Amazing 12-Day Midwest Family Adventure

The Midwest was never a place high on our bucket list. I started researching a new place to visit and found out how amazing and beautiful it was. Everywhere was even more beautiful in person. Our trip to the Midwest included Milwaukee, Door Country, the UP, lower Michigan, and ended in Chicago. It was an amazing circle!

Watch our adventure here

Quick Itinerary

Day 1

Day 2

Day 3

Day 4

Day 5

Day 6

Day 7

  • Lake Superior

Day 8

Day 9

Day 10

Day 11

Day 12

Detailed Itinerary

Day 1

Our day started at 2 am at home. The flight was for 5:15am, so we basically had an entire day in Milwaukee. Car rentals are cheaper away from the airport so we took an Uber to our Priceline hotel, Aloft, and left all of our bags there until check in. Milwaukee was super cheap. I got a hotel on the river for $100 total. It was in a great location. We walked to a swing playground placed under a bridge call Hanging Bridge Park. You can walk along the riverwalk that is really nice. They have a great store that is a lot like Whole Foods called The Farmers Market. The smoothies were delicious. We walked up the quirky Brady Street. There is a lot of restaurants and shops. We stopped in a super cute Italian grocery store called Glorioso’s for an Italian Beef sandwich. It was super good. We then walked to McKinley Park and Veterans Park. The parks are beautiful and right on the water. Our walk back was through a beautiful part of town. Milwaukee has some of the most beautiful churches and homes I have ever seen. I couldn’t stop taking pictures. IT was time for hotel check in so we got our room and our rental car at this point. After we headed to Eagle Park Brewing. They had great beers and really good food. We ordered the Buffalo Curry Chicken Sandwich with Karate Chopped Fries and the Chicken Tostadas. Both were really good. Next we headed to the Brewers game. Stub Hub had tickets for like $10 dollars a piece. Views anywhere in the stadium are great. We ended the night at Leon’s Custard. This place is kind of in a rough part of town, but it was super packed when we got there. We ordered 1 of each of the 4 custard flavors.

Leon’s Frozen Custard Milwaukee

Day 2

We headed to Door County. This is about a 2 hours from Milwaukee. We stopped at Trader Joes right outside of the city to get camping food. This trip we brought a one pot burner so we had really amazing camp meals. We camped in Peninsula State Park. It was so beautiful. We camped at Weborg Point Site 105. This was a great campground/campsite. Much smaller than all the others and our site was waterfront. Weborg Point is an amazing sunset and fishing spot. We set up camp then headed explored the park some. I found a moderate hike for us to do called Eagle Trail. This trail is about 3 miles. it is mostly along Green Bay. There are many caves and beautiful views along the trail. After we stopped at the beach in the state park. It is nice with plenty of picnic tables and a playground, but it stays packed.

Door County Sunset
Sunset at Weborg Point

Day 3

Door County is full of the cutest little towns. We drove through the whole peninsula to the end. There are 2 islands you can take a ferry to as well. We took 1 ferry to Washington Island. It was about $60 for all of us and our car. There are mopeds and bikes on the island to rent but a car is super easy. On the far side of the island is Schoolhouse Beach. This is one of the coolest beaches I have ever been to. It is a rock beach. I recommend wearing some kind of water shoe. The rocks are hard to walk on barefoot. We wore Tevas. The water is so clear and beautiful. It is pretty cold but once you get it it feels amazing. There is a little float out in the water you can swim to to jump off as well. There are 2 Lavender fields on the island. I recommend Fragrant Isle Lavender Farm. They have huge lavender fields to run through and a beautiful store. The other lavender farm does not let you walk through very much lavender. After getting back to the mainland we stopped at Door County Ice Cream Co. Delicious ice cream. My favorite was the Door County Cherry. We also got Death’s Door Chocolate. Both were so good. Sister Bay is definitely the biggest town along the peninsula. There is a huge playground right on the water. There is also a walkway that goes out to a dock and another floating dock for jumping in the water. This is where we spent most of the evening.

Schoolhouse Beach
Schoolhouse Beach

Day 4

Kayaking Lake Michigan is a very popular activity. We did the Cave Point tour with Door County Kayak Tours. It was the only company that let children of any age on the tour. It was so much fun kayaking through the waves of Lake Michigan. Much different than the flat bayous around home. After we stopped for lunch and a beer at Door County Brewing Co. They had a food truck with great food. We ordered cheese curds and a burger. The beers and food were delicious, especially after kayaking all morning. Door County has a ton of cherry orchards along the main highway. We stopped at one for a pit spitting contest. On our way out of Wisconsin we stopped in Green Bay to see Lambo Field. We could not get int he stadium but we still liked driving by, After, we had a 4 hour drive to our Airbnb in the UP.

Kayak Door County
Door County Kayak Tours

Day 5

Our Airbnb in the UP was great for a rest day. The owners were amazing. It was right on the water. There was a playground, fire pit, kayaks, grill, trampoline, and floating trampoline for us to use. The owners have 8 kids so our kids loved it! The first night they were roasting s’mores and invited us like we were family. The next day they brought us cinnamon rolls for breakfast and strawberry shortcake that night after dinner. They really were so great. It was located in Chassell, MI. Very small town. It is right outside of Houghton, MI, which is a little college town. In Houghton there is a super cute riverfront with a really cool bridge. There is the biggest playground of all time located here. The girls loved it. They played for at least 2 hours here. We tried our first pasty at Roy’s Pasties. We all really liked it. The bugs in the UP are ridiculous. You needs mosquito nets around your body to prevent bites. Spray is simply not enough for these bugs.

Michigan's Upper Peninsula
Playground in Houghton, MI

Day 6

Next we headed to Pictured Rocks National Lakeshore. We camped at Munising Tourist Park site K. This is a really small town. We hiked to Miner’s Falls, Miner’s Castle, and Miner’s Beach. All hikes were very easy. Miner’s Falls was the longest at about a 1 mile roundtrip. Miner’s Beach is so beautiful. Perfect spot to play in the water and walk along the beach finding rocks. We ended the night with a sunset cruise along Pictured Rocks. We booked these tickets in advance but it looked like you could buy them the day of. Be there early in line if you want an outer spot on the upper deck. I personally liked being below deck where you could stand on the back of the boat. They will not let you stand on the upper deck. While at the dock we saw another company that takes you on a pirate ship. That looked super cool!

Pictured Rocks National Lakeshore
View from Pictured Rocks Cruise

Day 7

This campsite was one of the best we have ever had. We decided to spend the day enjoying it, playing in the water and relaxing all day. There is an island infant of this part of Lake Superior so it makes the water super calm in this area. Another hike I wanted to do was Chapel Rock and Chapel Beach. It brings you to a beautiful rock with a lone tree and a beach with a small waterfall. It is about 6 miles roundtrip. We actually saw both on the cruise. We would have gone but out campsite was so good we decided to enjoy it. There are many other waterfalls in this area as well. I also wanted to explore Kitch-iti-kipi. This is a large spring with very clear water. There is a little barge that brings you across it. I believe it is about 10 dollars to get in the state park.

Lake Superior Campsite
Munising Tourist Park Site K

Day 8

Wake up early and make the 2 hour drive to St. Ignace and hop on the ferry to Mackinaw Island. This place is like no other place I have ever been. Only accessible by boat, this island reminds me of a car less little New England. Only transportation is foot, bike, or horse. You can rent bikes right by the dock or rent a horse and carriage. We rented 3 bikes and a burley for Jolene. It is pretty pricey but worth it to see the island. The island is 8 miles long, and we just made the circle around and stopped at sites as we saw them. The houses are beautiful. All hotels and housing was completely booked when I looked but I would love to stay on the island one day. The island is super packed. There are many restaurants if you get hungry. We chose to grab a small snack at the small corner grocery store to save money. There is a beautiful park at the elementary school with an amazing view of the water and Mackinaw Bridge. We caught the evening ferry back and camped at Wilderness State Park Site Y for the night which was only about 20 minutes from the ferry dock.

Mackinac Island
Biking around Mackinac Island

Day 9

Traverse City was out next destination. It was about 2 hours from our campsite. Traverse City is a pretty big town. We camped in Traverse City State Park Site 161. Perfect, large spot with a water view and right by the playground. There is also a bridge to go over the highway to the East Bay Beach. We actually splurged on lunch and at at The Filling Station. They had amazing pizzas with a really good beer selection. It is also kid friendly.

Sleeping Dunes National Lakeshore
Sleeping Bear Dunes National Lakeshore

Day 10

Our morning started with a sailboat tour in East Bay. This was super cute and fun for the girls. On this particular cruise they served ice cream. They have others where they serve alcohol, dinner, or brunch. Greilickville Harbor Park is across the street and it is an amazing little park right on the water. There is a beach, swings, volleyball net WITH a volleyball, and a playground. We spent the afternoon here then ate at The Filling Station again for dinner this night. One of the locals at the restaurant suggested a hike at the Sleeping Bear Dunes off Spiller Rd. It is not as crowded and brings you through beautiful wild flower fields before getting to an amazing view. It is about a 20-30 minute hike to get to the view. Definitely worth the hike.

Traverse City
Tall Ships Co Sailboat Tour

Day 11

Start the day early to make the 5 hour drive to Chicago. We arrived about 1:30 at the hotel. I got the hotel for about $150 on Priceline Express Deals. It was the W Lakeshore on the Magnificent Mile with a view of the water and navy pier. Parking at the hotel is $60 a night or you can go across the street and pay $30-$40 for the night. Out first stop was Lou Malnati’s Pizzeria. Call ahead and order especially if you are hungry because the deep dish pizza takes 45 minutes to cook, but it is definitely worth the wait. PRO TIP: If you are waiting for a table you can also order your pizza at the front desk while you wait for a table so the wait is shorter once you sit. After we walked to Millennium Park to see The Bean. There is also an amazing kids play area. There is a huge playground with tons of slides, swings, scooter track, rock climbing, and a bunch of other activities. After we walked along the Riverfront. This is a super cute picture spot. There are a ton of little bars/restaurants along the river that looked super cool to hang out at. They were packed with locals. We found a super cute coffee shop/small grocery store called Foxtrot. It had coffee, wine, liquor, fancy beer, ice cream, fancy snacks and grab and go meals. We hung out here for a little while. For dinner we had Seoul Taco. I highly recommend Seoul Taco. It was one of the best meals I have ever eaten. It is a fusion of Korean and Mexican food. The flavors were amazing. We ordered the Pro Tacos, Gogi Bowl, and the Gogi and Waffles. Everything was amazing.

Chicago
Chicago

Day 12

Our last day was pretty short. We spent the morning in Chicago. We walked to Navy Pier, drove by Wrigley Field, and ordered a pizza from Pequod’s. This one was good but I liked the first one better. We stopped at Pipeworks Brewing Co on our way out the city. They had great beer and really cool cans. They said their taproom will be opening soon. Our flight was that evening. It was a 1 hour drive to the Milwaukee airport for our flight home.

Chicago Deep Dish Pizza
Pequod’s Deep Dish Pizza

Have you ever been to the Midwest/Great Lakes region? Tell us your favorite stops and spots! This is definitely on our list to visit again.

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