003. First Time Flying with a Toddler & Why Kauai Should Be On Your List
My tips and lessons on traveling with a kid (after not flying for over 4 years) and reclaiming my love for travel after postpartum depression
As some of you know, Pearls of Jasmine started as a travel blog the year after I got married because I had a case of post-travel blues after coming back from Bora Bora. As a way to redirect my itch to travel again, I started writing it all down. “Pearls” was a nod to Bora Bora, “the Pearl of the Pacific,” as well as the “pearls” or experiential tips and advice I would be sharing.
The following month we would be doing our first backpacking trip ever to Havasupai, a land in the Grand Canyon owned by the Havasupai tribe and known for their mesmerizing aqua blue-green waters and incredible canyon waterfalls. I had so many questions from friends when I returned that the blog was a fantastic place to write down all I had learned and all the research, packing, and training we had done to prepare.
But after becoming a mom, travel became something that was put on the wayyyy back burner, despite it being a dream of mine to still be able to travel with my baby, as a way to disprove the naysayers. Postpartum depression took front and center stage in my life, and the memories of travel became so foreign, so unattainable that they actually made me more sad. All the taunts and warnings of “your life will be over” and “you’ll never travel the same again” or “forget being a travel blogger—your blog will become a mommy blog” seemed to come true.
I almost felt embarrassed and ashamed that I had naively rejected those ideas, but they came true anyway. And it felt like I lost a big part of my identity and what made me happy whenever I thought about traveling. I could barely keep myself together, barely figure out what my baby’s cries meant…how was I going to ever take her anywhere? But a big part of motherhood is merging your new and old identities and learning how to love and accept this new woman.
So when we were finally able to take my daughter to Hawaii this year over Mother’s Day, it felt very surreal and almost vindicating. We had babymooned in Oahu and I had always dreamed of taking her back after she was earthside. But by the time I was ready to consider flying with a one-year old, the pandemic completely capsized our plans.
Now here we are, four years later. It’s never too late to start. And though I don’t have flying tips for traveling with a baby, I do have some lessons learned from flying with a toddler and a new love for a new island. It’s not going to be some all-comprehensive blog post, but these were my big takeaways for first-time fliers!
Consider a “Test Flight” before a Longer Flight
I completely understand that ‘testing’ out a flight is definitely a big privilege, and even going to Hawaii is one as well. But if you can swing it, I highly recommend a “test flight” if this is your first time flying with a baby or a toddler and you have plans for a longer trip. And by “test flight,” I mean to make it a shorter flight. A few…mishaps (read on!)…happened on our first ever flight with our kiddo that I really think it helped us iron out the wrinkles for our longer 5-hour flight to Hawaii and reminded us not to repeat the same mistakes!
We were able to do our warm-up flight over Spring Break and try out flying on a more low-pressure trip to San Diego before embarking on our dream trip of Hawaii over Mother’s Day. As a cost-savings tip, Costco sometimes has Southwest gift cards on sale, so you can consider using those with flight sales too! I also had a bunch of points leftover from pre-pandemic times, so this helped me when looking to book for Hawaii. Southwest will also sometimes have sales on discounted point flights, so look out for those!
Lessons From Our Test Flight/Trip (1.5 hours):
If you have an older toddler, bringing the car seat onto the plane is not necessarily helpful. It’s one extra (bulky) item to carry with you through the aisles, and your toddler may not actually be more comfortable in it. For one, we realized our four-year old daughter was actually too tall when sitting in the car seat strapped to plane seat that her tray table could NOT fold down completely! It would hit her knees. My toddler is average height, so she’s not unusually long, but this was impractical. All her snacks and tablet and drinks and toys went onto MY tray…sigh.
So, gate check the car seat if you have an older toddler. We used a car seat cover you can easily buy on Amazon. There are more expensive padded ones too, but so far this has worked for us. If you’re worried about safety on the plane for a bigger kid, we borrowed a relative’s plane seat harness instead of the car seat, which was much more compact, and easy enough to put on. It’s expensive, but was pretty useful and we got one for ourselves too for travel again in a few months! The parents of the toddler sitting behind us asked us for the brand after they saw us using it too.
Do not lose your ID. I mean, this goes without saying, but this happened on our trip(!!) and was not realized until we got to the car rental counter! If this happens, file a report with the airline and airport immediately. We were so lucky to get it back from the airline(!), but not until after the trip was long over. It’s a pain in the butt to explain when you’re trying to get on your return flight, and you should account for extra time at the airport too to see if they will let you board. I’m glad this happened on this test flight though and not when we got to Hawaii! It made us extra vigilant, to say the least, and I’m glad we made it home.
My tip is to always store your ID somewhere close to you where you can be certain it won’t fall out (a zipped up wallet, zippered pocket, zipped backpack compartment, etc.). Back pockets are dangerous! Having a copy of an ID stored somewhere else safe in a compartment on your person is also not a bad idea.
Do not lose your phone. Again, this also goes without saying! But it actually happened on the way home! It was narrowly missed and found on the car rental that was almost returned and rented to someone else before we got onto our plane. WHEW! (As if explaining a lost ID wasn’t enough!) I’m just glad these scares happened on the first trip and that we got lucky because they totally would have completely ruined a great Hawaii trip. Same advice for wallet goes for phone—store it somewhere it won’t fall out and always check before you transition locations if you have it on you!
Also, a tip to store boarding passes on multiple phones. Just in case you need to rush through the airport and you did happen to lose your phone.It’s worth it to check some bags. I’m a person who hates checking in things because it’s faster not to wait for luggage claim and I am always anxious my things will get lost. Pre-kid life, my husband and I had carry-on packing down to an art. But with a toddler, honestly, it is just easier to have a few less items to keep an eye on or haul. AND, you need to pack so much more stuff when traveling with babies and toddlers! So we did check a larger suitcase for Hawaii.
Toilet seat covers are a saving grace whenever we go out, but even more so on the plane bathroom when you will likely have to crouch and be close to the bathroom floor. (*barf*) I don’t like to generate more waste/plastic, but I will reserve using these covers that cover almost the entire bowl. We really like them for tiny airplane bathrooms (and dirty public bathrooms) to avoid being close to the toilet bowl!
Snacks, screens, entertainment are your friends. Obvious tip, but just wanted to assuage that mom guilt— don’t sweat the screen time as much. You’re on vacation! But do download things before the trip (make sure it works)! We have the Amazon Fire HD Kids tablet, which is this “indestructible” cased Fire tablet and there’s a few different versions/colors/memory sizes.
And because some mamas have asked me for ideas, here are our other favorite things to bring for entertainment on planes (and cars):
-Melissa & Doug Reusable Water Books
-Accordion pop tubes
-Some sort of an Etch a Sketch
-Magic Ink coloring pads
-Go Fish Alphabet
-Good old stickers and paper; crayons and coloring pads
Basically, I think about flatter, smaller items to pack to save space. And hopefully it’s a toy that can be reused over and over. Games are great, but it does require more interaction and less independent play. The Go Fish is a little harder if your toddler is younger, but it happens to be my daughter’s favorite game right now and she’s gotten really good at learning phonics from it!
Try to bring new and novel items so your kid will stay more engaged. Target also sells the Magic Ink pads in the Dollar Spot section sometimes too!
My last tip is from a mama friend who says to rent your large equipment on babyquip.com (strollers, car seats, pack n plays, etc.). We haven’t tried this yet, but just putting it out there because it’s a great idea!
If you have more questions on the flight stuff, feel free to leave a comment!
Kauai—An Underrated Island to Take Kids
I always thought I would bring my daughter to Oahu as her first Hawaiian island, just to complete the circle of where we had babymooned. But my husband actually suggested we should try Kauai! I was slightly hesitant taking her so far to an island we’d never been before, especially for her first long-flight. But Kauai had always been a place I wanted to see, although I knew with a toddler, I wouldn’t experience it in the full capacity that I wanted to.
The woman I was four years ago probably would have been so anxious and wanted to control everything. But I decided to just give in to the unknown and not feel pressure to do it all on this trip. And I think that made for a beautiful vacation.
I was very pleasantly surprised by Kauai and fell in love with the slow rhythm, the lush greens, the wild chickens, and most of all—how much less crowded it was compared to Waikiki. I would highly recommend it to any families wanting a slower island experience—somewhere less busy and touristy but equally breathtaking and tranquil. I was worried there wouldn’t be enough to do, but honestly did not feel the need to be busy with a toddler, and we even squeezed in a waterfall hike with her to Ho’opi Falls!
I also would highly recommend a family stay at the Grand Hyatt Kauai in Poipu, where the southern part of the island tends to get a little less rain too. I booked with Chase points and it was totally worth it, especially with the Grand Club Access (breakfast, snacks, happy hour every day)!
There’s beautiful pools, water slides, lazy rivers, a man-made lagoon, parrots to visit, steps from the beach, a luau on site (which we did and it was really only worth it for the convenience), plenty of restaurants to choose from, and so much more. 50 acres of oceanfront fun, and we even met a family who had honeymooned there when it first opened in 1992 and now was back with their adult kids!
There’s plenty to do if you never want to leave the resort, but the island is not too big, and I’d say you should definitely venture out and dine out too! Check out Poipu Beach nearby for turtles, Shipwreck Beach on site for limestone caves, Lydgate Beach for littles, Smith’s for a grotto tour and garden luau. Waters in Kauai can be bigger in swells, but just be mindful in your research and you can find kid-friendly beaches.
We definitely didn’t do everything we could have, but I think just enjoying time together and marveling at my child taking in a new place was already more than magical. The pace was exactly what I was hoping for, and even at our resort, the pools didn’t feel crowded or full, even for Mother’s Day weekend!
If there’s more specifics you’d like, feel free to comment or reply to the newsletter email. :)
Tips on Family Photoshoots
While in Kauai, I knew I wanted to commemorate this first trip to Hawaii with family photos, so I booked our photographer right when I booked the trip 5 months in advance. This totally may not be up your alley as photoshoots can take up time and cut into a vacation with the scheduling, but I knew for this inaugural trip (and Mother’s Day), that this was a splurge and treat. And you’ll see the final photos scattered throughout this newsletter because I ended up loving them so much!
A few tips for planning a photoshoot:
Consider booking a date earlier in your trip so you have time to reschedule due to weather if necessary. Kauai is a rainier island and we almost had to reschedule, but our photographer kept a close eye on weather reports and it worked out!
Time zone change might play a factor. My daughter was up at 4am that first night (which is 7am PST) and would not go back to sleep! Our photographer originally suggested maybe even a sunrise shoot instead of sunset due to time zone changes/jet lag. I was a little skeptical, but she was right—it could have worked out! So consider that in your planning :)
Have your kid try on their outfit before the shoot. This is a big obvious statement, but guess who still forgot to do it?… Her dress ended up being a little longer on her than anticipated and I was really worried she was going to trip all over the sand, especially with her sandals on—which were also TOO small…ahhh! Luckily, the photographer said, no shoes! And that ended up working out even better. Whew!
Snack beforehand or have a dinner plan ready, if you’re doing a sunset shoot to avoid a hangry toddler afterwards. (Or breakfast plans for sunrise shoots.) We decided to just do room service dinner after since we had to wash off the sand and beach after our shoot. We weren’t planning to get wet, but those Kauai waves are no joke! They make for beautiful crests in photos though!
PC: Hannah McFall, highly recommend her!
Thanks for reading along! I know I’m not very concise, but this is why all these details are not in an Instagram post. In the next newsletter, it will be more essay format and story-telling about a hard parenting moment when my daughter slammed a door in my face for the first time. It should be out next week, so please subscribe (if you haven’t already) if you want to see it first in your inbox! I appreciate all the support and love on this endeavor. :)
xo,
Jasmine