I’ll admit, I’ve always had a soft spot for road trips. Growing up, I remember us taking tons of road trips across the states, from as far away as Kansas to South Carolina, Georgia to Texas, and everywhere in between (we never made it to the west coast though). Road trips as a kid are typically different though than those same road trips as an adult. As a kid, it’s all about the fun and games, the memories, and how much you can annoy your siblings. For the adults, it’s a lot more about the planning and preparation to ensure we arrive at our destinations in one piece.

Still, when we set a goal at the beginning of the year as a family to have at least one epic road trip, we didn’t know how it would turn out. I was just hoping that it would enable us (ok, me) to capture a bit of the magic of my road trip days from my childhood. Fortunately, in many ways it lived up to the hype in my head and in others it set a new standard of what I expect going forward. Here’s some of the lessons I learned from this summer’s epic road trip.

Lesson # 1: Find consistent alone time when you’re traveling with a crowd

In my case, our family of 6+ whichever extended family members are traveling or staying with us at the time is a crowd. Alone time comes at a premium, especially if you’re trapped in a vehicle for hours on end, or sharing a small accommodation for a night on a long road trip. Getting up early, walking around, and simply being by yourself are crucial. One morning while staying in a hotel in Louisville, I got up early (and by early I mean 8:45am…) and as quietly as I could, tip-toed out of our room while only managing to wake up 2 of the girls. I took my journal and a book and went downstairs to a quiet outdoor space to sit, read, and reflect.

Little did I know that immediately after leaving, the door closing woke up everyone in the room. At any rate, thirty minutes later I returned refreshed to find my family had went down to breakfast without me. During the days we were in Chicago, I woke up each morning, made some tea, and sat out on our AirBnB’s balcony looking down at the traffic below while I had my morning quiet time. Afterwards I was ready to face whatever shenanigans awaited me for the day.

Lesson # 2: Make time for shenanigans

So, usually we bring our bikes on every trip that we take. Sure it takes some effort to load up the bike rack with 5 bikes (and it can be a pain driving with an obstructed rear view), but I love having the option of biking around wherever we visit. This time we made the executive decision to leave the bikes home (read: my wife said no). Bummer. But, I was determined to make the most of it, especially once we got to Chicago, the pinnacle of our trip. Who knew that Chicago was known as such as bike-able city (for about 3-5 months out of the year)?

Well, not willing to miss out on any of the fun, I decided that it would be a great idea (read: terrible for everyone else) if we rented bikes to bike the length of Lakeshore Drive. I mean, really, while in Chicago, shouldn’t we do Chicago things? So, I rented the bikes, and even thought I’d rented the appropriate carrier for the little girls (one just like the one I left at home regretfully with our bikes). Upon arrival at the Navy Pier to pick up our equipment, I learned that instead I’d rented something called a tagalong, which essentially means that I would be riding a tandem bike with my 5 year old daughter (a newly minted bike rider by the way), and my wife would have to strap our 3 year old to her bike (something she’s never done) and the older two girls would have to ride semi-adult bikes (new for them too!). No one, and I mean no one, was happy with my executive decision as we stood in the 90 degree weather getting strapped into our helmets and bikes.

I can tell you that it didn’t start pretty (the girls crashed into each other within the first 5 minutes and London was more powerful than I thought she was as a peddler so we nearly ran off the path several times ourselves), but after about a half hour of riding folks were starting to get the hang of it. And despite all the glaring and mean mugging that I endured, I think that the girls appreciated the experience of doing something that scared them (or at least I think so…time will tell!). Little did I know that I would quickly be doing the same.

Lesson # 3: Do something that scares you

Ok, so here’s the thing, I don’t like elevators. I tend to avoid them unless absolutely necessary. Is it a phobia? Perhaps. Definitely. Maybe. Whatever. If given the choice between stairs and an elevator in a parking garage, I’m definitely taking the stairs. Well, as you can imagine that’s easy to do when you’re in small building like in our stops in Chattanooga or Nashville or Louisville. But what about big cities like Chicago where it seems every building presents your worst nightmare?

Another fun fact, apparently I’ve hid this kryptonite from my daughters well because they were all shocked to learn that I didn’t like elevators. It started in Louisville, when we stayed the night in a hotel there and our room was on the second floor. Given that it was only the second floor, and our room was literally right next to the stairs, there was a plausible rationale to simply use the stairs even if I had to carry luggage. Elevators got a bit harder to avoid in Chicago though. Fortunately our AirbnB was in only on the second floor so I got off easy there. But the question kept coming up, hey dad, why aren’t you using the elevator? It was getting harder to shrug it off as more convenient to use the stairs when it was clear I was willing to choose struggling to carry luggage up a flight of stairs over pressing a button.

But then came our trip to Navy Pier, where we had to park on the 6th floor of the parking deck (6th floor!) and then our excursion down the Magnificent Mile where again we found ourselves on the 6th floor of a parking deck. That’s where my wife refused to to play my stairs game and instead took the girls on the elevator while I took the stairs. Perhaps it was the fatigue from the day, or the desire not to walk in the dark, urine smelling stairwell of downtown Chicago, Either way, the jig was up, and now I had something to prove. So, at our next stop, my sister in law’s apartment complex, I didn’t even put up a fuss, I simply walked onto the elevator with the rest of the family and rode up to wait for it, the third floor. Such courage wasted for only 3 floors. Though that wasn’t the last time the girls asked me about my elevator riding (you would think that one show of courage would be enough sheesh…), it was my last elevator ride on that trip!

Lesson # 4: Pace yourself, road trips are a marathon not a sprint

I like to think that preparation is my superpower. I like to plan for multiple eventualities and you’ll rarely catch me out and about without snacks, water, books, first aid, whatever we might need. Sometimes what I don’t plan for is simply knowing when to call it. On our first day we were on the road for about 8 hours and that nearly broke us (on the first day!). We had to learn to do better, and that involved making more pit-stops, for longer periods of time. From then afterwards, we stopped every 2-3 hours, for at least 30-60 minutes. Sometimes to eat. Sometimes to use the rest room and walk around.

We finally found our rhythm. Sometimes that meant knowing that if was nearing 8 or 9pm, we’d better make our way somewhere for the evening to rest and recharge. Sometimes that meant pushing back our start time to mid-day to give us a chance to sleep in (thank God for late check-outs!).

One other interesting tidbit, at every stop, like clockwork some older guy (I assume a father himself) would walk up to me and remark incredulously, four girls? Wow! Good luck! So, that became a thing. Meanwhile, my wife was tagged as, the lady with a lot of kids whenever she had the unfortunate task of taking the girls somewhere by herself.

Lesson #5: Be open to learning something new about yourself and your fellow travelers

I learned from sharing a hotel suite that Riley tosses and turns in her sleep like her father. Every time I turned over, I heard her turning over in her bed. We’ve both got restlessness issues.

I learned that when London gets sleepy, she turns into a diva (Samantha’s words). That’s not too surprising. She’s kind of a diva when she’s wide awake as well.

I learned that even if you put the little ones back on the third row of the van, they’re still going to cause commotion, it’ll just be harder for you to reach them now.

I learned that Sloane loves to sing random lyrics, and she gets louder if you turn on music to drown her out.

I learned that Samantha and I still have a lot in common and we like being around each other (whew!). Spending a ton of concentrated time with your partner is a good test of a relationship. Will you run out of things to talk about? How soon will you need some space? On this road trip we found new things to laugh at together and new ways to laugh with (sometimes at) our children.

I learned that I actually like the people we’re raising. I mean, I would actually enjoy spending time with them if I didn’t have to. Olivia is witty and sarcastic, who wouldn’t want to have her on their team? London is hilarious and doesn’t seem to care if you think so or not, if Riley says it, it’s the truth, and Sloane leans so hard into being the baby that it’s stinking cute.

And as for me, well, I learned that I can survive a road trip with my family which is no small feat.

SDW3