One of our more popular posts recently has been Tips for Traveling with an Infant, but as you’ve likely seen from our more recent pictures/trip reports, Lily has definitely outgrown the infant label into a toddler – and an active one at that!  With that, traveling with her has introduced a new set of challenges, but more importantly, has made traveling more enjoyable in an entirely new way.  We’ve learned a ton of new tips and tricks over our past few trips, so we wanted to share the ones we think will be most helpful on your next trip with a toddler!

Full Disclosure: we’ve linked a couple of our favorite items below, and if you purchase through those links, we do earn a commission (at no cost to you). However, we would never recommend something that we haven’t personally used, and the income goes towards keeping this site updated!

Plan activities for your kiddo.

This may seem like something that’s obvious, but the emphasis is on ‘plan’; a common mistake made is assuming that your kiddo will just go with the flow or entertain themselves.  That happens sometimes, to be sure, but there are few things worse than a long car ride with a toddler that has nothing to keep their attention occupied. We actively try to limit Lily’s screen time, but for some of our longer car rides, we’ve found that a small tablet (we went with an Amazon Fire Tablet for Kids) has been instrumental in help keeping her entertained. We keep a lot of restrictions on it (we’ve specifically chosen both the movies and the games that she can watch/play), but let’s face it: keeping a kiddo entertained for a 5 hour car ride can be a lot of work on the adult doing so, and a 15 minute game/movie break here and there can help keep you refreshed for the trip as well. And at the end of the day, trips should be for parents as much as they are for kids!

Of course, one of the best things about toddlers is how little it takes to keep them entertained – Lily can still spend a surprising amount of time on the most minimal of activities, enjoying every minute of doing so thoroughly. We literally spent hours at the beach playing with shells and in the sand, and even though we had a small sandcastle building kit to do so, she would have been fine with out it. But the important thing wasn’t what we were doing (it didn’t require much planning), but we felt a ton of reassurance in knowing that we had a plan for each day.

Have a backup plan.

To build on our first point, a huge part of planning for a toddler is being flexible with those plans, and being able to adjust if that plan doesn’t go as you initially hoped. We’ve planned a number of activities that we thought Lily would absolutely love, and they were an absolute dud; when that’s happened, it’s never something that a quick coloring book or this drawing pad can’t fix! We always have a couple of different options (that are space-efficient) packed away into Lily’s diaper bag for exactly these moments that we have to switch gears quickly.

On the flip side of that scenario, we’ve found a ton of things that we budgeted minimal time for, but ended up spending extra time there because of how much Lily enjoyed it – those sorts of surprises are often some of the best discoveries of a trip. A big part of the flexibility that we try to maintain is setting aside time to stay at an activity a bit longer

You cannot be too over-prepared.

One of the best things about being a parent in today’s day and age are the sheer number of things that exist to help parents with traveling. More ofter than not, if you mention to yourself, “Wow, wouldn’t it be great if someone invented something that does x” – you’d be surprised at how many of those things already exist. For example, Lily slept in her Pack n’ Play up until the point that she outgrew it, and we loved how convenient it was to pack; so when she reached that point, we were dreading not having a sort of transition bed that was just as easy to travel with – but with a bit of research, we very easily found one: in this case, we settled on the Hiccapop – an inflatable mattress that has sides raised up to keep her secure, but also packs up very easily.

Lily had never slept on an inflatable mattress before, and fortunately our first use went very smoothly, but we largely attribute that to testing it out well beforehand, and letting Lily get familiar with it as we did so. We went through a full set-up in our dining room a few days prior to the trip to introduce Lily to it, and we let her see how to inflate the mattress, bounce around on it (only a bit of course), and reaffirmed that this was her new travel bed. It ultimately went super well, but we’re big believers that it wouldn’t not have gone as smoothly if we hadn’t made a point to prepare her for it well in advance.

One thing that we’ve found is that there are so many different tools and gadgets out there to make traveling as a parent easier. If you’ve thought “this shouldn’t be this difficult” at any point on a trip with a kiddo, there’s a pretty good chance that someone else thought that, and then created something to help. The best example of this that we’ve found was the Piggyback (seen below). As relatively frequent theme park travelers, we love a good fireworks show; however, with a toddler, those almost always involve holding up your kiddo… at the end of what was likely a very busy day. We stumbled upon the Piggyback online not having any idea that it existed, and it could not have been a better find. Lily loves riding on daddy’s shoulders or on his back, but when you’ve been standing in lines all day, it’s not always easy to carry her; this keeps her safely strapped in (essentially like a backpack), while still giving her the view up high to see the fireworks – it’s one of our favorite travel finds ever.

Similarly, when Lily flew for the first time, we weren’t sure how to handle the carseat situation; she’s no longer a “lap child,” but is still too small for the airplane seatbelts to adequately secure her (and planes obviously don’t have a carseat equivalent). But after a quick search or two, we found a plane seat safety harness that was a quick and easy addition to the plane seat, was easy to pack and carry, and still keep Lily as secure as we’d like. We never would have thought of something like that existing, but it quickly solved our dilemma, and made us feel way more secure about Lily’s first flight.

These are just a few of the things that we found helpful, but there are truly countless things like this out there. If you anticipate running into a particular problem while traveling with a toddler, it’s worth it to look around online to see what others have done to solve the problem – you’ll never believe what inventions are out there to help!

Enjoy your trip!

If you’re reading this post, you likely enjoy traveling – we’re making an assumption there, but given that this is a travel blog, it’s a pretty safe one. It’s super easy to get bogged down with the details, or to feel like traveling with a toddler is more work than it’s worth. But we could not disagree more: there is a genuine magic to traveling with toddlers. Those ages are all about discovery, so exploring a place that is completely different from their typical surroundings provides them with sensory overload in the best way.  

The best example we’ve seen is Lily’s trip to the beach – we hinted at it with one of the tips above, but she was absolutely fascinated by the sand (which conveniently required little prep on our part).  If you’d told us prior to the trip that we’d spend most of the time just playing in the sand, it would have seemed pretty dull; however, we quickly found that watching Lily explore the most simple activities was our favorite portion of the trip. And that’s likely the best advice we can offer: if you’re planning to travel with a toddler, you’ve actively chosen to set aside time to do so, so take advantage of that and explore with them!