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!