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Traveling with our teen

Santinas at della Santina

Traveling with our teen

Santina on the airplane

In the summer of 2009, my husband and I had a brand-new baby girl. We were broker than broke, but we had a dream of someday going to Italy. So we started a savings account and decided we could afford to put $50 into it every two weeks. We figured, we didn’t want to go until our baby girl was old enough that she didn’t need to be pushed in a stroller, could carry her own stuff, and, most importantly, would remember the experience years later.

As we approached her 14th birthday, that little savings account had grown to a nice sum. We had nowhere else we had to go for a family visit, we had some time, and there were no longer any pandemic restrictions to deal with. It was time. We booked our flights for March 2023. Our daughter would spend her spring break and 14th birthday in Italy.

The Planning

Olivia on an airplane

We had two and a half weeks to play with — a nice, long time, but not long enough that we could spend tons of time in any one place. We would fly into Venice, spend a couple days there, then travel by train to Lucca, eventually moving southward to Rome, then to Positano, which we’d call home for our last week of the nearly 18-day vacation.

I’d been to Europe before, and so had Dave. We’d even honeymooned in Ireland. Just ahead of smartphones, we’d relied on nothing but our wits, our senses of adventure, and a little AAA guidebook of bed & breakfasts in Ireland. It had all worked out just grand. But we’d never taken our offspring with us.

You know how the older you get, the more scared and anxious you get about stuff? Seems like it should be the opposite, but it isn’t. In fact, the more you learn about life, the more afraid you become of everything. I wasn’t afraid of foreign travel. But suddenly I was worried about our comfort level. I was worried about booking things early enough to not get stuck without tickets. I was worried about weight restrictions for bringing carry-on luggage onto airplanes. I was worried about having shoes that were comfortable enough. I was worried about all my clothes matching but also not looking too matchy-matchy and American. I was worried about where I would need my passport and what might happen if I lost it. I was worried about whether we had the right kinds of raincoats.

In short, I didn’t get much sleep in the weeks before we left. At one point, I had a full-on panic attack. In the middle of the night, it occurred to me that perhaps our passports might be expiring soon, so I had to get up at 3 a.m. and check.

Our daughter, for her part, is a self-confessed introverted homebody who had her own fears. Would anyone speak English in Italy? Would going through customs mean she’d be pulled into an office and strip-searched, like some movie or bizarre tale shared in a YouTube video?

And we played a role in her anxiety as well. Adamant that we could not, under any circumstances, lose our passports or any of our belongings, and having read too many stories about pickpockets, my husband and I (well, mostly I) talked excessively about the need to keep watch over our belongings. The poor thing was probably convinced that Italy was a nation of thieves.

The Trip

The first thing I should say here is that none of our fears were realized. We had packed perfectly, customs was a breeze, and we never lost a thing.

Oh, and we had THE BEST TIME.

Traveling with our teenager really opened our eyes to a lot of important things about international travel, and I believe it made the trip so much more enjoyable than it ever would have been without her.

Santina at della Santina
  • I cannot stress this enough: Pack light. You’ll never regret packing light. I’ve been to Europe twice before, and both times, I made the terrible mistake that newbies who glamorize Europe make. I wanted to look GOOD. I packed the cute shoes, the fashionable dress, the jewelry I didn’t usually get to wear. My suitcase was way too big, which really sucked when I was jet-lagged and sleep-deprived, dragging it from the train station down cobblestone streets to our hotel. Did I wear that stuff? Hell no. I also got blisters and sprained ankles from those “cute shoes” and generally felt miserable a lot of the time.
    The beauty of being older and wiser is that you stop giving a crap how you look in a foreign country. We were all about practicality. Our approach was, we can’t be parted from our bags on the way there. But we could bear it if we were parted coming home – all our other stuff is at home.
    That meant neutrals, things we could mix and match so we didn’t have to bring much. I went with black, white, and tan. It all went together. I packed four pairs of comfortable pants, three t-shirts, two long-sleeved tees, a lightweight jacket, a couple tank tops, and two pairs of sneakers. It lasted me two and a half weeks, and I was comfortable every day. All three of us did carry-on only, using similar neutral color palettes, and we never had to pay to check bags and risk losing any of it. Not only that but our airline, Lufthansa, has a strict weight limit for carry-on bags. We bought a luggage scale and did practice runs on packing in the weeks leading up to the trip. If it weighed too much, it had to go.
    It all paid off. We had no trouble sailing through check-in and security. And we just shook our heads and felt thankful as we watched folks struggle to lift giant, overpacked suitcases onto buses and up Positano’s notorious staircases. You’ll never regret the stuff you don’t pack.

Buy whatever’s missing when you get there.
They have stores there, too.

Santina family on a boat
  • Bring the comfortable shoes. Trust me on this: NO ONE CARES WHAT YOUR SHOES LOOK LIKE. But you will care how they feel when you are regularly walking 15,000-20,000 steps a day. Pack one or two extra-comfy pairs that go with everything and call it done.
  • Bring something warm. Traveling in off-season or shoulder season (which I recommend, because money) means you can expect chilly weather. Our 14-year-old would rather freeze her tail off than wear a jacket to school (Seriously, what do kids have against jackets?), so the only warm thing she’d brought was a cropped cardigan sweater (“It’s FINE, Mom! Jeez!”). It only took her 24 hours in damp Venice before my daughter admitted she was cold. Have at least one cozy item that can warm you on a chilly day, and count on layering up, so you can take off layers as you need to.
  • As much as you want to see it all, don’t try. On a two-week family trip, you need to face facts: You can’t see it all. You shouldn’t try to, because it will diminish all the experiences you have when you’re rushing to the next thing. You can have a whirlwind day or two, but then build in some time to really slow down and stay in one place for a bit. Immediately, get the idea OUT of your head that this is your last chance to see Europe. It’s not. Plan to return. It really, really shouldn’t be. The slow, staying-in-one-place days give everyone a chance to breathe and glimpse what it’s like to be a local. Don’t be so rigid about your itinerary.

Stop treating European travel as a once-in-a-lifetime deal.

Santinas in Pisa
Olivia eating gelato!
  • If you seem anxious, your kid will be anxious. All our talk about holding our possessions tightly, avoiding pickpockets, being aware of strangers … it freaked out our daughter. On one hand, it was a good thing. She rose to the occasion, became an infinitely more responsible and capable person, and we had zero trouble with theft. But it also may have made it harder on all of us, and anxiety can ruin a trip. Instead, have some backup plans just in case (save photos of passports and IDs in the cloud and buy some good locking luggage, for example), and then have a big family conversation about the what-ifs. Brainstorm, have some emergency “what-if” plans, and then talk about how stuff will inevitably happen, but that you’ll get through it no matter what.
  • Let your kid carry some of their own money. We put her in charge of a couple hundred dollars cash for her to use as she liked. Some went in the suitcase, some in her backpack, and some in her pocket. Before we left hotels or AirBNBs, we all did cash counts to be sure we knew how much we were headed out the door with and how much we were leaving behind. And then, as we were out sightseeing, if she started asking for gelato, we could say, “You have money, go get some. We’ll wait here.” The dawning realization of that freedom was apparent on her face; she felt so proud, so capable. Suddenly, she understood that she had a level of independence, and that truly made the trip more enjoyable for her.
  • Tickets and tours are good … sometimes. I used to be firmly anti-tour. I preferred spontaneous excursions, going where the wind took me, having an “authentic” experience. But that results in a lot of wasted time, and we didn’t want to waste a minute. Plus, with a kid who gripes, loudly, when her feet hurt, we were all about hitting it and quitting it. We booked tours with guides who led us through crowds to exactly the right spots, maximizing our time, showing us the highlights, and keeping us moving.
    Also, if there’s stuff you absolutely, positively must see – the bucket list stuff – buy your tickets early. Big tourist attractions, like St. Mark’s Basilica and Michelangelo’s David, sell out. If you must go, buy tickets early. Have a few things you know are booked, and then be flexible about the rest.
Shrimp with heads and tails

  • Get lost. No, really. Plan some time to aimlessly wander. See where that road goes. You never know where it could lead. It’s also a great skill to teach a kid – not to be paralyzed by fear of being lost, but that with your phone’s GPS and a little curiosity, you can accomplish great things.
  • It’s okay to look and feel foolish. So you went and got lost. Now what? Should you be the tourist and ask directions? What if you aren’t sure how to pronounce “grazie” or “buongiorno” or “s’il vous plait”? Just try. Give it a go. When you are a stranger in a strange land, you have to relinquish some control. You are just going to look stupid sometimes. Who cares? The locals will appreciate your efforts.
    For a lot of people, that’s scary. My daughter was used to seeing us in control, and it was important for her to see us being vulnerable and unafraid to look and sound silly. Big deal if we didn’t understand the menu or the bus schedule. So what if we butchered a German word. It’s the trying that counts. What’s the worse that can happen? Kids need to see that it’s not something to be afraid of.
    I saw a video recently about how in France, as in many European countries, they like kids to feel frustrated. There aren’t children’s menus in many restaurants there. There’s more of a sink-or-swim mentality. Here in the States, our kids are so used to having their every whim accommodated. But they NEED to understand frustration. They NEED to be put in vulnerable, challenging circumstances, because getting out of them is a LIFE SKILL. And the way you get them to push through it is 1) showing them that you do it all the time, and 2) making them.
Olivia in Italy
  • Carry water and snacks. This sounds a little babyish, but it’s important. We were walking a LOT. We were tired, and unused to the late hours Italian restaurants kept. My daughter grumped a lot about being hungry in the middle of activities. Having a few snacks and water bottles on hand make that bearable.
  • Insist on trying local cuisine, even if you’re scared. I will never forget my daughter’s face when the shrimp she ordered came complete with heads and tails. We are lucky to have a kid who has never been a picky eater. She’ll eat almost anything (except mayonnaise. Don’t do it.), and we’ve exposed her to plenty of gourmet foods. But she had no idea what to do with that shrimp. So I dug in there, showed her how to peel one, and took a bite. It was the best shrimp we ever ate. Don’t be afraid to try new things. You can get a burger at home. You’ll be so proud of yourself for trying it.
  • Give everyone a shot at picking activities. Rather than making our daughter follow us around for whatever we planned, we sat down each evening and talked about what we wanted to do in the days ahead. She got a chance to vote, to contribute ideas to the day’s agenda. It gave everyone an opportunity to be in charge and feel in control, and when something didn’t work out, we debriefed on how to avoid that going forward. Again, life skills.
  • Get out of your bubble. The biggest lesson we learned from traveling with our teen – or, at least, the biggest reminder we got – was how essential it is to get out of your safety bubble and see how people live in another country. The world is vast. It doesn’t revolve around you, and we need to be reminded of that. It opens your mind to ways of thinking and behaving that never would have occurred to you. It reminds you that your “big” problems aren’t that big. It gives you confidence, shows you what you’re capable of, and makes you a more empathetic and interesting human. You become more sensitive to other people and ways of life.

This point was driven home a day or two after we returned, when our shy, introverted, homebody daughter asked us, “When I’m a little older, could I go somewhere far away by myself?”

You betcha, kid. In fact, we insist upon it.

Jessica Santina is an award-winning freelance writer and editor based in Northern Nevada. Her credits include working as managing editor for three local/regional publications, being a managing partner in a Reno-based publishing company, and writing and editing for a wide variety of publications and organizations. See more of her work at

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