5 days in Kentucky Itinerary

5 days in Kentucky Itinerary

Created using Inspirock Kentucky tour planner

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Route & dates

5 days in Kentucky Itinerary

Start: New York City
Fly:  4​h 30​min
1
Frankfort
— 2 nights
Drive:  1​h
2
Louisville
— 1 night
Drive:  1​h 30​min
3
Lexington
— 1 night
Fly:  4​h 15​min
End: New York City

2
nights
Frankfort

Frankfort ©
Frankfort is the capital city of the Commonwealth of Kentucky and the seat of Franklin County. You've now added Kentucky Bourbon Trail to your itinerary. Your inner history buff will appreciate Shaker Village of Pleasant Hill and Lanier Mansion State Historic Site. Step off the beaten path and head to Historic District and Barton 1792 Distillery. Take a break from Frankfort with a short trip to Willett Distilling Company in Bardstown, about 1h 05 min away. There's more to do: brush up on your knowledge of spirits at Buffalo Trace Distillery.

Before you visit Frankfort, use our trip planner to discover what you can do and see there.

New York City to Frankfort is an approximately 4.5-hour flight. You can also do a combination of bus and flight; or drive. Traveling from New York City in December, you can expect nighttime temperatures to be little chillier in Frankfort, with lows of 31°F. Wrap up your sightseeing on the 3rd (Tue) to allow time to drive to Louisville.

Things to do in Frankfort

Historic Sites Breweries & Distilleries

Side Trips

Madison, Bardstown, Kentucky Bourbon Trail, Shaker Village of Pleasant Hill
Highlights from your plan
Shaker Village of Pleasant Hill ©
Shaker Village of Pleasant Hill
Lanier Mansion State Historic Site ©
Barton 1792 Distillery ©
Barton 1792 Distillery

1
night
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
On the 4th (Wed), stroll the grounds of Cave Hill Cemetery, then see the interesting displays at Conrad-Caldwell House Museum (Conrad's Castle), then see the interesting displays at Frazier History Museum, and finally admire the masterpieces at 21c Museum Hotel.

For ratings, where to stay, other places to visit, and tourist information, refer to the Louisville visit website .

Traveling by car from Frankfort to Louisville takes an hour. Alternatively, you can take a bus. In December, daily temperatures in Louisville can reach 48°F, while at night they dip to 33°F. Finish your sightseeing early on the 4th (Wed) to allow enough time to drive to Lexington.

Things to do in Louisville

Museums Historic Sites Shopping
Highlights from your plan
Cave Hill Cemetery ©
Cave Hill Cemetery
Frazier History Museum ©
Frazier History Museum

1
night
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 5th (Thu), explore the different monuments and memorials at Lexington Cemetery, then indulge your thirst for a good beer at Lexington Brewing & Distilling Co., then explore the galleries of Mary Todd Lincoln House, and finally look for all kinds of wild species at Raven Run Nature Sanctuary.

To see traveler tips, where to stay, reviews, and tourist information, you can read our Lexington trip planner.

You can drive from Louisville to Lexington in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 48°F in December, and nighttime lows around 32°F. Wrap up your sightseeing on the 5th (Thu) to allow time to travel back home.

Things to do in Lexington

Historic Sites Wildlife Parks
Highlights from your plan
Mary Todd Lincoln House ©
Mary Todd Lincoln House
Lexington Cemetery ©
Lexington Cemetery
Raven Run Nature Sanctuary ©
Raven Run Nature Sanctuary

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