I recently took a trip to Puerto Rico with my husband and our toddler… and while our time on the island was genuinely lovely, getting there and back was a very different story. My three-year-old had already been on ten flights before this one, so I went in thinking we had this whole “traveling with a toddler” thing figured out. But the combination of a rushed departure, a sudden wave of airplane anxiety from both of us, and airline traffic reductions that week turned our travel days into a full-on adventure — the kind you don’t brag about on Instagram.

It wasn’t smooth. There were tears, meltdowns, delays, and a few moments where I silently questioned all my life choices. But there were also lessons — big, humbling, practical lessons — about what actually helps toddlers travel well and what just adds to the chaos.

Even the messy trips teach us something, and this one taught me a lot.

What I Actually Did Well

1. I planned for entertainment.

I had activities, shows downloaded on the iPad, small toys — the whole arsenal. And honestly, these saved us more than once. I even got her to wear her headphones, which had never worked in the past. When I saw her locked in on her favorite cartoons, I thought, “Okay, we’ve made it.”
I was wrong.

2. I packed solid snacks.

This was clutch. Familiar foods gave her comfort when everything else felt overwhelming. She loves fruit, muffins, and milk, so having those prepped and ready to go made a huge difference. And for the milk, I packed powdered milk and mixed it right before she drank it — zero refrigeration stress and one very happy toddler.

3. I brought changes of clothes and planned bathroom breaks.

This kept the “big” emergencies away. We avoided outfit disasters and frantic mid-flight bathroom runs. But now that she’s older, we didn’t need nearly as much as I packed. Next time, I’ll pack lighter and save myself from carrying all that extra stuff.

What Didn’t Work (And Why It Mattered)

1. Sitting at the gate too long.

Toddlers plus waiting equals chaos. By the time we boarded, she was restless before we even stepped on the plane. We normally minimize gate time thanks to TSA PreCheck, but with the government shutdown and a checked bag, we arrived earlier than usual. Then our flight was delayed an hour. No bueno.

2. Boarding early.

Thank you, family boarding… but also, absolutely not. Boarding early meant she sat confined way too long before takeoff and got overwhelmed watching everyone rush in.
If you’re traveling with another adult, split up: one boards to set up the space, the other lets the toddler move until the very last minute. Total game changer.

3. Not using magnesium early enough.

I rely on drug-free magnesium drops to help her regulate, but we gave them too late. By then she was already in “nope” mode. Next time, I’ll give it at least 20 minutes before boarding.
(Always check with your healthcare provider before adjusting doses.)

4. Using melatonin.

This one missed completely. Instead of calming her, it made her crankier — not ideal at 30,000 feet. It might’ve been the timing, but I think I’m skipping melatonin next time and relying more on magnesium.

5. Not bringing candy.

Sometimes strategic bribery is the move. A lollipop during takeoff on the flight home helped with her ears, her focus, and her mood. I still regret not bringing any for the first flight.

6. Not getting her excited about the airplane.

Because we booked last-minute, we skipped our usual lead-up: talking about the plane, looking at pictures, pretending to pack together. At three, that buildup matters. She needs to feel part of the experience — not dragged through it.

Bringing It All Together

This trip reminded me that even with experience and all the right tools, traveling with little ones is unpredictable. And that’s okay. Every bumpy moment taught me something I can use next time — ways to prepare better, stay calmer, and support my daughter when the world feels big for her.

At the end of the day, the goal isn’t a perfect trip. It’s a meaningful one. And with the right preparation (and maybe a lollipop or two), you really can travel without losing your sanity.