I am a classic eldest daughter/recovering perfectionist and so it won’t surprise you when I say rules, systems, organization…it’s all part of who I am as a person, and how I plan any kind of travel.
When I think back on how I sobbed over wake windows, for example, I wish I could go back to my postpartum self and tell her that it didn’t matter as much as I thought it did. I just could not get myself to loosen up at all, often doing unhinged acts of motherhood to preserve the “correct” sleep window (not limited to driving around for literal hours at a time if my now-toddler fell asleep in the car because I could not transfer them successfully to their bed…every mom I know has their own version of this story.)
Travel has been such a gift for me as a mother, not just because it’s fun, but also because it has taught me, and forced me, to go with the flow and be present in those moments. I don’t throw all the rules out the window—I usually still enforce a bedtime that’s pretty close to our bedtime at home—but every time things don’t go according to plan (which, let’s face it, is every time), I come home a little wiser, a little more like, okay, it’s gonna be just fine.
But I’m not a digital nomad, and I don’t travel full time or even every weekend the way did in my ‘20s. That’s why I was so excited when Christina Haisfield, aka Jetset Christina, agreed to chat with me. She’s one of my favorite travel influencers, and she lives practically on the road with her two toddlers (aged 3.5 and 1). Because they travel so often, their regular routine is basically their travel routine.
Christina Haisfield on Travel with Toddlers
The thing I love about Christina’s blog and her content is that even when she’s in these incredible bucket-list locations, she never makes it feel out of reach. Her real-talk on how her travel style, career, and ambition shifted when having kids made me feel so seen, like yes, this is exactly how I feel…though I did not write this post from an overwater bungalow or five-star resort, unfortunately.
I feel like there’s no such thing as ‘focus’ anymore, at least not really. It’s more like everything is all over the place, all the time. You instinctively know where those little walking hearts are, at all times. And you know what they need. You try to focus on other things, but you can’t do so until you know they’re okay, their needs are met, they’re happy, they’re safe. And even when you know that, you’re still spinning all the time with thoughts like what am I going to make for dinner tonight did I remember to drop off that form at school and the other form for the neighborhood fundraiser shoot I’m in charge of the preschool class thanksgiving party when am I going to get to the grocery store what are we doing this weekend should we get a tree what time is that birthday party oh no i need a gift what was that store again that suzie said she shops at for birthday gifts let me text her oh the baby’s crying ugh weaning is so hard my boobs hurt and she won’t drink cows milk MILK shit we’re out of milk my toddler who will 10000% have a meltdown if i dont get some by dinnertime are these 3 year old meltdowns normal maybe i should chatgpt it just in case. A mother’s brain is like having 1000 tabs open all at once on a computer that’s overheating and spinning out of control. But she keeps going, one tab at a time. Sometimes ten tabs at a time. it’s just what moms do.
Ah, it’s like she peeled open my brain to write this! Here’s how she approaches traveling as a full-time influencer and business owner with two littles in tow:1
As a professional in the travel industry, I’m curious how your travel “style” changed before and after kids. Do you all travel together?
We do! My 3-year-old son has been on over 150 flights, to more than 15 countries, and my one-and-a-half year old daughter is catching up to him fast. Our travel style has always been vacation and leisure travel. We hustle hard at home so we can relax on vacation. We love tropical islands and five-star resorts that make it easy to travel as a family.
Before kids, we lived in Bali for 3 years, working on our business Kenny Flowers, because that’s where our manufacturers are. We’d also travel for my business, Jetset Christina, and lived out of a suitcase for years as digital nomads. In 2021 we got married and decided to “settle down”—really, somewhere to put our suitcases—in Charleston, SC. We’re still on the road a lot of the time, but we love our home as well.
You’re the first person I think of when I need a recommendation in the luxury travel space. When we’ve visited some of these big name resorts, sometimes the vibe makes me feel like toddlers don’t belong. How do you handle that?
I seek out resorts that encompass and really champion that family-friendly luxury. Rosewoods and Four Seasons and One&Only’s have been some of the best family-friendly resorts. I have a list of our favorite places we’ve stayed as a family in here.
That said, if we find ourselves somewhere that feels more adult-oriented, I don’t stress about it. I think it’s great for kids to learn how to adapt to different environments, and I whole-heartedly believe that families are just as entitled to a luxurious vacation as anyone else. A toddler shouldn’t ever be something to “shush,” and if someone is doing that, that’s their problem, not ours. (Editor’s note: Amen!)
I often see you on your blog traveling on serious long-haul destinations, like to Asia from Charleston. How do you handle such big trips with the littles?
Practice makes perfect! We started young on flying with both of my kids, so they get really excited about being on the airplane! I’m also a huge believer in our energy = their energy. If you’re stressed about a travel day, they will feel that, and they’ll be tough to travel with. But if you hype them up, get them excited, and get excited yourself—they will feed off of that!
It’s definitely not always easy, but when we’re on the plane for a long time, I like to think of it as just relocating for the day. We do all the same things we do at home, read books, play games, eat meals, nap, and so on. We just do them on the plane instead.
My son is now 3.5 and we’ve just this year started allowing screen time on the airplane so if there’s a TV he’ll watch a Disney movie or something like that, but we didn’t do any screens before 3 years old. I always thought I would need them on the plane but he really learned how to entertain himself by not having a screen. I pack a LOT of toys and books.
What’s your biggest travel advice when taking along little ones?
Travel as much as you can in the first year! And especially the first 9 months. It’s easy! Don’t stress over it. They are along for the ride.
For toddlers, talk to them about the trip leading up to it, and all about it afterwards! Involve them in all of the fun pieces of travel. My toddler loves to talk about airport security, the process of getting on the plane, packing for a trip, his favorite vacations, anything to solidify the experience and make it real for them. Don’t just spring it on them, include them in it!
And the best place to travel with toddlers is…
The Maldives. It’s my favorite destination in the world with or without kids!! The hotels are absolutely insane, private islands with 7-star service. Lots of young kids and so many fun things for them to do. We loved Six Senses Laamu and One&Only Reethi Rah as a family. And the Ritz-Carlton Mandapa in Bali had the best kids club I’ve ever seen!
Closer to home, our favorite is Four Seasons Maui, or Four Seasons Bora Bora! Both are incredible with families.
And the gear that Christina never leaves behind…
Slumberpod, snacks, cute matching Kenny Flowers outfits, a good quality camera for capturing the memories!
You’ve been all over the world. What’s your favorite memory traveling with your kids?
Impossible to pick just one! But I have this memory of staying up way past my kids’ bedtimes because it was a full moon on the beach, and we were watching the sun set and swimming in the ocean, and as the moon started to rise and it went to that beautiful blue-hour, no one wanted to leave. So we played in the sand until it was dark. The best memories are the spontaneous ones. The ones where you throw the plan or the “schedule” out the window, so I like to leave room in our travels for moments like that. ✨
Thank you so much, Christina! I love those kinds of moments as a family where you just break the rules a little. It’s often what creates family traditions that we take with us when we come home. Once on a beach vacation, my toddler ran out to the balcony to say goodnight to the moon and goodnight to the ocean, which hung low over the ocean. Now it’s something we do every night, whether we can see the moon or not.
Thanks for being here.
When I think about the gift of travel, it’s really the spontaneity I mean. The freedom to choose a long, lingering breakfast by the ocean or to pack a bag and go on a hike or to take a yoga class or to pop in to that cute shop just because it calls to you. One morning on our trip to St. Maarten we spent literally an hour collecting sea glass, just because. It’s one of my favorite memories of last year.
With my toddler, I’m trying to be more present in the everyday, to try and add that spontaneity. This is something that comes naturally to little ones—spend five minutes watching them navigate a new play area or playground and you’ll see how they just move to whatever strikes their fancy, no hemming and hawing whatsoever.
Here’s to finding that wow moment,
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.
