Real Talk with Real Moms || Traveling with Little Kids

(This post is part of our Real Talk with Real Moms series. Be sure to check out the other posts today from  Lovely Indeed ||  Studio DIY || The Proper Blog)

I have always known that I wanted to travel with my kids. For some people, my husband included, the idea of toting around tots in another time zone is a quick way to cue stress or anxiety, and understandably so. To me, though, the idea of getting to experience a new place with them by my side is my idea of living my best life. I have been to New York more than a dozen times, but getting to see the city last summer through the lens of a four-year-old Parker brings tears to my eyes right now just recalling it.

I read an article a couple of years ago written by Rachel Denning and it resonated with me so much. She wrote, “Deciding not to travel with your children while they are young ‘because they won’t remember’ the trips you take is a little like saying you’re not going to read to your children while they are young because they won’t remember the books you read. You read to your small children because of sounds they will hear, the words they will see, the skills they will acquire, and the habits you hope they will form. Traveling with young children is very much the same.” So much of childhood development happens in those early years “before they will remember”, but the experiences and exposures shapes their mind and the person they will become. They get to see new places, landscapes and people. They get to hear new languages, eat new foods and interact with new things. They learn to be adaptable. You are giving their mind entire new frames of reference.

Here’s a little secret, though, and perhaps my favorite thing about traveling as a family. I am my best mom self when on vacation. Seriously. I’m not worried about multi-tasking and getting work done. I’m not concerned with the laundry or some closet that needs to be organized. I’m not grocery shopping and planning our next meal. I’m fully present in the moment and eager to play and explore.

Ready to jet set? Here are few things I’ve learned along the way…

Set Realistic Expectations: The quicker that you can come to terms with the fact that your child will melt down at some point, you will forget to pack something important and you will come home more tired than you left, the better off you’ll be traveling with kids. Here’s the inescapable reality of traveling with kids, at least for me: The highs are higher and the lows are lower and it’s often times a roller coaster of both. At the end of the ride, though, I always want to go again.

Planning the Trip: I think that any destination is suitable for kids, but kids do change the itinerary. For example, we never could have made the long drives without stopping for breaks with the kids in Iceland. so we would have needed to extend the trip or do less. In Mexico City kids weren’t allowed on the architectural home tours so we likely would have swapped those out for some of the city’s amazing museums if the kids had been with us. As for flights, my kids are so much better in the morning than they are in the evening on a plane. On return flights, though, I like to plan it so that by the time we get home we don’t have too much time before bedtime. I was recently looking at flight options for Hawaii and there was a red eye return flight that landed back home at 6am which is basically my worst nightmare!

Packing: For starters, only kids who can pull their own suitcase get their own suitcase. Parker always begged to take her Hello Kitty suitcase on trips but I refused until she was old enough to take care of it herself. Consolidating luggage is super helpful for getting around efficiently. Consider what the kids will need to get around. Last summer we didn’t take a stroller to NYC or Martha’s Vineyard and had no regrets. I wore Ever everywhere and it was honestly the easiest solution. However, with Ever at 20 months we did take the stroller to D.C. with us and it was both an annoyance and a necessity. The nice thing about the stroller is that you can store other things in it– water bottles, purses, etc. I use packing cubes to keep things nice and organized in my suitcase. I learned the hard way to always pack two pairs of shoes for each kid because blisters. I can usually get away with just a pair or two of pajamas. No need to pack one for every night. I check as much baggage as I can because we are never going to be able to avoid baggage claim so it makes sense not to have to juggle it all the way to the gate.

On the Flight: Every kid is so different, but for me I always pack the following for each kid: at least one new activity that they haven’t seen before (both Parker and Ever loved these recently), something they love like a lovey or baby doll, headphones (I bought these for Ever for D.C.) and an iPad of stocked shows and movies (for Parker- Ever doesn’t have the attention span yet) and a snack pack (we have used these for two+ years). For anyone who doesn’t want to do screens, I recently found these at a local toy store and Parker is obsessed! On a flight, give Parker an iPad and it’s almost like she’s not there. Ever on the other hand makes her presence very known- ha! Also, I am the crazy person with multiple sanitizing wipes who wipes down every single surface as soon as we board, especially those tray tables!

The Schedule: It’s really important to prioritize what you really want to do and see and what is okay if you miss. When we were in New York, we took it really easy the first and third days and went hard for nine miles and eight hours on day two. Usually I like to plan one thing for the morning and one thing for the afternoon each day. If we have time to do other stuff, great, but it’s better to not try to jam too much into one day. Also, I find that my kids can go like two days napping on the go before it really starts to catch up with them. By day three they need a day back in their normal schedule to catch up on rest before they can really be on the go all day again without being just ridiculously grumpy. When Parker was three we did LA and Palm Springs and I totally didn’t make space for her normal schedule and by day 5 she was a total nightmare to be around.

Post-Trip Recovery: Re-entry is hard. If you can avoid it, don’t fly back on a Sunday night if you have a busy Monday. Give yourself and your family time to catch up on sleep, laundry, and get re-adjusted before going back into normal life.

If you’re looking for more travel tips, I wrote more on the subject here and you can read all of our trips we’ve taken with kids here

  1. These are really good tips!

    Effortlessly Sophisticated

  2. Savannah


    I don’t have kids yet, but you make traveling with kids look really good!

    • Jen Pinkston


      There are high highs and low lows, but always worth it!

  3. Elizabeth


    I love that quote so much! It’s a great perspective.

    • Jen Pinkston


      It has seriously been burned into my memory since I first read the words. It really articulated a feeling I had that I don’t think I was able to put words to.

  4. I’m curious what your favorite trip has been with kids so far? I would love to take my boys to hawaii!

    • Jen Pinkston


      Hawaii is so kid-friendly. We did Maui with Parker right before she turned two and had the best time! We are hoping to do Oahu at the end of this year. I really loved New York with the girls last year, but I feel like I have a great memory or two from every single trip we’ve done with them.

  5. Kristina


    So glad you guys brought this series back! It’s been my favorite even before I had kids!

    • Jen Pinkston


      Ah, thank you! You would be shocked how many emails I have received from people who don’t have kids who enjoy reading it! It’s one of my favorites too!

  6. Candice DePrang Boehm


    would love to hear your maui tips! we are headed to a small town in maui in late october when the kids will be 2.5 y & 7 MO.

  7. These are really practical tips! As a soon to be mom, I know I want to travel with my kids. Like you said, “they learn to be adaptable.” And even if my kid doesn’t remember, I will! I will definitely be referring to this post when I have a trip planned.


  8. My kids are all teenagers now. I used all of these tips, but had to learn all that on my own. Blogs were just starting when I was having my babies, no social media to help out. My biggest tip is to came home a full day before you have to be back at school or work. It was IMPERATIVE to getting us back to normal, and gave us the easiest transition back to our routines. And whenever I could, I would do laundry before I got home. It was amazing how one less chore gave me so much more time and energy.
    And as an aside, I think traveling with kids is really important. All of my kids had their first flights before they were 2 months old, and their first solo flights (to see grandparents) by 10 years old. They weren’t scared or worried because they had been in enough airports with us already. This past January, our 13 year old flew out to Chicago on a red eye at the very last minute. Booked the flight at 3pm, she was on the plane at midnight. She NEVER would have been able to do that if she hadn’t traveled as much as we have. Planes, trains, or automobiles, we have done them all. And I think my girls are better off for it.
    Thanks for passing on your wisdom to all the moms coming up behind you.