15 days in Kentucky & Wisconsin Itinerary

15 days in Kentucky & Wisconsin Itinerary

Created using Inspirock United States holiday planner

Make it your trip
— 3 nights
Bowling Green
— 2 nights
— 4 nights
Fly to La Crosse, Train to Wisconsin Dells
Wisconsin Dells
— 3 nights
— 2 nights



— 3 nights

Horse Capital of the World

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: Frankfort (Daniel Boone's Grave & Buffalo Trace Distillery), Versailles (Sun Valley Farm & Woodford Reserve Distillery) and Ark Encounter (in Williamstown). The adventure continues: explore the galleries of Kentucky Horse Park, look for all kinds of wild species at Coolmore America - Ashford Stud, sample the fine beverages at James E. Pepper Distillery, and indulge your thirst for a good beer at Lexington Brewing & Distilling Co..

For reviews, ratings, maps, and other tourist information, go to the Lexington attractions planner.

New York City to Lexington is an approximately 4-hour flight. You can also drive; or take a bus. When traveling from New York City in March, plan for somewhat warmer days and about the same nights in Lexington: temperatures range from 55°F by day to 34°F at night. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Bowling Green.

Things to do in Lexington

Museums · Parks · Breweries & Distilleries · Fun & Games

Side Trips

Bowling Green

— 2 nights
Bowling Green is a home rule-class city in and the county seat of Warren County, Kentucky, United States. On the 16th (Wed), take in the dramatic natural features at Lost River Cave, see the interesting displays at National Corvette Museum, and then explore the activities along Green River. Here are some ideas for day two: tour the pleasant surroundings at Fat Man's Misery, then explore the fascinating underground world of Mammoth Cave, and then tour the pleasant surroundings at Cedar Sink Trail.

For maps, where to stay, more things to do, and other tourist information, use the Bowling Green visit website.

Traveling by car from Lexington to Bowling Green takes 3 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Lexington to Bowling Green. In March, plan for daily highs up to 58°F, and evening lows to 37°F. Finish your sightseeing early on the 17th (Thu) to allow enough time to drive to Louisville.

Things to do in Bowling Green

Parks · Nature · Trails · Outdoors

Side Trip


— 4 nights

Derby City

Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Step out of Louisville to go to Loretto and see Maker's Mark, which is approximately 1h 10 min away. There's lots more to do: explore the fascinating underground world of Louisville Mega Cavern, sample the fine beverages at Copper & Kings American Brandy Distillery, steep yourself in history at Conrad-Caldwell House Museum (Conrad's Castle), and try your luck at Churchill Downs.

To see ratings, photos, more things to do, and more tourist information, refer to the Louisville trip planning app.

Traveling by car from Bowling Green to Louisville takes 2 hours. Alternatively, you can take a bus. Traveling from Bowling Green to Louisville, you'll lose 1 hour due to the time zone difference. In March, plan for daily highs up to 55°F, and evening lows to 36°F. Wrap up your sightseeing on the 21st (Mon) to allow time to travel to Wisconsin Dells.

Things to do in Louisville

Breweries & Distilleries · Museums · Historic Sites · Tours

Side Trips

Wisconsin Dells

— 3 nights

Waterpark Capital of the World

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Venture out of the city with trips to Madison (Olbrich Botanical Gardens, Wisconsin State Capitol, &more). The adventure continues: get engrossed in the history at Portage WWII History Museum, get to know the resident critters at Wisconsin Deer Park, do a tasting at Von Klaus Winery, and get interesting insight from Tours.

Plan my day in Wisconsin Dells using traveler tips and tourist information provided by Inspirock.

Traveling by combination of flight and train from Louisville to Wisconsin Dells takes 8 hours. Alternatively, you can drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 1 hour traveling from Louisville to Wisconsin Dells. Prepare for a bit cooler weather when traveling from Louisville in March: high temperatures in Wisconsin Dells hover around 40°F and lows are around 22°F. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Milwaukee.

Things to do in Wisconsin Dells

Parks · Outdoors · Museums · Adventure

Side Trips


— 2 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Start off your visit on the 25th (Fri): make a trip to Black Cat Alley, then admire the masterpieces at Milwaukee Art Museum, then admire the landmark architecture of Basilica of St. Josaphat, and finally sample the fine beverages at Great Lakes Distillery. Here are some ideas for day two: examine the collection at Harley-Davidson Museum, examine the collection at Chudnow Museum of Yesteryear, and then indulge your thirst for a good beer at Lakefront Brewery.

To see ratings, other places to visit, traveler tips, and more tourist information, read our Milwaukee trip planning app.

You can drive from Wisconsin Dells to Milwaukee in 2.5 hours. Other options are to take a train; or do a combination of train and bus. In March, plan for daily highs up to 41°F, and evening lows to 27°F. Cap off your sightseeing on the 26th (Sat) early enough to catch the flight back home.

Things to do in Milwaukee

Museums · Breweries & Distilleries · Historic Sites · Shopping

Kentucky travel guide

Caves · Specialty Museums · Distilleries
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.

Wisconsin travel guide

Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.