29 days in Wisconsin Itinerary

29 days in Wisconsin Itinerary

Created using Inspirock Wisconsin trip itinerary builder

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Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Milwaukee
1
Milwaukee
— 5 nights
Drive
2
Sheboygan
— 4 nights
Drive
3
Sister Bay
— 2 nights
Drive
4
Green Bay
— 4 nights
Drive
5
Madison
— 4 nights
Drive
6
La Crosse
— 3 nights
Drive
7
Bayfield
— 5 nights
Drive to Duluth International Airport, Fly to Kosice

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Milwaukee

— 5 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Explore the numerous day-trip ideas around Milwaukee: Lake Geneva (Geneva Lake Shore Path & Geneva Lake) and Racine (SC Johnson Headquarters & Wingspread). There's still lots to do: examine the collection at Harley-Davidson Museum, learn about wildlife with up-close encounters at Milwaukee County Zoo, sample the tasty concoctions at Lakefront Brewery, and learn more about the world around you at Milwaukee Public Museum.

For more things to do, other places to visit, maps, and other tourist information, read our Milwaukee trip maker app.

Kosice, Slovakia to Milwaukee is an approximately 17-hour combination of flight and car. The time zone difference when traveling from Kosice to Milwaukee is minus 7 hours. Expect a bit warmer evenings in Milwaukee when traveling from Kosice in September, with lows around 17°C. Wrap up your sightseeing on the 19th (Sun) early enough to drive to Sheboygan.

Things to do in Milwaukee

Historic Sites · Museums · Parks · Shopping

Side Trips

Sheboygan

— 4 nights
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Venture out of the city with trips to Horicon Marsh (in Mayville), Two Rivers (Mariners Trail & Rawley Point Bike Trails & Neshotah Park) and Cedar Valley Cheese (in Belgium). And it doesn't end there: admire the natural beauty at Bookworm Gardens, immerse yourself in nature at Fischer Creek State Recreation Area, tee off at Whistling Straits Golf Course - Straits and Irish, and join the crowd at Road America.

To see photos, maps, and more tourist information, use the Sheboygan road trip site.

Getting from Milwaukee to Sheboygan by car takes about an hour. Traveling from Milwaukee in September, Sheboygan is a bit cooler at night with lows of 12°C. Finish your sightseeing early on the 23rd (Thu) so you can travel to Sister Bay.

Things to do in Sheboygan

Parks · Nature · Outdoors · Museums

Side Trips

Sister Bay

— 2 nights
Sister Bay is a village in Door County, Wisconsin, United States. Kick off your visit on the 24th (Fri): take in the exciting artwork at Plum Bottom Gallery, then stop by Wood Orchard, then take in the exciting artwork at Edgewood Orchard Galleries, and finally admire the majestic nature at Peninsula State Park. Get ready for a full day of sightseeing on the 25th (Sat): learn about winemaking at Stone's Throw Winery, enjoy the sea views from Cana Island Lighthouse, then don't miss a visit to George Burr Gallery, and finally get outside with Outdoor Activities.

To see traveler tips, maps, and more tourist information, you can read our Sister Bay trip tool.

Traveling by car from Sheboygan to Sister Bay takes 2.5 hours. September in Sister Bay sees daily highs of 24°C and lows of 12°C at night. Cap off your sightseeing on the 25th (Sat) early enough to go by car to Green Bay.

Things to do in Sister Bay

Shopping · Tours · Nature · Wineries

Side Trips

Green Bay

— 4 nights

Home of the Packers

Home of the Green Bay Packers, the city of Green Bay centers around sports and is home to hundreds of notable football icons, including Brett Favre and Curly Lambeau.
Change things up with these side-trips from Green Bay: EAA Aviation Museum (in Oshkosh) and Sturgeon Bay (The Farm, Cave Point County Park, &more). The adventure continues: examine the collection at Green Bay Packer Hall of Fame, identify plant and animal life at Bay Beach Wildlife Sanctuary, meet the residents at NEW Zoo & Adventure Park, and find something for the whole family at Bay Beach Amusement Park.

To find reviews, ratings, where to stay, and tourist information, you can read our Green Bay online holiday builder.

Traveling by car from Sister Bay to Green Bay takes 1.5 hours. Expect a daytime high around 27°C in September, and nighttime lows around 13°C. Finish up your sightseeing early on the 29th (Wed) so you can go by car to Madison.

Things to do in Green Bay

Parks · Museums · Outdoors · Zoos & Aquariums

Side Trips

Madison

— 4 nights

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Change things up with these side-trips from Madison: Wisconsin River (in Sauk City), Baraboo (Baraboo Riverwalk, Devil's Lake State Park, &more) and Spring Green (The House on the Rock & Taliesin Preservation: Frank Lloyd Wright Visitor Center ). Next up on the itinerary: admire the natural beauty at Olbrich Botanical Gardens, kick your exploration up a notch at some of the top local zipline courses and adventure parks, make a trip to Memorial Union Terrace, and get a sense of history and politics at Wisconsin State Capitol.

To find other places to visit, traveler tips, photos, and tourist information, use the Madison road trip planning site.

You can drive from Green Bay to Madison in 2.5 hours. Alternatively, you can take a bus; or fly. In September, daytime highs in Madison are 28°C, while nighttime lows are 13°C. Cap off your sightseeing on the 3rd (Sun) early enough to go by car to La Crosse.

Things to do in Madison

Parks · Tours · Nature · Outdoors

Side Trips

La Crosse

— 3 nights
La Crosse is a city in the U.S. state of Wisconsin and the county seat of La Crosse County. Venture out of the city with trips to Elroy-Sparta State Trail (in Elroy) and Alma (Lock and Dam 4 & Buena Vista Park). And it doesn't end there: explore the striking landscape at Grandad Bluff, take in the spiritual surroundings of Franciscan Sisters of Perpetual Adoration Motherhouse, pause for some serene contemplation at Shrine of Our Lady of Guadalupe, and stroll around Riverside Park.

To see where to stay, other places to visit, ratings, and other tourist information, go to the La Crosse road trip site.

Traveling by car from Madison to La Crosse takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. October in La Crosse sees daily highs of 20°C and lows of 7°C at night. Wrap up your sightseeing on the 6th (Wed) to allow time to drive to Bayfield.

Things to do in La Crosse

Parks · Historic Sites · Trails · Outdoors

Side Trips

Bayfield

— 5 nights
Bayfield is a city in Bayfield County, Wisconsin, United States. Venture out of the city with trips to ABC Raceway (in Ashland), Copper Falls State Park (in Mellen) and Potato River Falls (in Hurley). The adventure continues: Head underground at Apostle Islands National Lakeshore Ice Caves, take an in-depth tour of Bayfield Maritime Museum, look for all kinds of wild species at Houghton Falls Nature Preserve, and take a peaceful walk through Apostle Islands National Lakeshore.

To find reviews, traveler tips, maps, and more tourist information, go to the Bayfield online itinerary planner.

Traveling by car from La Crosse to Bayfield takes 5.5 hours. Alternatively, you can do a combination of bus, flight, and car; or do a combination of train, bus, and taxi. Traveling from La Crosse in October, expect Bayfield to be a bit cooler, temps between 16°C and 3°C. Finish your sightseeing early on the 11th (Mon) so you can travel back home.

Things to do in Bayfield

Parks · Nature · Outdoors · Trails

Side Trips

Wisconsin travel guide

4.2
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.