Travel Stories

Flying Solo to Italy with Toddlers

Sometimes the best-laid plans are the first ones to fall apart. Last summer we planned a trip to Italy with our two daughters, Lily and Charlotte (ages 1 and 3, respectively). We rented a villa in Tuscany, forty-five minutes outside of Siena. I thought I had planned for everything — I even had a wonderful local host waiting for us in Italy upon arrival as part of the villa rental program we chose. A few days before our departure date, my husband informed that he couldn’t go on the trip with us, because of business. I was devastated! We had been planning this trip for almost six months and it would mean that I would have to fly with both of my very boisterous toddlers alone for over nine hours in coach! I was in a quandary. Could I endure the flight alone?
I knew we would have a wonderful time once we arrived, plus it would be a trip my older daughter would always remember. I couldn’t cancel — we had to go, even to just escape the heat of a New York City summer.
I knew there were a few things I could do to make the trip easier. First of all I went to the toy store. I bought new coloring books, new DVD movies, sticker books, lip gloss, nail polish, slinkys — anything to keep them occupied. I hand-wrapped fifty small items (even small things like life savers) for each leg of the trip. I had snacks in all shapes and sizes. I decided to bring a seat for my youngest, Lily, so she could sleep on the seat without slipping off. I shipped all of the bulky items in advance like diapers, baby food, and more toys.
We were ready! We arrived at the airport and I curb-checked our bags, so I wouldn’t have to carry them and the girls. I had Lily in a travel stroller and two carry-on bags. I then proceeded to walk them around everywhere to exhaust them (a tough undertaking). We had relay races up and down the corridors, ate fries and played twenty rounds of I Spy. When we boarded, I waited as long as possible to pull out any toys. Charlotte ended up being the star of this leg. She went to sleep in her seat and cooperated with me probably because she could sense how freaked out I was to be flying alone with them. Lily on the other hand was not a happy camper. She cried for about two hours before she finally fell asleep. I tried everything from bottles to rocking her to walking up and down the aisles. Nothing worked. She finally exhausted herself from all the screaming and passed out in my lap. I felt terribly for the people around us, but what was I to do?
I’m happy to report that the pain of dealing with the flight alone was worth it and the trip was wonderful. Charlotte learned how to make pizza with an Italian chef, over-dosed on gelato, and she took a ceramics class with local Italian children in the town’s square. She woke up in the morning to collect the fresh eggs from the chicken coop and cut flowers in a garden fit for a queen. I think they will always remember the fields of sunflowers at every turn.
On the return, I pulled out the rest of the toys and put on my clown face. We made friends with other passengers and they helped entertain them for the 10-hour flight to JFK. When we disembarked at least twenty people said “Bye Lily!” This experience made me less afraid to take trips with them on my own.
A friend of mine with four kids says that travels with children should be called trips not vacations — these trips are satisfying, but not relaxing.  Although it was a lot of work, it’s not the flight we dwell on … but the gelato and our incredible Italian garden — now those are fun to remember!
Fast Facts:
House Rental –
Travel Toys –
Pre-Travel Diaper Shipment –

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  • Laura,
    I feel for you. As a father of 5 boys and frequent traveler, I’ve been in your shoes many times. We are that family you see in the waiting lounge that other people are just desperately hoping are not seated near them on the plane! But things generally turn out just fine.
    Several tricks ‘n tips that I’ve found that help:
    – don’t try to control the outcome of your kids’ behavior – what will be will be, and if you’re uptight, chances are they will sense this and behave accordingly
    – let them get plenty of exercise before getting on the plane – doing laps around the waiting lounge works wonders
    – pack lots of snacks and beverages for the lounge and plane
    – pack some surprise presents and activities; introduce a new one each hour
    Glad the villa vacation experience on the other end made it all worthwhile!

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