The Travel Mistakes We Made So You Don’t Have To

Given that our Ciao Bambino team plans trips for a living, you might assume we breeze through airports without a hiccup, pace our itineraries perfectly and always pack the right number of baby outfits. We wish! The truth is, every one of us has had a travel moment that makes us cringe (and laugh) years later. We’ve boarded the wrong train, forgotten paperwork, misjudged our kids’ stamina and, in one memorable case, left a child behind at an ice cream parlor. But here’s the upside: Each of those moments taught us something, and the lessons we learned now help us steer our clients clear of the same mistakes. Here are some of our most memorable mishaps — consider them your shortcut to a smoother trip.

Our first time traveling internationally with our first baby was from Canada to New York City, a multigen festive trip with the grandparents. My baby had a diaper explosion on the plane and I thought, “Phew, thank goodness I brought an extra pair of baby clothes.”As soon as we landed, she had another diaper explosion and I did not have any backup clothes in the diaper bag (it was only a 1-hour flight, so I thought we’d be fine with our check-through luggage). After we went to baggage claim, we found out that our luggage was lost. Thankfully, the grandparents had packed a baby Santa suit, so our little one wore that outfit until we could make our way to Macy’s. Lesson learned: Pack multiple extra pairs of clothes in your carry-on for your baby and a spare for the parents! — Mandy Cecchetto, senior travel advisor

My early mistake: booking one hotel room with no door to separate our baby’s sleeping space, when we were all fighting jet lag. When we did this on our first trip with him, nobody got any sleep … including the guests in the rooms next door. Always book a suite or connecting rooms! In good-weather destinations, a deck or balcony is a great backup, giving you a spot to sit once your little one is asleep. — Amie O’Shaughnessy, founder and CEO

I was traveling with friends by train from Rome to Naples to spend a week on the Amalfi Coast. We checked the platform number that was printed on our tickets, boarded and settled into our seats, which were facing each other. We spread out our picnic on the tray tables and then … The conductor came on to welcome everyone on board the “nonstop train to Milan.” We were on the wrong train and the doors were about to close! We scooped up our picnic, grabbed our luggage, sprinted off to find the platform for the correct train to Naples, and hopped on as the doors were closing. Moral of the story: Train platforms change! Always make sure to read the board and reconfirm upon boarding that you’re on the right train. — Lynda Zuber, senior travel advisor

Upon arrival in Dublin on a trip with my best friend and her daughter, I learned I’d been “upgraded” from a smaller car to a Jaguar. Feeling posh, I accepted the upgrade, not knowing what a mistake that would be when trying to drive (on the other side of the road) through the rural roads along the Wild Atlantic Way! My best friend was riding shotgun and calmly would tell me when I was about to clip a hedge or the embankment was getting too close by lightly saying, “Maybe a little more to your side.” I was feeling quite confident after driving miles and miles down through the meandering coastal towns toward Killarney, where we would begin our journey ’round the ring of Kerry. Well, the evening we were pulling into Killarney, it was raining (shocker) and dark. My directions to the hotel seemed straightforward … until they weren’t. We found ourselves driving in circles on one-way narrow streets until I finally snapped and said I’m NOT going around that roundabout again, and swooped into a side street I could see connected to the main street that would finally take us to the hotel.

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As I slowly drove along, we started to notice that the alleyway was getting narrower and narrower, until we got to the point where we had to put the windows down and pull in the car mirrors. I continued to creep forward successfully until I spied two pole barriers about six inches in from the walls on either side of the alleyway exit. We sat in silence for a moment, all exchanged glances and then started laughing hysterically at the absurdity of our situation. I quickly eyed the distance between the barriers, considered the width of the Jag and said, “I think we can make it!” and proceeded to inch forward to increasingly louder shrieks of “No, Jill! Don’t do it! We can’t make it!” I turned to them with a sly grin and said, “Watch me!” and then, as the car body slowly rubbed its way through the two poles (thank you, car insurance), I deftly turned onto the street and into the hotel parking lot, where I promptly was rewarded with loud cheers, laughter and a much-deserved pint of Guinness. The bottom line: Don’t accept that car upgrade unless you know what you’re getting into. — Jill Dore, director of operations

On our family sabbatical in 2016, this mama bear was bound and determined to squeeze as much as we could into each day. The kids were young and, like all kids, would get worn out. It became a family joke because the three of them would stop in the middle of whatever they were doing and hang their heads. We coined it a “low battery moment” and they jokingly sometimes continue to do it to this day. It was a good reminder for me to go at a balanced pace while traveling/touring and to make sure they were well fed at all times. — Kim Bottoms, travel advisor

I had a pickpocketing incident in Italy, where I left my purse at the reception of the hotel because I felt safe … I walked around the corner to help some members [of the tour I was leading] and came back to sit down, and the bag was gone. My entire group was in the reception and nobody saw anything. Lesson learned, never let your guard down, especially when they’re when you’re arriving in a city for the first time and you just don’t have your bearings quite yet. — Cary Walker, senior travel advisor

We were traveling from Krakow, Poland, to Mallorca for two weeks of vacation. The kids were 2, 4 and 6 at the time. We had made arrangements for a rental car in Mallorca. When we arrived in Mallorca, we learned that we needed an international driver’s license to drive the car … which we didn’t have. We only had our U.S. license. Womp womp. That wasn’t great! — Loren Braunohler, travel advisor

I once returned a rental car to the wrong car agency. Literally dropped it in their parking lot and dropped the keys in their dropbox while trying to catch an early-morning flight with my kids when they were about 4 and 5. In my flustered single-mom state, I made the big “oops” and realized it only when I landed back home. I called the rental car company where I left the car, and they had no evidence that I had done so. I was, of course, freaked out, thinking, “It’s my word against theirs, and how will I ever prove I returned a car!” But I called the company whose car I had lost and let them know, and while they laughed, they also said, “Don’t worry, we’ll make sure we get our car back.” Thank goodness! I was wondering how I was going to explain that one to insurance. — Lissa Poirot, travel advisor

We took our four kids to Cinque Terre years ago (before I was an advisor) and, not understanding the rail situation there, got off at what appeared to be a deserted train station. We waited 2 to 3 hours there alone, wondering if we should hike to find another village, but not sure which direction and if the path was OK. Ultimately, we were picked up again, but to this day, I am very calculative on how I plan Cinque Terre for my clients and always recommend support there. — Amy Annis, senior travel advisor

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We were with two other families at a Cows Come Home Festival in Bavaria, Germany. We had six adults and eight kids in total with us — there were six girls close to the same ages and two boys, all between the ages of 7 and 12. We were at an ice cream parlor after the fest and all of the girls went to the bathroom before leaving. When they came out, we left, wandered around the town and shopped. As we were wandering back to the cars to leave, we passed by the ice cream parlor again, and out front was my 9-year-old daughter asking if we had forgotten her. I admitted we had by accident and apologized profusely. Thank goodness she was smart and stayed put like we always instructed our kids to do. She still brings it up, and she is 21 years old now. But she is not wrong to remind us! It was a horrible parenting moment, but I was so glad I had discussed what to do if we ever got lost from one another while traveling or out and about. And after that, we always did a headcount before moving on! — Kerry Rawcliffe, travel advisor

The Alhambra had been on my bucket list forever before my family and I got our first chance to see it on a 2019 trip to Spain. For reasons I’m still not sure about, I decided we didn’t need a guide or a tour. What was I thinking? We enjoyed the beauty and artistry of the palace, but we missed all the symbolism and layers of history that an expert could have brought to life. As we walked through room after room, I was looking with envy at all the people smarter than me who did have guides and were listening to stories that sounded fascinating (from the little snippets I could hear). Luckily, we returned to Andalucia this past spring and had a do-over … the experience was night and day. If you’ve dreamed of seeing a place for years, go the extra mile to make it special! — Lisa Frederick, director of marketing

On a trip to Paris, Switzerland and Italy when my kids were teenagers, we used all our euros in Paris, went to Switzerland, which uses a different currency, then trained to Milan. The ATM at the Milan train station was broken. We couldn’t even use the pay restroom! Then we went to get on the train to Lake Como. There were two trains next to each other … one to Tirano, one to Torino … very similar spellings. I showed my ticket to someone in uniform and pointed to the train I thought it was, and he nodded his head (he didn’t speak English). We got on the train with all our luggage … and it left 2 minutes early. Trains in Italy DON’T leave early! So I immediately knew we were on the wrong train. I went car to car to try and find someone to ask what to do. I finally found someone, and with his limited English and my guessing, I understood that he was saying to get off at the first stop and wait for a train coming back to Milan. We got off at the first stop, and it was a deserted train station. I called the lady we were staying with to tell her what happened, and she said, “You went the wrong direction!” Yup! Eventually another train came along, and we rushed to get on. By the time we reached our destination, the lady picked us up and we went to an ATM so we could have cash. We got to her house at midnight and she said, “Would you like some pasta?” We were not about to pass that up! So she cooked us pasta at midnight on our first day in Italy … crazy! Now I tell clients how to read the train board and to look at the train number, not the city name. — Helen Buckner, senior travel advisor

Relevant Links:

How family travel changes at every age and stage

Mindful travel tips with kids: How to live in the moment

How family travel creates resilient kids

Why travel insurance matters: One CB! advisor’s story

What kids learn from travel that they can’t learn in a classroom

18 summer vacations to take before your kids grow up

Editor’s note: This post was accurate when published. We advise checking independently for the latest information and updates. Ciao Bambino does not accept responsibility or liability for any errors or omissions in, or for any actions taken based on, the information presented.