21 days in Kentucky Itinerary

Created using Klarna Trips Kentucky journey planner
Make it your trip
Fly
1
Lexington
— 4 nights
Drive
2
Petersburg
— 1 night
Drive
3
Louisville
— 6 nights
Drive
4
Loretto
— 1 night
Drive
5
Owensboro
— 4 nights
Drive
6
Mammoth Cave National Park
— 4 nights
Fly

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Lexington — 4 nights

Horse Capital of the World

Get out of town with these interesting Lexington side-trips: Boone County Distilling Co. (in Independence), Ark Encounter (in Williamstown) and Frankfort (Kentucky River Tours, Buffalo Trace Distillery, &more). There's lots more to do: try to win big at Keeneland, immerse yourself in nature at Kentucky Horse Park, relax in the rural setting at Old Friends at Dream Chase Farm, and sample the fine beverages at James E. Pepper Distillery.

For where to stay, reviews, traveler tips, and other tourist information, read our Lexington trip itinerary maker website.

Atlanta to Lexington is an approximately 3-hour flight. You can also drive; or take a bus. Plan for a bit cooler nights when traveling from Atlanta in May since evenings lows in Lexington dip to 55°F. Cap off your sightseeing on the 27th (Sat) early enough to go by car to Petersburg.
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Side Trips
Find places to stay May 23 — 27:

Petersburg — 1 night

On the 28th (Sun), walk around England Idlewild Park, get a new perspective on nature at Creation Museum, and then get to know the fascinating history of Dinsmore Homestead.

For traveler tips, more things to do, where to stay, and more tourist information, go to the Petersburg day trip planning site.

You can drive from Lexington to Petersburg in 2 hours. In May, daytime highs in Petersburg are 75°F, while nighttime lows are 54°F. Finish your sightseeing early on the 28th (Sun) so you can drive to Louisville.
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Parks · Museums · Historic Sites
Side Trip
Find places to stay May 27 — 28:

Louisville — 6 nights

Derby City

Get out of town with these interesting Louisville side-trips: Lux Row Distillers (in Bardstown) and Elizabethtown (Swope's Cars of Yesteryear Museum & Freeman Lake Park). There's still lots to do: gain some tasty knowledge on a distillery tour, examine the collection at Muhammad Ali Center, snap pictures at The Big Four Bridge, and brush up on your knowledge of spirits at Kentucky Artisan Distillery.

To find maps, ratings, other places to visit, and more tourist information, go to the Louisville trip itinerary planning app.

Traveling by car from Petersburg to Louisville takes 2 hours. In May, daytime highs in Louisville are 77°F, while nighttime lows are 58°F. Finish up your sightseeing early on the 3rd (Sat) so you can go by car to Loretto.
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Side Trips
Find places to stay May 28 — Jun 3:

Loretto — 1 night

Start off your visit on the 4th (Sun): take in the spiritual surroundings of The Abbey of Gethsemani, sample the fine beverages at Maker's Mark, then sample the fine beverages at Limestone Branch Distillery, and finally learn about winemaking at Jesters Winery & Cafe.

To find more things to do, traveler tips, and more tourist information, go to the Loretto online trip itinerary maker.

Traveling by car from Louisville to Loretto takes 1.5 hours. Alternatively, you can drive. Traveling from Louisville in June, plan for a bit cooler nights in Loretto, with lows around 61°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Owensboro.
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Breweries & Distilleries · Historic Sites · Wineries
Side Trips
Find places to stay Jun 3 — 4:

Owensboro — 4 nights

Venture out of the city with trips to Paducah (Floodwall Murals, The National Quilt Museum, &more), Bowling Green (NCM Motorsports Park, National Corvette Museum, &more) and John James Audubon Museum (in Henderson).

For traveler tips, more things to do, reviews, and more tourist information, you can read our Owensboro attractions site.

Use the Route module to find suitable travel options from Loretto to Owensboro. Due to the time zone difference, you'll gain 1 hour traveling from Loretto to Owensboro. Traveling from Loretto in June, plan for a bit warmer nights in Owensboro, with lows around 67°F. Finish your sightseeing early on the 8th (Thu) so you can drive to Mammoth Cave National Park.
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Parks · Museums · Nature · Breweries & Distilleries
Side Trips
Find places to stay Jun 4 — 8:

Mammoth Cave National Park — 4 nights

Change things up with a short trip to Nolin Lake State Park in Mammoth Cave (about 36 minutes away). And it doesn't end there: explore the fascinating underground world of Mammoth Cave, explore the activities along Dog Creek Recreation Area, meet the residents at Kentucky Down Under Adventure Zoo, and get a dose of the wild on a nature and wildlife tour.

To find ratings, photos, and other tourist information, read our Mammoth Cave National Park day trip site.

Getting from Owensboro to Mammoth Cave National Park by car takes about 2 hours. June in Mammoth Cave National Park sees daily highs of 84°F and lows of 64°F at night. Wrap up your sightseeing on the 12th (Mon) to allow time to fly back home.
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Parks · Nature · Outdoors · Trails
Side Trips
Find places to stay Jun 8 — 12:

Kentucky travel guide

4.6
Caves · Distilleries · Specialty Museums
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.
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