Our First Family Road Trip: 5 Things We Did Right and 4 Lessons We Learned the Hard Way

In mid-September, we finally took the plunge.

After years of talking about how we wouldn’t let having kids stop us from traveling, M and I packed up our two young children and hit the road. Our plan: a weeklong family road trip through New England.

We had no idea what to expect. Our son, E, was a little over two and a half, and our daughter, S, was only five months old. How would they handle the long drives? What would we do if it rained and we were stuck indoors for days on end? Would E, who had been having some sleep troubles of late, do okay in unfamiliar beds? How many diapers should we pack, anyway?

With our SUV full of clothes and supplies and our hearts full of cautious optimism, we set off on a Friday night for a five-and-a-half-hour drive to our first stop, Rhode Island. What followed was a week that exceeded all of our expectations and a first family vacation we’ll never forget.

Along the way, we were happy to find that we had made some good decisions that set us up for success on the trip. We also learned a lot about how having young children changes the dynamic of travel and what we will make sure to do differently next time.

Today, I want to share five things we did right on our first family road trip as well as some of the lessons we learned on the road. I hope that our experiences help you in planning your own family road trip! Check them out, and I’d love to hear about your experiences traveling with kids – or your questions about it – in the comments!

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Did It Right: I Lowered My Expectations

While M and I usually have a lot of goals for what we want to see and do on vacation, I embarked on our family road trip trying to have almost no expectations at all. In fact, I booked almost nothing ahead of time: only our accommodations and the cog railway up Mt. Washington. I did my research as usual and had a good idea what was available in each of our destinations, but overall I tried to hold all plans loosely and just let the trip play out as it would.

For the most part, it worked out really well. By going into the trip with a “We’ll see how it goes!” attitude, I wasn’t disappointed when we didn’t cover a lot of ground or when we changed plans last-minute according to the kids’ needs or moods. (For example, we originally planned to stop in Portsmouth, New Hampshire on our drive between Boston and the White Mountains, but we abandoned the plan when both kids were still passed out as we were approaching the exit. They ended up sleeping almost the whole way to North Conway, enabling M and I enjoyed the peaceful, scenic drive.)

Since I had almost no expectations, there weren’t many real disappointments and we were able to genuinely enjoy each experience. We could relax (as much as one can with two small kids) and just enjoy the ride.

Lesson Learned: Expect a Few Meltdowns

If you have a toddler, you’re no stranger to meltdowns and tantrums. (If you are, please tell me your secret.) While on the whole E is pretty flexible and easygoing, he’s not immune to the occasional tantrums of toddlerhood. Insert a lot of new stimuli, some discombobulated sleep patterns, and unfamiliar environments, and a tantrum or two was practically inevitable.

(For example, we planned the aforementioned train ride up Mt. Washington for E, lover of all things in motion, but he broke down on way there when he found out the train would be going up a mountain. Your guess is as good as mine as to why this small fact bothered him so much, but by the time we arrived he had an absolute blast on the train. Toddlers, am I right?)

While overall E did great and we really didn’t experience many abnormal behavioral issues, I now have a much better understanding of the impact these changes and new stimuli can have on a toddler’s developing brain and body. We learned to have an extra dollop of grace for our little guy, as well as to communicate as much and effectively as possible to prepare him for what was coming next.

Did It Right: Our Packing Strategy Worked

Another area where I thought we did a good job was in packing. Thinking about the amount of stuff that four people would need over the course of a weeklong road trip – including a baby, which notoriously comes with a lot of stuff – was a bit overwhelming at first.

We tried to keep our packing as minimalist as possible as for the most part we succeeded. The back of our vehicle was full, but not jam-packed, and in the end there wasn’t much that we wished we had brought and we used almost everything we did.

Packing strategies for a family road trip deserve a lot more space than I can give them here, so don’t miss my lists of road trip essentials for babies and toddlers, as wells as the best travel gifts and gear for young kids.

Lesson Learned: Don't Forget the Night Light

One exception to my packing comments above, however, was that we forgot to bring a night light. In all my pre-trip planning and list-making, I never even thought about it.

Cut to us arriving to our first Airbnb in Rhode Island. It was well after 1:00 AM, and we had just endured a long, traffic-filled drive from the Philadelphia area. We had unloaded the car, set up the pack and play for S, blown up E’s travel toddler bed, and were all ready to turn in for the night. We switched off the light in E’s room… and realized that it was pitch black. Forcing the kid to sleep alone in a lightless, unfamiliar room was not an ideal way to start off our vacation.

Thankfully, our awesome hosts had put a night light in the bathroom that we were able to repurpose during our stay, but in the next two destinations we made do by leaving hall lights on with E’s door cracked. Next time, we bring our own.

Did It Right: We Booked Accommodations with Multiple Bedrooms

When considering where we would stay in each of the places we were going to visit, it didn’t take long before we ruled out standard hotel rooms. Our kids go to bed between 7:30 – 8:00 PM on a normal night, and M and I didn’t want to spend our evenings sitting around quietly in the dark while they slept. We also figured both kids would sleep better in separate rooms where they wouldn’t be distracted going to sleep or wake each other up in the middle of the night.

After checking different hotels, resorts, and other rental properties for suitable room configurations, we ended up booking three Airbnbs with two or three bedrooms each. Although it cost us more money (geez, Airbnb has gotten expensive!), it was absolutely worth it. M and I were able to enjoy our evenings together, the kids didn’t wake each other up, and we even had the benefit of some extra play and living space during the waking hours.

PS: Don’t miss my list of the pros and cons of Airbnb to help you plan your next trip!

Lesson Learned: Be Prepared to Do Laundry

I’ve never done laundry on a weeklong trip before, but on our first family road trip I did four loads. Between S’s many carseat blowouts and the general proclivity of toddler boys toward dirt and mess, we were ready to do laundry by our second stop.

Thankfully, two out of our three Airbnbs had in-unit washers and dryers, but we did not come prepared to use them. We ended up grabbing a small bottle of laundry detergent from the nearby grocery store. Next time, I’ll make sure to toss a few laundry pods into our suitcases so we don’t have to haul around a jug of detergent.

We were also fortunate that with naps and early bedtimes our need to do laundry didn’t inconvenience us much. Plus, we went home with half our clothes already washed and ready to be put away! That said, I’m definitely hoping that future trips won’t involve multiple wardrobe changes per day!

Did It Right: We Built a Good Itinerary

Another of our wins for this family vacation was that – at the risk of sounding boastful – we knocked it out of the park with the itinerary. New England was gorgeous and had tons of great things to do, including lots of opportunities to expend toddler energy. It was new and exciting to M and me while still being comfortable and easy to manage. And we built in lots of time so that we didn’t feel rushed and could move at a family-friendly pace.

Also, by choosing to do a road trip versus flying or taking other forms of transportation, we had lots of control over our schedule and could easily adjust according to our family’s needs. All of these factors combined to make a really memorable trip. It’s so gratifying that even now, nearly two months after we returned, E is still bringing up “our cation” on an almost daily basis.

I’ll be sharing the full itinerary with you in early 2022, so be on the lookout!

Lesson Learned: It's Hard to Avoid French Fries

It probably shouldn’t have surprised me how challenging it was to balance E’s diet on the road, but it did. Despite my best efforts, it felt like the kid ended his vacation sorely lacking in the fruit and vegetable department.

At home, we tend to eat out about once a week, so it’s no big deal if E has some French fries, chicken nuggets, or a plate that’s a little lacking in color for one night. On our road trip, however, we were eating out two to three meals per day, and we quickly learned how un-varied and lacking in nutrition most kids’ menus are. (And expensive! When did kids’ meals get to be $9-$14 dollars?!) It seemed that every meal came with fries, and we were mostly stuck with the same options: grilled cheese, chicken fingers, burger, and macaroni and cheese, with the occasional pasta, slice of pizza, or cheese quesadilla thrown in. It definitely became challenging to get E the fruits and vegetables he needed and to fill his belly without having French fries at every meal.

Our best solutions for this particular issue were to vary the kinds of cuisine we ate when possible and for M and I to share from our own plates as much as we could. Still, it was a long time before I served E another French fry after we got home!

Did It Right: We Went on the Vacation

For a lot of people, the thought of taking young kids on a vacation – especially one involving long car rides – can be really intimidating. Life with little ones can be hectic and unpredictable enough without adding in unfamiliar places, new foods, lengthy drives, and other variables. Even as a travel professional, I was a little nervous starting out on our first big adventure.

In the end, though, I am so glad that we took the plunge and took our kids on this first family vacation. There were a few less-than-Instagram-perfect moments, but overall we had an incredible time together. We saw a gorgeous part of the country, stretched and grew our kids through new experiences, and spent invaluable time together as a family.

I’m also a big believer in the idea that the more you do something in parenting, the easier it becomes. Here’s hoping that by starting early and continuing to prioritize spending time together in this way, travel will only get easier and more rewarding as our children grow.

So if you’re considering taking a family vacation with little ones but are intimidated or worried it might not work out, I say go. To borrow a well-known slogan, just do it. It might not be picture-perfect all the time, but it will be worth it.

And don’t forget, I’m here to help.