16 days in Wisconsin Itinerary

16 days in Wisconsin Itinerary

Created using Inspirock Wisconsin holiday planner

Plan created by another user. Make it yours

Route & dates

1
Milwaukee
— 3 nights
2
Madison
— 3 nights
3
Wisconsin Dells
— 3 nights
4
Sheboygan
— 3 nights
5
Sturgeon Bay
— 3 nights

3
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Milwaukee is known for museums, breweries & distilleries, and historic sites. Your plan includes some of its best attractions: explore the world behind art at Milwaukee Art Museum, savor the flavors at Food & Drink, steep yourself in history at Pabst Mansion, and examine the collection at Harley-Davidson Museum.

For other places to visit, traveler tips, reviews, and tourist information, read our Milwaukee trip planner.

Miami to Milwaukee is an approximately 7.5-hour flight. You can also drive; or take a bus. Traveling from Miami to Milwaukee, you'll gain 1 hour due to the time zone difference. Expect colder temperatures when traveling from Miami in May; daily highs in Milwaukee reach °F and lows reach °F. Wrap up your sightseeing on the 14th (Thu) to allow time to drive to Madison.

Things to do in Milwaukee

Museums Breweries & Distilleries Historic Sites
Find places to stay May 11 — 14:
Highlights from your plan
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum
Milwaukee County Zoo ©
Milwaukee County Zoo

3
nights
Madison

Madison ©
Madison might be the capital of Wisconsin, but students rather than politicians give the city its identity.
Explore the numerous day-trip ideas around Madison: Rotary Botanical Gardens (in Janesville) and Spring Green (The House on the Rock & Taliesin Preservation: Frank Lloyd Wright Visitor Center ). There's lots more to do: get a sense of history and politics at Wisconsin State Capitol, let your taste buds guide you at a local gastronomic tour, don't miss a visit to Capitol Square, and admire the natural beauty at Olbrich Botanical Gardens.

To find traveler tips, other places to visit, more things to do, and other tourist information, read our Madison route app.

Drive from Milwaukee to Madison in 1.5 hours. Alternatively, you can take a bus. May in Madison sees daily highs of °F and lows of °F at night. Cap off your sightseeing on the 17th (Sun) early enough to go by car to Wisconsin Dells.

Things to do in Madison

Parks Zoos & Aquariums Breweries & Distilleries

Side Trips

Spring Green, Rotary Botanical Gardens
Find places to stay May 14 — 17:
Highlights from your plan
Wisconsin State Capitol ©
Wisconsin State Capitol
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

3
nights
Wisconsin Dells

Wisconsin Dells ©
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.
Wisconsin Dells is known for theme parks, nightlife, and fun & games. Your plan includes some of its best attractions: whizz through the canopy at some of the top local zipline courses and adventure parks, have some family-friendly fun at Elusive Escape Rooms, admire the majestic nature at Devil's Lake State Park, and cool off at Noah's Ark Water Park.

To find more things to do, reviews, maps, and more tourist information, you can read our Wisconsin Dells trip planner.

You can drive from Madison to Wisconsin Dells in 1.5 hours. Alternatively, you can do a combination of bus and train. In May in Wisconsin Dells, expect temperatures between °F during the day and °F at night. Wrap up your sightseeing on the 20th (Wed) early enough to travel to Sheboygan.

Things to do in Wisconsin Dells

Theme Parks Outdoors Tours

Side Trip

Devil's Lake State Park
Find places to stay May 17 — 20:
Highlights from your plan
Noah's Ark Water Park ©
Noah's Ark Water Park
Zipline
Mt. Olympus Water & Theme Park ©
Mt. Olympus Water & Theme Park

3
nights
Sheboygan

Sheboygan ©
Sheboygan is a city in and the county seat of Sheboygan County, Wisconsin, United States. You'll find plenty of places to visit near Sheboygan: EAA Aviation Museum (in Oshkosh) and Green Bay (Green Bay Botanical Garden, Fonferek Glen County Park, &more). There's still lots to do: bet on your favorite at Road America, pause for some photo ops at Acuity Flagpole, and admire the natural beauty at Bookworm Gardens.

For reviews, ratings, maps, and more tourist information, read our Sheboygan vacation planning website.

Traveling by car from Wisconsin Dells to Sheboygan takes 2.5 hours. Expect a daytime high around °F in May, and nighttime lows around °F. Cap off your sightseeing on the 23rd (Sat) early enough to travel to Sturgeon Bay.

Things to do in Sheboygan

Museums Parks Theme Parks

Side Trips

Green Bay, EAA Aviation Museum, Road America
Find places to stay May 20 — 23:
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
Green Bay Packer Hall of Fame ©
Green Bay Packer Hall of Fame
Green Bay Botanical Garden ©
Green Bay Botanical Garden

3
nights
Sturgeon Bay

Sturgeon Bay ©
Sturgeon Bay is a city in and the county seat of Door County, Wisconsin, United States. Explore the numerous day-trip ideas around Sturgeon Bay: Sister Bay (Boat Tours & Water Sports & Waterfront Park), Fish Creek (Sunset Beach Park & Peninsula State Park) and Cana Island Lighthouse (in Baileys Harbor). There's lots more to do: experience rural life at The Farm, walk around Cave Point County Park, view the masterpieces at Edgewood Orchard Galleries, and examine the collection at Door County Maritime Museum.

Planning Sturgeon Bay trip won't be overwheling when you use's Insprock itinerary maker.

Getting from Sheboygan to Sturgeon Bay by car takes about 2 hours. In May, plan for daily highs up to °F, and evening lows to °F. Wrap up your sightseeing by early afternoon on the 26th (Tue) to allow enough time to travel back home.

Things to do in Sturgeon Bay

Parks Museums Historic Sites

Side Trips

Fish Creek, Sister Bay, Cana Island Lighthouse
Find places to stay May 23 — 26:
Highlights from your plan
Peninsula State Park ©
Peninsula State Park
The Farm ©
The Farm
Boat Tours & Water Sports

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