The Perfect Wisconsin Itinerary: A 5-Day Road Trip

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We’ve called Wisconsin home for a few years now. When we first moved here, we thought we hated the state. We used to drive through it and it took soooo long and seemed all the same. However, after living here, we’ve become proud cheese heads. Okay so we don’t actually wear the cheese hats but we like living here. So if you’re planning to visit this amazing state filled with some really great places to visit – from amazing natural areas to hip towns – consider following this one week Wisconsin itinerary as you travel around the state to see the best it has to offer. 

The Perfect Wisconsin ItineraryToggle Table of Content

Itinerary 

Day 1 – Madison

Start your Wisconsin road trip in Madison, the capital. You can fly into the airport in town and rent a car.

Visit the Henry Vilas Zoo in the morning. This is a fun zoo and the kiddos of all ages will love it. Henry Vilas Zoo is a free zoo that is really splendid. 

Henry Vilas Zoo
Henry Vilas Zoo

Next, explore the Olbrich Botanical Gardens. These beautiful gardens are fun to explore for all ages. And the best part, they’re free if you visit before noon on Wednesday or Saturday. Admission is $6 during regular hours. 

Olbrich Botanical Gardens
Olbrich Botanical Gardens

Then explore downtown Madison in the afternoon. Start with a walk around the capitol building and then take a tour of the building. 

Spend the rest of your afternoon exploring the businesses (and bars/breweries) downtown. We love the Great Dane Pub and Brewing Co. as they have great food and drinks. 

Next, drive 1 hour to Wisconsin Dells and stay the evening there. If you follow this Wisconsin itinerary, you’ll stay two nights here. Here are some of our recommendations for places to stay:

  • Budget – camping at Mirror Lake State Park or Devil’s Lake State Park
  • Comfort – Dells Resorts
  • Luxury – Kalahari Resorts and Water Park (This is a great option for the kiddos! But not worth the extra money if you aren’t going to play in the resort.)

Day 2 – Wisconsin Dells

On day two of your Wisconsin itinerary, eat breakfast at Mr. Pancake. Don’t eat anywhere else. I’ve never so strongly recommended a breakfast restaurant in my life. Consider trying the banana split waffle – which is a banana split served on a waffle and a completely appropriate breakfast food. And do not order eggs and bacon at the restaurant and then complain that they weren’t worth the wait, I’m talking to you dude-who-sat-next-to-us – they clearly specialize in breakfast-desserts. Get here early as tables fill up quick.

Mr. Pancake
Mr. Pancake

Next, spend the morning exploring Devil’s Lake State Park. This park is a bit south of Wisconsin Dells but worth the side trip. Hiking at this park is great or you can explore the beach with the family.

Devil's Lake State Park
Devil's Lake State Park

In the afternoon, spend your day doing something fun in the Dells. There are plenty of fun things to do in Wisconsin Dells to suit any travel style. Spend the day at a waterpark, Timbavati Wildlife Parkdoing a river tour, or drinking wine. 

For dinner you should enjoy the perfectly wonderful experience of a Wisconsin supper club. We recommend either the Del-Bar or Ishnala. This is one of the top things to do in Wisconsin and the Dells is the best place to try it in this Wisconsin itinerary. 

We’ll take a moment to explain how a super club works. First, get a reservation, if they’ll take one. Next, arrive at least a half hour early for your reservation. Sit at the bar and order an old fashioned (this is a requirement). Next, eat dinner. Expect a multi-course meal with some fancy type of meat as the main course – fish or red meat. Then, go back to the bar and order an after-dinner drink, which should involve a milkshake with alcohol in it. Roll out of the restaurant miserably full and part ashamed/part proud of the amount of food you consumed. And there you have the quintessentially Wisconsin experience of a supper club.

Stay the night again in the Dells.

Day 3 – Green Bay

Wake up in the morning and potentially have breakfast again at Mr. Pancake – that’s really the only place we eat breakfast in the Dells. Then drive the 2.5 hours to Green Bay.

First, visit Lambeau Field and the Packer hall of fame if you’re a football fan. This is the best place to get the cheesy Wisconsin souvenir of a classic cheese hat. If football isn’t for you, consider checking out the National Railroad Museum.

Wisconsin cheese hats

After visiting Green Bay, head to Door County and start exploring. Consider exploring part of the Door County Wine Trail in the evening. 

Stay the evening in Door County. You’ll be staying here for two nights of this Wisconsin itinerary. Here are some of our recommendations:

  • Budget – camping in Peninsula State Park
  • Comfort – Parkwood Lodge or another old fashioned lodge
  • Luxury – Any B&B in Door County – this is the romantic option and there are tons of options. 
Cave Point County Park
Cave Point County Park

Day 4 – Door County

Spend the day enjoying Door County. There are plenty of things to see here to fill your day. We’ve put together our favorite things to do on the Peninsula. Choose a few and check them out!

For dinner, consider trying a famous Door County fish boil. You get dinner and a show out of one of these. If fish isn’t your thing, check out other things to eat in Door County in our post here. 

Fish Boil - Door County
Fish Boil

Day 5 – Milwaukee

Start your day bright and early and head straight for Milwaukee. On your way there, stop at one of the great Lake Michigan beaches for a swim in this salt free sea. We recommend stopping at Kohler-Andrae State Park. Once you’ve had a refreshing swim wherever you choose, finish the 2.5 hour drive to Milwaukee. 

Door County Beach

Once in Milwaukee, check out the Milwaukee Art Museum and/or the Harley-Davidson Museum, depending on how much time you have left in the day.

Next, spend the evening doing the most Wisconsin of things: drinking beer by a lake. The two most popular breweries to visit in Milwaukee are Miller and Lakeside. We think you should visit both.

Either fly out of the Milwaukee airport in the evening or stay one night in town and fly out the following morning. Home rental options are amazing in Milwaukee and serve a variety of budgets and locations, we’d recommend staying in one of these neat places. 

Want to Adjust the Itinerary

If you have extra time to spend in Wisconsin, we recommend staying 1-2 extra days in Door County. Consider inserting our complete Door County vacation into your Wisconsin itinerary. 

If you have even more time to add to your Wisconsin road trip, consider adding additional stops. We have plenty to choose from here. 

National Freshwater Fishing Museum
National Freshwater Fishing Museum - World's Largest Muskie

If you have less time, you could cut time from Green Bay and Madison. However, you’ll still need at least 4 days to complete a road trip throughout the state though.

If you only have a few days, we recommend that you pick one place and fully explore it. We think this Door County itinerary is the best long weekend in Wisconsin. 

Stavkirke Church
Stavkirke Church

We hope you enjoy this Wisconsin itinerary as much as we have and we think you’ll have a great time in the heart of the Midwest. If you have any questions or tips for a Wisconsin itinerary, please leave them in the comments below. 


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This Post Has 4 Comments

  1. Go Wander Wild

    This Wisconsin guide is incredibly helpful. You’ve really thought through everything you need to know before planning a trip. Thank you for this helpful resource. Saving this guide for later!

    1. Paula

      Thanks! I hope you’re able to make it out here soon 🙂

  2. Mary Westerbeke

    As a lifelong Cheesehead I throughly enjoyed your itinerary. You totally nailed the supper club experience. Of course I could offer more suggestions for travel highlights in the state. If you are looking for ideas for future feature articles consider The Apostle Islands, the Mississippi River bluffs near Prairie du Chien, New Glarus with its brewery and Spotted Cow beer, and Kettle Morraine area which cannot be rivaled for fall color. Enjoy your travels mbfromnb

    1. Paula

      Thanks! The Apostle Islands and the Mississippi River are actually some of our favorite road trips. I just have to sit down and write about them 🙂 But we’ll definitely have to get to New Glarus at some point. It’s been on the list for a while and we just have never made it there.

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