Hotels North America Travel

Traveling With A Toddler

Sale PSA: A camel cashmere bicolor coat from Max Mara, now 40% off, a draped short sleeve romper from Halogen, now under $55 (I picked up one in black), a pretty and quite sexy little black dress from Bailey 44, now under $150, and a pretty embroidered summer dress from SEA (why is everything from this brand so pretty and so $$?), now under $200. 

We just returned from a trip to Maui with baby Feather – a sort of another “babymoon” before #2 arrives, and while they’re fresh in my mind, I thought I’d share some of my learnings about traveling with a toddler.

If you have younger children, I also wrote earlier about traveling with a baby, if you’re interested!

1. Buy a seat. This is just my opinion, but once you have a kid of a certain size and wriggliness, I’d buy them a seat on the plane. I know, having a free lap baby is super tempting, and there’s always the chance that you could luck out and there’ll be empty seats, but I will say that on our way to and from Hawaii, there were empty seats in our row all the way until boarding, and then the plane filled up completely. And I really don’t know what we would have done without a seat. I think it would have been torturous (especially since I’m pregnant). Instead, our toddler sat pretty much the whole way to and from happily in his car seat, which he was very familiar with, and I felt that he was safe in case of turbulence. He didn’t sleep though. We’ve never gotten him to really sleep on a plane. It remains a pipe dream.

By the way, we used this stroller to carry the car seat through the airport, and we were the envy of all parents. It not only makes it so easy to transport your car seat, but wheels right onto the plane, and also doubles as a stroller through the airport. So, so recommended. We didn’t bring a separate stroller.

2. The hotel matters. That is, if you’re staying at a hotel, and not renting an apartment. I’ve come to terms that I’m a hotel person, and when you have a baby/toddler, I think a hotel choice really matters. At a resort especially, I’d check for two things – a kid’s club, and ample child friendly menu/dining options. We felt fortunate that our hotel of choice, the Four Seasons Wailea, was so toddler friendly – we didn’t have to pack wipes, there was a great crib, adorable toys in our room, toys at the beach, a kid’s pool, and the staff were used to children and the occasional tantrum…perfect.

This was the kid’s club…once they turn five you can leave them in here alone (see ya!) all day, for the staff to supervise, with lots of fun activities. Until then, they had a great toddler area, as well as toys and books you could check out and take back to your room. This was a godsend.

Some of the food options for our toddler – every morning he had a custom waffle and omelet, and on our last evening he even enjoyed this amazing Spaghetti Carbonara. He’d already exhausted every option on the kid’s menu and he eats so much that the waiter ordered him this. Yes..and all free! The savings here can add up…some kids eat a ton! At Four Seasons Maui, the policy it goes all the way up to five years.

3. It’s time for screen time. Again, a personal thing. Yeah, I really try to limit my kid’s screen time at home….but on vacation? Let your brain turn to mush, my love. Mommy needs to enjoy her dinner. Room service has arrived? Let’s get that TV turned on.

And on the plane? Game over…it was basically unlimited tablet access. Travel is stressful enough…it’s expensive, and supposed to be a vacation for the parents too. So in that spirit, I’d relax some of your rules. I will say that I had made my peace with our toddler going *crazy* over the screen because we are pretty strict with it at home, but for whatever reason, he tired of it himself after maybe ~15 minutes or so at a go. I think that was the limit of his attention span, so it wasn’t like he was zoning out for hours at a time (which I as an adult am fully capable of, and in fact dream of). So tiger parents, don’t worry. Let your little darling watch some TV. You can finish your drink and everyone will be happy.

4. And finally….book some “me” time. Toddlers are demanding, no? There were times when my husband and I were both so stressed, it felt like we were serving an emperor with a penchant for capital punishment. We’d be at a quiet restaurant and little one would start fidgeting…and we’d both leap into action. “Where’s the truck? Where’s the tablet? Oh god, my entree hasn’t arrived yet! Is there time to eat?”

In order to avoid the idea that we’d just flown and paid all this money purely to satisfy the whims of a tiny tyrant, we both booked multiple treatments at the excellent Four Seasons spa,and our only regret was that we didn’t do more. We basically took turns each day on who got to go, and always booked it during his nap, so the other person could relax, too.

Remember: vacations are not just about surviving them. You should enjoy them too! That’s really the key to continuing to travel with kids, in my opinion. Make it something you want to do again.

Please share any of your advice/learnings about traveling with a toddler!

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  • Michelle
    May 8, 2017 at 11:07 am

    Great tips and I am a subscriber of all of them! They are valid whether you have toddlers or in my case, school age kids. We flew to Tokyo when the twins were 18 months old and I paid for two seats for them. There was no way we are going to deal with two squirmy toddlers on our laps for 10+ hours. It is not as if we could hand them to each other because we would each have one! The airline makes a difference too. Some airlines are more lax with seating arrangements e.g. with one airline, I could let one sleep on the 3 across seat (head on my lap) and one sleep on the floor below lined with blankets. We definitely have to be vigilant and aware of safety with this arrangement.

    I love Four Seasons Wailea and could not imagine going anywhere else. Service was excellent, the room was spacious (2 queen sized beds plus a queen sized sofa bed), food was awesome and free for the twins (double win!), awesome spa, free kids club, lotsa nice amenities poolside throughout the day and no cabana or resort fee!!! We only used the kids club one day cos they were happy just playing in the pool all day long. Plus, unfortunately, they all caught a virus at the start of the trip so I had to keep them close to me. Prior to the trip, I had visions of all three going to Kids Camp 😛 so we could enjoy couple spa treatments. Next trip!

    We have very restricted screen time at home too. We never started regular screen time so they don’t a habit so they don’t request for screen time. But when we travel, on the plane, at our destination, it’s no hands barred screen time, basically knock yourselves out with cartoons unless it’s time for outside play or bed time.

    Like you, we took turns going to the spa, it was so blissful despite being marred by text messages from the husband about stolen kids goggles, haha!

    • Katherine
      May 8, 2017 at 1:14 pm

      Michelle, love all the tips! You are right, we have so many in common, ha! I’m sad I didn’t get to make it to GW to visit your jeweler.

      Can I ask what room you guys get? With one kid we had the regular room but we were thinking with multiple we need to get suite next. What has been your experience? Thank you!

      • Michelle
        May 9, 2017 at 1:19 pm

        There’s always the next Maui trip! 🙂 I am so looking forward to going back but it won’t be this year …

        For now, 99% of the time we get a regular room, not a suite. Budget just doesn’t really permit when I am paying for 5 air tickets plus many nights *sweat* We usually turn off the lights for the girls to go to sleep (but one of us can be in the bathroom showering or something) and when they are knocked out (varies from 5-20 mins depending on how tired they are), we can turn on some lights or the TV, talk etc., and it doesn’t wake them up. Only once we got a suite and that was in HK and it wasn’t too crazy expensive so that worked out. Else I do try to ensure we have at least 2 queen beds + 1 rollaway bed. But some hotel rooms in Japan are small and hard to accommodate so we have had to make do with 3 twin beds. Not the most comfortable stay but we got by.

        One other thing, my girls love to read but honestly, all the books or small toys we/they pack in their backpacks goes unused on the plane or at our destination (experience from 3 trips!) so we will likely lighten the load and not pack those stuff. Books gets heavy and even little toys adds up! On the plane, their eyes were glued to the screen and at our destinations, they were busy soaking in the sights, enjoy outside activities and getting new souvenirs. So by the end of the trip, we ended up with both un-played toys we brought along plus new ones we picked up along the way.

        But I will always pack their coloring books/plain paper and crayons as it occupies them at restaurants while waiting for their food. This doesn’t apply when we eat at street food places 😀

        • Katherine
          May 11, 2017 at 7:34 am

          Great points! And I’m so glad to hear that the regular size room for you (which at FS Wailea is already quite big!!). We are struggling right now as we’ll have a little baby and toddler next time we travel (requiring two cribs) but I think once we have two sleeping in beds it would be much easier for the rooms.

  • Melissa
    May 8, 2017 at 11:00 pm

    Great tips that I didn’t consider. If you’re traveling with more than one child, I would highly recommend booking a suite, even though it’s much pricier than just a room.
    For Packing: Type and print a check list of all the items that you will need for the trip. You can reuse this list for future trips. Alternatively, you can use the iPhone’s reminder app for this purpose.
    Don’t forget to pack anything that your child uses to help them sleep, such as a sound machine, favorite stuffed animal, blanket, night light, or music player.
    Use a separate duffel bag or suitcase for each person. If using duffel bags, choose different colors for each person or monogram the bags for easy identification.
    Check the weather ahead so you can pack accordingly.
    Pack a separate carry-on bag with necessities like diapers and wipes as well as snacks, toys, and drinks (milk, water). For snacks, I like puffs and yogurt treats. I include some new toys and stickers for entertainment. I always pack an empty straw sippy cup because it doesn’t spill.
    If you’re planning on nursing, pack a nursing cover.
    Hope this is helpful.

  • Vivian
    May 9, 2017 at 10:16 am

    Even though I don’t have kids I just enjoy reading all the travel with baby series from you! I got married to a Tiger Family and I have seen all these strict rules applied to my niece and nephew during vacation.. They have dietary restrictions due to religious belief and also set 2 hours nap time at certain time (Imagine everyone needs to run back to hotel room at 2pm because kids need a nap). No kidding I was scared cuz it seems there’s no flexibility and I would never imagine to travel with young toddlers. Sorry for all the whining but your story just put a smile on my face.

    • Katherine
      May 11, 2017 at 7:35 am

      Thanks Vivian! And enjoy your wonderful, child free travel ha 🙂

  • Anonymous
    May 9, 2017 at 11:28 am

    Very helpful post! We haven’t made the jump yet with our 1 yr old beyond long car trips, but we are hoping to do some flying with him in the near future. The stroller you linked looks like a Godsend. Definitely will pickthat up. What kind of carseat do you guys use with it? Just curious (I know the stroller is compatible with a few brands). Thank you so much for your advice!

  • Lindsay
    May 10, 2017 at 12:27 pm

    We purchased a car seat for our LO for our upcoming trip even though it’s only a few hours and I’ll do so for any trip we take.

    Aside from comfort (I’m one of those people who falls asleep before we even take off!) it is MUCH safer. A little background…the aviation industry does not require it because statistically, even ‘lap-babies’ is much safer than riding in a car but more importantly, it would mean a LOT less business for airlines! It always seemed crazy to me that we require bags (even small purses!) to be secured or under the seat but not a baby with fragile developing bones! That recent Aeroflot flight to Bangkok had 3 babies injured (reportedly with spine injuries, the same type of injury typical of incorrectly/not restrained children in cars).

    Sorry for the scare but hoping to share because what originated as a logistically/economical decision has now become such the norm that people think it’s actually SAFER when it’s not!

  • Revanche @ A Gai Shan Life
    May 10, 2017 at 10:18 pm

    Welcome back from vacation!

    We’ve flown several times with JuggerBaby now: San Diego, Hawaii, Seattle, and overseas to Asia. We’ve never used zir car sear on the plane, we just checked it, omg with a full stroller. We had planned to allow screen time when ze was still an infant but botched it so ultimately ze just played with us. As a toddler, ze doesn’t need limits on screen time at home because after 20 minutes, ze will voluntarily ask to turn the tv off. Even if we wanted to use the tv as a babysitter, we couldn’t 😉

    The real magic screen is one that’ll play music for zir to dance to but that’s really not plane appropriate.

    On our most recent trip, we had great luck with small plane packs of toys: reusable stickers, a deck of cards, some bead necklaces, little matching tiles from the dollar bin at Target and a small bag of Legos. That meant happy toddler play for HOURS. Also, never travel without books, though we limit it to four small books for carryons.

  • littie luxury list
    May 11, 2017 at 7:47 pm

    I totally follow these tips too! Our little one took her first transcontinental trip at 4 months and I miss those days. She is so active as a toddler and while we limit screen time (it was/is a good incentive for potty time though!) all rules go out the window when we travel, especially on long hauls. We took the direct from SIN-SFO and it was pretty brutal. But the travel is the easiest part and we always have to deal with jetlag.
    I do love kids clubs now too. My little one this week said she wanted to go to the Maldives. We are blessed to be able to travel, but I’m still not taking a toddler to luxury resorts all the time!