41 days in Wisconsin Itinerary

41 days in Wisconsin Itinerary

Created using Inspirock Wisconsin trip itinerary maker

Make it your trip
Drive
1
Madison
— 3 nights
Drive
2
Wisconsin Dells
— 5 nights
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3
La Crosse
— 4 nights
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4
Bayfield
— 3 nights
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5
Oshkosh
— 3 nights
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6
Sturgeon Bay
— 4 nights
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7
Sheboygan
— 3 nights
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8
Milwaukee
— 5 nights
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9
Sister Bay
— 3 nights
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10
Hubertus
— 2 nights
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11
Appleton
— 3 nights
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12
Milton
— 2 nights
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Madison

— 3 nights

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
You'll find plenty of places to visit near Madison: Spring Green (The House on the Rock & Arcadia Books). There's still lots to do: get a sense of history and politics at Wisconsin State Capitol, identify plant and animal life at Owens Conservation Park, make a trip to Memorial Union Terrace, and get to know the resident critters at Henry Vilas Zoo.

To find traveler tips and more tourist information, go to the Madison road trip app.

Chicago to Madison is an approximately 2.5-hour car ride. You can also take a bus; or fly. In May, plan for daily highs up to 70°F, and evening lows to 48°F. Finish your sightseeing early on the 4th (Mon) so you can drive to Wisconsin Dells.

Things to do in Madison

Parks · Shopping · Zoos & Aquariums · Museums

Side Trip

Wisconsin Dells

— 5 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.
Plan for a day of cool, family-friendly fun on the 5th (Tue) at Noah's Ark Water Park. There's still lots to do: admire nature's wide array of creatures at Wisconsin Deer Park, make a trip to Carr Valley Cheese, immerse yourself in nature at Devil's Lake State Park, and see the interesting displays at Circus World.

To find ratings, photos, traveler tips, and other tourist information, you can read our Wisconsin Dells tour itinerary maker website.

Drive from Madison to Wisconsin Dells in an hour. Alternatively, you can do a combination of bus and train. In May in Wisconsin Dells, expect temperatures between 68°F during the day and 46°F at night. Finish your sightseeing early on the 9th (Sat) so you can drive to La Crosse.

Things to do in Wisconsin Dells

Museums · Theme Parks · Parks · Nature

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. Change things up with these side-trips from La Crosse: Rush River Produce (in Maiden Rock) and Crystal Cave (in Spring Valley). And it doesn't end there: explore the striking landscape at Grandad Bluff, pause for some serene contemplation at Shrine of Our Lady of Guadalupe, take in the spiritual surroundings of Franciscan Sisters of Perpetual Adoration Motherhouse, and admire the natural beauty at Riverside International Friendship Gardens.

To find maps, photos, where to stay, and more tourist information, you can read our La Crosse trip itinerary maker.

You can drive from Wisconsin Dells to La Crosse in 1.5 hours. Alternatively, you can take a train. Expect a daytime high around 71°F in May, and nighttime lows around 50°F. Finish your sightseeing early on the 13th (Wed) so you can drive to Bayfield.

Things to do in La Crosse

Parks · Historic Sites · Nature

Side Trips

Bayfield

— 3 nights
Bayfield is a city in Bayfield County, Wisconsin, United States. Apostle Islands Cruise Service has been added to your itinerary. Get out of town with these interesting Bayfield side-trips: Potato River Falls (in Hurley) and Copper Falls State Park (in Mellen). There's lots more to do: explore the fascinating underground world of Apostle Islands National Lakeshore Ice Caves, get engrossed in the history at Bayfield Maritime Museum, take in the exciting artwork at Stone's Throw Art Gallery, and stop by Apostle Islands Booksellers.

To see other places to visit, ratings, reviews, and more tourist information, read our Bayfield holiday builder tool.

You can drive from La Crosse to Bayfield in 5.5 hours. Alternatively, you can do a combination of bus, flight, and car; or do a combination of train, bus, and taxi. Plan for a bit cooler temperatures traveling from La Crosse in May, with highs in Bayfield at 62°F and lows at 38°F. Wrap up your sightseeing on the 16th (Sat) to allow time to travel to Oshkosh.

Things to do in Bayfield

Nature · Parks · Outdoors · Tours

Side Trips

Oshkosh

— 3 nights
Oshkosh is a city in Winnebago County, Wisconsin, United States, located where the Fox River enters Lake Winnebago from the west. The Outlet Shoppes at Oshkosh has been added to your itinerary. Explore Oshkosh's surroundings by going to Green Bay (Green Bay Packer Hall of Fame, Bay Beach Wildlife Sanctuary, &more), Horicon Marsh (in Mayville) and Scray Cheese (in De Pere). Next up on the itinerary: see the interesting displays at EAA Aviation Museum.

For where to stay, reviews, and tourist information, read Oshkosh online trip builder.

Traveling by car from Bayfield to Oshkosh takes 5 hours. Alternatively, you can do a combination of car and flight. Traveling from Bayfield in May, you can expect nighttime temperatures to be a bit warmer in Oshkosh, with lows of 48°F. Wrap up your sightseeing on the 19th (Tue) early enough to travel to Sturgeon Bay.

Things to do in Oshkosh

Museums · Wildlife · Parks · Theme Parks

Side Trips

Sturgeon Bay

— 4 nights
Sturgeon Bay is a city in and the county seat of Door County, Wisconsin, United States. Venture out of the city with trips to Cana Island Lighthouse (in Baileys Harbor), Ellison Bay Pottery Studios (in Ellison Bay) and Peninsula State Park (in Fish Creek). The adventure continues: relax in the rural setting at The Farm, stroll around Cave Point County Park, get outside with Door County Charters, and pause for some serene contemplation at Washington Island Stavkirke.

For where to stay, reviews, maps, and more tourist information, go to the Sturgeon Bay trip builder site.

Traveling by car from Oshkosh to Sturgeon Bay takes 2 hours. When traveling from Oshkosh in May, plan for a bit cooler days in Sturgeon Bay, with highs around 62°F, while nights are about the same with lows around 44°F. Cap off your sightseeing on the 23rd (Sat) early enough to travel to Sheboygan.

Things to do in Sturgeon Bay

Parks · Historic Sites · Nature · Outdoors

Side Trips

Sheboygan

— 3 nights
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Step out of Sheboygan to go to Belgium and see Cedar Valley Cheese, which is approximately 30 minutes away. There's much more to do: bet on your favorite at Road America, examine the collection at Sheboygan County Historical Museum, cool off at Blue Harbor Resort & Conference Center Water Park, and explore the world behind art at John Michael Kohler Arts Center.

For other places to visit, ratings, reviews, and tourist information, use the Sheboygan trip itinerary planner.

Getting from Sturgeon Bay to Sheboygan by car takes about 2 hours. May in Sheboygan sees daily highs of 65°F and lows of 44°F at night. Wrap up your sightseeing on the 26th (Tue) early enough to drive to Milwaukee.

Things to do in Sheboygan

Museums · Parks · Theme Parks · Nightlife

Side Trips

Milwaukee

— 5 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
When in Milwaukee, make a side trip to see SC Johnson Headquarters in Racine, approximately Racine away. And it doesn't end there: get to know the resident critters at Milwaukee County Zoo, contemplate in the serene atmosphere at St. Stanislaus Oratory, take an in-depth tour of Chudnow Museum of Yesteryear, and browse the eclectic array of goods at Milwaukee Public Market.

To see more things to do, ratings, and more tourist information, read our Milwaukee trip maker app.

You can drive from Sheboygan to Milwaukee in an hour. May in Milwaukee sees daily highs of 66°F and lows of 47°F at night. Finish up your sightseeing early on the 31st (Sun) so you can go by car to Sister Bay.

Things to do in Milwaukee

Shopping · Historic Sites · Neighborhoods · Parks

Side Trip

Sister Bay

— 3 nights
Sister Bay is a village in Door County, Wisconsin, United States. You've now added Sister Bay Scenic Boat Tours to your itinerary. Get ready for a full day of sightseeing on the 1st (Mon): stop by Wood Orchard and then take a tour by water with Sister Bay Scenic Boat Tours.

To see maps, other places to visit, ratings, and other tourist information, use the Sister Bay trip tool.

Drive from Milwaukee to Sister Bay in 3.5 hours. Alternatively, you can do a combination of bus and car; or do a combination of flight and car. Traveling from Milwaukee in May, plan for little chillier nights in Sister Bay, with lows around 42°F. On the 3rd (Wed), wrap the sightseeing up by early afternoon so you can travel to Hubertus.

Things to do in Sister Bay

Parks · Nature · Shopping · Historic Sites

Side Trips

Hubertus

— 2 nights
Hubertus is an unincorporated community in the village of Richfield and the town of Erin in Washington County, Wisconsin, United States. Holy Hill has been added to your itinerary. Start off your visit on the 3rd (Wed): tour the pleasant surroundings at Veterans Memorial Park. Keep things going the next day: take in the exciting artwork at The Pink Llama Gallery, explore the landscape on two wheels at Ozaukee Interurban Trail, and then snap pictures at Cedarburg Covered Bridge.

Ask Inspirock to suggest an itinerary and make planning a trip to Hubertus fast, fun, and easy.

Traveling by car from Sister Bay to Hubertus takes 3.5 hours. In June, plan for daily highs up to 75°F, and evening lows to 56°F. Wrap up your sightseeing by early afternoon on the 5th (Fri) to allow time for travel to Appleton.

Things to do in Hubertus

Parks · Trails · Outdoors · Historic Sites

Side Trips

Appleton

— 3 nights
Appleton is a city in Outagamie (mostly), Calumet, and Winnebago counties in the U.S. state of Wisconsin. The History Museum at the Castle has been added to your itinerary. Start off your visit on the 6th (Sat): browse the exhibits of Hearthstone Historic House Museum, examine the collection at The History Museum at the Castle, and then identify plant and animal life at Gordon Bubolz Nature Preserve. Get ready for a full day of sightseeing on the next day: see the interesting displays at Green Bay Packer Hall of Fame, admire the natural beauty at Green Bay Botanical Garden, and then get your game on at Badger Sports Park.

To find photos, more things to do, other places to visit, and more tourist information, you can read our Appleton trip planner.

Traveling by car from Hubertus to Appleton takes 1.5 hours. In June, daily temperatures in Appleton can reach 75°F, while at night they dip to 56°F. On the 8th (Mon), wrap the sightseeing up by early afternoon so you can travel to Milton.

Things to do in Appleton

Parks · Museums · Wildlife · Fun & Games

Side Trip

Milton

— 2 nights
Milton is a city in Rock County, Wisconsin, United States. Milton House Museum has been added to your itinerary. On the 8th (Mon), get lost in a book at Dwight Foster Public Library. Get ready for a full day of sightseeing on the 9th (Tue): steep yourself in history at Milton House Museum, then take an in-depth tour of Hoard Historical Museum, and then get some fabulous bargains at Johnson Creek Premium Outlets.

To see photos, traveler tips, more things to do, and tourist information, you can read our Milton trip itinerary planner.

Drive from Appleton to Milton in 2.5 hours. Expect a daytime high around 80°F in June, and nighttime lows around 59°F. On the 10th (Wed), wrap the sightseeing up by early afternoon so you can drive back home.

Things to do in Milton

Shopping · Historic Sites · Museums · Parks

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.