Aren’t you excited for a post that isn’t about Disney? I love Disney, but I was ready to move on, too. These planning posts are going to all start off pretty similar. When we begin planning our trip, the first thing I do is research.

1. What states haven’t we visited?
2. Should we fly or drive?
3. How many states can we realistically fit in?
4. What is the route to get to each place?
5. What are the things we want to do at each place?

I create spreadsheets like this that I fill out as we add detail. Is it a lot? Yes. Does it work for me? Also, yes.

For our summer 2025 trip, it started out with two trip options – fly into Seattle and do a loop of states there, or drive north (actual direction not area of the country) and visit some Midwestern states.

We didn’t start planning this one early enough to benefit on finding cheap, or even affordable flights, to Seattle. It’s not a cheap place to fly into from this region already, and the flights were VERY expensive this close to the trip. I wish I could remember exactly, but it was weeks, and not months, before we left that we started planning. Why? Travel volleyball. Enough said.

Midwestern states it was! We decided to drive north and get: Nebraska, Iowa, South Dakota, North Dakota and Wisconsin. Each state was easily drivable of each other with only a slightly long drive home. When looking at things to do, the only real things we knew that were for sure on this was Mount Rushmore, Mall of America and Milwaukee.

Knowing the states and those three things, I sat down with my trusty Excel spreadsheet and mapped out a route that was realistic and doable for us. On a trip where we stop at several places and states, we typically take about ten days. That gives us time to not rush and add things to the to-do list if we run across something that looks fun or interesting.

We decided this would be our schedule:

• Leave on Wednesday, May 28 and drive to Omaha, NE
• Thursday, May 29 drive to Keystone, SD
• Saturday, May 31 drive to Jamestown, ND
• Sunday, June 1 drive to Minneapolis, MN
• Wednesday, June 4 drive to Milwaukee, Wi
• Saturday, June 7 drive home

Where is Iowa on this list? Well, remember the rules? You have to at least stop and do something in the state and airports don’t count. Iowa was a stop, not a destination. We stopped and got snacks and viewed lots and lots of farmland along the way.

As I started researched South Dakota, I found a lot of blog posts about Badlands National Park. We decided to add it as a waypoint on our way to Keystone. It was about 6.5 hours from Omaha and a little less than 2 hours to Keystone from the Badlands. We decided to add it as a hiking stop for the afternoon. Let me be clear – you aren’t going to hear me say that often – a hiking stop. This girl doesn’t love a hike.

When researched Keystone, I discovered Custer State Park and the Black Hills. Because I’m not a hiker, I found the 1880 Train that ran from Keystone to Hill City and back. I booked us tickets on that. A great way to see the Black Hills and not have to hike! I thought I cheated the system. I did not. Just wait for the trip recap. We had heard that the best time to visit Mount Rushmore was in the evening and watch the lighting ceremony. We made plans to ride the train in the morning/afternoon, explore Keystone and visit Mount Rushmore Friday evening. Then we’d drive through Custer State Park on our way to North Dakota.

North Dakota was a challenge. We had originally planned to stay in Fargo, but it was their annual race weekend. We didn’t want to pay the expensive prices for hotels since it was an event weekend or have to deal with the race route on our way out of the city. I began searching for anything cool or fun. I’m sorry, North Dakota, but, ummm…. I thought we might could stay at a ranch and go horseback riding. It was either insanely expensive or you had to bring your own horses. I did find these cool covered wagons that had been made into yurt-type things, but that was on the opposite side of the state. I did find one thing, however. Jamestown – home of the World’s Largest Buffalo Statue. What’s a road trip without at least one cheesy attraction?? Jamestown, here we come.

Next up: Minnesota. We knew we wanted to visit the Mall of America, so Minneapolis was our primary destination. While researching other things to do, I found where we could white water raft. The place wasn’t far from Duluth, MN and Duluth sat right on Lake Superior. New state and new great lake! Sold. Our amended scheduled looked like this:

• Leave on Wednesday, May 28 and drive to Omaha, NE
• Thursday, May 29 drive to Keystone, SD
  • Stop at Badlands National Park to hike
• Saturday, May 31 drive to Jamestown, ND
  • Drive through Custer State Park
• Sunday, June 1 drive to Duluth, MN
• Monday, June 2 drive to Minnesota
  • Stop to white water raft
• Wednesday, June 4 drive to Milwaukee, Wi
• Saturday, June 7 drive home

Lastly, Milwaukee. This one was easy to plan. Since it was a walkable city, for the most part, we picked an area and just decided to do whatever in the moment. We knew we’d be tired and so we decided to play this part by ear.

Now that we had our states, our route and our major activities, we started finding places to stay. When I’m finding places, or we’re on a trip like this, I look for and consider several things. If it’s more than one night, I typically attempt to find an Airbnb or Vrbo for a couple of reasons. It’s always good to have some space. We’re in close quarters in a car and I like to spread out and have some quiet. Most important – laundry. I make sure to find a place where we can do laundry. It helps us not have a ton to do when we come home, but also helps keep our packing to a minimum. I’ll talk a little more about packing in another post. If it’s a one night stay, I typically find a hotel.

• For Omaha, we stayed in a hotel in a walkable part of the city.
• In Keystone, we booked this cabin. We loved it!
• In Jamestown, it was a hotel. There weren’t a lot of options here.
• In Duluth we stayed here at Fitger’s Inn. Highly recommend!
• In Minneapolis, we booked this house. The theming! It was so cute and so fun! Absolutely would stay here again.
• In Milwaukee, we booked this apartment. It was a great location. This was another great place.

Up next: food. You know what I discovered? Very few places would require reservations. And with as few set-in-stone plans as we had? We just decided to wing it. We ended up researching places as we were driving. Honestly, it was great this way. No pressure to stick to a plan and it sometimes helped pass the time. There was a lot of car time.

Lastly, transportation. Sometimes on trips, we take my car. Other times, we rent a car. It depends on the number of people going with this, and the amount of stuff required. We like to rent cars when we can. We can usually make it in a small SUV that gets way better gas mileage than my car gets, and it puts the miles and wear and tear on a rental. We decided rental.

That, my friends, was our quick trip planning. All of this was done within a Saturday. It took the whole Saturday, but it was worth it. I’m about to start thinking about this year’s vacation, but it’ll be down to the wire like this trip. Travel volleyball, man. It’s not for the weak.

Until next time: Stay curious, stay caffeinated, and stay a little LindSwept.