5 days in Kentucky Itinerary

5 days in Kentucky Itinerary

Created using Inspirock Kentucky trip planner

This plan was created by another user. Make it your plan

Route & dates

5 days in Kentucky Itinerary

Start: Chicago
Fly:  3​h 30​min
1
Paducah
— Few hours
Drive:  3​h 45​min
2
Louisville
— 2 nights
Drive:  1​h 30​min
3
Lexington
— 2 nights
Fly:  3​h 15​min
End: Chicago

few
hours
Paducah

Paducah ©
Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Start off your visit on the 3rd (Sat): learn about winemaking at Purple Toad Winery and then take a leisurely stroll along Paducah Riverwalk.

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

Chicago to Paducah is an approximately 3.5-hour flight. You can also do a combination of flight and car; or drive. Expect a daytime high around 87°F in August, and nighttime lows around 67°F. Finish your sightseeing early on the 3rd (Sat) so you can drive to Louisville.

Things to do in Paducah

Historic Sites Wineries
Highlights from your plan
Purple Toad Winery ©
Purple Toad Winery
Paducah Riverwalk ©
Paducah Riverwalk

2
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Kick off your visit on the 4th (Sun): explore the world behind art at 21c Museum Hotel, sample the fine beverages at The Bulleit Frontier Whiskey Experience at Stitzel-Weller, examine the collection at Conrad-Caldwell House Museum (Conrad's Castle), then contemplate the long history of Locust Grove, and finally sample the fine beverages at Copper & Kings American Brandy Distillery. Get ready for a full day of sightseeing on the 5th (Mon): brush up on your knowledge of spirits at Kentucky Peerless Distilling Co, contemplate the long history of My Old Kentucky Home, then sample the fine beverages at Barton 1792 Distillery, and finally wander the streets of Old Louisville.

For photos, other places to visit, more things to do, and other tourist information, read our Louisville trip planner .

Traveling by car from Paducah to Louisville takes 4 hours. Alternatively, you can fly; or take a bus. You'll lose 1 hour traveling from Paducah to Louisville due to the time zone difference. In August, plan for daily highs up to 86°F, and evening lows to 68°F. Cap off your sightseeing on the 5th (Mon) early enough to go by car to Lexington.

Things to do in Louisville

Historic Sites Breweries & Distilleries Museums

Side Trip

Bardstown
Highlights from your plan
Historic Locust Grove ©
Historic Locust Grove
Barton 1792 Distillery ©
Barton 1792 Distillery

2
nights
Lexington

Lexington ©
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
On the 6th (Tue), take in nature's colorful creations at Ashland: The Henry Clay Estate, relax in the rural setting at Old Friends at Dream Chase Farm, then explore the different monuments and memorials at Lexington Cemetery, then sample the fine beverages at Bluegrass Distillers, and finally sample the tasty concoctions at West Sixth Brewing. Here are some ideas for day two: sample the fine beverages at Barrel House Distillery, brush up on your knowledge of spirits at Four Roses Bourbon - Warehouse and Bottling Facility, then steep yourself in history at Old Fort Harrod State Park, then take in the exciting artwork at Kentucky Artisan Center at Berea, and finally look for gifts at Tater Knob Pottery and Farm.

For photos, maps, more things to do, and more tourist information, refer to the Lexington route planning website .

You can drive from Louisville to Lexington in 1.5 hours. Alternatively, you can take a bus. August in Lexington sees daily highs of 85°F and lows of 65°F at night. Cap off your sightseeing on the 7th (Wed) early enough to travel back home.

Things to do in Lexington

Historic Sites Breweries & Distilleries Shopping

Side Trips

Berea, Old Friends at Dream Chase Farm, Four Roses Bourbon - Warehouse and Bottling Facility, Old Fort Harrod State Park
Highlights from your plan
Old Fort Harrod State Park ©
Old Fort Harrod State Park
Tater Knob Pottery and Farm ©
Tater Knob Pottery and Farm
Lexington Cemetery ©
Lexington Cemetery

Similar Plans

6 days in Kentucky BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, beaches, historic sites, wildlife, popular sights PREFERENCES: July, teens, kids, culture, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 8 days in United States BY A USER FROM PHILIPPINES July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, teens, kids, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Kentucky BY A USER FROM UNITED STATES July, outdoors, relaxing, historic sites, museums, wildlife, slow & easy, popular sights PREFERENCES: July, outdoors, relaxing, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 8 days in Kentucky BY A USER FROM CANADA August, kids, outdoors, historic sites, museums, popular sights PREFERENCES: August, kids, outdoors, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Kentucky BY A USER FROM CANADA August, kids, relaxing, historic sites, museums, wildlife, slow & easy, popular & hidden gems PREFERENCES: August, kids, relaxing, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 8 days in Kentucky BY A USER FROM UNITED STATES October, teens, outdoors, historic sites, museums, popular sights PREFERENCES: October, teens, outdoors, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Kentucky BY A USER FROM UNITED STATES August, historic sites, museums, slow & easy, popular sights PREFERENCES: August, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Slow & easy 6 days in Kentucky BY A USER FROM UNITED STATES August, culture, relaxing, historic sites, museums, slow & easy, popular sights PREFERENCES: August, culture, relaxing, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Slow & easy 8 days in Kentucky & Dayton BY A USER FROM UNITED STATES June, kids, historic sites, museums, popular & hidden gems PREFERENCES: June, kids, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 6 days in Kentucky BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 6 days in Indianapolis, Kentucky & Cave in Rock BY A USER FROM UNITED STATES August, outdoors, relaxing, romantic, historic sites, wildlife, popular & hidden gems PREFERENCES: August, outdoors, relaxing, romantic, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 4 days in Kentucky BY A USER FROM UNITED STATES August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife, popular sights PREFERENCES: August, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans