With a little one, I’ve learned that if I don’t plan to leave the house beforehand, I just won’t. There are SO many excuses to pull from: It’s cold, it’s dark, it’s rainy, there are chores to be done, we’re already deep into play, I think the flu is going around, it’s probably too much to fit in, I’m tired, well now it’s naptime…
The same is true of longer trips. In our house, trip planning falls to me (yes, typically a female-coded assignment, but as someone who is a travel writer and who worked at Tripadvisor for several years, my partner defers to my expertise here). And so while I have a host of new year’s resolutions, which I’m sure surprises no one who regularly reads this newsletter, I also spend a lot of time reflecting on what worked and what didn’t in the last year of toddler travel.
Manifesting long Maine summers, the way life should be!
The tricky thing about this is…each year has been completely different, stage-wise, activity-wise, capability-wise. And so one event that worked in 2024 (a very adorable night-lights Halloween walk) became a disaster in 2025 for reasons I still do not understand. On the flip side, in 2025 we have been able to travel further, for longer, and with more “different” experiences—art museums, nice restaurants, live music, actual tourist attractions instead of just playgrounds—which has been rewarding all on its own.
Set the right expectations ahead of time.
Here are my wishes for you:
May you experience pure joy and wonder watching your toddler experience something new for the first time, or thousandth time.
May you get to share something you love doing with your toddler and have them “get it” in a way only kids can.
May you hold fast to your boundaries and routines where they make sense (for us, bedtime) and allow yourself to be loosey-goosey on the rest (hello, vacation chicken nuggets.)
May you slow down and see every small detail that makes up a place, even if you only get 0.25 miles from the trailhead.
May you wish on every star, say goodnight to every moonrise, collect seashells, pick berries, eat midmorning ice cream, and all those good vacation things.
May you breathe through the inevitable meltdowns and remember that you could be at home, doing the same thing. ⭐
Choosing the right place makes it much easier to have a good time.
We’ve aged out of the most wiggly stage of toddlerdom and into a really, really fun stage where my toddler can engage with what we’re doing in new and fun ways. Instead of toting them around in a carrier, we’re walking…slowing me down, yes, but in a really good way. We’re waving at bus drivers and making small talk with shopkeepers and designating places as “our favorite playground.” We did not go far this year for a variety of reasons, but we did have many adventures out of the house:
- St. Maarten – After the lovely Mirva Lempiainen recommended the island, I casually looked at our points ratios and found an incredible deal for the JW Marriott—a true “plop” vacation that was just what we needed in March.
- Portland, ME – I love this little city so much. We stop overnight on the way to and from our family’s place in Maine and oh, so much delicious food this year (s/o to Il Leone Peaks, Terlingua, Izakaya Minato, Evo, and Standard Baking Co.) We capped off our year with a trip here to take the Polar Express and wow, was it magical.
- Williamstown, MA – I took my first solo trip with my toddler this past year and it’s one of our best weekends ever. Lots of art—MASS MoCa was SO toddler friendly, I loved it—and little cafe dates and exploring the outdoors. 10/10 can’t wait to go back.
Some of the best advice I received last year.
My favorite, favorite part of being a journalist is that every day I get to learn something new. Usually from folks wiser and more educated than myself! Case in point: Each month I interview a parent/caregiver for their baby and toddler travel advice. A few gems from the year (a longer post on this coming soon…it was so hard to pick my favorites!)
Before you begin, think intentionally about your trip.
“What am I trying to achieve from this trip? Because if I’m envisioning that we’re going on these long hikes and doing the types of things I did before I had my son, that’s not going to be feasible. I get to decide what’s going to make this travel opportunity feel good to me, and it looks different than it did before.” – Aliza Sir from Platonic Love
When planning a trip, play defense…
“With little kids you need some unstructured, low key way for them to play and not be all scheduled out. Ideally you want it to be, let’s play in the pool, let’s play at the beach. Even if you do go to a busier place, like we’re doing my sister’s 40th birthday at Disneyland, and we still have downtime scheduled.” – Lisa Sibbett from the Auntie Bulletin
That includes how you eat out, since most of your meals while traveling are at restaurants:
“With the littlest ones, I try my best to keep them out of the high chair before food arrives. In my experience, the high chair has a time limit. If there are two adults available, I recommend someone take the little one on a walk nearby, or in the restaurant’s waiting area, or wherever you can get. Get some wiggles out before strapping them in.” – Hillary Dixler Canavan from What Are We Having?
And finally, two solid pieces of advice during hard moments…
“You just have to do the hard thing again and again, and, like a muscle straining to lift a heavy weight, it’ll get easier over time.” – Tori Simokov from Window Seat
And…
“Remember that every day is a series of moments, and if you have a difficult time at one moment, you can always come back from it and make the next moment better.” – Matthew Buccelli from Creative Parenting Club
Thanks for being here.
Going owling in honor of Jane Yolen’s Owl Moon. No, it’s not midnight lol it’s just 4 PM in New England.
Part of these resolutions come from many, many mom conversations on playgrounds and dodging snowballs and sitting cross-legged on library floors. There’s this general sense that none of us are doing “enough” even while we’re chasing after little ones doing a variety of Enrichment Activities (TM) or simple let-them-playtime. With this newsletter, I never want you to feel like ohmygosh, look at them going all these fancy places, I could never.
Because you could, I promise. One of my very first newsletters was all about scaffolding—the Montessori concept where you progress your skillset in chunks, as in, learning to pincer grasp before using tongs before holding a pencil—the same is true of your travel skills as a parent. Your local library is a great place to start if you’re not booking a plane ticket just yet.
To giving your kiddos the world,
Kayla
If you liked this post, please consider supporting my work. I’m just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.
This post was originally published on Travel with Toddlers. Subscribe for more real-talk travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
