58 days in Kentucky Itinerary

58 days in Kentucky Itinerary

Created using Inspirock Kentucky trip maker

Make it your trip
Fly
1
Lexington
— 12 nights
Drive
2
Covington
— 6 nights
Drive
3
Louisville
— 12 nights
Drive
4
Owensboro
— 5 nights
Drive
5
Bowling Green
— 8 nights
Drive
6
Hopkinsville
— 7 nights
Drive
7
Paducah
— 7 nights
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Lexington

— 12 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.
Change things up with these side-trips from Lexington: Versailles (Woodford Reserve Distillery, Sun Valley Farm, &more), Four Roses Bourbon - Warehouse and Bottling Facility (in Coxs Creek) and Shaker Village of Pleasant Hill (in Harrodsburg). The adventure continues: try to win big at Keeneland, relax in the rural setting at Old Friends at Dream Chase Farm, sample the fine beverages at Castle & Key Distillery, and admire the sheer force of Cumberland Falls State Resort Park.

To find photos, ratings, traveler tips, and more tourist information, read Lexington online trip maker.

Tucson to Lexington is an approximately 8-hour flight. You can also drive; or take a bus. The time zone difference moving from Mountain Standard Time (MST) to Eastern Standard Time (EST) is 2 hours. Traveling from Tucson in May, things will get little chillier in Lexington: highs are around 76°F and lows about 55°F. Wrap up your sightseeing on the 13th (Wed) to allow time to travel to Covington.

Things to do in Lexington

Parks · Breweries & Distilleries · Historic Sites · Nature

Side Trips

Covington

— 6 nights
Covington is a city in Kenton County, Kentucky, located at the confluence of the Ohio and Licking Rivers. Explore Covington's surroundings by going to Ark Encounter (in Williamstown), Kentucky Speedway (in Sparta) and Augusta (1811 Historic Jail & O'Neil Landing). The adventure continues: learn more about the world around you at Creation Museum, walk around Devou Park, enjoy some diversion at George Rogers Clark Park, and make a trip to Roebling Murals on the Floodwalls of Covington, KY.

Inspirock's itinerary builder makes planning a Covington trip simple and quick.

Traveling by car from Lexington to Covington takes 1.5 hours. Expect a daytime high around 75°F in May, and nighttime lows around 53°F. Wrap up your sightseeing on the 19th (Tue) to allow time to travel to Louisville.

Things to do in Covington

Museums · Parks · Breweries & Distilleries · Childrens Museums

Side Trips

Louisville

— 12 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Change things up with these side-trips from Louisville: Maker's Mark (in Loretto), Bardstown (Preservation Distillery, Barton 1792 Distillery, &more) and Limestone Branch Distillery (in Lebanon). There's still lots to do: try your luck at Churchill Downs, see the interesting displays at Louisville Slugger Museum & Factory, sample the fine beverages at Copper & Kings American Brandy Distillery, and browse the exhibits of Conrad-Caldwell House Museum (Conrad's Castle).

For maps, more things to do, other places to visit, and more tourist information, read Louisville tour itinerary planner.

You can drive from Covington to Louisville in 2 hours. In May in Louisville, expect temperatures between 77°F during the day and 58°F at night. Finish up your sightseeing early on the 31st (Sun) so you can travel to Owensboro.

Things to do in Louisville

Breweries & Distilleries · Parks · Museums · Historic Sites

Side Trips

Owensboro

— 5 nights
Owensboro is a home rule-class city in and the county seat of Daviess County, Kentucky, United States. Explore the numerous day-trip ideas around Owensboro: Bill Monroe's Home Place (in Rosine), Henderson (John James Audubon Museum, Audubon State Park, &more) and Everly Brothers Monument (in Central City). Next up on the itinerary: walk around Smothers Park, don't miss a visit to World's Largest Sassafras Tree, brush up on your knowledge of spirits at O.Z. Tyler Distillery, and admire the natural beauty at Western Kentucky Botanical Garden.

For reviews, more things to do, and other tourist information, read our Owensboro online route builder.

Traveling by car from Louisville to Owensboro takes 2 hours. Due to the time zone difference, you'll gain 1 hour traveling from Louisville to Owensboro. In May in Owensboro, expect temperatures between 77°F during the day and 58°F at night. Finish your sightseeing early on the 5th (Fri) to allow enough time to drive to Bowling Green.

Things to do in Owensboro

Parks · Nature · Wineries · Historic Sites

Side Trips

Bowling Green

— 8 nights
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. You'll find plenty of places to visit near Bowling Green: Campbellsville (Tebbs Bend - Green River Bridge Battlefield & Atkinson-Griffin Log House-Confederate Hospital), Mammoth Cave National Park (Tall Man's Misery, Mammoth Cave, &more) and Horse Cave (Kentucky Down Under Adventure Zoo, Hidden River Cave and American Cave Museum, &more). The adventure continues: see the interesting displays at National Corvette Museum, Head underground at Diamond Caverns, take in the dramatic natural features at Lost River Cave, and experience rural life at Chaney's Dairy Barn.

For more things to do, ratings, traveler tips, and tourist information, refer to the Bowling Green route maker tool.

You can drive from Owensboro to Bowling Green in 1.5 hours. Expect a daytime high around 87°F in June, and nighttime lows around 66°F. Finish your sightseeing early on the 13th (Sat) so you can drive to Hopkinsville.

Things to do in Bowling Green

Parks · Nature · Museums · Outdoors

Side Trips

Hopkinsville

— 7 nights
Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. Explore Hopkinsville's surroundings by going to Cadiz (Lake Barkley Marina & Woodlands Nature Station), Golden Pond (The Elk and Bison Prairie & Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium) and Don F Pratt Museum (in Fort Campbell). And it doesn't end there: sample the fine beverages at Casey Jones Distillery, experience rural life at Christian Way Farm & Mini Golf, contemplate the long history of Trail of Tears Commemorative Park and Heritage Center, and sample the tasty concoctions at Hopkinsville Brewing Company.

For photos, traveler tips, where to stay, and other tourist information, use the Hopkinsville day trip planner.

Drive from Bowling Green to Hopkinsville in 1.5 hours. In June in Hopkinsville, expect temperatures between 85°F during the day and 67°F at night. Wrap up your sightseeing on the 20th (Sat) early enough to drive to Paducah.

Things to do in Hopkinsville

Parks · Wildlife · Breweries & Distilleries · Museums

Side Trips

Paducah

— 7 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), Kenlake State Park (in Hardin) and Columbus-Belmont State Park (in Columbus). The adventure continues: admire the masterpieces at The National Quilt Museum, get engrossed in the history at Lloyd Tilghman House and Civil War Museum, take a leisurely stroll along Paducah Riverwalk, and don't miss a visit to Floodwall Murals.

Plan a Paducah trip in moments using our itinerary builder.

You can drive from Hopkinsville to Paducah in 1.5 hours. In June, daytime highs in Paducah are 87°F, while nighttime lows are 67°F. On the 27th (Sat), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Paducah

Parks · Museums · Historic Sites · Nature

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.