Leave Room in Your Itinerary to Break the Rules
How Christina Haisfield aka Jetset Christina travels around the world with 2 toddlers.
đ Hello!! Lots of new faces here, welcome! Iâm so happy youâre here. Every month, Iâll be bringing you interviews from travel experts/caregivers from around the globe as part of Travel with Toddlersâbecause as we all know, every! kid! is! different! I want to include a wide range of voices here, so if you or someone you know would like to be featured, comment/reply and let me know.
I am a classic eldest daughter/recovering perfectionist and so it wonât surprise you when I say rules, systems, organizationâŚitâs 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 didnât 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 âcorrectâ 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 bedâŚevery mom I know has their own version of this story.)
Travel has been such a gift for me as a mother, not just because itâs fun, but also because it has taught me, and forced me, to go with the flow and be present in those moments. I donât throw all the rules out the windowâI usually still enforce a bedtime thatâs pretty close to our bedtime at homeâbut every time things donât go according to plan (which, letâs face it, is every time), I come home a little wiser, a little more like, okay, itâs gonna be just fine.
But Iâm not a digital nomad, and I donât travel full time or even every weekend the way did in my â20s. Thatâs why I was so excited when Christina Haisfield, aka Jetset Christina, agreed to chat with me. Sheâs 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 Christinaâs blog and her content is that even when sheâs 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 feelâŚthough I did not write this post from an overwater bungalow or five-star resort, unfortunately.
I feel like thereâs no such thing as âfocusâ anymore, at least not really. Itâs 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 canât do so until you know theyâre okay, their needs are met, theyâre happy, theyâre safe. And even when you know that, youâre 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 Iâm 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 babyâs crying ugh weaning is so hard my boobs hurt and she wonât drink cows milk MILK shit weâre 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 motherâs brain is like having 1000 tabs open all at once on a computer thatâs overheating and spinning out of control. But she keeps going, one tab at a time. Sometimes ten tabs at a time. itâs just what moms do.
Ah, itâs like she peeled open my brain to write this! Hereâs 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, Iâm curious how your travel âstyleâ 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 thatâs where our manufacturers are. Weâd 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 âsettle downââreally, somewhere to put our suitcasesâin Charleston, SC. Weâre still on the road a lot of the time, but we love our home as well.
Youâre the first person I think of when I need a recommendation in the luxury travel space. When weâve visited some of these big name resorts, sometimes the vibe makes me feel like toddlers donât 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&Onlyâs have been some of the best family-friendly resorts. I have a list of our favorite places weâve stayed as a family in here.
That said, if we find ourselves somewhere that feels more adult-oriented, I donât stress about it. I think itâs 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 shouldnât ever be something to âshush,â and if someone is doing that, thatâs their problem, not ours. (Editorâs 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! Iâm also a huge believer in our energy = their energy. If youâre stressed about a travel day, they will feel that, and theyâll be tough to travel with. But if you hype them up, get them excited, and get excited yourselfâthey will feed off of that!
Itâs definitely not always easy, but when weâre 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 weâve just this year started allowing screen time on the airplane so if thereâs a TV heâll watch a Disney movie or something like that, but we didnât 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.
Related:
Whatâs 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. Itâs easy! Donât 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. Donât just spring it on them, include them in it!
And the best place to travel with toddlers isâŚ
The Maldives. Itâs 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 Iâve 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 behindâŚ
Slumberpod, snacks, cute matching Kenny Flowers outfits, a good quality camera for capturing the memories!
Youâve been all over the world. Whatâs your favorite memory traveling with your kids?
Impossible to pick just one! But I have this memory of staying up way past my kidsâ 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 âscheduleâ out the window, so I like to leave room in our travels for moments like that. â¨
Thank you so much, Christina! I love those kinds of moments as a family where you just break the rules a little. Itâs 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 itâs something we do every night, whether we can see the moon or not.
Now, on to this weekâs recs:
This weekâs rapid-fire recs.
Disclosure: This section may contain affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. I promise Iâll only ever recommend products Iâve actually used and loved.
On choosing an itinerary. Great advice from Maggie.
Itâs destination roundup seasonâŚnot sure some of these are on my toddler-friendly list, but I miss the days when Iâd collage the spreads from these pieces in every travel magazine.
Been watching Taylor Swiftâs The End of an Era (Disney+) and ahhh I know Iâm a huge Swiftie (I was there at âthe rainiest rain show that ever rain showedâ), but itâs just fascinating to see all the moving parts behind the show.
Call me a millennial all you want, this suitcase is still going strong 10+ years in.
ICYMI
Thanks for being here.
When I think about the gift of travel, itâs 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. Itâs one of my favorite memories of last year.
With my toddler, Iâm trying to be more present in the everyday, to try and add that spontaneity. This is something that comes naturally to little onesâspend five minutes watching them navigate a new play area or playground and youâll see how they just move to whatever strikes their fancy, no hemming and hawing whatsoever.
Hereâs to finding that wow moment,
Kayla
Thank you for supporting Travel with Toddlers! If you liked this issue, please like it, share it, subscribe, or you can buy me a coffee. It really does mean a lot. Iâm just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdownsâI sincerely hope this helps you do the same.
This interview has been lightly edited for clarity and brevity.
What an honor to be a part of one of my favorite corners of Substack!!!! Thank you so much for chatting with me, Kayla! I loved this conversation on travel and ways to make it even more special as a family!