20 days in Wisconsin Itinerary

20 days in Wisconsin Itinerary

Created using Inspirock Wisconsin trip itinerary planner

Make it your trip
Fly
1
Sturgeon Bay
— 3 nights
Drive
2
Chippewa Falls
— 4 nights
Drive
3
Wisconsin Dells
— 4 nights
Drive
4
Sheboygan
— 3 nights
Drive
5
Milwaukee
— 5 nights
Fly

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Sturgeon Bay

— 3 nights
Sturgeon Bay is a city in and the county seat of Door County, Wisconsin, United States. Deepen your sense of the past at sights like Cana Island Lighthouse and Eagle Bluff Lighthouse. Get some cultural insight at Von Stiehl Winery and Lautenbach's Orchard Country. Get out of town with these interesting Sturgeon Bay side-trips: Off The Wheel Pottery (in Egg Harbor) and The Ridges Sanctuary (in Baileys Harbor). Next up on the itinerary: learn about winemaking at Door Peninsula Winery, view the masterpieces at Plum Bottom Gallery, walk around Cave Point County Park, and take in nature's colorful creations at The Garden Door.

To see reviews, ratings, photos, and more tourist information, use the Sturgeon Bay trip planner.

New York City to Sturgeon Bay is an approximately 6.5-hour flight. You can also drive; or do a combination of bus and car. Due to the time zone difference, you'll gain 1 hour traveling from New York City to Sturgeon Bay. Traveling from New York City in June, things will get a bit cooler in Sturgeon Bay: highs are around 72°F and lows about 54°F. Wrap up your sightseeing on the 19th (Sat) to allow time to travel to Chippewa Falls.

Things to do in Sturgeon Bay

Wineries · Historic Sites · Parks · Shopping

Side Trips

Chippewa Falls

— 4 nights
Chippewa Falls is a city located on the Chippewa River in Chippewa County in the U.S. state of Wisconsin. Your cultural itinerary includes sights like River Bend Vineyard & Winery and ELMARO Vineyard. Venture out of the city with trips to Brigadoon Winery (in Tripoli), Fred Smith's Wisconsin Concrete Park (in Phillips) and Tenba Ridge Winery (in Blair). There's much more to do: indulge your thirst for a good beer at Jacob Leinenkugel Brewing Company, look for gifts at Chippewa Candy Shop, and learn about winemaking at Munson Bridge Winery.

To find maps, more things to do, ratings, and other tourist information, read Chippewa Falls trip planning website.

Traveling by car from Sturgeon Bay to Chippewa Falls takes 3.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Sturgeon Bay in June, expect nights in Chippewa Falls to be about the same, around 56°F, while days are somewhat warmer, around 78°F. Wrap up your sightseeing on the 23rd (Wed) to allow time to travel to Wisconsin Dells.

Things to do in Chippewa Falls

Wineries · Breweries & Distilleries · Historic Sites · Parks

Side Trips

Wisconsin Dells

— 4 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.
Your cultural itinerary includes sights like Taliesin Preservation: Frank Lloyd Wright Visitor Center and Wollersheim Winery & Distillery. Visit H.H. Bennett Studio & Museum and Swiss Historical Village for their historical value. Explore Wisconsin Dells' surroundings by going to Rock N Wool Winery (in Poynette) and New Glarus Brewing Company (in New Glarus). There's still lots to do: get a dose of the wild on Original Wisconsin Ducks, kick your exploration up a notch at some of the top local zipline courses and adventure parks, do a tasting at Von Klaus Winery, and stop by Kernel Popcorn's Factory.

For maps, traveler tips, other places to visit, and tourist information, go to the Wisconsin Dells trip builder site.

You can drive from Chippewa Falls to Wisconsin Dells in 2.5 hours. In June, daytime highs in Wisconsin Dells are 77°F, while nighttime lows are 57°F. Cap off your sightseeing on the 27th (Sun) early enough to travel to Sheboygan.

Things to do in Wisconsin Dells

Wineries · Outdoors · Tours · Historic Sites

Side Trips

Sheboygan

— 3 nights
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. Get some historical perspective at Wade House and St. Mary's Church. Your cultural itinerary includes sights like The Blind Horse Winery and Kerrigan Brothers Winery. Get out of town with these interesting Sheboygan side-trips: Horicon Marsh (in Mayville), Scray Cheese (in De Pere) and Armstrong Apples, Orchard & Winery! (in Campbellsport). There's much more to do: tee off at Whistling Straits Golf Course - Straits and Irish, appreciate the history behind Big Cow, Antoinette, enjoy some music at John Michael Kohler Arts Center, and learn about winemaking at LedgeStone Vineyards.

For where to stay, traveler tips, maps, and other tourist information, refer to the Sheboygan trip maker website.

Traveling by car from Wisconsin Dells to Sheboygan takes 2.5 hours. In June in Sheboygan, expect temperatures between 74°F during the day and 55°F at night. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Milwaukee.

Things to do in Sheboygan

Wineries · Historic Sites · Wildlife · Outdoors

Side Trips

Milwaukee

— 5 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Get a sense of the local culture at Historic Third Ward and Basilica of St. Josaphat. Get some historical perspective at Pabst Mansion and North Point Water Tower. Explore Milwaukee's surroundings by going to Lake Mills (Bartel's Beach & Lewis Station Winery), Ten Chimneys (in Genesee Depot) and Cedar Creek Winery (in Cedarburg). There's lots more to do: sample the tasty concoctions at Lakefront Brewery, admire the masterpieces at Milwaukee Art Museum, indulge your taste buds at Food & Drink, and brush up on your knowledge of spirits at Great Lakes Distillery.

To find ratings, maps, more things to do, and other tourist information, refer to the Milwaukee trip website.

You can drive from Sheboygan to Milwaukee in an hour. In June, daily temperatures in Milwaukee can reach 76°F, while at night they dip to 58°F. Finish up your sightseeing early on the 5th (Mon) so you can catch the flight back home.

Things to do in Milwaukee

Historic Sites · Breweries & Distilleries · Wineries · Outdoors

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.