Traveling With Toddlers

By Meghan Rossi

Hi there!  This summer we were so lucky to have the opportunity to travel.  We took the boys to five states! We experienced everything from warm beaches to cool mountains. Through trains, planes and rental cars we learned a ton about traveling as a family.

One of my biggest learning experiences was traveling solo with the boys.  I managed four flights, and even one family reunion, solo with the boys.  Just me and two toddlers (ages 4 and 2) navigating airports, security, connections, rental cars (no better workout than to solo install two car seats in blistering sun while your toddlers threaten to run into oncoming traffic, ha!), and hotels.

Ever watched American Ninja Warrior? Yeah, go ahead and get that ultimate challenge in your head as you imagine me in the airport with a luggage cart, stroller and two boys ages 4 and 2. Kane is at the age where he is relatively happy to follow instructions, and is completely content with his videos and snacks. Arlo? Like a caged wild animal on a plane! It’s intense.

First up, best thing you can do is plan ahead. About a month out, I’ll begin researching baby gear rental companies, highly accredited babysitting/ nanny agencies, and urgent care & hospitals at destination. 

I check baby gear availability & pricing and make my order. Typically, I will rent a full size crib for Arlo (2-years-old, and because many hotel cribs are small & he can climb out which makes nap/ overnight sleep a nightmare), a baby monitor (because luggage scans have zapped mine in the past), a white noise machine (if it’s priced right & I can’t fit mine in suitcase), and I always order a box of diapers and case of water if they have them offered. I have even ordered a small set of toys, hiking back pack, car seats and strollers in the past.

  • Crib
  • White noise machines
  • Monitor
  • Diapers
  • Bottled Water
  • Have also done: hiking back pack, toys, car seats, and strollers.

For the babysitting/ nanny agency I begin with an online search of nanny agencies in my destination.  Search their website to see if they offer temporary sitters/ nannies to traveling parents.  I then research the company, read reviews from various sites, email them, set up a phone call… and if I like their communication (to check professionalism), if they do background checks, etc.  I then move forward with interviewing their suggested sitters. 

I need a temporary sitter when traveling for work, because I like having my kids with me while they’re still young enough to miss school, but I do need a sitter when I have meetings and events.

When we are on vacation, I’ve hired a sitter strategically for one or two mom-dad moments on the trip.  Like a couple’s spa afternoon or a couple’s brunch or dinner.  I’m a believer in that the stronger your relationship, the stronger your entire family unit.  It’s definitely a good idea to take a few hours out for mom & dad time during a family vacation.  We do try to schedule in afternoons when the boys are in nap time, or at night after a full day of fun together.

As for urgent care and hospital, there has hardly been a time we’ve traveled with our young kiddos with building immune systems that someone hasn’t gotten an ear infection, stomach bug or virus. I always know ahead of time where there are hospitals and urgent care clinics.  I travel with a thermometer to take their temperatures at any given moment, and I travel with a first-aid kit along with children’s fever medicine and vitamins so I can save time having to hunt down a pharmacy.

Now that I’ve worked ahead on baby gear, babysitting for mama-dada quality time, and healthcare, I work on packing.  I start by making a list of everything I need on the road by category: travel clothes, day clothes, night clothes, sleeping, bath time, feeding, diapers, travel and healthcare.  Then I make a list of everything I need within those categories. Here’s an abbreviated example:

  • Travel clothes, light jacket, shirt, pants, socks, shoes + backup shirt & pants
  • Day clothes, 5x shirts, 3x shorts, 3x pants, socks, 2x swimsuit, 3x shoes, 5x undies
  • Night clothes, 4x dinner outfits
  • Sleeping, 5x PJs, lovey, sound machine, pacifier, blanket, bedtime books, night light
  • Bath time, shampoo/ body wash, toothbrush, toothpaste, hairbrush, gel, nail clippers, body lotion.
  • Feeding, 2x water cups, 2x snack cups, 2x reusable snack bag (for babies add travel spoon/ fork, bottles, disposable placemats, etc)
  • Diapers, 20x day diapers, 10x night diapers, cream, wipes
  • Travel, backpacks, tablets, headphones, lollipops (ears on airplane), change of clothes, snacks, water, coloring books, stickers, car seats, stroller + gate check bag, and photo ID.
  • Healthcare, outlet plug covers, children’s fever medicine, vitamins, nose drops, essential oils, thermometer.

I begin laying out all items above in an unused guest bedroom at least a week in advance. It lets me know what I need to grab at the store or order from Amazon, and I close up their suitcase at least two days before we leave.  This includes wiping down Arlo’s travel stroller, and their travel car seats.  Everything is prepped and ready to go. 

The kiddos are all set, aside from a few last-minute travel items that need to be packed morning of travel. I leave a note tapped to their suitcase with a list of the last-minute items to add before leaving the house. It gives me peace of mind knowing I have that list to help me remember on the hectic travel day.

Quick Resource checklist:

  • Baby gear rental companies
  • Travel gear: car seats, umbrella stroller, safety wrist band for toddler.
  • Highly Reviewed and Insured Babysitting/ Nanny Agency
  • Packing Cubes to organize day/ night outfits, sleep, etc.
  • Travel Docs: Passports (photo ID), shot records, health insurance card
  • Healthcare Prep (medical facilities and healthcare items)
  • Change of Clothes (child & parent) for travel days
  • Airplane fun items (tablets, headphones, coloring, stickers, lollipops)
  • Reusable water bottles, snack cups, etc.
  • Peanut Butter and Jelly Sandwiches, mic drop!

On travel day, I have everything packed and ready to go.  We are all in our comfy gear, sneakers, and have backup outfits in our bags.  Lots of snacks, water cups ready to get us through any flights delays.  Tablets fully charged and downloaded with their favorite shows and games (for non-WiFi moments), hand sanitizer & wipes (eek! So many airplane germs), and we are ready to rock ‘n roll. 

Take it slow. Breathe. Stretch when you first wake up, and throughout the travel day.  And by all means – DON’T FORGET THE LOLLIPOPS! I purchase a bag of organic lollipops from the grocery store and stick them in our travel bags, suitcases, diaper changing bag, and basically anywhere they’ll fit. I use them as a bribe to get Arlo back in the stroller after security, we use them for take-off and landing, and for any rewards necessary throughout travel.  They never get them at home, and only for travel, so it keeps them extra special to the boys.

Whip out those homemade snack boxes on the flight and you’re a hero. I pack them with a mix of crackers, fruits, veggies… all carefully cut small for safe in-flight eating.  You can bring individual packets of peanut or almond butter, snack pouches, etc. Anything that won’t spoil.

My absolute clutch move: pack PBJs.  It can take a long time to de-board plane, get luggage, get to car, and over to your hotel or rental home.  Once you’re in the car headed to your hotel, whip out the PBJs for a well-balanced power house snack that everyone will be saying, “THANK THE LORD” after the hectic airport travel rush.

Oh, and last but certainly not least a note to parents: wear a black shirt, sneakers and make sure your pants have pockets when you’re traveling.  There will be spills, there will be the need for stuffing things in pockets, and sneakers for chasing. J

I’m happy to answer any additional questions either in the comments below or on Instagram at @meggomcrossi

Happy Trails!


To see many of the essential travel products listed above, please visit and click Travel Gear.