Tips for Traveling with a 5 month old


I hesitate writing this post because I am absolutely sure it will jinx us for future trips, but alas, here we go.

I’m just going to say it. Henry was amazing on his first official vacation. Dare I say he was even more behaved than he is at home? Granted, we’ve been taking him to Vermont since he was a wee 4 week old so I suppose he’s a bit seasoned, but this was the first time we hopped on a plane and put our parenting to a real test. It was the first time I truly had the “is this worth it??” moment. And it was. It really was. Here’s how we tackled everything to make it not only seamless, but really really fun.

The Airport


This is huge when you have a little one. Get it. It takes like 5 minutes of paper work, but it will save you hours of annoyance. Andrew and I had Global Entry and TSA Precheck before Henry was born - but it was just a luxury then. Now it’s a must. We breezed through security like no big deal with Henry. Even with a cooler full of breast milk and puree pouches (both just in case), a stroller, a car seat and carry ons. I’m pretty sure the entire line wanted to stand up and cheer at our efficiency. It might be one of my proudest traveling moments.


I’m still on the fence on this one. On our way to Florida we checked our stroller and car seat and just wore Henry through security. I loved this because I hate having a bunch of stuff on me at an airport. On our way back, we took the stroller and car seat into the airport because it was nap time (I still wore him through security). Both really worked out well, and I wanted to try out both scenarios. I think for our upcoming trip to Spain I’ll bring the car seat / stroller combo into the airport just to have it since we’ll have longer wait times. Although the bonus with checking the car seat / stroller combo is that you can pack it to the gills with stuff (diapers, laundry, etc) - and it’s like a free checked bag. So really, either work depending on your scenario.


Henry loved the airport because he could smile at so many new faces. We used these random kind strangers as free entertainment, and Henry thought the airport was the happiest place on earth. I also brought a blanket that I could throw on the ground before take off so he had a few solid moments to “get his wiggles out” (as we call it). I know I hate being stuck in a seat for hours on an airplane, and if I could get my wiggles out beforehand, I would too.

Tips for traveling with a 5 month old Gasparilla Travel Guide from Abby Capalbo
Tips for traveling with a 5 month old Gasparilla Travel Guide from Abby Capalbo

On the Flight


If you do gate check your stroller and car seat and you have an Uppa Baby Vista Travel Set, I highly recommend getting the travel bags if you travel a bunch (here is the stroller bag and here is the car seat bag). They will fully replace your stroller if it’s in these bags and they get damaged. And we’ve all seen how they throw those bags around.


This was crucial when boarding the flight so I had free hands for everything else. We used this one since it’s a tad smaller than the Ergo and we knew I would be wearing him.


I bought a few new (cheap) toys to bring on the flights to introduce to Henry when he started getting bored. They worked wonders, and then we had toys for the trip too.


We flew Southwest to and from Florida, so we got extra lucky because no one really chooses to sit next to a baby on a flight. So we got our own row both ways. That totally spoiled us. Mostly during his massive blow out on the way home (too much information?). I have heard people say ask the flight attendant if the flight is full every time you board with a baby to see if you might get so lucky. On our way to Spain next month, we know we won’t get that lucky - but we did reserve a bassinet in hopes that will give us some wiggle room.


Everyone will tell you this, and it really is the most important tip - make sure your baby is nursing, sucking on a pacifier or taking a bottle during take off and descent. This will help their poor ears from popping.

The Vacation


If your baby is used to being on some sort of routine, a vacation can really shake them up. Remember that feedings and naps are the most important thing (for everyone) to make sure the day goes well. We planned our walks or lunches or beach time around when we thought Henry would need a nap. And we basically planned everything around his feedings (because the boy likes to eat). It resulted in a really happy baby the entire time (we called this overly happy alter ego - “Vacation Henry”), and more importantly, parents who actually got to enjoy their vacation!

Bedtime is another thing Henry takes super seriously, so we made sure he was in bed at 6:55pm on the dot every day (after his bath of course - which we used this blow up bath tub) - and then got a babysitter to sit and watch him sleep while we had a date night. (*The Gasparilla Inn is known to be very family friendly resort, and all baby sitters are actually staff members at the inn - so we felt very comfortable leaving him. Plus we were literally across the street).


If you have a little one, you know that sleep rules all. We booked a tad late for the hotel we were staying at, and we knew Henry would be sleeping right next to us. This sent me in a bit of a panic because Henry likes his own, super dark room for sleeping. But I found the Slumberpod, and boy did that thing work like magic! It made me a little nervous at first to zip him up - but he slept better than ever! We also brought a used sheet from home, his sleep sack and his lovey to make sure he felt extra cozy.

*one thing we did realize is that the Nanit isn’t the best for traveling. WE LOVE THIS MONITOR, and it was sort of a bummer that it didn’t work on an unsecure network (which we totally get). So make sure to check and see if your hotel has secure wireless before bringing this monitor or bring a back up.


Here is what we brought that really, truly helped us. We used every little thing on this list multiple times (we did end up leaving the jumper at home because we just didn’t want another thing to carry - but it will be useful for more local trips!). We also were introduced to Totts Travel before we left, and they sent an amazing package of everything we needed (diapers, disposable bibs, swim diapers, tylenol, etc). And that was a HUGE help!

(Images are clickable)

I hope this all helps! Let me know if you have any questions in the comments! xo