South · United States
Kentucky
Bourbon, bluegrass, thoroughbreds and the wild Appalachian outdoors.
Discover Kentucky
Kentucky is the home of bourbon, the Kentucky Derby and some of the most beautiful horse country on earth — but it's also Mammoth Cave, the Red River Gorge, Appalachian music towns and a riverfront capital in Louisville. Compact distances make it easy to pair a city stay with a distillery trail and a day in the hills.
Watch
Kentucky in motion
Recommended Drives
Suggested itineraries
10 days
The Classic Kentucky Loop
Route: A circular drive taking in Kentucky's iconic landscapes, gateway towns, and signature stays.
Our most-requested itinerary for first-time visitors to Kentucky — a balance of headline sights and quiet, off-grid retreats.
7 days
Kentucky Hidden Corners
Route: Lesser-known back roads, working ranches, and locally-owned inns across Kentucky.
Designed with our regional partners for travellers who have already seen the postcards and want the unfiltered version.
19 days · Chicago to New Orleans
Get Your Vibe On I-65
Route: Chicago → Indianapolis → Louisville → Nashville → Florence/Muscle Shoals → Huntsville → Birmingham → Montgomery → Orange Beach/Gulf Shores → Mobile → New Orleans
End-to-end on Interstate 65 from the Great Lakes to the Gulf — Chicago's skyline, Indy's Motor Speedway, Louisville bourbon, Nashville's Music City, the legendary Muscle Shoals studios, Huntsville's Space & Rocket Center, Birmingham's Civil Rights heritage, Montgomery's history, the white-sand Alabama Gulf Coast, historic Mobile and a New Orleans finale.
- •Chicago — Millennium Park, the Bean, Navy Pier & Magnificent Mile
- •Indianapolis — Motor Speedway, Eiteljorg Museum & the Cultural Trail
- •Louisville — Kentucky Derby Museum, Bourbon Trail, Muhammad Ali's home & Louisville Slugger Museum
- •Nashville — Ryman Auditorium, Country Music Hall of Fame, Grand Ole Opry & Printer's Alley
- •Florence/Muscle Shoals — Muscle Shoals Sound Studio, Alabama Music Hall of Fame, W.C. Handy's birthplace & Frank Lloyd Wright's Rosenbaum House
- •Huntsville — U.S. Space & Rocket Center, Botanical Garden, Burritt on the Mountain & The Orion amphitheater
- •Birmingham — Civil Rights District, Vulcan statue, Barber motorcycle museum & James Beard kitchens
- •Montgomery — Civil Rights Memorial Center, Rosa Parks Museum, Hank Williams Museum & State Capitol
- •Orange Beach & Gulf Shores — Gulf State Park, sugar-white beaches, Fort Morgan & The Wharf
- •Mobile — birthplace of Mardi Gras, USS Alabama Battleship, Bellingrath Gardens & Dauphin Island
- •New Orleans — French Quarter, Creole cuisine, jazz & riverboats on the Mississippi
15 days · Nashville loop
Bourbon, Bluegrass & Horse Country
Route: Nashville → Tullahoma → Pigeon Forge → Lexington → Versailles → Cincinnati → Indianapolis → Louisville → Owensboro → Nashville
A DriveAmerica-curated fly-drive through the heart of bourbon and bluegrass country — Nashville's honky-tonks and Ryman Auditorium, Tennessee whiskey at Jack Daniel's and George Dickel, Dollywood and the Smokies in Pigeon Forge, thoroughbred farms and Keeneland racecourse in Lexington, the Kentucky Bourbon Trail (Wild Turkey, Buffalo Trace, Woodford Reserve, Jim Beam and Maker's Mark), Cincinnati's riverfront, Indianapolis's craft distillery scene, Churchill Downs and the Kentucky Derby Museum in Louisville and the Bluegrass Music Hall of Fame in Owensboro. Offered by our DriveAmerica partner ATI.
- •Day 1 — Nashville: Ryman Auditorium, bluegrass venues & Nelson's Green Brier Distillery
- •Day 2 — Nashville to Tullahoma: Jack Daniel's in Lynchburg, Miss Mary Bobo's, Short Springs waterfalls & George Dickel at Cascade Hollow
- •Day 3 — Tullahoma to Pigeon Forge: WDVX Blue Plate Special in Knoxville & Dollywood in the foothills of the Smokies
- •Day 4 — Pigeon Forge to Lexington: Daniel Boone National Forest & the Kentucky Music Hall of Fame in Mount Vernon
- •Days 5–7 — Lexington: Darley at Jonabell, Keeneland racecourse, Blue Door Smokehouse BBQ & Claiborne Farm
- •Day 8 — Lexington to Versailles: WinStar Farm, Lane's End, Wild Turkey, Buffalo Trace, Woodford Reserve & Ashford Stud
- •Day 9 — Versailles to Cincinnati: the Purple People Bridge, Newport riverfront & New Riff Distilling
- •Day 10 — Cincinnati to Indianapolis: 12.05 Distillery, West Fork Whiskey, Hotel Tango & dinner at Bluebeard
- •Day 11 — Indianapolis to Louisville: Churchill Downs, the Kentucky Derby Museum, Stitzel-Weller (Bulleit) & Doc Crow's on Whiskey Row
- •Day 12 — Louisville to Owensboro: Jim Beam American Stillhouse, Oscar Getz Museum of Whiskey History & Maker's Mark in Loretto
- •Day 13 — Owensboro: Bluegrass Music Hall of Fame & Museum and O.Z. Tyler Distillery
- •Day 14 — Owensboro back to Nashville via Rosine and the Bill Monroe Museum, home of the 'father of bluegrass'
- •Day 15 — Nashville: return car at BNA for departure
8 days · Cincinnati loop
Explore Kentucky
Route: Cincinnati → Newport/Covington → Lexington → Red River Gorge → Berea → Cumberland Falls → Mammoth Cave → Bowling Green → Land Between the Lakes → Paducah → Owensboro → Louisville → Cincinnati
A DriveAmerica-curated fly-drive through the very best of Kentucky — Northern Kentucky's B-Line bourbon bars, Lexington's thoroughbred farms and Keeneland, outdoor adventures in the Red River Gorge, the Folk Arts capital of Berea, Cumberland Falls' famous moonbow, Mammoth Cave National Park, the National Corvette Museum in Bowling Green, the Elk & Bison Prairie at Land Between the Lakes, Paducah's UNESCO quilt heritage, the Bluegrass Music Hall of Fame in Owensboro and Churchill Downs, Whiskey Row and the Louisville Slugger Museum in Louisville. Offered by our DriveAmerica partner ATI.
- •Day 1 — Cincinnati arrival to Newport/Covington: BB Riverboats, Newport on the Levee & the B-Line bourbon trail
- •Day 2 — Newport/Covington to Lexington: Old Friends thoroughbred retirement farm in Georgetown, Kentucky Horse Park, Keeneland Racecourse & the Distillery District
- •Day 3 — Lexington to Berea via Red River Gorge: Natural Bridge State Resort Park, Boone Creek zip lines or the Gorge Underground kayak tour, then the Kentucky Artisan Center in Berea
- •Day 4 — Berea to Bowling Green: Kentucky Music Hall of Fame, Cumberland Falls (the 'Niagara of the South'), Mammoth Cave National Park & the National Corvette Museum
- •Day 5 — Bowling Green to Paducah via Land Between the Lakes: Casey Jones Distillery, the Elk & Bison Prairie, Patti's 1880's Settlement & Paducah's National Quilt Museum and floodwall murals
- •Day 6 — Paducah to Owensboro: Bluegrass Music Hall of Fame & Museum, Green River Distilling Co. on the Bourbon Trail, Smothers Park & Reid's Orchard
- •Day 7 — Owensboro to Louisville: Kentucky Derby Museum, Churchill Downs, the Belle of Louisville, Muhammad Ali Center, Louisville Slugger Museum & Whiskey Row
- •Day 8 — Louisville to Cincinnati departure
Top Places To Visit
The unmissable Kentucky
Kentucky's capital city
Begin your journey amid the cultural heart of Kentucky.
A signature national or state park
Untouched landscapes that define the Kentucky experience.
A coastal or scenic byway
An unhurried drive past viewpoints, diners, and small towns.
An iconic small town
Local craftsmanship, regional cuisine, and Kentucky hospitality.
Simple Things To Do
Fun things to do in Kentucky
A quick-hit list of ideas for first-time visitors to Kentucky, inspired by Kentucky Tourism.
Drive the Kentucky Bourbon Trail
18 distilleries across the Bluegrass — Maker's Mark, Woodford Reserve, Buffalo Trace and Wild Turkey — with tastings, rickhouse tours and the official Bourbon Trail Passport.
Experience the Kentucky Derby
The 'most exciting two minutes in sports' at Churchill Downs in Louisville every first Saturday in May — or visit the Kentucky Derby Museum year-round for a behind-the-scenes tour of the track.
Tour Horse Country in Lexington
Working thoroughbred farms, the Kentucky Horse Park and Keeneland Race Course — drive the rolling pastures and white-fenced lanes around the horse capital of the world.
Go underground at Mammoth Cave
The longest known cave system on the planet and a UNESCO World Heritage Site — ranger-led tours from gentle historic walks to lantern-lit Wild Cave adventures.
Hike & climb the Red River Gorge
Sandstone arches, cliff lines and waterfalls in the Daniel Boone National Forest — world-class rock climbing, scenic byways and Kentucky's own 'Natural Bridge'.
Explore Louisville's riverfront
The Louisville Slugger Museum, Muhammad Ali Center, NuLu's restaurants and the Big Four pedestrian bridge across the Ohio River — plus Bourbon Row downtown.
Cruise the Bluegrass Music Highway
From Owensboro's Bluegrass Music Hall of Fame to Renfro Valley and the eastern Kentucky hill towns — the birthplace of Bill Monroe and the sound that named a state.
Step back at Shaker Village
Pleasant Hill near Harrodsburg — the largest restored Shaker community in America, with 34 original 19th-century buildings, working farm, trails and a country inn.
Discover Cumberland Falls
The 'Niagara of the South' in southeastern Kentucky — one of the few places on earth to see a regular moonbow on clear full-moon nights.
Sample the Kentucky food scene
Hot Brown sandwiches, burgoo, country ham, beer cheese and bourbon-barrel everything — try Proof on Main in Louisville and Holly Hill Inn near Lexington.
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