If you’re reading this, you’re probably waiting for the punchline. But I’m here to encourage you that with the right entourage and tools, you, too, can travel abroad with your toddler(s). AND have a great time! (There’s still no punchline.)
Note that this was not our first rodeo traveling with our kids. By the time we flew to Italy in September of 2025, Sofia had been on probably two dozen flights and Luca on half a dozen. Sofia was 28 months old and Luca was 14 months old at this time. I wasn’t worried about the flights or any jetlag. I was mainly concerned that I packed the right items to insure we’d have the most enjoyable trip.
This meant I spent a lot of time researching how to travel with your toddler and what you should pack for them to make their trip (and yours) the best it could be. Because we weren’t just going to a beach where there were essentially no rules, I knew I had to be organized. Italy is busy, crowded, and our itinerary was not packed with a child-friendly agenda. Therefore, I had to make sure I built in PLENTY of time for delays, playtime, tantrums and anything else expected or unexpected. Additionally, I had to make sure we had the right travel tools to get us around, and toys to keep the kiddos occupied in moments when we needed them to be (i.e., in stores, during meals, etc.). None of this is obviously failproof, but my god did all this planning and research make a difference!
So without further ado, to guarantee your experience is more calm than chaotic, here are my vetted and approved “must haves” for traveling with your toddler(s):
- Activity Bag. Keke Activity Bag – the PERFECT zipped bag to hold your kiddo’s activities and toys! This was literally a lifesaver. We took this with us everywhere so Sofia always had her toys to play with. Instead of buying the subscription that comes with the Keke Activity Bag, I had fun at dollar stores before our trip getting curated items I knew Sof would love (dinosaurs, coloring books, hot wheels, play cards, etc.). This was also the ideal size bag because Sofia could hold it herself (big handles), it slide perfectly into our stroller’s basket (with room to spare for other items), AND it fit within the exact dimensions of her JetKids’ luggage (top closed, no issues). You’re welcome.
- Entourage. Helpful Helpers – get yourself a reliable entourage! We would NOT have attempted this trip to the Amalfi Coast and Tuscany without my parents. Period the end. They helped us every step of the way, from carrying bags to kids, and from filling milk bottles to wine glasses, they did it all in step with me and Simran every day. They made our trip enjoyable, allowing us time off to shop or eat a meal alone, and vice versa. It was absolutely a team effort, and all the more enjoyable because they understood the assignment. Shout-out to them for being the BEST travel companions we could as for 🙂
Professional photos by Alyona Podoba
- Shopping Bag Hook. The Mommy Hook – this large and lightweight shopping bag carrier hook lightens your load when shopping, increases stroller storage space and makes carrying your purchases easy and convenient. It also keeps your individual bags secured together and on your stroller in case of run-by thieves!
- Travel Stroller. Stokke® YOYO³ stroller from 6 months – less than 15 lbs of absolute perfection that you can throw over your shoulder and go (strap included and you can also purchase the travel backpack (highly recommend)), which you’ll need to go over cobblestone and up and down stairs abroad; easily foldable to fit in the overhead compartment of any public transit; and customizable (0-6 months, 6 months+, colors, accessories, etc.). We also bought the YOYO® Connect, which makes your single stroller a double stroller. You could also buy two separate strollers if that makes more sense, but we liked having them connected. (One less separate thing to keep track of!). And make sure to get four cup holders so there’s plenty of spots for alcoholic beverages, milk cups and water bottles #protip.
- Travel Suitcase + Plane Bed. Stokke® JetKidsâ„¢ Travel Bundle​ – airline-approved ride-on luggage that turns any seat into a bed; carry-on compatible, with ample storage and a practical top opening; little ones (2-7 years old) can ride on it, be pulled along, or pull it along themselves; adjustable strap allows parents to carry over their shoulder; comes with sticker set for customization. The bundle includes an expandable backpack, which can fit inside the BedBoxâ„¢, or be attached to it. I kept the kids’ snacks, milk bottles and water bottles in their backpacks and kept their bags hanging on the outside of their suitcases for easy access and to free up space in the diaper bag.
This type of trip is not for the faint of heart. We were lucky we had my parents willing and able to help us navigate Italy with two toddlers. I can understand if you don’t have the same helpful helpers as us that this type of trip can seem impossible. And you might be 100% correct. But if nothing else, I’m here to tell you this IS possible and as I always say, the memories outweigh any of the tough moments.
Now, off you go. You’ve got this!
