Beyond Travel Anxiety: How Family Trips Build Your Story (Even With Toddlers)

It was the end of a long summer break. I had spent most of it toting my three kids to and from the beach, solo. We'd spent some time as a family in Maine, and the kids had done a few weeks of day camp, but by mid-August, I was more than ready for school to start. The magic of summer had worn off, the kids were ready for some structure, and I was more than ready for a break.

That's when my husband's parents invited us to attend a family reunion in Lake George, NY. I remember physically flinching when the invite happened. But the earnest look on my father-in-law's face when he invited us was too sweet to refuse. He couldn’t wait to show off his grandkids to his cousins. He wanted to take them to the arcade and to see the lake.

I had spent almost the entire summer solo parenting the kids, my husband was working in NJ, and just the thought of packing everyone up for a long weekend, fighting traffic through a 5-hour drive on my own with a 9, 7, and 4-year-old was enough to make me weep.

The morning we were leaving, my youngest woke up with a scratchy throat. The sky was thick with an impending summer storm, and it was a Friday... which meant we could expect lots and lots of traffic. We packed up the car with snacks, cozy blankets, our clothes and swim suits, and the kids' scooters. I put on a kid-friendly podcast (no screens to avoid carsickness) and off we went.

We were about an hour past Boston when my little one started crying because she couldn't find her owl. She already wasn't feeling great, and “Owl” was her security blankie (with an owl head). She needed it to fall asleep and she couldn't get comfortable. I had a split second of panic. Could I have forgotten to pack her owl? No way. I would never do that. I moved right on from that thought and passed back a book for her to look at and thankfully she fell asleep.

Traffic started moving, and the rest of the ride was fine. We arrived in Lake George around the same time my husband arrived from NJ and the kids had all fallen asleep in the car, so they were ready for the late dinner reservation with the extended family that evening. Everyone was happy…until bedtime.

My husband was in the hotel bathroom helping the kids get washed and ready for bed, I was laying out jammies and plugging in the sound machine, and that's when I started looking for Owl. My seven-year-old came in and started helping me search through our bags. "Mommy, I think I know where Owl is," she said in a slow and slightly panicked voice, "Sloane had her in the playroom right before we left. She was building a house and I bet she left her in there..."

I almost cried. I was exhausted from driving, I didn't want to come on this trip anyway, and now we'd be up all night wishing for Owl. Traveling with the kids was getting to be too much...

My little one came out of the bathroom, climbed into bed, asked for Owl, and I broke the news. She cried, and then suddenly, my sweet nine-year-old had an idea. He took some rubber bands, a washcloth, and a marker and made her "Owl's Cousin." By some grace of the universe, it worked. She happily clutched "Owl's Cousin" and fell fast asleep. For the remainder of the weekend, she proudly held Owl’s Cousin in one hand and her Papa's hand in the other. We went from the arcade to the candy store to the pool and back again. The kids had a blast, and more importantly, their grandparents were so happy we made the trip. We all look back fondly on that weekend and, eight years later, we still talk about Owl's Cousin, the really fun playground at the hotel, and scootering through the puddles in the rain.

I've spent the years since then redefining what successful family travel looks like. It's not about checking off the must-see attractions or maintaining the same rules and routines you have at home. It's about creating a different kind of rhythm—one that becomes a shared adventure that changes all of you in unexpected ways. My in-laws have since passed, and that was one of the last trips we took with them. I am so glad we said yes.

And that's the thing about traveling with children—behind the logistics, exhaustion, forgotten comfort items, and occasional tears lies the possibility for connection that shapes your family story. These moments become the memories your children carry into adulthood, the stories they'll tell their own children someday.

Travel exposes children to different cultures, environments, languages, and ways of living that simply can't be replicated through books or screens. Is it a privilege to travel with kids? Yes. Can it be challenging? At times, yes. But I wholeheartedly believe that successful travel with kids is one part preparation, two parts mindset, and a thousand percent worth it.

Over the years, our family has developed traditions and approaches that have transformed our travels from endurance events into genuine adventures. I'd love to share some of these with you—both the small rituals that have become treasured traditions and the strategies that have saved us from countless meltdowns (both kid and parent kinds).

Here are a few of our favorite travel traditions that we’ve returned to time and time again:

Night swimming in the pool with glow sticks and goggles

There’s something so special to little kids about going down to the pool after the sun goes down, it’s such a memory maker.

Dinner at the pool or beach

Skip the hurried showers, and overtired kids and instead stay late at the pool or the beach. Order food to your loungers. Let the kids graze and keep playing while you and your partner sit and eat. My husband loves to try the local food wherever we go, so this was always a great way to enjoy it without carting overtired kids around.

Passing on the Fun

This one is kinda weird, but for some reason my kids loved doing it. At the end of our trip, the kids would gather any pool toys, inner tubes, sand toys that we picked up along the way and pick another family with kids who just arrived and pass it on to them. They felt so big and important offering up their toys, and were always met with such happy, gracious smiles from others.

Get Ready to Transform Your Own Family Travel Experience:

After years of trial and error, I’ve put all my hard-earned knowledge into “Family Travel Decoded: Your Realistic Guide to Traveling With Kids” - and I'd love to share it with you.

Here’s What's Inside:

• Pre-trip planning strategies that set you up for success before you even leave home

• Essential packing tips (including what to bring in your carry-on to avoid meltdowns)

• Screen-time strategies that won't leave you feeling guilty

• Practical approaches to managing big feelings during travel days

• Creating comfort zones in unfamiliar places

• How to make sure parents get a break too (because it should be a vacation for everyone!)

I hope you enjoyed this blog! If you want to keep up with more Workspace for Children content, follow along on Instagram by clicking HERE.

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TIPS FOR NYC WITH KIDS

It’s Spring Break over here, so there is no school this week.  The kids and I made a list of things we would want to do with our time and NYC was high on the list.  We are very lucky to live a short train ride away (about 50 min.) so that made it an easy YES.  

We had loose plans to take the train to NY Penn Station, walk to Madison Square Park, play and eat lunch, and then head to the Math Museum.  But… the day was too beautiful to spend inside.  Here’s how it all went down. 

The big kids walked to the train station and Sloane scootered.  She is six, and too old for a stroller.  Her tiny little legs have a hard time keeping up with the big kids sometimes.  Before we left, we talked about bringing the scooter.  We called it her “commuter scooter”  and we chatted about how riding a scooter in the city is WAY different than taking runs up and down out street.  It’s different because we didn’t wear a helmet, which is usually a non-negotiable.  It was different because instead of riding independently, she had to stay right next to me and if she wanted, I would pull her along.  It’s so easy to “tow” your child with THIS scooter.  Two feet on, and I can easily pull her along and steer.  

Sloane’s face when she saw the subway….

We took an 10:38 train in.  We got to the station a little early and I let the children each choose lifesavers or gum for the train ride.  I know they’d be fine with nothing, but for me, it’s the little things in life, and I like to make our adventures special.  We rode the train in and walked across town to Madison Square Park and ate at Shake Shack.  The kids had never been there before, and it did not disappoint.  Next stop in the plan was to go across the street to Mo Math, The National Math Museum, but the kids asked to go to the playground first.  Sure, why not (see me being flexible over here?!)?

The kids played and I sat in the sun, feeling good.  I watched them run, squeal and climb, when I suddenly decided that the weather was too perfect to head inside to a museum.  Their favorite NYC playground is the one in Union Square but I wanted to try something new.  I did a quick Google search and decided on The Ancient Playground in Central Park. I called the kids over and asked them if they still wanted to go to a museum or if they were up for a new adventure.  Guess which one they picked?

We headed off to the Subway and hopped on.  It didn’t occur to me before, but Sloane had somehow never ridden the Subway! She was mesmerized and it was the absolute cutest thing.  Nate and Ruby played their favorite game of “spot the rats” in the tracks while Sloane asked me a billion and one questions about how the subway works.  We got on and the train was pretty empty.  The kids seriously had the best time holding on and riding the bumps.  I fought my inner germ-phobe and went along with it.  I am so glad I did.  They LOVED it.  

It was an easy trip into Central Park and we headed into the playground.  Kids were off and running and again, I was sitting on a bench in NYC on this beautiful Spring day.  Besides a few hiccups with Sloane, we could’ve stayed for hours, but I know from experience that it is SO important to quit while you are ahead.  I knew we still had to get back downtown and get on a train back to Maplewood before the evening commute began.  I enticed them with ice cream cones and off we went.  

We made it back down to Penn Station and as luck would have it, a train to Maplewood was boarding.  Thank goodness, because at that point we were all getting a bit tired. We made it home in one piece and I am so grateful for another adventure in the books. 

Here are my quick takeaways:

1. Front end load. Pack snacks and water, wipes, and layer clothing.  Knowing that basic needs are easily met means you can relax.

2. Follow your child’s lead.  We literally went to the city to play at the playground.  Could we have done that at home? Sure, but it was way more special this way.  The kids had a blast and since they were happy, my job was much easier.  

3. Quit while you are ahead.  Remember NOT to stretch them to their limits.  It can be tempting to stay when you are having fun, but ending on a high note is so much better.  

4. Have a plan but be flexible. We switched it up today and instead of the museum, we hit up a new playground.

5. You know your child best.  Think about what you will need to do in order to meet their needs and keep them feeling successful.  For us, this was bringing along the scooter for Sloane.  I knew she’d feel tired and frustrated trying to keep up on foot.  The scooter was a total game changer.  

Get out of your comfort zone and adventure with your kids! It will not always be as smooth as today was, but it is SO worth it.  The adventures that don’t go well are learning experiences for everyone, and they will only make your next adventure easier.  

I hope you found this post helpful.  If you want to hear more from me, please be sure to subscribe to my blog and join the conversation over on Instagram.  

-Lizzie