Kentucky
5
Day Itinerary •
USA
Five days in Kentucky lets you explore the full extraordinary breadth of the Bluegrass State, from the finest bourbon distilleries on earth and the magnificent Thoroughbred horse farms of the Bluegrass to the longest cave system in the world at Mammoth Cave, the extraordinary Red River Gorge and the remarkable Cumberland Falls. This route covers the complete Kentucky experience. The extraordinary Maker's Mark and Buffalo Trace distilleries, the Keeneland morning workouts and Kentucky Horse Park, the magnificent Mammoth Cave National Park, the extraordinary Red River Gorge arches and the remarkable Daniel Boone country of eastern Kentucky.
Best Time To Visit
April to June or September to November
Getting There
Fly into Louisville (SDF) or Lexington (LEX)
Getting Around
Rental car essential throughout Kentucky
Budget Per Day
Approx $100 to $170 per person per day
Difficulity
Easy to moderate, some cave and gorge hiking
DAY 1
KENTUCKY BOURBON TRAIL
MORNING
MAKER'S MARK AND BARDSTOWN BOURBON TRAIL
Maker's Mark Distillery in Loretto is the most extraordinary bourbon distillery setting in Kentucky, its extraordinary red-shuttered black buildings beside Hardin's Creek and the remarkable hand-dipped wax bottle experience giving the finest distillery visit on the Trail. Bardstown, the Bourbon Capital of the World, gives the finest historic bourbon town experience in Kentucky with the Heaven Hill Bourbon Experience, the Oscar Getz Museum of Whiskey History and the extraordinary Old Talbott Tavern since 1779. Maker's Mark approx $16. Drive: 1 hr drive
MIDDAY
BUFFALO TRACE AND WILD TURKEY DISTILLERIES
Buffalo Trace in Frankfort is the most historic distillery in America, continuously operating since 1792 and home of the legendary Pappy Van Winkle and Blanton's Single Barrel bourbons. The extraordinary free tour gives the finest distillery experience on the Trail. Wild Turkey nearby, with master distillers Jimmy and Eddie Russell, gives the most extraordinary father-son distilling legacy in bourbon history. The Wild Turkey visitor center above the Kentucky River is extraordinary. Buffalo Trace free, Wild Turkey approx $15. Drive: 45 min drive
AFTERNOON
LOUISVILLE, THE MOST EXTRAORDINARY BOURBON CITY
Louisville is the most extraordinary bourbon city in Kentucky, its extraordinary NuLu neighborhood of independent restaurants and bars, the remarkable Louisville Slugger Museum and the Evan Williams Bourbon Experience on Whiskey Row giving the finest urban bourbon experience in the state. The Kentucky Derby Museum at Churchill Downs is the finest horse racing museum in America. The Great Lawn at Louisville Waterfront Park gives the finest Ohio River view in the city. Slugger Museum free.
💎 HIDDEN GEM
The extraordinary Evan Williams Bourbon Experience on Louisville's Whiskey Row is the finest urban bourbon distillery tour in Kentucky, its extraordinary recreation of the original 1783 Evan Williams distillery on the Ohio River giving the most extraordinary immersive bourbon history experience in Louisville. Entry approx $16. The finest hidden bourbon gem in Louisville.
🍽 WHERE TO EAT
Breakfast: Old Talbott Tavern, Bardstown The most legendary tavern in Kentucky since 1779. Extraordinary Kentucky country breakfast. | Lunch: Kurtz Restaurant, Bardstown The finest Kentucky home cooking since 1937. Extraordinary burgoo stew and hot brown sandwich. | Dinner: Proof on Main, Louisville The finest restaurant in Louisville. Extraordinary local Kentucky produce and outstanding bourbon.
DAY 2
BLUEGRASS HORSE COUNTRY
MORNING
KEENELAND RACE COURSE MORNING WORKOUTS AND HORSE FARMS
Keeneland Race Course in Lexington offers the most extraordinary free morning horse experience in America, its extraordinary morning workouts from 6am to 10am during training season giving access to Thoroughbred horses training on one of the finest racecourses in the world. The surrounding Bluegrass horse farm landscape of white plank fences, limestone walls and rolling pastures dotted with horse barns is the most extraordinary rural landscape in America. Workouts free. Drive: 1.5 hr drive
MIDDAY
KENTUCKY HORSE PARK AND INTERNATIONAL MUSEUM OF THE HORSE
The Kentucky Horse Park is the most extraordinary equine attraction in the world, its extraordinary 1,200-acre working horse farm containing over 50 breeds, the International Museum of the Horse, the graves of Man o' War and other legendary champions and the extraordinary Hall of Champions parade of retired Thoroughbreds giving the finest horse culture experience in the Bluegrass. Entry approx $20. Drive: 20 min drive
AFTERNOON
LEXINGTON DOWNTOWN AND THE DISTILLERY DISTRICT
Lexington's extraordinary Distillery District gives the finest craft spirits experience in the Bluegrass, its extraordinary cluster of urban craft distilleries including Barrel House Distilling, Town Branch Bourbon and the remarkable James E. Pepper Distillery, resurrected in a 19th-century stone distillery building, giving the finest new wave Kentucky bourbon experience. The extraordinary Thoroughbred Center training facility morning tours are unmissable. Town Branch approx $12.
💎 HIDDEN GEM
The extraordinary Headley-Whitney Museum in Lexington is the finest hidden cultural gem in Kentucky, its extraordinary jeweled bibelots and the remarkable shell grotto created by George Headley giving the most extraordinary small private museum experience in the Bluegrass. Entry approx $8. Almost entirely unknown to visitors on the Bourbon Trail.
🍽 WHERE TO EAT
Breakfast: Winchell's, Lexington The finest diner breakfast in Lexington. Extraordinary local Kentucky eggs and strong coffee. | Lunch: Parkette Drive-In, Lexington The most legendary drive-in in Lexington since 1951. Extraordinary Kentucky burgoo and local beef burger. | Dinner: Jonathan at Gratz Park, Lexington The finest restaurant in Lexington. Extraordinary local Kentucky produce in a historic inn.
DAY 3
MAMMOTH CAVE NATIONAL PARK
MORNING
MAMMOTH CAVE NATIONAL PARK, THE LONGEST CAVE SYSTEM ON EARTH
Mammoth Cave National Park contains the longest known cave system on earth at over 420 miles of mapped passages, its extraordinary formations of gypsum flowers, flowstone, stalactites and stalagmites in a labyrinthine network beneath the Kentucky knobs giving the finest cave experience in America. The Historic Tour gives the most extraordinary 2-hour guided experience through the Grand Avenue, Mammoth Dome and the Bottomless Pit. The cave maintains a constant 54 degrees year-round. Entry approx $15. Drive: 1.5 hr drive
MIDDAY
GREEN RIVER CANOE TRAIL AND MAMMOTH CAVE WILDERNESS
The Green River through Mammoth Cave National Park is the most extraordinary river paddling experience in Kentucky, its extraordinary 25-mile canoe trail through the park wilderness past the cave entrances, limestone bluffs and old-growth forest giving the finest waterway experience in the Bluegrass State. The River Styx Spring where the cave's underground rivers emerge into the Green River is extraordinary. Canoe rentals from Green River Canoeing approx $35. Drive: 30 min walk
AFTERNOON
MAMMOTH CAVE HOTEL PORCH AND SUNSET IN THE KNOBS
The Mammoth Cave Hotel veranda at sunset gives the most extraordinary evening in Mammoth Cave National Park, its extraordinary views over the Kentucky knobs landscape surrounding the park from the oldest national park hotel porch in the eastern United States giving the finest end to a day underground. The park's extraordinary darkness at night gives extraordinary stargazing above the cave system. Hotel dining room and porch free to visit.
💎 HIDDEN GEM
The extraordinary Frozen Niagara section of Mammoth Cave gives the most extraordinary cave formation experience in the park, its extraordinary flowstone cascade of calcite resembling a frozen waterfall in the finest short cave tour in the system. Entry approx $8. The Frozen Niagara Tour is 75 minutes and far less crowded than the Historic Tour.
🍽 WHERE TO EAT
Breakfast: Mammoth Cave Hotel dining room Extraordinary cave country breakfast before the Historic Tour. Local Kentucky eggs and strong coffee. | Lunch: Picnic at Green River Pack lunch from the hotel. The extraordinary Green River bank picnic in the park wilderness. | Dinner: Mammoth Cave Hotel dining room The finest dining near the cave. Local Kentucky cuisine with extraordinary knobs landscape views.
DAY 4
RED RIVER GORGE
MORNING
RED RIVER GORGE NATURAL BRIDGE AND CATHEDRAL ARCH COUNTRY
Red River Gorge Geological Area contains the most extraordinary concentration of natural arches in the eastern United States, its 100-plus sandstone arches in the Daniel Boone National Forest giving a landscape entirely unlike the rest of Kentucky. The Natural Bridge at 78 feet long and 65 feet high is the finest arch. The extraordinary Chimney Top Rock trail at 1.8 miles gives the finest canyon panorama. The Nada Tunnel, a 900-foot one-lane railroad tunnel, is the most extraordinary road experience in Kentucky. All free. Drive: 1.5 hr drive
MIDDAY
INDIAN ARCH AND THE ROCK BRIDGE TRAIL
Indian Arch is the most extraordinary rock shelter in Red River Gorge, its extraordinary 90-foot curved sandstone overhang forming a natural amphitheater in the finest example of the Gorge's geological diversity. The Rock Bridge Trail gives the most extraordinary 0.6-mile loop past a natural arch over Swift Camp Creek. The extraordinary Rough Trail gives the finest ridge walk in the Gorge through old-growth forest. All free in Daniel Boone National Forest. Drive: 20 min drive
AFTERNOON
SKY BRIDGE AND THE PRINCESS ARCH
Sky Bridge is the most extraordinary accessible arch in Red River Gorge, its extraordinary 90-foot sandstone span crossing a ravine with the Gorge landscape visible through the arch opening on a 0.9-mile loop trail. Princess Arch nearby is the most beautiful arch in the Gorge, its extraordinary smooth sandstone curves framing a perfect oval window through the rock. The Auxier Ridge trail gives the finest elevated view of the Gorge. All free.
💎 HIDDEN GEM
The extraordinary Courthouse Rock in Red River Gorge is the finest hidden viewpoint in the area, its extraordinary freestanding sandstone tower accessible by a short scramble giving a 360-degree Gorge view entirely unknown to visitors on the main trails. Free. The most extraordinary hidden gem in the Red River Gorge.
🍽 WHERE TO EAT
Breakfast: Miguel's Pizza, Slade The most legendary climbing cafe in Kentucky. Extraordinary wood-fired pizza and strong coffee. | Lunch: Miguel's Pizza Outstanding wood-fired pizza in the finest outdoor setting near Red River Gorge. | Dinner: Natural Bridge State Resort Park dining room The finest dining near the Gorge. Local Kentucky cuisine with extraordinary forest views.
DAY 5
CUMBERLAND FALLS AND EASTERN KENTUCKY
MORNING
CUMBERLAND FALLS, THE NIAGARA OF THE SOUTH
Cumberland Falls is the most extraordinary waterfall in Kentucky, its extraordinary 125-foot-wide curtain of the Cumberland River plunging 68 feet into a mist-filled gorge giving the finest waterfall experience in the eastern United States. Cumberland Falls is one of only two places on earth where a moonbow, a rainbow created by moonlight, appears regularly on clear nights around the full moon. The extraordinary State Resort Park surrounding the falls gives the finest lodge in eastern Kentucky. Entry free. Drive: 1.5 hr drive
MIDDAY
CUMBERLAND GAP NATIONAL HISTORICAL PARK
Cumberland Gap is the most extraordinary historic mountain pass in America, the natural gap in the Cumberland Mountains through which Daniel Boone led the Wilderness Road expedition in 1775 opening the way west for hundreds of thousands of settlers. The extraordinary Pinnacle Overlook at 2,440 feet gives the finest three-state view of Kentucky, Virginia and Tennessee in any national park. The Gap itself is the most important geographic feature in the history of American westward expansion. Entry free. Drive: 45 min drive
AFTERNOON
MIDDLESBORO AND THE KENTUCKY APPALACHIANS
Middlesboro is the most extraordinary small city in eastern Kentucky, the only city in America built inside a meteor impact crater, its extraordinary circular street plan following the 300-million-year-old impact structure. The surrounding Pine Mountain State Resort Park gives the finest ridge hiking in eastern Kentucky, its extraordinary Chained Rock above Pineville attached to the cliff by an enormous chain placed in 1933 to reassure townspeople the rock would not fall. Park entry free.
💎 HIDDEN GEM
The extraordinary Cumberland Falls moonbow is the most extraordinary natural optical phenomenon in North America, its extraordinary lunar rainbow appearing in the mist of the falls on clear nights around the full moon in one of only two such reliable moonbow locations on earth. Free with park entry. Check moon phase calendar before visiting. The most extraordinary hidden natural wonder in Kentucky.
🍽 WHERE TO EAT
Breakfast: Cumberland Falls State Resort dining room Extraordinary breakfast at the finest state resort in eastern Kentucky before the falls walk. | Lunch: Cumberland Falls park cafe Outstanding casual lunch beside the Niagara of the South. Local Kentucky ingredients. | Dinner: Ol'Barn Restaurant, Corbin The finest restaurant in Corbin. The original Harland Sanders Cafe where KFC was born is next door.
Where To Stay
Bardstown or Louisville, Night 1 Old Talbott Tavern or 21c Museum Hotel Louisville. Approx $100 to $220. Lexington or Mammoth Cave, Nights 2 to 3 21c Lexington or Mammoth Cave Hotel. Approx $100 to $200 per night. Slade or Corbin, Nights 4 to 5 Natural Bridge State Resort or Cumberland Falls State Resort. Approx $90 to $160.
Top Tips
1. Book Mammoth Cave Historic Tour at recreation.gov weeks ahead. The cave is a constant 54 degrees year-round.
2. Cumberland Falls moonbow: one of only two places on earth with a regular moonbow. Check moon phases before going.
3. Keeneland morning workouts are free from 6 to 10am during training season. The finest free horse experience.
4. Bourbon Trail passport: collect stamps at 18 distilleries for the official certificate. Free to collect.
5. Red River Gorge rock climbing is the finest in the eastern US. Miguel's Pizza in Slade has a gear rental board.
6. Louisville's NuLu neighborhood has the finest independent restaurants in Kentucky. The Louisville Slugger Museum is free.
Total Budget
$100 to $170/day