60 days in Wisconsin Itinerary

60 days in Wisconsin Itinerary

Created using Inspirock Wisconsin trip planner

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Make it your trip
Fly to Chicago O'Hare, Bus to Madison
1
Madison
— 9 nights
Drive
2
Chippewa Falls
— 8 nights
Drive
3
Bayfield
— 8 nights
Drive
4
Washington Island
— 3 nights
Drive
5
Fish Creek
— 5 nights
Drive
6
Green Bay
— 8 nights
Drive
7
Sheboygan
— 8 nights
Drive
8
Milwaukee
— 10 nights
Fly

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Madison

— 9 nights

The City of Four Lakes

Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Step off the beaten path and head to Wollersheim Winery & Distillery and Beer Tastings & Tours. Explore Madison's surroundings by going to Zipline (in Wisconsin Dells), International Crane Foundation (in Baraboo) and Lewis Station Winery (in Lake Mills). There's still lots to do: explore the world behind art at Overture Center for the Arts, indulge your thirst for a good beer at Wisconsin Brewing Company, take in the spiritual surroundings of First Unitarian Meeting House of Madison, and admire the natural beauty at Olbrich Botanical Gardens.

To see more things to do, ratings, traveler tips, and more tourist information, refer to the Madison trip planner.

Stockholm, Sweden to Madison is an approximately 14.5-hour combination of flight and bus. You can also fly. Due to the time zone difference, you'll gain 7 hours traveling from Stockholm to Madison. Traveling from Stockholm in June, expect Madison to be somewhat warmer, temps between 30°C and 17°C. Finish up your sightseeing early on the 10th (Thu) so you can travel to Chippewa Falls.

Things to do in Madison

Museums · Parks · Wineries · Breweries & Distilleries

Side Trips

Chippewa Falls

— 8 nights
Chippewa Falls is a city located on the Chippewa River in Chippewa County in the U.S. state of Wisconsin. Eschew the tourist crowds and head to River Bend Vineyard & Winery and Lake Wissota State Park. Explore Chippewa Falls' surroundings by going to Villa Bellezza (in Pepin), ELMARO Vineyard (in Trempealeau) and Soldiers Walk Memorial Park (in Arcadia). There's lots more to do: sample the tasty concoctions at Leinie Lodge, explore the landscape on two wheels at Old Abe Trail, sample the fine beverages at Chippewa River Distillery & Brewster Brothers Brewing Company, and learn about winemaking at Cottage Winery and Vineyard.

To find where to stay, photos, maps, and more tourist information, go to the Chippewa Falls vacation maker tool.

You can drive from Madison to Chippewa Falls in 3 hours. June in Chippewa Falls sees daily highs of 30°C and lows of 15°C at night. Wrap up your sightseeing on the 18th (Fri) early enough to travel to Bayfield.

Things to do in Chippewa Falls

Breweries & Distilleries · Parks · Wineries · Outdoors

Side Trips

Bayfield

— 8 nights
Bayfield is a city in Bayfield County, Wisconsin, United States. Eschew the tourist crowds and head to Spas and Kayaking & Canoeing. Venture out of the city with trips to Ashland (Maslowski Beach & Prentice Park), Ironwood (Historic Ironwood Museum & Downtown Miners Mural) and Little Star Beach Park (in Manitowish Waters). There's much more to do: do a tasting at Hauser's Superior View Orchard, look for gifts at Apostle Islands Booksellers, explore the fascinating underground world of Apostle Islands National Lakeshore Ice Caves, and identify plant and animal life at Big Ravine Trail.

For reviews and tourist information, read our Bayfield itinerary builder app.

Traveling by car from Chippewa Falls to Bayfield takes 3 hours. Prepare for a bit cooler weather when traveling from Chippewa Falls in June: high temperatures in Bayfield hover around 26°C and lows are around 10°C. Wrap up your sightseeing on the 26th (Sat) early enough to travel to Washington Island.

Things to do in Bayfield

Parks · Outdoors · Nature · Beaches

Side Trips

Washington Island

— 3 nights
Washington Island is located about northeast of the tip of Door Peninsula in Door County, Wisconsin. Step off the beaten path and head to Schoolhouse Beach and Sand Dunes Beach Park. Next up on the itinerary: take in the architecture and atmosphere at Washington Island Stavkirke, experience rural life at Island Lavender Farm Market, examine the collection at Jacobsen Museum, and don't miss a visit to Fair Isle Books & Gifts.

To find traveler tips, ratings, where to stay, and tourist information, read Washington Island trip itinerary site.

You can drive from Bayfield to Washington Island in 7.5 hours. You'll lose 1 hour traveling from Bayfield to Washington Island due to the time zone difference. In June, daytime highs in Washington Island are 24°C, while nighttime lows are 12°C. Cap off your sightseeing on the 29th (Tue) early enough to go by car to Fish Creek.

Things to do in Washington Island

Museums · Outdoors · Beaches · Parks

Fish Creek

— 5 nights
Fish Creek is an unincorporated community located in Door County, Wisconsin, United States, within the town of Gibraltar and is located on Highway 42 along Green Bay.HistoryThe first settler of Fish Creek was Increase Claflin and his family circa 1844, but the village founder is considered to be entrepreneur Asa Thorp. You'll discover tucked-away gems like Lautenbach's Orchard Country and The Ridges Sanctuary. And it doesn't end there: enjoy the sea views from Eagle Bluff Lighthouse, indulge in some personalized pampering at The Spa at Sacred Grounds, take in the exciting artwork at J. Jeffrey Taylor, and take a tour by water with Boat Tours & Water Sports.

To see reviews, other places to visit, traveler tips, and more tourist information, you can read our Fish Creek sightseeing planning site.

You can drive from Washington Island to Fish Creek in 1.5 hours. You'll gain 1 hour traveling from Washington Island to Fish Creek due to the time zone difference. In June, plan for daily highs up to 26°C, and evening lows to 14°C. Wrap up your sightseeing on the 4th (Sun) early enough to drive to Green Bay.

Things to do in Fish Creek

Outdoors · Golf · Parks · Historic Sites

Side Trips

Green Bay

— 8 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 discover tucked-away gems like Badger State Brewing Company and Bay Beach Wildlife Sanctuary. Explore the numerous day-trip ideas around Green Bay: Ahnapee Brewery (in Algoma) and Kerrigan Brothers Winery (in Freedom). Next up on the itinerary: admire the natural beauty at Green Bay Botanical Garden, do a tasting at LedgeStone Vineyards, walk around Fonferek Glen County Park, and get in on the family fun at Bay Beach Amusement Park.

For reviews, photos, ratings, and tourist information, use the Green Bay trip website.

Getting from Fish Creek to Green Bay by car takes about 1.5 hours. In July in Green Bay, expect temperatures between 32°C during the day and 17°C at night. Finish your sightseeing early on the 12th (Mon) so you can drive to Sheboygan.

Things to do in Green Bay

Parks · Outdoors · Breweries & Distilleries · Wildlife

Side Trips

Sheboygan

— 8 nights
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Explore hidden gems such as Whistling Straits Golf Course - Straits and Irish and John Michael Kohler Arts Center. The adventure continues: admire the natural beauty at Bookworm Gardens, stroll around Indian Mounds Park, indulge your thirst for a good beer at 3 Sheeps Brewing Company, and appreciate the history behind Acuity Flagpole.

Find out how to plan Sheboygan trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Green Bay to Sheboygan takes 1.5 hours. Expect a daytime high around 30°C in July, and nighttime lows around 17°C. Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Milwaukee.

Things to do in Sheboygan

Parks · Outdoors · Golf · Nature

Side Trips

Milwaukee

— 10 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Eschew the tourist crowds and head to Pieper Porch Winery & Vineyard and North Beach Park. Venture out of the city with trips to Racine (Wind Point Lighthouse & SC Johnson Headquarters), Kenosha (Civil War Museum & Kenosha Sculpture Walk) and Cedar Creek Winery (in Cedarburg). There's much more to do: explore the world behind art at Milwaukee Art Museum, indulge your thirst for a good beer at Milwaukee Brewing Co., examine the collection at Harley-Davidson Museum, and grab your bike and head to Ozaukee Interurban Trail.

To find traveler tips, maps, photos, and other tourist information, go to the Milwaukee trip itinerary planner.

You can drive from Sheboygan to Milwaukee in an hour. In July, daily temperatures in Milwaukee can reach 31°C, while at night they dip to 20°C. Finish up your sightseeing early on the 30th (Fri) so you can travel back home.

Things to do in Milwaukee

Museums · Outdoors · Parks · Breweries & Distilleries

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.