60 days in Kentucky Itinerary

60 days in Kentucky Itinerary

Created using Inspirock Kentucky trip maker
Make it your trip
Fly
1
Paducah
— 6 nights
Drive
2
Hopkinsville
— 6 nights
Drive
3
Bowling Green
— 8 nights
Drive
4
Louisville
— 18 nights
Drive
5
Lebanon
— 3 nights
Drive
6
Lexington
— 12 nights
Drive
7
Covington
— 6 nights
Drive to Cincinnati Northern Kentucky International Airport, Fly to Boston

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Paducah — 6 nights

Paducah is a home rule-class city in and the county seat of McCracken County, Kentucky, United States. Explore Paducah's surroundings by going to Kuttawa Harbor Marina (in Kuttawa), Ben E. Clement Mineral Museum (in Marion) and Kentucky Lake (in Gilbertsville). Next up on the itinerary: do a tasting at Purple Toad Winery, admire the masterpieces at The National Quilt Museum, pause for some serene contemplation at St. Francis de Sales Catholic Church, and stroll around Bob Noble Park.

To plan Paducah vacation without wasting time, ask Inspirock to design an itinerary.

Boston to Paducah is an approximately 7-hour flight. You can also fly; or drive; or take a bus. Traveling from Boston to Paducah, you'll gain 1 hour due to the time zone difference. While traveling from Boston, expect somewhat warmer days and about the same nights in Paducah, ranging from highs of 49°F to lows of 32°F. Wrap up your sightseeing on the 9th (Thu) early enough to drive to Hopkinsville.
Parks · Historic Sites · Museums · Wildlife
Side Trips

Hopkinsville — 6 nights

Hopkinsville is a home rule-class city in and the county seat of Christian County, Kentucky, United States. You'll find plenty of places to visit near Hopkinsville: Golden Pond (The Elk and Bison Prairie & Land Between the Lakes NRA, Golden Pond Visitor Center & Planetarium), Preservation Station Market And Event Center (in Owensboro) and Trover Wellness Park (in Madisonville). The adventure continues: sample the fine beverages at Casey Jones Distillery, look for gifts at Griffin's Studio, pause for some photo ops at Everly Brothers Monument, and stroll around Trail of Tears Commemorative Park and Heritage Center.

To find photos, where to stay, maps, and more tourist information, you can read our Hopkinsville trip planner.

You can drive from Paducah to Hopkinsville in 1.5 hours. In December, plan for daily highs up to 49°F, and evening lows to 33°F. Finish up your sightseeing early on the 15th (Wed) so you can go by car to Bowling Green.
Parks · Wildlife · Shopping · Breweries & Distilleries
Side Trips

Bowling Green — 8 nights

Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. You'll find plenty of places to visit near Bowling Green: Kentucky Down Under Adventure Zoo (in Horse Cave), Diamond Caverns (in Park City) and Mammoth Cave National Park (Green River, Echo River, &more). There's lots more to do: examine the collection at National Corvette Museum, steep yourself in history at Riverview at Hobson Grove, get engrossed in the history at South Union Shaker Village, and walk around Fountain Square Park.

To find maps and more tourist information, use the Bowling Green trip itinerary site.

Drive from Hopkinsville to Bowling Green in 1.5 hours. Expect a daytime high around 51°F in December, and nighttime lows around 33°F. Wrap up your sightseeing on the 23rd (Thu) to allow time to drive to Louisville.
Parks · Nature · Outdoors · Trails
Side Trips

Louisville — 18 nights

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
You'll find plenty of places to visit near Louisville: Bardstown (Lux Row Distillers, My Old Kentucky Home, &more), Elizabethtown (Freeman Lake Park, Swope's Cars of Yesteryear Museum, &more) and Clermont (Bernheim Arboretum & Forest & James B. Beam Distilling Co.). There's lots more to do: explore the fascinating underground world of Louisville Mega Cavern, learn insider's secrets on a distillery tour, snap pictures at The Big Four Bridge, and sample the fine beverages at Copper & Kings American Brandy Distillery.

To find ratings, traveler tips, where to stay, and tourist information, read Louisville trip itinerary builder app.

You can drive from Bowling Green to Louisville in 2 hours. Another option is to take a bus. You'll lose 1 hour traveling from Bowling Green to Louisville due to the time zone difference. In December in Louisville, expect temperatures between 48°F during the day and 33°F at night. Cap off your sightseeing on the 10th (Mon) early enough to go by car to Lebanon.
Breweries & Distilleries · Museums · Historic Sites · Parks
Side Trips

Lebanon — 3 nights

Lebanon is a home rule-class city in Marion County, Kentucky, in the United States. Change things up with these side-trips from Lebanon: Danville (Wilderness Trail Distillery & The Great American Dollhouse Museum), Abraham Lincoln Birthplace National Historical Park (in Hodgenville) and The Abbey of Gethsemani (in Trappist). Next up on the itinerary: sample the fine beverages at Limestone Branch Distillery and contemplate the long history of William Whitley House.

To find maps, where to stay, traveler tips, and tourist information, you can read our Lebanon trip itinerary builder site.

You can drive from Louisville to Lebanon in 1.5 hours. Expect a daytime high around 41°F in January, and nighttime lows around 23°F. Cap off your sightseeing on the 13th (Thu) early enough to go by car to Lexington.
Historic Sites · Breweries & Distilleries · Museums
Side Trips

Lexington — 12 nights

Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
You'll find plenty of places to visit near Lexington: Brush Arbor Appalachian Pioneer Homestead (in Renfro Valley), Ark Encounter (in Williamstown) and Frankfort (Castle & Key Distillery, Buffalo Trace Distillery, &more). There's still lots to do: indulge your thirst for a good beer at West Sixth Brewing, take a memorable drive along Old Frankfort Pike, indulge in some personalized pampering at some of the best spas, and brush up on your knowledge of spirits at James E. Pepper Distillery.

To find photos, where to stay, and more tourist information, read Lexington road trip planning website.

Drive from Lebanon to Lexington in 1.5 hours. In January, daily temperatures in Lexington can reach 41°F, while at night they dip to 24°F. Finish up your sightseeing early on the 25th (Tue) so you can travel to Covington.
Breweries & Distilleries · Parks · Museums · Outdoors
Side Trips

Covington — 6 nights

Covington is a city in Kenton County, Kentucky, located at the confluence of the Ohio and Licking Rivers. Get out of town with these interesting Covington side-trips: Dinsmore Homestead (in Burlington), EAT Gallery (in Maysville) and EarthJOY Tree Adventures (in Germantown). The adventure continues: sample the fine beverages at Boone County Distilling Co., snap pictures at Newport Southbank Bridge a.k.a. Purple People Bridge, buy something for everyone on your list at Newport on the Levee, and get outside with England idlewild park.

To see maps, where to stay, and more tourist information, you can read our Covington trip itinerary builder site.

Traveling by car from Lexington to Covington takes 1.5 hours. January in Covington sees daily highs of 39°F and lows of 22°F at night. Finish up your sightseeing early on the 31st (Mon) so you can travel back home.
Breweries & Distilleries · Outdoors · Shopping · Fun & Games
Side Trips

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.