If you’re travelling with kids for the first time, this is a post for you!

This is a story about our first travel adventure as a family and the lessons I learned from travelling with kids for the first time. I’m sharing these lessons, so that YOUR first time travelling with kids will be much smoother!

I’d travelled quite a bit before I had kids, usually just with carryon luggage for a week or two, so thought I knew what I was doing. And I figured even with kids, no problem, I’d just bring an extra suitcase for them.


It turns out that there’s a bit more to it…..

Our first international adventure –and also the boys’ first flight – was definitely a learning experience!

I’m here to share the lessons that I learned, so that YOUR first time travelling with kids will be a bit smoother.

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Up until now, my travel style had been to pick an international destination, spend a week or two there and do some sightseeing, while wandering around and exploring the city. I loved to stop and have a coffee (or fancier drink) at a café and spend some time people watching.  

And yes, I realized now that I had toddlers with me, the wandering around, admiring architecture and people watching at a café while enjoying a leisurely drink wasn’t going to happen. But somehow I thought that we might still have a similar type of vacation. So for my first trip with kids, I booked a 10 hour flight to the south of Italy.

It probably wasn’t the best idea.

Although we still had a good time, there were a few mishaps and it wasn’t as smooth as I’d expected – really, not sure why I expected that though!

Southern Italy is a fantastic place and I would highly recommend going there, BUT maybe choose somewhere closer, with a shorter flight (and less jet lag) when you’re travelling with kids for the first time.

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Lessons Learned from Travelling with Kids
for the First Time

Our flight was an overnight flight, which was great as it didn’t seem like a ten-hour flight when we slept most of it! Well, the boys slept easily, as it was WAY past their bedtime when we boarded, but I had a harder time sleeping and kept checking on the boys.

Just before landing, I woke the boys up. One was up and ready to go but the other was still sleepy and wanted to be carried. I hadn’t thought about that AND how I would get our two carry-on bags off the plane, while carrying a sleepy child.

1. Arriving and Gate-Checked Items

Another surprise was when we started to leave the plane and realized we had to climb down the steps to the tarmac. The jets were still going and the noise and wind were a little scary for the boys.

We were the last ones to disembark so I didn’t even have someone to help get us all down!

We managed though, with me carrying both suitcases in one hand and trying to convince the boys down the steps while holding onto the railing.

Lesson Learned #1: Don’t bring excess carry-on luggage. You’ll need your hands free! A backpack per kid and a bag for mom or parents is plenty.

Read more | Best Carry-on Luggage for Families

Once we were on the tarmac, things improved! But there was no stroller as I’d expected!

We walked across to the airport and waited –outside- in a long line to get through customs. The line snaked outside of the airport building, which was nice and warm and gave the boys things to look at.

After about an hour of waiting in line (no priority lines for little kids and families at this airport…), we finally made it through customs and the boys got their first passport stamp. Even though we had no luggage, because I (mistakenly!) thought it would be easier with only carry-on bags, we had to still pick up our gate-checked stroller.

Lesson Learned #2: Gate-checked items don’t always get returned to you at the final gate of your flight. Although that’s customary on most flights to larger airports where they have the jet bridge to exit the plane, in smaller airports that’s not always the case and you may find your gate-checked items at the luggage claim.

3. Arrange Transport from the Airport

A friend’s husband was coincidentally on the same flight as us and had offered to drive us to our hotel. He met us at the baggage area (I guess we weren’t too hard to spot!) and we were off! What a nice offer, as it was about a 45-minute drive to our hotel.

The scenery along the way was absolutely stunning and if I hadn’t been craving a nice hot shower and some breakfast, we could have stopped along the way. 

If you don’t have someone picking you up, or you’re not renting a car at the airport, make sure you arrange transport AHEAD of time. Gone are the days when you travelled solo and could just find a bus or train once you arrived at the airport.

Some hotels may offer airport transfers and although there is a fee, it’s usually well worth it! If not, check ahead of time to see if you can pre-book a taxi or shuttle to your accommodations.

Lesson Learned #3: Make sure you have transportation from the airport arranged ahead of time. Luckily we did, but if our friend hadn’t offered, I’m not sure I would have thought of it before we arrived, with all the other packing, prep and paperwork that’s required for travelling with kids for the first time.

4. Check the Directions Ahead of Time

Arriving in Tropea, I didn’t realize that the hotel we had booked was really a B&B and wasn’t a big hotel that was well known. Although I’d written the address down, I hadn’t thought to get specific directions.

Luckily, my friend’s husband spoke fairly decent Italian and was able to ask locals for directions to where we were staying. None of the little streets have signs, at least not like they do in larger cities. Without him and some basic Italian, I never would have found the address on our own!

Lesson Learned #4: Write down exact addresses and directions before leaving! (I usually do this, I think this time I just had other worries about the trip on my mind).

5. Confirm Accommodation

Once we finally found the right place, it turned out the apartment wasn’t even ready for us. There had been some miscommunication through Booking.com and they weren’t expecting us.

We were able to leave our bags and went on a hunt to find another place to stay that night.

By the time we found somewhere else, went back and got our suitcases, it was almost 6 pm and we had been travelling for a VERY long time. We were glad to get in, have a shower and find something to eat before we all crashed and slept straight through to late morning. The bonus was that we didn’t experience any jet lag at all! 

Lesson Learned #5: Confirm accommodation ahead of time and make sure to have the confirmation number handy – write it down, save in on your phone or screen shot it!

**Side note – the mixup was not the fault of Booking.com, and we have used them exclusively for all of our other travels without any problem at all. We highly recommend them!


6. Strollers and Cobblestones Don’t Mix Too Well

One of the nice things about Tropea, as with many other European towns, is that it some of the town is pedestrian-only and many of the streets are cobblestone. Which certainly adds to the charm of the town, but strollers are NOT great on the uneven cobblestones.

If you are bringing a stroller when travelling with kids for the first time, an umbrella stroller may seem like a great idea, as they are light weight and fold small but it will be very hard to push on the streets.

We had a larger style City Mini, and even with those tires, it was hard to manage on many of the streets. Although I didn’t think it would be great to take on the plane, I constantly wished for the large tires on my double running stroller!

I also had this bright idea that one of the boys could ride in the stroller and the other could stand behind on the stroller board (or I could wear him in a wrap and I could balance some of the suitcases on the board). Either way, the stroller board is definitely NOT a good idea on cobblestones. Stick with a double stroller if you have two kids.  

Lesson Learned#6: Strollers aren’t great on cobblestones, especially umbrella strollers. Skip the lightweight strollers and bring something with wider tires, but keep in mind many European streets can be narrow, so a large stroller isn’t great either.

7. Bring Snacks

Although the food in Italy, or wherever you are headed may be fantastic, kids can be picky and it’s wise to bring some snacks from home.

Just in case.

Even if your kids love the food, there will times that those snacks will come in handy.

Like when you’re waiting in a long line to go through customs on arrival.

Or while you’re out exploring.

Or when you’re finally got everybody and all the ‘stuff’ to the beach and then someone is hungry.

Or during that long, day-time plane ride home.  

Lesson Learned #7: Bring snacks. Lots of snacks. (Fruit and liquid snacks aren’t allowed through customs, even some dried fruit is prohibited, but granola bars, rice cakes and dry cereal are good options.)

The rest of our time in Italy went much more smoothly! We spent some time on the beach and some time exploring. The boys napped in the stroller (yes, squished into a single stroller) while I did some sightseeing and I even managed to stop at a café for a leisurely drink during one of those naps!

Even with some hiccups and a tough first day (or two), it was still a great vacation. In fact, I just looked at those first few days as lessons learned, made notes not to do it again, and our next trip was much smoother! (Although there were some mishaps and adventures on that trip too, but it wasn’t due to my lack of planning. That’s a story for another day.)

Now that I’ve learned these lessons the hard way, I’m sharing them with you so that your first time travelling with kids will be easier!

Final Thoughts: Lessons Learned from Travelling with Kids for the First Time

Lots of lessons were learned on that first trip as a family.

I felt like such a beginner traveller, even though I had travelled a fair bit solo. But travelling with kids for the first time is a completely different experience!

Plus you’ve got so many more things to consider, that it’s easy to forget some of the basic things.

#1. Don’t take carry-on. Next time I will definitely bring a large backpack!

#2. Don’t assume that your stroller will be at the gate.

#3: Arrange your transportation from the airport ahead of time.

#4. Write down exact addresses and directions before leaving!

#5. Confirm accommodation ahead of time.

#6. Strollers and cobblestones don’t mix well.

#7. Pack extra snacks!

And lastly, have a great time! Let us know how your first time travelling with kids goes!

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  1. This is a great article! I have a 3 1/2 year old son, so all the tips and advice are super helpful. Definitely some great tips.

  2. Awesome post! I remember what it was like to travel with young kids! If you are not well prepared, its gonna be a LOOOOONG day!

  3. Great post! You are so right about the cobblestones! I’m from Rome and my sister and friends with kids always struggle with the strollers 😀

  4. Such a great post. Wish I knew about these before I first traveled with my daughter. Thank you for sharing! I’ll definitely keep this in mind the next time I travel.

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