By Sinaiyouth 
I’m a classic older daughter/recovering perfectionist and so it won’t surprise you when I talk about rules, systems, organization…it’s all part of who I am as a person and how I plan any type of trip.
When I think about how I sobbed during waking 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. I just couldn’t relax at all, often doing messy acts of motherhood to preserve the “correct” sleep window (not limiting myself to driving for literal hours at a time if my now toddler fell asleep in the car because I couldn’t successfully transfer him to his bed…every mom I know has their own version of this story.)
Travel has been a true gift to me as a mother, not only because it is fun, but also because it has taught 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 always stick to a bedtime pretty close to our bedtime at home – but whenever things don’t go as planned (which, let’s face it, is every time), I come home a little wiser, a little more like, ok, it will be fine.
But I’m not a digital nomad and I don’t travel full time or even every weekend like I 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 practically lives on the road with her two toddlers (ages 3.5 and 1). Because they travel so often, their usual routine is essentially their travel routine.
Christina Haisfield on traveling with toddlers
What I love about Christina’s blog and her content is that even when she is in these incredible must-see places, she never feels out of reach. His real talk about how his travel style, career, and ambition changed when he had kids made me feel so seen, like yes, that’s exactly how I feel…although I sadly didn’t write this post from an overwater bungalow or five-star resort.
I feel like “focus” doesn’t exist anymore, at least not really. It’s more like everything is everywhere, all the time. You instinctively know where these 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 that until you know they’re okay, their needs are met, they’re happy, and they’re safe. And even when you know that, you still run around all the time with thoughts like what am I going to make for dinner tonight, have I remembered to drop off this form at school and the other form for the neighborhood fundraiser? I’m in charge of the preschool class’s Thanksgiving party. When will I go to the grocery store? hurt and she doesn’t drink cow’s milk MILK shit we’re out of milk my toddler is 10000% going to collapse if I don’t have any by dinner time are these 3 year old tantrums normal maybe I should discuss it just in case. A mother’s brain is like having 1,000 tabs open at once on a computer that overheats and spins out of control. But she keeps going, one tab at a time. Sometimes ten tabs at a time. that’s just what moms do.
Ah, it’s as if she opened my brain to write this! Here’s how she approaches the journey as a full-time influencer and business owner with two little people under her belt:1
As a travel industry professional, I’m curious how your travel “style” changed before and after kids. Do you all travel together?
We do it! My 3-year-old son has taken over 150 flights to over 15 countries, and my 1.5-year-old daughter is quickly catching up. Our travel style has always been vacations and leisure trips. We work hard at home so we can relax on vacation. We love tropical islands and five-star resorts that make family travel easy.
Before having children, we lived in Bali for 3 years and worked on our business Kenny Flowers, as that is where our manufacturers are located. We also traveled for my company, Jetset Christina, and lived out of a suitcase for years as digital nomads. In 2021, we got married and decided to “settle down” – basically, somewhere to settle down – in Charleston, South Carolina. We’re still on the road most of the time, but we also love our home.
You are the first person I think of when I need a luxury travel recommendation. When we’ve visited some of these famous resorts, sometimes the ambiance makes me feel like little ones don’t belong. How do you deal with this?
I look for resorts that truly embrace and champion that family luxury. Rosewoods, Four Seasons and One&Only are some of the best family resorts. I have a list of our favorite places we have stayed as a family here.
That said, if we’re in a place that seems more adult oriented, I don’t worry about it. I think it’s great for children to learn to adapt to different environments, and I wholeheartedly believe that families have just as much right to a luxurious vacation as anyone else. A toddler should never be something to be “silenced”, and if someone does that, it’s their problem, not ours. (Editor’s note: Amen!)
I often see you on your blog traveling to serious long-haul destinations, like Asia from Charleston. How to manage such big trips with the little ones?
Practice makes perfect! We started flying very young with my two children, so they Really excited to be on the plane! I also believe enormously in our energy = their energy. If you are stressed from a day of travel, they will feel it and it will be difficult to travel with them. But if you exalt them, excite them and yourself, they will feed off it!
It’s definitely not always easy, but when we’re on the plane for a long time, I like to think of it as simply to relocate for the day. We do all the same things we do at home, read books, play games, eat meals, take a nap, etc. We just do them on the plane.
My son is now 3.5 and we started allowing screen time on the plane this year, so if there is a TV he will watch a Disney movie or something, but we didn’t do any screen time until he was 3. I always thought I’d need it on the plane, but he’s really learned how to entertain himself without a screen. I bring A LOT of toys and books.
What’s your biggest travel tip when taking your little ones?
Travel as much as you can in the first year! And especially the first 9 months. It’s easy! Don’t stress about it. They are there for the journey.
For little ones, tell them about the trip before, and all about it after! Involve them in all the fun parts of the trip. My toddler loves talking about airport security, the process of getting on the plane, getting ready for a trip, his favorite vacation, anything that can solidify the experience and make it real for him. Don’t just throw it at 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 children!! The hotels are absolutely crazy private islands with 7-star service. Lots of young children and so many fun things 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 the Four Seasons Maui, or Four Seasons Bora Bora! The two are amazing as a family.
And the gear Christina never leaves behind…
Slumberpod, snacks, cute matching Kenny Flowers outfits, a good quality camera to capture the memories!
You have traveled all over the world. What is your best travel memory with your children?
Impossible to choose just one! But I have this memory of staying up way past my kids’ bedtime because it was a full moon on the beach, and we were watching the sun go down and swimming in the ocean, and as the moon started to rise and it got to this beautiful blue hour, no one wanted to leave. So we played in the sand until it got dark. The best memories are the most spontaneous. The ones where we throw the plan or “schedule” out the window, so I like to leave room in our travels for moments like that. ✨
Thank you very much Christine! I like these kinds of family moments where we break the rules a little. This is often what creates family traditions that we take with us when we come home. One day, on a beach vacation, my toddler ran onto the balcony to say goodnight to the moon and goodnight to the ocean, which was floating above 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 of the gift of travel, I’m really talking about spontaneity. The freedom to choose a long, lingering breakfast by the ocean or pack a bag and go for a hike or take a yoga class or stop by that cute boutique just because it calls your name. One morning on our trip to St. Maarten, we spent literally an hour collecting sea glass, just like that. It’s one of my best memories from last year.
With my toddler, I try to be more present on a daily basis, to try to add this spontaneity. It’s something that comes naturally to toddlers: Spend five minutes watching them navigate a new playground or playground and you’ll see how they simply move towards what they please, without any hesitation or hesitation.
Here’s to finding that wow moment,
Kayla
If you liked this article, please consider supporting my work. I’m just a mom at heart trying to create essential memories for our entire family while minimizing meltdowns. I sincerely hope this helps you do the same.
This article was originally published on Traveling with Toddlers. Subscribe for more actionable travel tips, toddler-friendly itineraries and proven gear recommendations.