31 days in Wisconsin Itinerary

31 days in Wisconsin Itinerary

Created using Inspirock Wisconsin travel route planner

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Make it your trip
Drive
1
Milwaukee
— 5 nights
Drive
2
Sheboygan
— 4 nights
Drive
3
Sister Bay
— 4 nights
Drive
4
Green Bay
— 4 nights
Drive
5
Bayfield
— 4 nights
Drive
6
La Crosse
— 4 nights
Drive
7
Madison
— 5 nights
Fly

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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.
Change things up with these side-trips from Milwaukee: Lake Geneva (Geneva Lake & Geneva Lake Shore Path). There's still lots to do: examine the collection at Harley-Davidson Museum, get a new perspective on nature at Milwaukee Public Museum, contemplate the long history of Pabst Mansion, and learn about wildlife with up-close encounters at Milwaukee County Zoo.

To find photos, traveler tips, ratings, and other tourist information, go to the Milwaukee trip builder tool.

Chicago to Milwaukee is an approximately 1.5-hour car ride. You can also take a train; or take a bus. In September, daily temperatures in Milwaukee can reach 74°F, while at night they dip to 58°F. Wrap up your sightseeing on the 9th (Thu) early enough to drive to Sheboygan.

Things to do in Milwaukee

Museums · Parks · Outdoors · Shopping

Side Trip

Sheboygan

— 4 nights
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Explore Sheboygan's surroundings by going to Horicon Marsh (in Mayville), Two Rivers (Mariners Trail & Rawley Point Bike Trails & Neshotah Park) and Wisconsin Maritime Museum (in Manitowoc). Next up on the itinerary: admire the natural beauty at Bookworm Gardens, immerse yourself in nature at Kohler-Andrae State Park, don't miss a visit to Walldogs, and play a few rounds at Whistling Straits Golf Course - Straits and Irish.

To see more things to do, maps, photos, and tourist information, you can read our Sheboygan trip itinerary maker tool.

Getting from Milwaukee to Sheboygan by car takes about an hour. Traveling from Milwaukee in September, plan for little chillier nights in Sheboygan, with lows around 51°F. Wrap up your sightseeing on the 13th (Mon) to allow time to travel to Sister Bay.

Things to do in Sheboygan

Parks · Outdoors · Nature · Museums

Side Trips

Sister Bay

— 4 nights
Sister Bay is a village in Door County, Wisconsin, United States. Sister Bay is known for shopping, adventure, and fun & games. Your trip includes some of its best attractions: get a new perspective on things with Boat Tours & Water Sports, take in the exciting artwork at Edgewood Orchard Galleries, sample the tasty concoctions at Door County Brewing, and visit a coastal fixture at Cana Island Lighthouse.

To see traveler tips, where to stay, other places to visit, and other tourist information, read Sister Bay vacation planning website.

You can drive from Sheboygan to Sister Bay in 2.5 hours. September in Sister Bay sees daily highs of 70°F and lows of 51°F at night. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Green Bay.

Things to do in Sister Bay

Parks · Nature · Shopping · Museums

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.
You'll find plenty of places to visit near Green Bay: Sturgeon Bay (The Farm, Cave Point County Park, &more). The adventure continues: examine the collection at Green Bay Packer Hall of Fame, get outside with Green Bay Bullfrogs Baseball, admire the natural beauty at Green Bay Botanical Garden, and stroll through Bay Beach Wildlife Sanctuary.

For where to stay, reviews, more things to do, and other tourist information, read our Green Bay trip builder site.

You can drive from Sister Bay to Green Bay in 1.5 hours. Expect a daytime high around 74°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 21st (Tue) so you can drive to Bayfield.

Things to do in Green Bay

Parks · Museums · Theme Parks · Outdoors

Side Trip

Bayfield

— 4 nights
Bayfield is a city in Bayfield County, Wisconsin, United States. Take a break from Bayfield with a short trip to Copper Falls State Park in Mellen, about 50 minutes away. And it doesn't end there: Head underground at Apostle Islands National Lakeshore Ice Caves, get outside with Outdoor Activities, hike along Meyers Beach Sea Caves, and take an in-depth tour of Bayfield Maritime Museum.

To find more things to do, maps, reviews, and tourist information, read Bayfield travel route planning site.

Traveling by car from Green Bay to Bayfield takes 6 hours. Alternatively, you can fly; or do a combination of bus and car. In September, daily temperatures in Bayfield can reach 71°F, while at night they dip to 48°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to La Crosse.

Things to do in Bayfield

Nature · Parks · Outdoors · Museums

Side Trips

La Crosse

— 4 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), Buena Vista Park (in Alma) and Chippewa Falls (Leinie Lodge & Jacob Leinenkugel Brewing Company). Next up on the itinerary: explore the striking landscape at Grandad Bluff, pause for some serene contemplation at Shrine of Our Lady of Guadalupe, walk around Riverside Park, and explore the engaging exhibits at Children's Museum of La Crosse.

To find photos, traveler tips, other places to visit, and tourist information, refer to the La Crosse trip itinerary maker site.

Getting from Bayfield to La Crosse by car takes about 5.5 hours. Other options: do a combination of car, flight, and bus; or do a combination of taxi, bus, and train. In September, La Crosse is a bit warmer than Bayfield - with highs of 78°F and lows of 57°F. Cap off your sightseeing on the 29th (Wed) early enough to go by car to Madison.

Things to do in La Crosse

Parks · Historic Sites · Breweries & Distilleries · Nature

Side Trips

Madison

— 5 nights

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Get out of town with these interesting Madison side-trips: Devil's Lake State Park (in Baraboo), Wisconsin Dells (Wisconsin Deer Park, Zipline, &more) and Spring Green (The House on the Rock & Taliesin Preservation: Frank Lloyd Wright Visitor Center ). And it doesn't end there: admire the natural beauty at Olbrich Botanical Gardens, ponder the world of politics at Wisconsin State Capitol, see the interesting displays at National Mustard Museum, and make a trip to Capitol Square.

To see more things to do, maps, ratings, and other tourist information, use the Madison itinerary maker website.

Drive from La Crosse to Madison in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. In September in Madison, expect temperatures between 75°F during the day and 53°F at night. Wrap up your sightseeing on the 4th (Mon) early enough to fly back home.

Things to do in Madison

Parks · Museums · Outdoors · Tours

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.