There was a time when I saw two paths forward with my life: Sell all of my belongings and do the “digital nomad” thing around the world…or buy a house in the suburbs and settle in. I don’t regret my choice (COVID shut down travel only a few months after closing on the house, omg) but I do think sometimes about the “ghost ship” where I followed the itinerary I dreamed about through Europe and Asia. Someday, I hope to bring my toddler to these places, too. But I still dream about doing the digital nomad thing.
That’s why I am so excited to bring you my very first interview, with one of the coolest writers I know—Ashley R. Cummings. Though we’ve never met in person, we hang out in the same freelance writer spaces, and her newsletter, Life In A Backpack, totally inspired me to start my own newsletter, Travel with Toddlers.
Ashley R. Cummings on Travel with Toddlers
Someday my kid will also look at the camera when I tell them to!
Though Ashley’s kids are slightly outside the toddler/pre-k bubble (they’re 9 and 11 now), they’re travel pros at this point. I firmly believe that even though your kids “won’t remember it,” the memories and skills they build while traveling as little kids creates a foundation for smoother (and more fun!) trips when they’re older.
Here’s what she had to say about it:
FV: Tell me about one of the first trips you took when your kids were little.
“One of the first trips I took my kids on was to Oahu, Hawaii. We went and stayed with a family friend, and it was amazing. [Editor’s note: OMG, if I could handle a flight that long from Boston, I would *totally* do Hawaii again.]
The plane ride with a 2-year-old and a 6-month-old was a bit stressful. But Hawaii was waiting on the other end of the trip—so WORTH IT! If you’re going to travel with little kids, I recommend a place with wide open, beautiful spaces and lots of kid-friendly activities. Oahu has a little bay called Shark’s Cove on the North Shore where the water is really shallow and calm. Great place for kids.”
FV: It may not feel like it in the moment, but take it from a mom who knows: Babies are actually much more flexible than toddlers (and kids.) What is the biggest advice you would give to new parents who want to travel?
“Go literally anywhere. Babies are portable.
And don’t stress out. Most everyone has children and gets it if they cry or are fussy on the plane. If they cry, who cares? It’s good for their ears.”
FV: For toddlers, it’s all about the entertainment. What was your top tip for making trips go smoothly?
“Go to the dollar store and get a ton of little prizes and snacks. Wrap them up and put them in a cute backpack that the kid is responsible for. Then, let them open up one prize to play with on the plane every hour or so. [Editor’s note: I LOVE this idea and will be trying it out in a few months when we fly to Orlando.]
Now, my kids each have a travel backpack. They put books, art supplies, and small toys in there. It’s a great way to keep them entertained without having to rely on electronics.”
FV: The most kid-friendly way to travel is…
“I’d say cruises are the most kid-friendly. Maybe this is basic, but I like Carnival. The new ships are super nice. The kid clubs are fun and a great way for you and your spouse to get alone time together.
Do your research on what kind of cruise you want to go on, and how you want to travel. For example, we went on a Disney cruise and it was SO EXPENSIVE and not that great—especially for the price. I’d say skip Disney, unless you absolutely love the characters. If so, it will be magical. We care more about the destinations.”
FV: And the best kid-friendly destination is…
“Mexico. Mexico is so family-friendly. We spent 6 months in La Paz in Baja California Sur, which is basically heaven.
[Editor’s Note: I googled this just to see what “heaven” looked like and um, yeah.]
I enrolled my kids in a Montessori school there so we could settle in and make friends. My kids (and I) made a ton of friends there, and we miss it all of the time. The city has good food, cool museums, and beautiful beaches. It also has a boardwalk where people get together, exercise, and hang out. If you’re going to go to Mexico, La Paz is wonderful.”
FV: Traveling with toddlers isn’t always easy. What was a travel hiccup you experienced and how did you recover when your kids were young?
“Once, one of our children had an epic blowout on the plane. [Editor’s note: We’ve all been there!] We had to buy all new clothing at our layover. My advice is to pack 2-3 outfits for planes for them and for yourself if you get caught in the crossfire.”
FV: You’re on the go more than your average family. How have you made traveling “work” for your family, and what advice do you have for someone who wants to do the same?
“There are no rules about traveling. If you want to go, do it. Don’t worry about what other people say. Do what works for you and your family.” 🌎
You’re in charge of how much or little you travel.
I love Ashley’s mindset about being in charge of your travel. Sometimes it’s easy to get caught up in feeling like “if you go to X destination you MUST do this/try that/experience this thing” and y’know what? With a toddler, you might just be at the playground, and that’s okay.
The memories you make are less about where you are and more about choosing a trip that’s right for your family, in that moment of your lives. A great reminder to stay present and to book places that you enjoy being in, not ticking off major sites.
Thanks for being here.
As always, thanks for reading! If you liked this issue, definitely go check out Ashley R. Cummings’ newsletter Life In A Backpack. In the meantime, I just got back from a week doing some wonderful, low-key peak foliage hiking in the White Mountains. It’s something we’ve been doing every year since having a kid, but the chiillllest version of it. Our only elevation gain came via Loon’s gondola, we ordered Thai food from the same restaurant every night, and did a post-nap dip in the indoor pool every day. Basically, the best.
Talk soon,
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.
