All About Our First Big Roadtrip With Kids

MY PLAN for our first long roadtrip with kids: Leave for first leg of trip to Wisconsin at 8 am. Stay on the road until we are past Chicago. After that, get a hotel room and spend the night.

Remember when I wrote that I needed to lower my expectations when traveling? Yeah, I forgot to do that.

Reality of Taking a Roadtrip With Kids

I had to push back the start time until 9 am when we decided to take the pets to be boarded and pick up the rental car the morning we were leaving. My husband left late to take in our animals, so I figured we’d be leaving closer to 9:30. He returns and calls the car rental company.  There are NO CARS available yet.

What?! We had a reservation!

I start to freak out internally. “We aren’t going to make it to Chicago until rush hour,” I think.  We are supposed to call back in 45 minutes. Husband disappears for awhile. That was probably for the best. He was packing. The kids and I play outside. It’s threatening rain.

I say to the kids, “it will rain at the most inconvenient time.” They ignored my prediction.

Flash forward To The “Free” Upgrade

When my husband pulls into the driveway with the rental, I was excited to see that it was a SUV. “Free upgrade,” he says. I wasn’t sure if this was worth my sanity. It’s not raining yet. He pulls out one car seat and starts to install it into the rental car. It starts to rain.

Just as I predicted.

Actual time of departure: 12:22 PM, eastern standard

My original plan was to break the driving into two days. However, even with our late departure time, we decided to push on through to our destination. The kids did really well on the very long drive. We had a few toys and also two reasonably priced tablets so they could play games. We arrived at our destination in Wisconsin at 11:30 pm.

The kids didn’t sleep very much while on the move, so I thought it wouldn’t take long to get them settled for bed.

Wrong. I was so very wrong.

They would not go to sleep the first night. I had that expectation. I knew it and it was part of the reason we decided to drive the whole way in one day. We hoped for only one bad night, instead of two or more. It was 3 am before they went to sleep! Torture, man.

The good thing?

They slept until 8:30 am!

We were fairly refreshed. We had breakfast, went swimming, and took the kids in the car for a nap (and also to do some errands and visiting). Naps were short, but long enough to keep their moods stable. We visited with family and they had a sand pit and digger toy in the backyard. The kids loved this! If we hadn’t had the option to visit my cousin’s home, we would’ve gone to a park with a playground.

The view from grandma's magical sleepy dust room. The pool. The glorious pool! The smaller one in the foreground is the hottub. It was perfect! I'm pretty certain the hottub was the reason I was so mellow.

The view from grandma’s magical sleepy dust room. The pool. The glorious pool! The smaller one in the foreground is the hottub. It was perfect! I’m pretty certain the hottub was the reason I was so mellow.

The Festivities Start

We were invited to a pizza and beer party that evening. It was in a restaurant with nowhere for the kids to play. Our kids were starting to meltdown. The other little kids were melting down. We left pretty early and headed back to the hotel. My mom and sister were also scheduled to arrive later in the evening and I wanted to be there for them. I was excited! It was also an excellent way to get the 2 year old into a carrier on my back (check out these toddler carriers), so we could “go see grandma when she gets here,” while also calming her down for sleep. Actually, I think the carrier helped prevent a pre-bedtime meltdown for both of us.

My extended family members ended up taking over the lobby to chat and drink that evening. I still had the two year old on my back. She was so tired and nothing was working to get her to sleep. We tried hallways, our room, and even outside.

Grandma’s Magical Sleepy Dust

“I want to go to grandma’s room,” she peeped. Since my mom and sister were in the lobby, their was empty, dark, and quiet. Only 90 seconds later and she was asleep. My husband and son were in our room, so I was able to lay her down and go back to the lobby and enjoy some conversation with my family!

As far as traveling goes, this wasn’t an exploration mission. We went to Wisconsin solely for a family wedding. I had visited 20 years prior and remembered it to be a beautiful place. I wanted to explore and also visit with the family that was gathered. There were more expectations placed upon us, in that regard. Exploration was very limited due to our obligations.

The kids adjusted surprisingly well to all the changes thrown at them in the first 2 days. It was a far cry from our first roadtrip a year prior.

Wedding Day!

On the day of the wedding, we were able to keep to a routine close to our normal one. Thankfully, the wedding was scheduled after our usual nap time. We went swimming after breakfast and napped in the car after lunch.

We arrived at the wedding 3 minutes late. I despise being late because it generally stresses me out. However,  the kids weren’t waiting around for the wedding to start and they didn’t have time to get bored! They were able to enjoy it and sit through the entire thing. I was really surprised. I did bring a few toys for them and it helped. We also sat in the back of the church, just in case we needed to make a quick exit.

Colorful ninja toys that really paid for themselves.

Ninjas and superheroes. Totally wedding appropriate, right?

As if it had been planned for the children’s comfort…

After the wedding, there was a long break before the reception and we went swimming again. Another huge advantage for us was staying in the same hotel as the reception was being held. If this is at all possible for you, it is worth it. My kids ate dinner, played with a cousin who is a mom of six, and then were ready to leave. This was my side of the family, so my husband took charge of the kids and took them upstairs for awhile.

My daughter needed me after a bit, but that was easily solved. I put the two year old in a arrier on my back and danced with her. When she seemed ready to sleep, we went to Grandma’s room again. Grandma’s room’s sleepy magic worked a second time! After I took her to our room, I was able to return to the reception. It was glorious.

This is the kind of pictures you can take when you don't have babies attached to you, so you have a few sips of a drink. I'm thinking of becoming a professional wedding photographer!

This is the kind of picture you can take when you don’t have babies attached to you, so you have a few sips of a drink. I’m thinking of becoming a professional wedding photographer!

We returned home the following day and decided to once again do all the driving in one stretch. This worked very well for us again.

It’s a long drive to Wisconsin…

My husband confided that he had dreaded the trip. I was concerned at the beginning, when we started out the trip so far off my plan. The trip exceeded my best case scenario expectations, even with one child waking up and screaming in the hotel every night around 2 am (because that happened and I want you to know it wasn’t all roses and sunshine).

What worked well:

Our children’s ages. They are old enough at ages 2.5 and 3.5 to play and entertain themselves for short stretches. The electronics were a factor in making the long car rides and the evenings at the hotel go well. We don’t allow them to play these at home, so the kids were excited to play their games (and no judgement from me if you do use games and such all the time – there are plenty of positive studies on screen time for kids).

Our room was also a little bigger than a usual hotel room and there was space to play.

What didn’t work so well

We didn’t actively schedule time for play with our cousin’s kids and it didn’t come together. The activities with family were adult-oriented. I would’ve liked to have a babysitter, but that wasn’t an option for us.

Celiac concerns

We ate a lot of fast food. My usual go-to is Wendy’s. I discovered Dairy Queen has a celiac menu, so I got a Blizzard and I shouldn’t have. After the fact, I realized that I couldn’t control for the person ahead of me having a gluten item in their blizzard. The Dilly bars are gluten free and I would choose that next time (as always, reconfirm every time, because ingredients can change).

The hotel had a hot continental breakfast, but I ate Chex cereal and milk. If I can’t verify the ingredients, I don’t eat it.

I found out in advance which items at the wedding reception would be safe for me. This is worth doing, if possible, so you won’t go hungry. The staff didn’t seem to know about celiac, so I was very glad I asked the bride* well in advance. In fact, because I asked about it, the caterer made all of the salads with gluten-free dressing. I’m so thankful for people who take food restrictions seriously!

*Not all brides will be able to be so accommodating, but it is better to know in advance if you’ll be able to eat the provided food.

Where did you go on your first long trip with children? Did you travel when your kids were babies or toddlers?


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