrie). There's lots more to do: sample the fine beverages at Casey Jones Distillery, appreciate the history behind Everly Brothers Monument, contemplate the long history of Trail of Tears Commemorative Park and Heritage Center, and stroll through Christian Way Farm & Mini Golf.

Use Inspirock's suggestions to plan your Hopkinsville trip and find the best activities and attractions for your vacation.

You can drive from Paducah to Hopkinsville in 1.5 hours. In January in Hopkinsville, expect temperatures between 44°F during the day and 27°F at night. Finish your sightseeing early on the 29th (Wed) so you can drive to Bowling Green.

Things to do in Hopkinsville

Parks · Museums · Wildlife · Breweries & Distilleries

Side Trips

Bowling Green

— 7 nights
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. Venture out of the city with trips to Mammoth Cave National Park (Cedar Sink Trail, Mammoth Cave, &more), Cub Run Cave (in Cub Run) and Owensboro (Smothers Park, World's Largest Sassafras Tree, &more). There's lots more to do: see the interesting displays at National Corvette Museum, contemplate in the serene atmosphere at St. Joseph Catholic Church, contemplate the long history of Riverview at Hobson Grove, and take an in-depth tour of South Union Shaker Village.

To see photos, ratings, traveler tips, and tourist information, read our Bowling Green day trip site.

Traveling by car from Hopkinsville to Bowling Green takes 1.5 hours. In January, daily temperatures in Bowling Green can reach 45°F, while at night they dip to 26°F. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Louisville.

Things to do in Bowling Green

Parks · Nature · Outdoors · Museums

Side Trips

Louisville

— 12 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Explore the numerous day-trip ideas around Louisville: Bardstown (Willett Distilling Company, Lux Row Distillers, &more), Abraham Lincoln Birthplace National Historical Park (in Hodgenville) and Elizabethtown (Veterans Memorial & Swope's Cars of Yesteryear Museum). There's much more to do: Head underground at Louisville Mega Cavern, indulge your taste buds at Food & Drink, contemplate the long history of Conrad-Caldwell House Museum (Conrad's Castle), and test your problem-solving skills at popular escape rooms.

For reviews, where to stay, traveler tips, and more tourist information, use the Louisville online road trip planner.

Drive from Bowling Green to Louisville in 2 hours. Alternatively, you can take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. In February, daytime highs in Louisville are 47°F, while nighttime lows are 29°F. Wrap up your sightseeing on the 17th (Mon) to allow time to travel to Covington.

Things to do in Louisville

Breweries & Distilleries · Museums · Historic Sites · Parks

Side Trips

Covington

— 7 nights
Covington is a city in Kenton County, Kentucky, located at the confluence of the Ohio and Licking Rivers. Explore the numerous day-trip ideas around Covington: Maysville (The Old Pogue Distillery, EAT Gallery, &more), Ark Encounter (in Williamstown) and Augusta (O'Neil Landing & 1811 Historic Jail). There's lots more to do: observe the fascinating underwater world at Newport Aquarium, head outdoors with England idlewild park, sample the fine beverages at New Riff Distillery, and see the interesting displays at Creation Museum.

To find reviews, photos, other places to visit, and tourist information, read Covington online visit planner.

Drive from Louisville to Covington in 2 hours. In February in Covington, expect temperatures between 43°F during the day and 25°F at night. Wrap up your sightseeing by early afternoon on the 24th (Mon) to allow time for the car ride back home.

Things to do in Covington

Museums · Parks · Breweries & Distilleries · Childrens Museums

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.